Organic electroluminescent material and device thereof
By using a new compound with Formula 1 structure in OLED devices as the main material of organic electroluminescent devices, the efficiency and life problems of existing OLED blue phosphorescent devices are solved, and the effects of high power efficiency and longer life are achieved.
Patent Information
- Application Number
- CN202311822216.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-12-27
- Publication Date
- 2025-06-27
AI Technical Summary
The blue phosphorescence devices of existing OLEDs have problems such as blue unsaturation, short device life and high operating voltage, and the efficiency of phosphorescence OLEDs in high brightness situations is rapidly reduced.
A novel compound with a specific structure of Formula 1 is used as the main material of the organic electroluminescent device, and the efficiency and performance of the device are improved by providing an organic layer with Formula 1 structure in the device.
Maintaining high power efficiency in OLED devices, providing better device performance and longer life, solving the efficiency and life problems of blue phosphorescence devices.
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Figure CN120208934A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a compound having the structure of Formula 1, and an organic electroluminescent device, a compound composition and an electronic device comprising the compound. Background Art
[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 photoreceptors, organic field effect quantum dots (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device that included an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light emitting layer (Applied Physics Letters, 1987, 51(12):913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light emitting diodes (OLEDs). The 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 a cathode and an anode. Since OLEDs are a self-emitting solid-state device, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as fabrication on flexible substrates.
[0004] OLEDs can be classified into three different types according to their emission mechanisms. The OLED invented by Tang and van Slyke is a fluorescent OLED. It only uses singlet emission. The triplets generated in the device are wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metals in complexes as emitters. Therefore, it is able to harvest both singlets and triplets, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs have directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from 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 and polymer OLEDs according to the form of the materials used. Small molecules refer to any organic or organometallic materials that are not polymers. As long as they have an exact structure, the molecular weight of small molecules can be very large. Dendrimers with a well-defined structure are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emitting groups. If post-polymerization occurs during the manufacturing process, small molecule OLEDs can turn into polymer OLEDs.
[0006] There are various methods for manufacturing OLEDs. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. If the materials can be dissolved or dispersed in a solvent, small molecule OLEDs can also be manufactured by solution methods.
[0007] The emission color of OLEDs can be achieved through the structural design of the emitting materials. OLEDs can include one or more emitting layers to achieve the desired spectrum. For green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue color unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid reduction of the efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, more saturated emission spectra, higher efficiency, and longer device lifetimes are desired.
[0008] US2022285627A1 discloses an electroluminescent element, wherein the electron transport region contains a general formula The compound, although its specific structure discloses the following structure However, the compounds of this type that it focuses on are used as a blocking layer material on the light-emitting layer to improve the performance of the device, and it does not disclose a compound formed by a triazine group having a naphthylphenyl group connected to a specific position of dibenzofuran through a biphenylene group, nor does it disclose or teach the special advantages of such compounds as a host material.
[0009] However, there is still room for improvement in the reported triazine materials at present. To meet the increasing demands in the industry, especially for high efficiency, new materials still need to be further researched and developed. SUMMARY OF THE INVENTION
[0010] The present invention aims to provide a series of compounds having the structure of Formula 1 to solve at least part of the above problems. The compounds can be used as host materials in organic electroluminescent devices. These novel compounds can maintain high efficiency in the devices and provide better device performance.
[0011] According to an embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:
[0012]
[0013] Wherein,
[0014] X1 to X 10 are each independently selected from C, N or CR x each time it appears, and one of X1 to X5 is C, and one of X6 to X 10 is C, and the two are connected by a single bond;
[0015] W1 to W7 are each independently selected from N or CR w each time they appear;
[0016] Y1 to Y9 are each independently selected from C, N or CR y each time they appear, and one of Y1 to Y5 is C, and one of Y6 to Y9 is C, and the two are connected by a single bond;
[0017] Y 10 to Y 13 are each independently selected from N or CR y each time they appear;
[0018] Z is each independently selected from O, S or Se each time it appears;
[0019] R x , R w , R yEach time it appears, it is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
[0020] Ar is selected from substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or combinations thereof.
[0021] According to another embodiment of the present invention, an organic electroluminescent device is also disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer contains a compound having the structure of Formula 1, and the specific structure of the compound is as shown in the foregoing embodiments.
[0022] According to another embodiment of the present invention, a compound composition is also disclosed, which contains a compound having the structure of Formula 1, and the specific structure of the compound is as shown in the foregoing embodiments.
[0023] According to another embodiment of the present invention, an electronic device is also disclosed, which includes an organic electroluminescent device, and the specific structure of the organic electroluminescent device is as shown in the foregoing embodiments.
[0024] According to another embodiment of the present invention, the use of a compound having the structure of Formula 1 as a host material is also disclosed, and the specific structure of the compound is as shown in the foregoing embodiments.
[0025] According to another embodiment of the present invention, the use of a compound having the structure of Formula 1 as an organic light-emitting layer is also disclosed, and the specific structure of the compound is as shown in the foregoing embodiments.
[0026] The novel compounds with the structure of Formula 1 disclosed in the present invention can be used as host materials in electroluminescent devices. These novel compounds can maintain high power efficiency in the devices and provide better device performance. Brief Description of the Drawings
[0027] Figure 1 It is a schematic diagram of an organic light-emitting device that can contain the compounds and compound compositions disclosed herein.
[0028] Figure 2 It is another schematic diagram of an organic light-emitting device that can contain the compounds and compound compositions disclosed herein. Detailed Description of the Embodiments
[0029] OLEDs can be fabricated on various substrates, such as glass, plastic, and metal. Figure 1 The organic light-emitting device 100 is schematically and non-limitingly shown. The figures are not necessarily drawn to scale, and some layer structures in the figures can also be omitted as needed. The device 100 can include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of US Patent US7,279,704B2, and the entire content of the above patent is incorporated herein by reference.
[0030] Each of these layers has more instances. For example, U.S. Patent No. 5,844,363, incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. 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, incorporated herein by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., 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, incorporated herein by reference in its entirety. U.S. Patents Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entireties, disclose examples of cathodes including a composite cathode having a thin metal layer such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of the blocking layer are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in their entireties. Examples of the injection layer are provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety.
[0031] The above-described layered structure is provided by way of non-limiting examples. The function of the OLED can be achieved by combining the various layers described above, or some layers can be completely omitted. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, the light-emitting layer can have two different light-emitting materials to achieve a desired emission spectrum.
[0032] In one embodiment, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. The organic layer can include one or more layers.
[0033] The OLED also requires a packaging layer, such as Figure 2 Schematically and non-limitingly shows an organic light-emitting device 200, which is Figure 1In contrast, a encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function 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 outside the OLED device. Multilayer thin film encapsulation is described in U.S. Patent US7,968,146B2, the entire content of which is incorporated herein by reference.
[0034] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) with the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.
[0035] The materials and structures described herein can also be used in other organic electronic devices listed above.
[0036] As used herein, "top" means farthest from the substrate, and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" "on" the second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer "contacts" the second layer, there may be other layers between the first and second layers. For example, even though there are various organic layers between the cathode and the anode, the cathode can still be described as being "disposed" "on" the anode.
[0037] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and / or deposited from a liquid medium.
[0038] When it is believed that the ligand directly contributes to the photosensitive properties of the emissive material, the ligand can be called "photosensitive". When it is believed that the ligand does not contribute to the photosensitive properties of the emissive material, the ligand can be called "auxiliary", but the auxiliary ligand can change the properties of the photosensitive ligand.
[0039] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can exceed the 25% spin statistics limit by delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0040] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets but on the conversion between the triplet state and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap for the energy state conversion. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with the increase in temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative decay from the triplet state, the fraction of the singlet excited state refilled may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of electro-generated excitons.
[0041] The characteristics of E-type delayed fluorescence can be seen in the exciplex system or a single compound. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in these donor-acceptor type compounds usually results in a small ΔE S-T . These states can include CT states. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) to an electron acceptor moiety (such as an N-containing six-membered aromatic ring).
[0042] Definition of substituent terms
[0043] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.
[0044] Alkyl - as used herein, includes straight-chain and branched-chain alkyls. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyls include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. 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 can be optionally substituted.
[0045] Cycloalkyl - As used herein, cycloalkyl includes cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 ring 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. Additionally, the cycloalkyl group can be optionally substituted.
[0046] Heteroalkyl - As used herein, heteroalkyl is formed by replacing one or more carbons in an alkyl chain with heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, phosphorus atoms, silicon atoms, germanium atoms, 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, 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, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl group can be optionally substituted.
[0047] Alkenyl - As used herein, it encompasses straight-chain, branched-chain, and cyclic olefin groups. The 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-methylethenyl, styryl, 2,2-diphenylethenyl, 1,2-diphenylethenyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, the alkenyl group can be optionally substituted.
[0048] Alkynyl - As used herein, linear alkynyl is encompassed. The alkynyl can be an alkynyl having 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylacetylenyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.
[0049] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, chrysene, phenanthrene, fluorene, pyrene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl include phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 4-p-terphenyl, 3-p-terphenyl, 2-p-terphenyl, 4-m-terphenyl, 3-m-terphenyl, 2-m-terphenyl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-4-p-terphenyl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl. Additionally, the aryl can be optionally substituted.
[0050] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are considered. The non-aromatic heterocyclic group includes 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 atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl and tetrahydrothienyl. Additionally, the heterocyclic group can be optionally substituted.
[0051] Heteroaryl - As used herein, refers to non - fused and fused heteroaromatic groups that can contain 1 to 5 heteroatoms, with at least one heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Isoaryl also refers to heteroaryl. The heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2 - azaborolane, 1,3 - azaborolane, 1,4 - azaborolane, borazole and its nitrogen analogs. Additionally, the heteroaryl can be optionally substituted.
[0052] Alkoxy - As used herein, is represented by -O - alkyl, -O - cycloalkyl, -O - heteroalkyl or -O - heterocycloalkyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocycloalkyl are the same as those described above. The alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. Additionally, the alkoxy can be optionally substituted.
[0053] Aryloxy - As used herein, is represented by -O - aryl or -O - heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 - 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. Additionally, the aryloxy can be optionally substituted.
[0054] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,
[0055] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.
[0056] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.
[0057] Alkylgermyl – As used herein, it encompasses alkyl-substituted germyl groups. The alkylgermyl group can be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of the alkylgermyl group include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tritert-butylgermyl, triisobutylgermyl, dimethyltert-butylgermyl, methylditert-butylgermyl. Additionally, the alkylgermyl group can be optionally substituted.
[0058] Arylgermyl – As used herein, it encompasses germyl groups substituted with at least one aryl or heteroaryl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of the arylgermyl group include triphenylgermyl, phenyldibiphenylgermyl, diphenylbiphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyltert-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.
[0059] In terms such as azadibenzofuran and azadibenzothiophene, the term "aza" means that one or more C-H groups in the corresponding aromatic moiety are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other similar compounds having two or more nitrogens in the ring system. Those of ordinary skill in the art can readily envision other nitrogen analogs of the above-mentioned aza derivatives, and all such analogs are determined to be included in the terms described herein.
[0060] In the present disclosure, unless otherwise defined, when any one of the terms consisting of the following groups is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocycloalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxy, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxy, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more substituents selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocycloalkyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxy, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.
[0061] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered equivalent.
[0062] In the compounds mentioned in the present disclosure, the hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred due to their enhanced device efficiency and stability.
[0063] Among the compounds mentioned in the present disclosure, polysubstituted refers to the range including disubstituted up to the maximum available substitution. When a substituent in the compounds mentioned in the present disclosure indicates polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its connecting structure, and the substituent present at multiple available substitution positions can be of the same structure or different structures.
[0064] Among the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally connect to form a ring, otherwise adjacent substituents in the compound cannot connect to form a ring. Among the compounds mentioned in the present disclosure, adjacent substituents can optionally connect to form a ring, which includes both the case where adjacent substituents can connect to form a ring and the case 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 spiro ring, bridged ring, fused ring, etc.), and an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, 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.
[0065] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:
[0066]
[0067] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:
[0068]
[0069] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms further away connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:
[0070]
[0071] In addition, the expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonding to the position where the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
[0072]
[0073] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:
[0074]
[0075] Wherein,
[0076] X1 to X 10 are the same or different each time they appear and are selected from C, N or CR x , and one of X1 to X5 is C, and one of X6 to X 10 is C, and the two are connected by a single bond;
[0077] W1 to W7 are the same or different each time they appear and are selected from N or CR w ;
[0078] Y1 to Y9 are the same or different each time they appear and are selected from C, N or CR y , and one of Y1 to Y5 is C, and one of Y6 to Y9 is C, and the two are connected by a single bond;
[0079] Y 10 to Y 13 are the same or different each time they appear and are selected from N or CR y ;
[0080] Z is the same or different each time it appears and is selected from O, S or Se;
[0081] R x ,R w ,R yEach occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0082] Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof.
[0083] As used herein, "Y1 to Y9 are each independently selected from C, N, or CR each time they occur" y and one of Y1 to Y5 is C, one of Y6 to Y9 is C, and the two are connected by a single bond" is intended to mean that the six-membered ring containing Y1 to Y5 and the six-membered ring containing Y6 to Y9 are directly connected, and the connecting atoms are C, and the two Cs are connected by a single bond.
[0084] As used herein, "X1 to X 10 are each independently selected from C, N, or CR each time they occur" x and one of X1 to X5 is C, one of X6 to X 10 is C, and the two are connected by a single bond" is intended to mean that the six-membered ring containing X1 to X5 and the six-membered ring containing X6 to X 10 are directly connected, and the connecting atoms are C, and the two Cs are connected by a single bond.
[0085] According to one embodiment of the present invention, X2, X3, or X4 is selected from C, and X8 or X9 is selected from C.
[0086] According to one embodiment of the present invention, the compound has a structure represented by any one of Formulas 1-1 to 1-4:
[0087]
[0088]
[0089] Wherein,
[0090] W1 to W7 are each independently selected from N or CR, the same or different each time they appear w ;
[0091] Y1 to Y9 are each independently selected from C, N or CR, the same or different each time they appear y , and one of Y1 to Y5 is C, one of Y6 to Y9 is C, and the two are connected by a single bond;
[0092] Y 10 to Y 13 are each independently selected from N or CR, the same or different each time they appear y ;
[0093] X1 to X 10 are each independently selected from N or CR, the same or different each time they appear x ;
[0094] Z is each independently selected from O, S or Se, the same or different each time it appears;
[0095] R x , R w , R y are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, isocyano, and combinations thereof;
[0096] Ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or combinations thereof.
[0097] According to one embodiment of the present invention, wherein, R w , R yEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof.
[0098] According to one embodiment of the present invention, wherein R w , R y Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, methyl, phenyl, deuterated naphthyl, deuterated phenyl, pyridyl, vinyl, naphthyl, biphenyl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, cyano, adamantyl, tert-butyl, trifluoromethyl, carbazolyl, 9,9-dimethylfluorenyl, and combinations thereof.
[0099] According to one embodiment of the present invention, wherein Y1 to Y9 each occurrence is the same as or different from and is selected from C or CR y , and one of Y1 to Y5 is C, one of Y6 to Y9 is C, and the two are connected by a single bond; Y 10 to Y 13 Each occurrence is the same as or different from and is selected from CR y ;
[0100] R y Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof.
[0101] According to one embodiment of the present invention, wherein Y1 to Y9 each occurrence is the same as or different from and is selected from C or CR y , and one of Y1 to Y5 is C, one of Y6 to Y9 is C, and the two are connected by a single bond; Y 10 to Y 13 Each occurrence is the same as or different from and is selected from CR y ;
[0102] R y Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, methyl, phenyl, deuterated naphthyl, deuterated phenyl, pyridyl, vinyl, naphthyl, biphenyl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, cyano, adamantyl, tert-butyl, trifluoromethyl, carbazolyl, 9,9-dimethylfluorenyl, and combinations thereof.
[0103] According to one embodiment of the present invention, Y3 or Y4 is selected from C, and Y6 or Y7 is selected from C.
[0104] According to one embodiment of the present invention, W1 to W7 are each independently selected from CR w ;
[0105] R w which is the same as or different from each other at each occurrence and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, and combinations thereof.
[0106] According to one embodiment of the present invention, W1 to W7 are each independently selected from CR w ;
[0107] R w which is the same as or different from each other at each occurrence and is selected from the group consisting of hydrogen, deuterium, halogen, methyl, phenyl, deuterated naphthyl, deuterated phenyl, pyridyl, vinyl, naphthyl, biphenyl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, cyano, adamantyl, tert-butyl, trifluoromethyl, carbazolyl, 9,9-dimethylfluorenyl, and combinations thereof.
[0108] According to one embodiment of the present invention, Z is selected from O or S.
[0109] According to one embodiment of the present invention, Z is selected from O.
[0110] According to one embodiment of the present invention, X1 to X 10 are each independently selected from CR x ;
[0111] R x which is the same as or different from each other at each occurrence and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, and combinations thereof.
[0112] According to one embodiment of the present invention, X1 to X 10 are each independently selected from CR x ;
[0113] R xEach occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, methyl, phenyl, pyridyl, cyclopentyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, adamantyl, tert-butyl, trifluoromethyl, carbazolyl, and combinations thereof.
[0114] According to one embodiment of the present invention, Ar is selected from substituted or unsubstituted aryl having 6 - 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 20 carbon atoms, or combinations thereof.
[0115] According to one embodiment of the present invention, Ar is selected from the group consisting of phenyl, biphenyl, deuterated naphthyl, deuterated phenyl, terphenyl, naphthyl, phenylnaphthyl, phenanthryl, triphenylene, pyrimidinyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, and combinations thereof.
[0116] According to one embodiment of the present invention, the compound is selected from the group consisting of Compound A-1 to Compound A-200, and the specific structures of Compound A-1 to Compound A-200 are shown in Claim 9.
[0117] According to one embodiment of the present invention, in the structures of Compound A-1 to Compound A-200, the hydrogen can be partially or completely replaced by deuterium.
[0118] According to another embodiment of the present invention, an organic electroluminescent device is also disclosed, which includes:
[0119] An anode,
[0120] A cathode,
[0121] And an organic layer disposed between the anode and the cathode, wherein the organic layer contains a compound having the structure of Formula 1, and the specific structure of the compound is as described in any of the foregoing embodiments.
[0122] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, a hole-transporting layer, or an electron-blocking layer.
[0123] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, and the compound is a host material.
[0124] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, and the light-emitting layer contains a second compound, and the second compound is selected from the structures shown in any one of Formula 2-1 to Formula 2-3:
[0125]
[0126] Wherein,
[0127] In Formulas 2-1 to 2-3, Ar 31 to Ar 35 is the same as or different from each other each time it appears, and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0128] L 31 to L 35 is the same as or different from each other each time it appears, and is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
[0129] X is the same as or different from each other each time it appears, and is selected from O, S, CR 21 R 22 or NR 23 ;
[0130] R 31 to R 37 is the same as or different from each other each time it appears, and represents single substitution, multiple substitution or no substitution;
[0131] R 31 to R 37 and R 21 to R 23 is the same as or different from each other each time it appears, and is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
[0132] Adjacent substituents R 21 to R 22 and R 31 to R 37can optionally be connected to form a ring.
[0133] In this text, "adjacent substituents R 31 to R 37 can optionally be connected to form a ring" is intended to mean that between adjacent substituents R 31 among adjacent substituents R 32 among adjacent substituents R 33 among adjacent substituents R 34 among adjacent substituents R 35 among adjacent substituents R 36 among adjacent substituents R 37 among adjacent substituents R 21 to R 22 among these, any one or more of these groups of substituents can be connected to form a ring. Obviously, these adjacent groups of substituents can also all not be connected to form a ring.
[0134] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, and the second compound is a host material.
[0135] According to one embodiment of the present invention, in the organic electroluminescent device, where the second compound has a structure represented by any one of Formula 2-4 to Formula 2-14:
[0136]
[0137]
[0138] In Formula 2-4 to Formula 2-14,
[0139] Ar 31 Ar 32 Ar 34 and Ar 35 are each independently selected, each time they appear, from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
[0140] L 31 to L 35 are each independently selected, each time they appear, from a single bond, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, or combinations thereof;
[0141] X is each independently selected, each time it appears, from O, S, CR 21 R 22 or NR 23 ;
[0142] R 31 to R 38 each occurrence is the same as or different from each other and represents mono-substitution, multi-substitution or no substitution;
[0143] R 31 to R 38 and R 21 to R 23 each occurrence is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0144] Adjacent substituents R 21 to R 22 and R 31 to R 38 can optionally be connected to form a ring.
[0145] As used herein, "adjacent substituents R 21 to R 22 and R 31 to R 38 can optionally be connected to form a ring" is intended to mean that between adjacent substituents R 31 , between adjacent substituents R 32 , between adjacent substituents R 33 , between adjacent substituents R 34 , between adjacent substituents R 35 , between adjacent substituents R 36 , between adjacent substituents R 37 , between adjacent substituents R 38 , between adjacent substituents R 21 to R 22Among them, any one or more of these substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.
[0146] According to one embodiment of the present invention, wherein each occurrence of X is the same or different and is selected from O, S or NR 23 .
[0147] According to one embodiment of the present invention, wherein each occurrence of X is the same or different and is selected from NR 23 .
[0148] According to one embodiment of the present invention, wherein the R 31 to R 38 Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof; adjacent substituents R 31 to R 38 can optionally be connected to form a ring.
[0149] According to one embodiment of the present invention, wherein the R 31 to R 38 Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuteriomethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl, phenylpyridyl, and combinations thereof; adjacent substituents R 31 to R 38 can optionally be connected to form a ring.
[0150] According to one embodiment of the present invention, wherein the L 31 to L 35 Each occurrence is the same or different and is selected from the group consisting of: single bond, substituted or unsubstituted arylene having 6-18 carbon atoms, substituted or unsubstituted heteroarylene having 3-18 carbon atoms, and combinations thereof.
[0151] According to one embodiment of the present invention, wherein the L 31 to L 35 Each occurrence is the same or different and is selected from the group consisting of: single bond, phenylene, naphthylene, biphenylene, terphenylenylene, triphenylene, pyridylene, thienylene, dibenzofuranylene, dibenzothiophenylene, and combinations thereof.
[0152] According to one embodiment of the present invention, wherein said Ar 31 to Ar 35 , R 21 to R 23 are each independently selected, each time they appear, from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, and combinations thereof.
[0153] According to one embodiment of the present invention, wherein said Ar 31 to Ar 35 , R 21 to R 23 are each independently selected, each time they appear, from the group consisting of: methyl, ethyl, phenyl, deuterated phenyl, methylphenyl, fluorophenyl, tert-butylphenyl, tri-deuterated methylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylene, and combinations thereof.
[0154] According to one embodiment of the present invention, wherein said second compound is selected from the group consisting of compound H-1 to compound H-156, and the specific structures of said compound H-1 to compound H-156 are shown in claim 16.
[0155] According to one embodiment of the present invention, in the preparation of the device, when the compound of the present invention and the second compound are co-evaporated with a luminescent material to form a light-emitting layer, the light-emitting layer can be formed by co-evaporating the compound of the present invention, said second compound and the luminescent material from different evaporation sources respectively, or by placing a mixture of the compound of the present invention and said second compound pre-mixed in the same evaporation source, and then co-evaporating with the luminescent material placed in another evaporation source to form the light-emitting layer. This pre-mixing method can further save evaporation sources.
[0156] According to one embodiment of the present invention, in the organic electroluminescent device, said organic layer is a light-emitting layer, and said light-emitting layer contains at least one phosphorescent luminescent material.
[0157] According to one embodiment of the present invention, wherein said phosphorescent luminescent material is a metal complex, and said metal complex has the general formula of M(L a ) m (L b ) n (L c ) q ;
[0158] M is selected from metals having a relative atomic mass greater than 40;
[0159] L a ,L b and L c are the first ligand, the second ligand, and the third ligand coordinated with the M, respectively; L a ,L b and L c can optionally be connected to form a polydentate ligand;
[0160] L a ,L b and L c are the same or different; m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q is equal to the oxidation state of the M; when m is greater than or equal to 2, multiple Ls a are the same or different; when n is 2, two Ls b are the same or different; when q is 2, two Ls c are the same or different;
[0161] L a is the same or different each time it appears and is selected from the structures shown in Formula 3:
[0162]
[0163] wherein,
[0164] Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
[0165] Ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;
[0166] Ring D and Ring E are fused via U a and U b ;
[0167] U a and U b are the same or different each time they appear and are selected from C or N;
[0168] R d and R e are the same or different each time they appear and represent mono-substituted, multi-substituted, or unsubstituted;
[0169] V1 to V4 are the same or different each time they appear and are selected from CR v or N;
[0170] R d ,R e and R vEach occurrence is the same as or different from each other and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
[0171] Adjacent substituents R d , R e and R v can optionally be connected to form a ring;
[0172] L b and L c Each occurrence is the same as or different from each other and is selected from any one of the following structures:
[0173]
[0174] Wherein,
[0175] R a , R b and R c Each occurrence is the same as or different from each other and represents mono - substitution, multi - substitution, or no substitution;
[0176] X b Each occurrence is the same as or different from each other and is selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;
[0177] X c and X d Each occurrence is the same as or different from each other and is selected from the group consisting of: O, S, Se and NR N2 ;
[0178] R a , R b , Rc , R N1 , R N2 , R C1 and R C2 Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0179] Said ligand L b , L c In the structure of, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be connected to form a ring.
[0180] In this context, adjacent substituents R d , R e , R v can optionally be connected to form a ring, which is intended to mean that when there are substituents R d , substituent R e , substituent R v , among which adjacent substituent groups, such as between adjacent substituents R d , between adjacent substituents R e , between adjacent substituents R v , between adjacent substituents R d and R e , between adjacent substituents R d and R v between adjacent substituents Re With R v Among them, any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, when there are substituents R d , substituent R e , substituent R v , these substituent groups may also not be connected to form a ring.
[0181] In this article, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be connected to form a ring, which is intended to represent adjacent substituent groups among them. For example, between two substituents R a , between two substituents R b , between 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 , and between R C1 and R C2 , any one or more of these substituent groups can be connected to form a ring. For example, Among the adjacent substituents R a , R b in it can optionally be connected to form a ring, which can form one or more of the following structures including but not limited to:
[0182] Wherein, W is selected from O, S, Se, NR w1 or CR w Rw1 ; wherein said R w1 , R a ’, R b ’ are defined the same as said R a . Obviously, these substituents may also not be connected to each other to form a ring.
[0183] According to an embodiment of the present invention, in formula 3, two adjacent substituents R e are connected to form a ring.
[0184] According to an embodiment of the present invention, in formula 3, two adjacent substituents R e are connected to form a 5-membered unsaturated carbon ring, a 5-membered heteroaryl ring or a benzene ring.
[0185] According to an embodiment of the present invention, in formula 3, ring D is a 6-membered heteroaryl ring, and ring E is a benzene ring or a 6-membered heteroaryl ring.
[0186] According to an embodiment of the present invention, in formula 3, ring D is a 6-membered heteroaryl ring, and ring E is a 5-membered heteroaryl ring or a 5-membered unsaturated carbon ring.
[0187] According to an embodiment of the present invention, in formula 3, ring D is a 6-membered heteroaryl ring, ring E is a benzene ring or a 6-membered heteroaryl ring, and two adjacent substituents R e are connected to form a benzene ring or a 6-membered heteroaryl ring.
[0188] According to an embodiment of the present invention, in formula 3, ring D is a 6-membered heteroaryl ring, ring E is a 5-membered heteroaryl ring or a 5-membered unsaturated carbon ring, and two adjacent substituents R e are connected to form a benzene ring or a 6-membered heteroaryl ring.
[0189] According to an embodiment of the present invention, in formula 3, at least one or two groups of adjacent substituents in R d , R e , R v are connected to form a ring. For example, two substituents R d are connected to form a ring, or two substituents R e are connected to form a ring, or two substituents R v are connected to form a ring, or a substituent R d and a substituent R e are connected to form a ring, or a substituent R d and a substituent R v are connected to form a ring, or a substituent R e and a substituent R v are connected to form a ring, or two substituents R d are connected to form a ring while two substituents R eCombine to form a ring, or two substituents R d Combine to form a ring while two substituents R v Combine to form a ring, or two substituents R e Combine to form a ring while two substituents R v Combine to form a ring, substituent R e With substituent R v Combine to form a ring while two substituents R v Combine to form a ring, or substituent R d With substituent R v Combine to form a ring while two substituents R v Combine to form a ring; R d 、R e 、R v When more groups of adjacent substituents in R, R, R combine to form a ring, a similar situation occurs.
[0190] According to an embodiment of the present invention, in the organic electroluminescent device, the phosphorescent light-emitting material is a metal complex, and the metal complex has the general formula M(L a ) m (L b ) n ;
[0191] M is selected from metals with a relative atomic mass greater than 40;
[0192] L a , L b are the first ligand and the second ligand coordinated with the M respectively; L a , L b can optionally combine to form a polydentate ligand;
[0193] m is 1, 2 or 3; n is 0, 1 or 2; the sum of m and n is equal to the oxidation state of the M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, two L b can be the same or different;
[0194] L a is the same or different each time it appears and is selected from the structure shown in Formula 3:
[0195]
[0196] Wherein,
[0197] Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
[0198] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
[0199] Ring D and ring E are connected via Ua and U b fused;
[0200] U a and U b each occurrence being the same as or different from one another and independently selected from C or N;
[0201] R d and R e each occurrence being the same as or different from one another and representing mono-substituted, multi-substituted or unsubstituted;
[0202] V1 to V4 each occurrence being the same as or different from one another and independently selected from CR v or N;
[0203] R d ,R e and R v each occurrence being the same as or different from one another and independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0204] adjacent substituents R d ,R e and R v can optionally be linked to form a ring;
[0205] wherein the ligand L b each occurrence being the same as or different from one another and independently selected from the following structures:
[0206]
[0207] Wherein, each of R1 to R7 is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, sulfhydryl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.
[0208] According to one embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b is the same or different each time it appears and is selected from the following structures:
[0209]
[0210] Wherein, at least one of R1 to R3 is selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, or combinations thereof; and / or at least one of R4 to R6 is selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, or combinations thereof.
[0211] According to one embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b is the same or different each time it appears and is selected from the following structures:
[0212]
[0213] Wherein, at least two of R1 to R3 are the same or different each time they appear and are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and / or at least two of R4 to R6 are the same or different each time they appear and are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.
[0214] According to one embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b is the same or different each time it appears and is selected from the following structures:
[0215]
[0216] Wherein, at least two of R1 to R3 are the same or different each time they appear and are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and / or at least two of R4 to R6 are the same or different each time they appear and are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
[0217] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent light-emitting material is an Ir complex, a Pt complex or an Os complex.
[0218] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent light-emitting material is an Ir complex and has a structure represented by any one of Ir(L a )(L b )(L c ), Ir(L a )2(L b ), Ir(L a )(L b )2, Ir(L a )2(L c ) or Ir(L a )(L c )2.
[0219] According to one embodiment of the present invention, wherein L aIt has a structure represented by Formula 3 and contains at least one structural unit selected from the group consisting of a 6-membered fused 6-membered aromatic ring, a 6-membered fused 6-membered heteroaromatic ring, a 6-membered fused 5-membered aromatic ring, and a 6-membered fused 5-membered heteroaromatic ring.
[0220] According to an embodiment of the present invention, in the organic electroluminescent device, wherein L a It has a structure represented by Formula 3 and contains at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline, and aza-phenanthrene.
[0221] According to an embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains a ligand L a , the L a is the same or different each time and is optionally any one selected from the group consisting of the following structures:
[0222]
[0223]
[0224] According to an embodiment of the present invention, wherein, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains a ligand L b , the L b is the same or different each time and is optionally any one selected from the group consisting of the following structures:
[0225]
[0226]
[0227] According to an embodiment of the present invention, wherein, in the organic electroluminescent device, the phosphorescent material is selected from the group consisting of the following structures:
[0228]
[0229]
[0230]
[0231]
[0232]
[0233] According to another embodiment of the present invention, a compound composition is also disclosed, which contains a compound having a structure represented by Formula 1, and the specific structure of the compound is as shown in any one of the foregoing embodiments.
[0234] According to one embodiment of the present invention, the compound composition comprises a second compound, and the second compound is selected from the structures represented by any one of Formula 2-1 to Formula 2-3:
[0235]
[0236] In Formula 2-1 to Formula 2-3, Ar 31 to Ar 35 are each independently selected, identically or differently each time they appear, from substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
[0237] L 31 to L 35 are each independently selected, identically or differently each time they appear, from a single bond, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
[0238] X is each independently selected, identically or differently each time it appears, from CR 21 R 22 , NR 23 , O or S;
[0239] R 31 to R 37 are each independently selected, identically or differently each time they appear, to represent mono-substituted, multi-substituted or unsubstituted;
[0240] R 31 to R 37 , R 21 to R 23Each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0241] Adjacent substituents R 21 to R 22 ,R 31 to R 37 can optionally be linked to form a ring.
[0242] According to another embodiment of the present invention, an electronic device is also disclosed, which includes an organic electroluminescent device, and the specific structure of the organic electroluminescent device is as shown in any of the foregoing embodiments.
[0243] According to another embodiment of the present invention, an application of a compound having the structure of Formula 1 as a host material is also disclosed, and the specific structure of the compound is as shown in the foregoing embodiments.
[0244] According to another embodiment of the present invention, an application of a compound having the structure of Formula 1 as an organic light-emitting layer is also disclosed, and the specific structure of the compound is as shown in the foregoing embodiments.
[0245] In combination with other materials
[0246] The materials for specific layers in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the devices. The combinations of these materials are described in detail in paragraphs 0132-0161 of US Patent Application US2016 / 0359122A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.
[0247] The materials described herein as being specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combinations of these materials are described in detail in paragraphs 0080 - 0101 of US Patent Application US2015 / 0349273A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.
[0248] 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 received from commercial sources. The synthesized products were structurally confirmed and characterized using one or more conventional devices in the art, including but not limited to nuclear magnetic resonance spectrometers from Bruker, liquid chromatographs, liquid chromatography-mass spectrometers, gas chromatography-mass spectrometers, differential scanning calorimeters from Shimadzu, fluorescence spectrometers from Shanghai Lingguang Technology, electrochemical workstations from Wuhan Koster, sublimators from Anhui Beike, etc., by methods well-known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using conventional devices in the art, including but not limited to evaporation coaters produced by Angstrom Engineering, optical test systems, lifetime test systems produced by Suzhou FushiDa, ellipsometers produced by Beijing Liangtuo, etc., by methods well-known to those skilled in the art. Since those skilled in the art are aware of the relevant content such as the use of the above devices and test methods, and can obtain the inherent data of the samples determinately and without being affected, the above relevant content will not be elaborated further in this patent.
[0249] Examples of material synthesis:
[0250] The preparation method of the compounds of the present invention is not limited. Typically but not restrictively, the following compounds are used as examples, and their synthetic routes and preparation methods are as follows:
[0251] Synthesis Example 1: Synthesis of Compound A-1
[0252] Step 1: Synthesis of Intermediate 3
[0253]
[0254] Under nitrogen protection, intermediate 1 (5.6 g, 22.7 mmol), intermediate 2 (5.8 g, 25 mmol), tetrakis(triphenylphosphine)palladium (2.5 g, 2.2 mmol), potassium carbonate (9.4 g, 68.0 mmol), and a solvent (tetrahydrofuran / water: 70 / 35 mL) were added to a three-necked flask, and then the temperature was raised to 70 °C and reacted overnight. After the reaction was completed, it was cooled, extracted with dichloromethane, the organic phase was washed with water, and the organic phase was obtained after liquid separation. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated to remove the solvent, and the crude product was purified by column chromatography with petroleum ether / dichloromethane = 9 / 1 to obtain white solid intermediate 3 (6.2 g, yield 77%).
[0255] Step 2: Synthesis of intermediate 5
[0256]
[0257] Under nitrogen protection, intermediate 3 (6.2 g, 17.5 mmol), intermediate 4 (6.7 g, 26.4 mmol), palladium acetate (380 mg, 1.7 mmol), X-Phos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (1.6 g, 3.4 mmol), potassium acetate (5.1 g, 52.0 mmol), and toluene (87 mL) were added to a three-necked flask, and then the temperature was raised to 100 °C and reacted overnight. After the reaction was completed, it was cooled, extracted with dichloromethane, and the organic phase was washed once with saturated sodium bicarbonate aqueous solution, water, and saturated brine respectively. The organic phase was obtained after liquid separation. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated to remove the solvent, and the crude product was purified by column chromatography with petroleum ether / dichloromethane = 1 / 2 to obtain white solid intermediate 5 (5.4 g, yield 69%).
[0258] Step 3: Synthesis of compound A-1
[0259]
[0260] Under nitrogen protection, intermediate 5 (5.4 g, 12.1 mmol), intermediate 6 (4.7 g, 12.1 mmol), tetrakis(triphenylphosphine)palladium (1.3 g, 1.1 mmol), potassium carbonate (5 g, 36.2 mmol), and a solvent (toluene / ethanol / water: 40 / 10 / 10 mL) were added to a three-necked flask, and then the temperature was raised to 100 °C and reacted overnight. After the reaction was completed, it was cooled and the solid crude product was obtained by filtration. The crude product was recrystallized with toluene to obtain white solid compound A-1 (4.7 g, yield 57%). The product was confirmed to be the target product with a molecular weight of 677.2.
[0261] Synthesis Example 2: Synthesis of compound A-51
[0262] Step 1: Synthesis of Intermediate 9
[0263]
[0264] Under nitrogen protection, intermediate 7 (4 g, 10.8 mmol), intermediate 8 (2.1 g, 11.0 mmol), tetrakis(triphenylphosphine)palladium (1.2 g, 1.0 mmol), potassium carbonate (4.5 g, 32.6 mmol), and solvent (toluene / ethanol / water: 40 / 10 / 10 mL) were added to a three-necked flask. Then, the temperature was raised to 70 °C and the reaction was carried out overnight. After the reaction was completed, it was cooled, extracted with dichloromethane, and the organic phase was washed with water. After liquid separation, the organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was concentrated and removed. The crude product was purified by column chromatography with petroleum ether / dichloromethane = 10 / 1 to obtain white solid intermediate 9 (3.6 g, yield 94%).
[0265] Step 2: Synthesis of Intermediate 10
[0266]
[0267] Under nitrogen protection, intermediate 9 (3.6 g, 10.2 mmol), intermediate 4 (3.9 g, 15.4 mmol), palladium acetate (220 mg, 1 mmol), X-Phos (940 mg, 2 mmol), potassium acetate (2.9 g, 29.5 mmol), and toluene (50 mL) were added to a three-necked flask. Then, the temperature was raised to 100 °C and the reaction was carried out overnight. After the reaction was completed and cooled, it was extracted with dichloromethane, and the organic phase was washed once with saturated sodium bicarbonate aqueous solution, water, and saturated brine respectively. After liquid separation, the organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was concentrated and removed. The crude product was purified by column chromatography with petroleum ether / dichloromethane = 1 / 1 to obtain white solid intermediate 10 (3.4 g, yield 75%).
[0268] Step 3: Synthesis of Compound A-51
[0269]
[0270] Under nitrogen protection, intermediate 10 (3.4 g, 7.6 mmol), intermediate 6 (3 g, 7.6 mmol), tetrakis(triphenylphosphine)palladium (924 mg, 0.8 mmol), potassium carbonate (3.1 g, 22.4 mmol), and solvent (toluene / ethanol / water: 24 / 6 / 6 mL) were added to a three-necked flask. Then, the temperature was raised to 100 °C and the reaction was carried out overnight. After the reaction was completed, it was cooled and filtered to obtain a solid crude product. The crude product was recrystallized with toluene to obtain white solid compound A-51 (2.5 g, yield 49%). The product was confirmed to be the target product with a molecular weight of 677.2.
[0271] Synthesis Example 3: Synthesis of Compound A-101
[0272] Step 1: Synthesis of Intermediate 13
[0273]
[0274] Under nitrogen protection, Intermediate 11 (8 g, 21.6 mmol), Intermediate 12 (4.1 g, 21.6 mmol), tetrakis(triphenylphosphine)palladium (2.4 g, 2.1 mmol), potassium carbonate (8.9 g, 64.4 mmol), and solvent (toluene / ethanol / water: 64 / 16 / 16 mL) were added to a three-necked flask. Then, the temperature was raised to 70 °C and the reaction was carried out overnight. After the reaction was completed, it was cooled, extracted with dichloromethane, and the organic phase was washed with water. After liquid separation, the organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed by concentration. The crude product was purified by column chromatography with petroleum ether / dichloromethane = 8 / 1 to obtain white solid Intermediate 13 (6.7 g, yield 87%).
[0275] Step 2: Synthesis of Intermediate 14
[0276]
[0277] Under nitrogen protection, Intermediate 13 (6.7 g, 18.9 mmol), Intermediate 4 (7.2 g, 28.4 mmol), palladium acetate (425 mg, 1.9 mmol), X-Phos (1.8 g, 3.8 mmol), potassium acetate (5.5 g, 56.0 mmol), and toluene (90 mL) were added to a three-necked flask. Then, the temperature was raised to 100 °C and the reaction was carried out overnight. After the reaction was completed and cooled, dichloromethane was added for extraction, and the organic phase was washed once with saturated sodium bicarbonate aqueous solution, water, and saturated brine respectively. The organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed by concentration. The crude product was purified by column chromatography with petroleum ether / dichloromethane = 1 / 2 to obtain white solid Intermediate 14 (5.5 g, yield 65%).
[0278] Step 3: Synthesis of Compound A-101
[0279]
[0280] Under nitrogen protection, intermediate 14 (5.5 g, 12.3 mmol), intermediate 6 (4.8 g, 12.3 mmol), tetrakis(triphenylphosphine)palladium (1.3 g, 1.1 mmol), potassium carbonate (5 g, 36.2 mmol), and solvent (toluene / ethanol / water: 40 / 10 / 10 mL) were added to a three-necked flask, and then the temperature was raised to 100 °C and reacted overnight. After the reaction was completed, it was cooled and filtered to obtain a solid crude product, and the crude product was recrystallized with toluene. A white solid compound A-101 (5 g, yield 60%) was obtained. The product was confirmed to be the target product with a molecular weight of 677.2.
[0281] Synthesis Example 4: Synthesis of Compound A-141
[0282] Step 1: Synthesis of Intermediate 15
[0283]
[0284] Under nitrogen protection, intermediate 11 (8 g, 21.6 mmol), intermediate 8 (4.1 g, 21.6 mmol), tetrakis(triphenylphosphine)palladium (2.4 g, 2.1 mmol), potassium carbonate (8.9 g, 64.4 mmol), and solvent (toluene / ethanol / water: 80 / 20 / 20 mL) were added to a three-necked flask, and then the temperature was raised to 70 °C and reacted overnight. After the reaction was completed, it was cooled, extracted with dichloromethane, the organic phase was washed with water, and after liquid separation, the organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was concentrated and removed. After the crude product was purified by column chromatography with petroleum ether / dichloromethane = 8 / 1, a white solid intermediate 15 (6.9 g, yield 90%) was obtained.
[0285] Step 2: Synthesis of Intermediate 16
[0286]
[0287] Under nitrogen protection, intermediate 15 (6.9 g, 19.5 mmol), intermediate 4 (7.4 g, 29.1 mmol), palladium acetate (425 mg, 1.9 mmol), X-Phos (1.8 g, 3.8 mmol), potassium acetate (5.7 g, 58.5 mmol), and toluene (100 mL) were added to a three-necked flask, and then the temperature was raised to 100 °C and reacted overnight. After the reaction was completed and cooled, it was extracted with dichloromethane, and the organic phase was washed once with saturated aqueous sodium bicarbonate solution, water, and saturated brine respectively. The organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was concentrated and removed. After the crude product was purified by column chromatography with petroleum ether / dichloromethane = 1 / 1, a white solid intermediate 16 (6.5 g, yield 75%) was obtained.
[0288] Step 3: Synthesis of Compound A-141
[0289]
[0290] Under nitrogen protection, intermediate 16 (5.7 g, 12.7 mmol), intermediate 6 (5 g, 12.7 mmol), tetrakis(triphenylphosphine)palladium (1.3 g, 1.1 mmol), potassium carbonate (5.3 g, 38.3 mmol), and solvent (toluene / ethanol / water: 40 / 10 / 10 mL) were added to a three-necked flask. Then, the temperature was raised to 100 °C and the reaction was carried out overnight. After the reaction was completed, it was cooled and filtered to obtain a solid crude product. The crude product was recrystallized with toluene to obtain white solid compound A-141 (4.4 g, yield 51%). The product was confirmed to be the target product with a molecular weight of 677.2.
[0291] Those skilled in the art should be aware that the above preparation method is only an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.
[0292] Device Example 1
[0293] First, a glass substrate having a 120-nm-thick indium tin oxide (ITO) anode was cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate was dried in a nitrogen-filled glove box to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The following specified organic layers were sequentially evaporated onto the ITO anode by thermal vacuum at a rate of about 10 -8 Torr. Compounds HT and HI were co-evaporated and used as the hole injection layer (HIL, weight ratio 97:3) with a thickness of Compound HT was used as the hole transport layer (HTL) with a thickness of 400 Compound EB was used as the electron blocking layer (EBL) with a thickness of Then, the compound A-1 of the present invention as the first host, compound H-137 as the second host, and compound RD as the dopant were co-evaporated and used as the emitting layer (EML, weight ratio 49:49:2) with a thickness of Compound HB was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compounds ET and lithium 8-hydroxyquinoline (Liq) were co-evaporated as the electron transport layer (ETL, weight ratio 40:60) with a thickness of Finally, Lithium 8-hydroxyquinoline (Liq) with a thickness of was evaporated as the electron injection layer (EIL), and aluminum was evaporated as the cathode. Then, the device was transferred back to the glove box and encapsulated with a glass cover to complete the device.
[0294] Device Example 2
[0295] The implementation of Device Example 2 is the same as that of Device Example 1, except that Compound A-51 of the present invention is used instead of Compound A-1 of the present invention as the first host in the emitting layer (EML).
[0296] Device Example 3
[0297] The implementation of Device Example 3 is the same as that of Device Example 1, except that Compound A-101 of the present invention is used instead of Compound A-1 of the present invention as the first host in the emitting layer (EML).
[0298] Device Comparative Example 1
[0299] The implementation of Device Comparative Example 1 is the same as that of Device Example 1, except that Compound B is used instead of Compound A-1 of the present invention as the first host in the emitting layer (EML).
[0300] Device Comparative Example 2
[0301] The implementation of Device Comparative Example 2 is the same as that of Device Example 1, except that Compound C is used instead of Compound A-1 of the present invention as the first host in the emitting layer (EML).
[0302] The detailed device layer structures and thicknesses are shown in the following table. For the layers where more than one material is used, they are doped with different compounds in the recorded weight ratios.
[0303] Table 1 Partial Device Structures of Device Examples and Comparative Examples
[0304]
[0305]
[0306] The material structures used in the device are shown as follows:
[0307]
[0308]
[0309] Table 2 lists the maximum emission wavelengths (λ 2 ), and power efficiencies (PE) of the device examples and device comparative examples measured under the condition of a constant brightness of 1000 cd / cm max ).
[0310] Table 2 Device Data
[0311] Device ID <![CDATA[λ max (nm)]]> PE [lm / W] Example 1 623 29.1 Example 2 622 28.8 Example 3 623 28.1 Comparative Example 1 623 26.4 Comparative Example 2 621 26.5
[0312] Discussion:
[0313] As can be seen from the data in Table 2, the maximum emission wavelengths of the examples and the comparative examples are basically the same. The difference between Example 1 and Comparative Example 1 is only the connection position of the triazine group on dibenzofuran through a biphenylene group. In terms of power efficiency, compared with Comparative Example 1, Example 1 has a significant increase of 10.2%. The difference between Example 2 and Comparative Example 2 is only the different naphthylphenyl groups. In terms of power efficiency, compared with Comparative Example 2, Example 2 has a significant increase of 8.7%. It is not easy to significantly improve the efficiency while keeping the maximum emission wavelength basically the same. Due to the particularity of the compound with the structure of Formula 1, the spatial configuration of the molecule is more conducive to device film formation and not easy to crystallize, thus obtaining better device performance. The above data show that a compound with the structure of Formula 1 formed by connecting a triazine group with specific substituents (naphthylphenyl) through a biphenylene group at a specific position on dibenzofuran and its similar structures can obtain higher device efficiency and better device performance when applied to an organic electroluminescent device.
[0314] In addition, the compounds of the present invention with different connection positions of the biphenylene group used in Example 3 can still achieve power efficiencies comparable to those of Examples 1 and 2, and have increases of 6.4% and 6% respectively in terms of power efficiency compared with Comparative Examples 1 and 2. These data once again prove that the compounds of the present invention with the structure of Formula 1 can obtain better device performance, such as power efficiency, when applied to an organic electroluminescent device.
[0315] From the above results, it can be seen that the compounds with the structure of Formula 1 disclosed in the present invention can be used as host materials to improve the device performance and achieve high efficiency. Therefore, it has broad commercial development prospects and application values.
[0316] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be obvious to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not intended to be restrictive.
Claims
1. A compound having the structure of Formula 1: Wherein, X1 to X 10 each occurrence is independently selected from C, N or CR x , and one of X1 to X5 is C, and one of X6 to X 10 is C, and they are connected by a single bond; W1 to W7 are each independently selected from N or CR, each occurrence being the same or different w ; Y1 to Y9 are the same as or different from each other each time they appear and are each independently selected from C, N or CR y , and one of Y1 to Y5 is C, one of Y6 to Y9 is C, and the two are connected by a single bond; Y 10 to Y 13 each occurrence being the same as or different from one another and independently selected from N or CR y ; Z is the same or different each time it appears and is selected from O, S or Se; R x , R w , R y each occurrence independently is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Ar is selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, or a combination thereof.
2. The compound according to claim 1, wherein X2, X3 or X4 is selected from C, X8 or X9 is selected from C; Preferably, the compound has a structure represented by any one of Formula 1-1 to Formula 1-4: Wherein, W1 to W7 are each independently selected from N or CR, the same or different each time they appear w ; Y1 to Y9 are each independently selected from C, N or CR, the selections being the same or different each time Y1 to Y9 appear; y and one of Y1 to Y5 is C, and one of Y6 to Y9 is C, and the two are connected by a single bond; Y 10 to Y 13 each occurrence being the same as or different from each other and independently selected from N or CR y ; X1 to X 10 each occurrence is independently selected from N or CR x ; Z is the same or different each time it appears and is selected from O, S or Se; R x ,R w ,R y each occurrence of which is the same as or different from and is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, isocyano, and combinations thereof; Ar is selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, or a combination thereof.
3. The compound according to claim 1 or 2, wherein, Y1 to Y9 are each independently selected from C or CR, the selections being the same or different each time y , and one of Y1 to Y5 is C, and one of Y6 to Y9 is C, and the two are connected by a single bond; Y 10 to Y 13 are each independently selected from CR y ; R y each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; Preferably, R y is the same or different each time it appears and is selected from the group consisting of hydrogen, deuterium, halogen, methyl, phenyl, deuterated naphthyl, deuterated phenyl, pyridyl, vinyl, naphthyl, biphenyl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, cyano, adamantyl, tert-butyl, trifluoromethyl, carbazolyl, 9,9-dimethylfluorenyl, and combinations thereof.
4. The compound according to claim 1 or 2, wherein, Y3 or Y4 is selected from C, Y6 or Y7 is selected from C.
5. The compound according to claim 1 or 2, wherein, Each occurrence of W1 to W7 is independently selected from CR w ; R w each occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and combinations thereof; Preferably, R w is the same or different each time it appears and is selected from the group consisting of hydrogen, deuterium, halogen, methyl, phenyl, deuterated naphthyl, deuterated phenyl, pyridyl, vinyl, naphthyl, biphenyl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, cyano, adamantyl, tert-butyl, trifluoromethyl, carbazolyl, 9,9-dimethylfluorenyl, and combinations thereof.
6. The compound according to claim 1 or 2, wherein Z is selected from O or S; preferably, Z is O.
7. The compound according to claim 2, wherein X1 to X 10 each occurrence being the same as or different from each other and independently selected from CR x ; R x Each occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and combinations thereof; Preferably, R x is the same or different each time it appears and is selected from the group consisting of hydrogen, deuterium, halogen, methyl, phenyl, pyridyl, cyclopentyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, adamantyl, tert-butyl, trifluoromethyl, carbazolyl, and combinations thereof.
8. The compound according to claim 1 or 2, wherein Ar is selected from a substituted or unsubstituted aryl group having 6 - 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 20 carbon atoms, or a combination thereof; Preferably, Ar is selected from the group consisting of: phenyl, biphenyl, deuterated naphthyl, deuterated phenyl, terphenyl, naphthyl, phenylnaphthyl, phenanthryl, triphenylene, pyrimidinyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, and combinations thereof.
9. The compound according to claim 1, wherein the compound is selected from the group consisting of Compound A-1 to Compound A-200: Optionally, the hydrogen in the structures of Compound A-1 to Compound A-200 can be partially or completely replaced by deuterium.
10. An organic electroluminescent device, comprising: An anode, A cathode, An organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 to 9.
11. The organic electroluminescent device according to claim 10, wherein the organic layer is a light-emitting layer, a hole transport layer or an electron blocking layer; Preferably, the organic layer is a light-emitting layer, and the compound is a host material.
12. The organic electroluminescent device according to claim 10, wherein the organic layer is a light-emitting layer, and the organic layer further comprises a second compound, the second compound is a host material, and the second compound has a structure represented by any one of Formula 2-1 to Formula 2-3: Wherein, In Formulas 2-1 to 2-3, Ar 31 to Ar 35 are each independently selected, each time they appear, from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; L 31 to L 35 each occurrence independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or combinations thereof; X is the same as or different from O, S, CR each time it appears 21 R 22 or NR 23 ; R 31 to R 37 each occurrence independently represents unsubstituted, monosubstituted, or polysubstituted, either the same or different each time it appears; R 31 to R 37 ,R 21 to R 23 each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R 31 to R 37 may optionally be linked to form a ring.
13. The organic electroluminescent device according to claim 10, wherein the organic layer is a light-emitting layer, and the light-emitting layer comprises at least one phosphorescent light-emitting material.
14. The organic electroluminescent device according to claim 13, wherein the phosphorescent light-emitting material is a metal complex, and the metal complex has the general formula of M(L a ) m (L b ) n (L c ) q . M is selected from a metal having a relative atomic mass greater than 40; L a , L b and L c are respectively the first ligand, the second ligand, and the third ligand coordinated with the M; L a , L b and L c can optionally be connected to form a polydentate ligand; L a , L b and L c may be the same or different; m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q is equal to the oxidation state of said M; when m is greater than or equal to 2, multiple L a may be the same or different; when n is 2, two L b may be the same or different; when q is 2, two L c may be the same or different; L a each time it appears, is the same as or different from and is selected from the structures represented by formula 3: Wherein, Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring; Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaryl ring or a 6-membered heteroaryl ring; Ring D and ring E are fused via U a and U b fused; U a and U b are the same as or different from each other, each independently selected from C or N each time they appear; R d and R e each occurrence independently represents unsubstituted, mono-substituted, or poly-substituted, identically or differently, every time it appears; V1 to V4 are each independently selected from CR v or N; R d , R e and R v each occurrence, independently of one another, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R d , R e and R v can optionally be linked to form a ring; L b and L c each occurrence being the same as or different from any one of the following structures: Wherein, R a , R b and R c each independently represents, when it appears each time, mono-substitution, poly-substitution, or no substitution; X b each occurrence is the same as or different from and is selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d each occurrence of which is the same as or different from and is independently selected from the group consisting of O, S, Se and NR N2 ; R a ,R b ,R c ,R N1 ,R N2 ,R C1 and R C2 is independently selected, each time it appears, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R a ,R b ,R c ,R N1 ,R N2 ,R C1 and R C2 can optionally be joined to form a ring.
15. A compound composition, comprising the compound according to any one of claims 1 to 9.
16. The compound composition according to claim 15, comprising a second compound, the second compound having a structure represented by any one of Formula 2-1 to Formula 2-3: In Formulas 2-1 to 2-3, Ar 31 to Ar 35 are each independently selected, each time they appear, from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; L 31 to L 35 each occurrence is the same as or different from and is independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof; X is the same as or different from each other each time it appears and is selected from CR 21 R 22 , NR 23 , O or S; R 31 to R 37 each occurrence independently represents mono-substitution, multi-substitution or no substitution, identically or differently; R 31 to R 37 ,R 21 to R 23 each occurrence is the same or different and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Preferably, the second compound is selected from the group consisting of Compound H-1 to Compound H-156:
17. An electronic device, comprising the organic electroluminescent device according to any one of claims 10 to 14.
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