An electroluminescent device
By using a new combination of compounds with H1-L1-Ar1 and H2-L2-Ar2 structures in organic electroluminescent devices, the problems of reduced efficiency and insufficient device performance in the prior art are solved, and longer life and higher life are achieved Efficient electroluminescent effect.
Patent Information
- Application Number
- CN202011397603.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2020-12-04
- Publication Date
- 2025-02-11
- Estimated Expiration
- 2040-12-04
AI Technical Summary
The efficiency of existing organic electroluminescent devices is rapidly reduced under high brightness, and blue phosphorescent devices have problems such as blue unsaturation, short device life and high operating voltage, which is difficult to meet the industry's demand for improving device performance.
A novel compound combination is used as the host material of the electroluminescent device, which comprises a first compound having a H1-L1-Ar1 structure and a second compound having a H2-L2-Ar2 structure. This combination is used in organic layers, which can significantly improve device life and provide better device performance.
By using new compound combinations, the lifespan of organic electroluminescent devices is significantly improved and provides better device performance, which can meet the industry's demand for high efficiency, long life and high efficiency.
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Figure CN114613924B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to an organic electronic device, such as an organic electroluminescent device, and more particularly to an organic electroluminescent device comprising a novel compound combination of at least a first compound having an H1-L1-Ar1 structure and a second compound having an H2-L2-Ar2 structure in an organic layer, and an electronic device comprising the organic electroluminescent device. Background Art
[0002] Organic electronic devices include but are not limited to the following categories: 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 devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light emitting devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an arylamine hole transport layer and a tri-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 is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and the anode. Since OLEDs are self-luminous solid-state devices, 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 on flexible substrates.
[0004] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet light emission. The triplet generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet light emission from heavy metals containing complexes as emitters. Therefore, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). 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 triplet to singlet. 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 based on the form of the material used. Small molecules are any organic or organometallic material that is not a polymer. Small molecules can have a large molecular weight as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.
[0006] There are various OLED manufacturing methods. 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. Small molecule OLEDs can also be manufactured by solution methods if the material can be dissolved or dispersed in a solvent.
[0007] The emission color of OLED can be achieved by the structural design of the luminescent material. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, it is expected to have a more saturated emission spectrum, higher efficiency and longer device life.
[0008] KR1020150077220A discloses an organic electroluminescent compound, an organic optical compound having the following structure The disclosed compound X1 may be N(Ar1), but it does not disclose or teach the use of the compound X1 together with an organic compound containing an aza macrocycle fused with indole and pyrrole and similar structures as a host material.
[0009] US20180337340A1 discloses an organic electroluminescent compound and an organic electroluminescent device comprising the same, which comprises an organic layer, wherein the organic layer contains one or more hosts, and the first host is an organic optical compound having the following structure:
[0010] However, it does not disclose or teach the use of organic compounds containing an aza macrocycle fused with indole and pyrrole and similar structures as a host material.
[0011] However, there is still room for improvement in the various host materials reported so far. In order to meet the industry's increasing demand, selecting appropriate host materials for combination is a more efficient research and development method. In order to meet the industry's increasing demand for device performance, new material combinations still need further research and development. Summary of the invention
[0012] The present invention aims to provide an electroluminescent device comprising a novel compound combination in an organic layer to solve at least part of the above problems. The novel compound combination comprises a combination of a first compound having an H1-L1-Ar1 structure and a second compound having an H2-L2-Ar2 structure. This novel material combination can be used as a host material of an electroluminescent device. This novel material combination can greatly improve the device life and provide better device performance.
[0013] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0014] anode,
[0015] cathode,
[0016] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a first compound and a second compound; and the first compound is different from the second compound;
[0017] The first compound has a structure of H1-L1-Ar1; and H1 has a structure represented by Formula 1:
[0018]
[0019] In Formula 1, A1, A2 and A3 are selected from N or CR at each occurrence, the same or different, and Ring A, Ring B and Ring C are selected from a carbocyclic ring having 5 to 30 carbon atoms or a heterocyclic ring having 3 to 30 carbon atoms at each occurrence;
[0020] R x Each occurrence, identically or differently, indicates mono-, poly- or non-substitution;
[0021] Adjacent substituents R, R x can optionally be linked to form a ring;
[0022] L1 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;
[0023] Ar1 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;
[0024] The second compound has a structure of H2-L2-Ar2;
[0025] The H2 has a structure represented by Formula 2;
[0026]
[0027] In formula 2,
[0028] Each time Z1-Z3, Z6-Z8 appears, they are selected from CR z1 or N, Z4 and Z5 are selected from CR each time they appear, either identically or differently z2 , and the two substituents R in Z4 and Z5 z2 Connect to form a ring;
[0029] Ar2 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;
[0030] L2 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;
[0031] R, R x , R z1Each occurrence is identically or differently 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 heterocyclyl 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 cycloalkyl having 6 to 30 carbon atoms Aryloxy, 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0032] R z2 Each occurrence is identically or differently selected from the group consisting of: hydrogen, 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 heterocyclyl 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 cycloalkyl having 6 to 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0033] Adjacent substituent R z1 , R z2 Can optionally be linked to form a ring.
[0034] According to another embodiment of the present invention, a display assembly is disclosed, which includes the electroluminescent device shown in the above embodiment.
[0035] The present invention discloses an electroluminescent device comprising a novel compound combination in an organic layer, wherein the novel compound combination comprises a combination of a first compound having an H1-L1-Ar1 structure and a second compound having an H2-L2-Ar2 structure, and the novel material combination can be used as a main material of the electroluminescent device. The novel material combination can greatly improve the device life and provide better device performance. BRIEF DESCRIPTION OF THE DRAWINGS
[0036] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the electroluminescent device disclosed herein.
[0037] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the electroluminescent device disclosed herein. DETAILED DESCRIPTION
[0038] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.
[0039] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.
[0040] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. 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 sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.
[0041] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
[0042] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1The difference is that an 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 that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.
[0043] 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) of 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, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.
[0044] The materials and structures described herein may also be used in other organic electronic devices listed above.
[0045] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.
[0046] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.
[0047] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
[0048] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0049] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.
[0050] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the 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 by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).
[0051] Definition of Substituent Terms
[0052] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.
[0053] Alkyl - as used herein, includes straight chain and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-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. In addition, the alkyl group may be optionally substituted.
[0054] Cycloalkyl - as used herein, includes cyclic alkyl. Cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl 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, 4,4-dimethylcyclohexyl are preferred. In addition, cycloalkyl can be optionally substituted.
[0055] Assorted alkyl - as used herein, assorted alkyl comprises one or more carbons in the alkyl chain and is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom and boron atom and is replaced by heteroatoms. Assorted alkyl can be an assorted alkyl with 1 to 20 carbon atoms, preferably an assorted alkyl with 1 to 10 carbon atoms, more preferably an assorted alkyl with 1 to 6 carbon atoms. The example of assorted alkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. Additionally, heteroalkyl groups can be optionally substituted.
[0056] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.
[0057] Alkynyl - as used herein, encompasses straight chain alkynyl. Alkynyl may be an alkynyl containing 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, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl may be optionally substituted.
[0058] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadrenyl. In addition, the aryl group may be optionally substituted.
[0059] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.
[0060] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is an aryl group, wherein ...
[0061] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. 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, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.
[0062] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.
[0063] 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,
[0064] 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.
[0065] 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.
[0066] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.
[0067] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, means that any one of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms. The invention also includes an alkyl group, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclyl group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
[0068] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.
[0069] In the compounds mentioned in this disclosure, 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. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.
[0070] In the compounds mentioned in the present disclosure, polysubstitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituent existing in multiple available substitution positions can be the same structure or different structures.
[0071] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring, as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, 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.
[0072] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0073]
[0074] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0075]
[0076] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
[0077]
[0078] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0079] anode,
[0080] cathode,
[0081] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a first compound and a second compound; and the first compound is different from the second compound;
[0082] The first compound has a structure of H1-L1-Ar1; and H1 has a structure represented by Formula 1:
[0083]
[0084] In Formula 1, A1, A2 and A3 are selected from N or CR at each occurrence, the same or different, and Ring A, Ring B and Ring C are selected from a carbocyclic ring having 5 to 30 carbon atoms or a heterocyclic ring having 3 to 30 carbon atoms at each occurrence;
[0085] R x Each occurrence, identically or differently, indicates mono-, poly- or non-substitution;
[0086] Adjacent substituents R, R x can optionally be linked to form a ring;
[0087] L1 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;
[0088] Ar1 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;
[0089] The second compound has a structure of H2-L2-Ar2;
[0090] The H2 has a structure represented by Formula 2;
[0091]
[0092] In formula 2,
[0093] Each time Z1-Z3, Z6-Z8 appears, they are selected from CR z1 or N, Z4 and Z5 are selected from CR each time they appear, either identically or differently z2 , and the two substituents R in Z4 and Z5 z2 Connect to form a ring;
[0094] Ar2 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;
[0095] L2 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;
[0096] R, R x , R z1 Each occurrence is identically or differently 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 heterocyclyl 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 cycloalkyl having 6 to 30 carbon atoms Aryloxy, 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0097] R z2 Each occurrence is identically or differently selected from the group consisting of: hydrogen, 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 heterocyclyl 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 cycloalkyl having 6 to 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0098] Adjacent substituent R z1 , R z2Can optionally be linked to form a ring.
[0099] In this embodiment, the adjacent substituents R, R x can be optionally connected to form a ring, which is intended to indicate that adjacent substituent groups, such as between substituents R, x between the substituents R and R x 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.
[0100] In this embodiment, the adjacent substituent R z1 , R z2 can be optionally connected to form a ring, which is intended to represent adjacent substituent groups in Formula 2, for example, adjacent substituents R in Z1-Z3 z1 Between, adjacent substituents R in Z6-Z8 z1 The substituent R in Z3 z1 With the substituent R in Z4 z2 The substituent R in Z3 z1 With the substituent R in Z5 z2 The substituent R in Z6 z1 With the substituent R in Z4 z2 between, and the substituent R in Z6 z1 With the substituent R in Z5 z2 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.
[0101] According to one embodiment of the present invention, in Formula 1, the ring A, ring B and ring C are selected from a 5-membered carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms, the same or different when they appear each time.
[0102] According to one embodiment of the present invention, in Formula 1, the ring A, ring B and ring C are selected from a 5-membered carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring, the same or different when they appear each time.
[0103] According to one embodiment of the present invention, in the first compound, H1 has a structure represented by Formula 1-a:
[0104]
[0105] wherein A1 to A3 are selected from N or CR at each occurrence, the same or different, and X1 to X 10 Each occurrence is selected from N or CR, either identically or differently x ;
[0106] R, R x Each occurrence is identically or differently 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 heterocyclyl 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 cycloalkyl having 6 to 30 carbon atoms Aryloxy, 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0107] Adjacent substituents R, R x Can optionally be linked to form a ring.
[0108] In this context, adjacent substituents R, R x can be optionally connected to form a ring, which is intended to indicate that adjacent substituents R can be optionally connected to form a ring, and is also intended to indicate that adjacent substituents R in X1 to X3 x can be optionally connected to form a ring, and is also intended to represent adjacent substituents R in X4 to X6 x can be optionally linked to form a ring, and is also intended to represent X7 to X 10 The adjacent substituent R x can be optionally linked to form a ring; and, is also intended to represent adjacent substituents R and R x can be optionally linked to form a ring, for example, between A1 and X3, and / or between A3 and X 10 and / or X6 and X7 can be optionally connected to form a ring. x Alternatively, they may not be connected to form a ring. In this case, adjacent substituents R are not connected to form a ring, and / or adjacent substituents R x nor are they connected to form a ring, and / or adjacent substituents R and R x They also do not connect to form a ring.
[0109] According to one embodiment of the present invention, in Formula 1-a, R, R xeach occurrence is identically or differently 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 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 amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof;
[0110] Adjacent substituents R, R x Can optionally be linked to form a ring.
[0111] According to one embodiment of the present invention, in Formula 1 or Formula 1-a, R and R x At least one of the following is selected from deuterium, 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.
[0112] According to one embodiment of the present invention, in Formula 1 or Formula 1-a, R and R x At least one of them is selected from deuterium, phenyl, biphenyl, or pyridyl.
[0113] According to one embodiment of the present invention, in Formula 1-a, the adjacent substituents R between A1 to A3 and the adjacent substituents R between X1 to X3 are x , the adjacent substituents R between X4 and X6 x , and X7 to X 10 Adjacent substituents R x , at least one of these adjacent substituent groups is connected to form a ring.
[0114] In this embodiment, at least one of the adjacent substituent groups is connected to form a ring, which is intended to represent the adjacent substituent groups present in Formula 1-a, for example, two adjacent substituents R in A1 and A2, two adjacent substituents R in A2 and A3, and two adjacent substituents R in X1 and X2. x , two adjacent substituents R in X2 and X3 x , two adjacent substituents R in X4 and X5 x , two adjacent substituents R in X5 and X6 x , two adjacent substituents R in X7 and X8 x , two adjacent substituents R in X8 and X9 x , as well as X9 and X 10Two adjacent substituents R x , at least one of these substituent groups is connected to form a ring.
[0115] According to one embodiment of the present invention, in the first compound, the H1 is selected from the group consisting of the following structures:
[0116]
[0117]
[0118]
[0119]
[0120]
[0121]
[0122]
[0123] In this example, "*" indicates the position in the structure of H-1 to H-139 that is connected to L1.
[0124] According to one embodiment of the present invention, the hydrogen in H-1 to H-139 can be partially or completely replaced by deuterium.
[0125] According to one embodiment of the present invention, in Formula 2, the two substituents R in Z4 and Z5 are z2 The rings are connected to form a ring having at least 6 ring atoms.
[0126] According to one embodiment of the present invention, in Formula 2, the two substituents R in Z4 and Z5 are z2 The rings are connected to form a ring having at least 7 ring atoms.
[0127] According to one embodiment of the present invention, in the second compound, H2 has a structure represented by any one of Formula 2-1 to Formula 2-8:
[0128]
[0129] In Formula 2-1 to Formula 2-8,
[0130] Each time Z1-Z3, Z6-Z8 appears, they are selected from CR z1 or N;
[0131] Z h1 -Z h8 Each occurrence is selected from CRzh or N;
[0132] Z m Selected from CR zm or N;
[0133] Z n Selected from CR zn R zn , O, S or NR zn When Z n Selected from CR zn R zn When two R zn Can be the same or different;
[0134] R z1 , R zh , R zm , R zn each occurrence is identically or differently 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 heterocyclyl 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 cycloalkyl having 6 to 30 carbon atoms Aryloxy, 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0135] Adjacent substituent R z1 , R zh , R zm , R zn Can optionally be linked to form a ring.
[0136] In this context, adjacent substituents R z1 , R zh , R zm , R zn can be optionally connected to form a ring, which is intended to represent adjacent groups of substituents, for example, adjacent substituents R in Z1-Z3 z1 Between, adjacent substituents R in Z6-Z8 z1 Between adjacent substituents R zh Between adjacent substituents Rzh and R zm Between adjacent substituents R zn Between, and adjacent substituents R zh and R zn 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.
[0137] According to one embodiment of the present invention, in Formula 2-1 to Formula 2-8, R z1 , R zh , R zm , R zn each occurrence being identically or differently 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 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 amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof;
[0138] Adjacent substituent R z1 , R zh , R zm , R zn Can optionally be linked to form a ring.
[0139] According to one embodiment of the present invention, in the second compound, H2 has a structure represented by any one of Formula 2-1 to Formula 2-8:
[0140]
[0141] In Formula 2-1 to Formula 2-8,
[0142] Each time Z1-Z3, Z6-Z8 appears, they are selected from CR z1 ;
[0143] Z h1 -Z h8 Each occurrence is selected from CR zh or N;
[0144] Z m Selected from N;
[0145] Z n Select from O, S or NRzn ;
[0146] R z1 , R zh , R zn each occurrence is identically or differently 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 heterocyclyl 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 cycloalkyl having 6 to 30 carbon atoms Aryloxy, 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0147] Adjacent substituent R z1 , R zh , R zn Can optionally be linked to form a ring.
[0148] In this context, adjacent substituents R z1 , R zh , R zn can be optionally connected to form a ring, which is intended to represent adjacent groups of substituents, for example, adjacent substituents R in Z1-Z3 z1 Between, adjacent substituents R in Z6-Z8 z1 Between adjacent substituents R zh Between adjacent substituents R zn Between, and adjacent substituents R zh and R zn 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.
[0149] According to one embodiment of the present invention, in the second compound, H2 has a structure represented by any one of Formula 2-1 to Formula 2-8:
[0150]
[0151] In Formula 2-1 to Formula 2-8,
[0152] Each time Z1-Z3, Z6-Z8 appears, they are selected from CR z1 ;
[0153] Z h1 -Z h8 Each occurrence is selected from CR zh or N;
[0154] Z m Selected from N;
[0155] Z n Select from O, S or NR zn ;
[0156] R z1 , R zh , R zn each occurrence being identically or differently 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 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 amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof;
[0157] Adjacent substituent R z1 , R zh , R zn Can optionally be linked to form a ring.
[0158] According to one embodiment of the present invention, wherein said H2 is selected from the group consisting of H-1 to H-139 and the following structures:
[0159]
[0160]
[0161]
[0162] In this example, “*” indicates the position in the structure of H2-1 to H2-53 that is connected to L2.
[0163] According to one embodiment of the present invention, the hydrogen in H2-1 to H2-53 can be partially or completely replaced by deuterium.
[0164] According to one embodiment of the present invention, in the first compound and the second compound, at least one of Ar1 and Ar2 is selected from substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms in the same or different manner each time it appears. For example, Ar1 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, and Ar2 is selected from substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms; or Ar1 is selected from substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, and Ar2 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms; or Ar1 and Ar2 are selected from substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms in the same or different manner each time they appear.
[0165] According to one embodiment of the present invention, in the first compound and the second compound, Ar1 and Ar2 each appear identically or differently and have a structure represented by any one of the following structures:
[0166]
[0167] Wherein, Z is selected from O, S, CR z R z ,SiR z R z , NR z , B.R. z or PR z ; When there are two R z When two R z Can be the same or different;
[0168] R Ar The same or different at each occurrence indicates mono-, poly- or no substitution;
[0169] R z , R Ar each occurrence is identically or differently 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 6-30 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 amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof;
[0170] Adjacent substituent R z , R Ar Can optionally be linked to form a ring.
[0171] In this embodiment, It represents the position in the structure of Ar1 and Ar2 to which L1 and L2 are connected respectively.
[0172] In this context, adjacent substituents R z , R Ar can be optionally connected to form a ring, which is intended to indicate adjacent groups of substituents, such as adjacent substituents R z Between adjacent substituents R Ar Between, and adjacent substituents R z With R Ar 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.
[0173] According to one embodiment of the present invention, in the first compound and the second compound, Ar1 and Ar2 each appear identically or differently and have a structure represented by any one of the following structures:
[0174]
[0175] Z is selected from O, S, CR z R z ,SiR z R z or NR z ; When there are two R z When two R z Can be the same or different;
[0176] R Ar The same or different at each occurrence indicates mono-, poly- or no substitution;
[0177] R z , R Ar each occurrence is identically or differently 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 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof;
[0178] Adjacent substituent R z , R Ar Can optionally be linked to form a ring.
[0179] In this embodiment, It represents the position in the structure of Ar1 and Ar2 to which L1 and L2 are connected respectively.
[0180] According to one embodiment of the present invention, in the first compound and the second compound, Ar1 and Ar2 each appear identically or differently and have a structure represented by any one of the following structures:
[0181]
[0182] Z is selected from O, S, CR z Rz,SiR z R z or NR z ; When there are two R z When two R z Can be the same or different;
[0183] R Ar The same or different at each occurrence indicates mono-, poly- or no substitution;
[0184] R z , R Ar each occurrence being identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, 9-phenylcarbazolyl, naphthylphenyl, phenylpyridinyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, silyfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, triphenylene, terphenyl, and combinations thereof;
[0185] Adjacent substituent R z , R Ar Can optionally be linked to form a ring.
[0186] In this embodiment, It represents the position in the structure of Ar1 and Ar2 to which L1 and L2 are connected respectively.
[0187] According to one embodiment of the present invention, in the first compound and the second compound, Ar1 and Ar2 are selected from the following structures when they appear the same or differently:
[0188]
[0189]
[0190] In this embodiment, It represents the position in the structure of Ar-1 to Ar-53 to which L1 and L2 are connected respectively.
[0191] According to one embodiment of the present invention, the hydrogen in Ar-1 to Ar-53 can be partially or completely replaced by deuterium.
[0192] According to one embodiment of the present invention, in the first compound and the second compound, L1 and L2 are selected from the group consisting of the following groups at each occurrence, either identically or differently: a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, and combinations thereof.
[0193] According to one embodiment of the present invention, in the first compound and the second compound, L1 and L2 are selected from the group consisting of: single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzofuranyl, dibenzothiophenylene, pyridylene, thiophenylene, and combinations thereof, the same or different each time they appear.
[0194] According to one embodiment of the present invention, each time L1 and L2 appear, they are identically or differently selected from the group consisting of the following structures:
[0195]
[0196]
[0197] In this embodiment, in the structures of L-1 to L-27, "*" indicates the position of the structure of L1 or L2 connected to H1 or H2. It indicates the position in the structure of the L1 or L2 to which the Ar1 or Ar2 is connected.
[0198] According to one embodiment of the present invention, the hydrogen in the structures of L-1 to L-27 can be partially or completely replaced by deuterium.
[0199] According to one embodiment of the present invention, the first compound has a structure of H1-L1-Ar1, wherein H1 is selected from any one of the group consisting of H-1 to H-139, L1 is selected from any one of the group consisting of L-0 to L-27, and Ar1 is selected from any one of the group consisting of Ar-1 to Ar-53. Optionally, hydrogen in the structure of the first compound can be partially or completely replaced by deuterium.
[0200] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound 1-1 to compound 1-322, and the compounds 1-1 to compound 1-322 have a structure of H1-L1-Ar1, wherein H1, L1 and Ar1 are respectively selected from the structures listed in the following table:
[0201]
[0202]
[0203]
[0204]
[0205]
[0206] According to one embodiment of the present invention, the hydrogen in the compounds 1-1 to 1-322 can be partially or completely replaced by deuterium.
[0207] According to one embodiment of the present invention, the second compound has a structure of H2-L2-Ar2, wherein H2 is selected from any one of the group consisting of H-1 to H-139, H2-1 to H2-53, L2 is selected from any one of the group consisting of L-0 to L-27, and Ar2 is selected from any one of the group consisting of Ar-1 to Ar-53. Optionally, hydrogen in the structure of the second compound can be partially or completely replaced by deuterium.
[0208] According to one embodiment of the present invention, the second compound is selected from the group consisting of compounds 1-1 to 1-322, compounds 2-1 to 2-316, and the compounds 2-1 to 2-316 have a structure of H2-L2-Ar2, wherein H2, L2 and Ar2 are respectively selected from the structures listed in the following table:
[0209]
[0210]
[0211]
[0212]
[0213] According to one embodiment of the present invention, the hydrogen in the compounds 1-1 to 1-322 and 2-1 to 2-316 can be partially or completely replaced by deuterium.
[0214] According to an embodiment of the present invention, the organic layer is a light-emitting layer, and the first compound and the second compound are host materials.
[0215] According to an embodiment of the present invention, the light-emitting layer further comprises at least one phosphorescent light-emitting material.
[0216] According to one embodiment of the present invention, in the light-emitting layer, the at least one phosphorescent material is a metal complex having M(L a ) m (L b ) n (Lc ) q The general formula of
[0217] M is selected from metals with a relative atomic mass greater than 40;
[0218] L a , L b , L c are the first ligand, the second ligand and the third ligand coordinated with the M respectively; L a , L b , L c can optionally be linked to form a multidentate ligand;
[0219] L a , L b , L c can be the same or different; m is 1, 2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of m, n, q 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, the two L b Can be the same or different;
[0220] L a It has a structure as shown in Formula 3:
[0221]
[0222] in,
[0223] Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
[0224] 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;
[0225] Ring D and Ring E via U a and U b condense;
[0226] U a and U b is selected identically or differently at each occurrence from C or N;
[0227] R d , R e Each occurrence of the same or different means mono-, poly- or no-substitution;
[0228] Each time V1-V4 appears, they are selected from CR v or N;
[0229] R d , R e , R vEach occurrence is identically or differently 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 heterocyclyl 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 cycloalkyl having 6 to 30 carbon atoms Aryloxy, 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0230] Adjacent substituent R d , R e , R v can be optionally linked into a ring;
[0231] L b , L c Each occurrence is identically or differently selected from any one of the following structures:
[0232]
[0233]
[0234] in,
[0235] R a , R b and R c Each occurrence is identical or different, indicating mono-, poly-, or unsubstituted;
[0236] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;
[0237] X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;
[0238] R a , R b , Rc , R N1 , R N2 , R C1 and R C2 Each occurrence is identically or differently 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 heterocyclyl 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 cycloalkyl having 6 to 30 carbon atoms Aryloxy, 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0239] The ligand L b , L c In the structure of a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.
[0240] In this context, adjacent substituents R d , R e , R v can be optionally connected to form a ring, which is intended to indicate that when there is a substituent R d , Substituent R e , Substituent R v When adjacent substituent groups, such as adjacent substituents R d Between and adjacent substituents R e Between and adjacent substituents R v Between and adjacent substituents R d With R e Between and adjacent substituents R d With R v Between and adjacent substituents R e With R v Any one or more of these adjacent substituent groups can be linked to form a ring.d , Substituent R e , Substituent R v When the substituent groups are not linked to form a ring.
[0241] In this embodiment, the adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and R C1 Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, the substituent R a and R N2 Between, the substituent R b and R N2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0242] According to one embodiment of the present invention, in the light-emitting layer, the at least one phosphorescent material is a metal complex having M(L a ) m (L b ) n The general formula of
[0243] M is selected from metals with a relative atomic mass greater than 40;
[0244] L a , L bare the first ligand and the second ligand coordinated with the M respectively; L a , L b can optionally be linked to form a multidentate ligand;
[0245] 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 M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, the two L b Can be the same or different;
[0246] L a It has a structure as shown in Formula 3:
[0247]
[0248] in,
[0249] Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
[0250] 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;
[0251] Ring D and Ring E via U a and U b condense;
[0252] U a and U b is selected identically or differently at each occurrence from C or N;
[0253] R d , R e Each occurrence of the same or different means mono-, poly- or no-substitution;
[0254] Each time V1-V4 appears, they are selected from CR v or N;
[0255] R d , R e , R vEach occurrence is identically or differently 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 heterocyclyl 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 cycloalkyl having 6 to 30 carbon atoms Aryloxy, 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0256] Adjacent substituent R d , R e , R v can be optionally linked into a ring;
[0257] Wherein the ligand L b Has the following structure:
[0258]
[0259] wherein R1 to R7 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 heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl 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 cycloalkyl having 6 to 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 amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
[0260] According to one embodiment of the present invention, in the metal complex, the ligand L b Has the following structure:
[0261]
[0262] Among them, at least one of R1-R3 is selected from 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, or a combination thereof; and / or at least one of R4-R6 is selected from 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, or a combination thereof.
[0263] According to one embodiment of the present invention, in the metal complex, the ligand L b Has the following structure:
[0264]
[0265] Among them, at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof, the same or different at each occurrence; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof, the same or different at each occurrence.
[0266] According to one embodiment of the present invention, in the metal complex, the ligand L b Has the following structure:
[0267]
[0268] wherein at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof, the same or different at each occurrence; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof, the same or different at each occurrence.
[0269] According to one embodiment of the present invention, in the device, the at least one phosphorescent light-emitting material is an Ir complex, a Pt complex or an Os complex.
[0270] According to one embodiment of the present invention, in the device, the at least one phosphorescent light-emitting material is an Ir complex having Ir(L a )(L b )(L c )、Ir(L a )2(L b )、Ir(L a )2(L c ) or Ir(L a )(L c )A structure shown in any one of 2.
[0271] According to one embodiment of the present invention, in the electroluminescent device, the at least one phosphorescent material is an Ir complex and contains a ligand L a , the L a The compound has a structure as shown in Formula 3 and comprises at least one structural unit selected from the group consisting of a 6-membered and 6-membered aromatic ring, a 6-membered and 6-membered heteroaromatic ring, a 6-membered and 5-membered aromatic ring and a 6-membered and 5-membered heteroaromatic ring.
[0272] According to one embodiment of the present invention, in the electroluminescent device, the at least one phosphorescent material is an Ir complex and contains a ligand L a , the L a The compound has a structure as shown in Formula 3 and comprises at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.
[0273] According to one embodiment of the present invention, in the electroluminescent device, the at least one phosphorescent material is an Ir complex and contains a ligand L a , the L a Each occurrence is identically or differently selected from any one of the group consisting of:
[0274]
[0275] According to one embodiment of the present invention, in the electroluminescent device, the at least one phosphorescent material is an Ir complex and contains a ligand L b , the L b Each occurrence is identically or differently selected from any one of the group consisting of:
[0276]
[0277] According to one embodiment of the present invention, in the electroluminescent device, the at least one phosphorescent material is selected from the group consisting of the following structures:
[0278]
[0279]
[0280]
[0281]
[0282] According to another embodiment of the present invention, a display assembly is disclosed, which includes an electroluminescent device. The specific structure of the electroluminescent device is as shown in any of the above embodiments.
[0283] Combination with other materials
[0284] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned 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.
[0285] The materials described herein as 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 light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned 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.
[0286] Compound synthesis:
[0287] Synthesis Example 1: Synthesis of Compound 1-89
[0288] Step 1: Synthesis of intermediate 3
[0289]
[0290] Under nitrogen protection, intermediate 1 (5 g, 20.2 mmol), intermediate 2 (3.5 g, 22.3 mmol), tetrakis(triphenylphosphine)palladium (230 mg, 0.2 mmol), potassium carbonate (5.6 g, 40.4 mmol), toluene (Tol, 50 mL), ethanol (50 mL) and water (20 mL) were added to a three-necked flask and reacted at 100° C. for 16 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with water, concentrated to remove the solvent, and the crude product was purified by column chromatography (PE / DCM=10 / 1) to obtain 5 g of intermediate 3 as a white solid (yield: 89%).
[0291] Step 2: Synthesis of Compound 1-89
[0292]
[0293] Under nitrogen protection, intermediate 3 (1.85g, 6.66mmol), intermediate 4 (2g, 6.06mmol), tris(dibenzylideneacetone)dipalladium (54mg, 0.06mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (50mg, 0.12mmol), sodium tert-butoxide (1.2g, 13.3mmol) and xylene (80mL) were added to a three-necked flask and reacted at 140°C for 16h. After the reaction was completed, it was cooled to room temperature, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, and the solvent was removed by concentration. After the crude product (purified by column chromatography PE / DCM=6 / 1), 2g of compound 1-89 (yield: 59%) was obtained as a yellow solid. The product was confirmed to be the target product with a molecular weight of 572.2.
[0294] The present invention does not limit the preparation method of the selected first compound and the second compound. Those skilled in the art can prepare them by conventional synthesis methods, or refer to the synthesis method of the above-mentioned compounds 1-89, or can refer to patent applications such as US20180337340A1, CN111868210A, CN202010270250.2, CN202010285016.7, CN202010268985.1, CN202010285026.0, CN202010720191.4, CN202010825242.X, etc., and the preparation method thereof will not be described in detail here. The preparation method of the organic electroluminescent device is not limited, and the preparation method of the following embodiment is only an example and should not be construed as a limitation. Those skilled in the art can make reasonable improvements to the preparation method of the following embodiment based on the prior art. Exemplarily, the ratio of the first compound and the second compound is not particularly limited, and those skilled in the art can reasonably select within a certain range based on the prior art. For example, based on the total weight of the light-emitting layer material, the total weight of the first compound and the second compound accounts for 99.5% to 80.0% of the total weight of the light-emitting layer, and the weight ratio of the first compound to the second compound is between 1:99 and 99:1; or, the weight ratio of the first compound to the second compound can be between 20:80 and 99:1; or, the weight ratio of the first compound to the second compound can be between 50:50 and 90:10. In the embodiment of the device, the characteristics of the device are also tested using conventional equipment in the field (including but not limited to the evaporation machine produced by Angstrom Engineering, the optical test system and life test system produced by Suzhou Fushida, the ellipsometer produced by Beijing Liangtuo, etc.), using methods familiar to those skilled in the art. Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, and can obtain the inherent data of the sample with certainty and without influence, the above-mentioned related contents will not be elaborated in this patent.
[0295] Device Embodiment
[0296] Device Example 1
[0297] First, the glass substrate with a 120nm 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 organic layers specified below were placed in a vacuum of approximately 10 -8 Torr's case The compound HI was used as a hole injection layer (HIL) with a thickness of Compound HT was used as a hole transport layer (HTL) with a thickness of Compound EB is used as an electron blocking layer (EBL) with a thickness of Then, compound 1-107 as the first host, compound 2-25 as the second host, and phosphorescent compound RD (the weight of compound RD accounts for 2% of the total weight of the light-emitting layer) are co-evaporated to form an emission layer (EML) with a thickness of Compound HB was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron transport layer (ETL) with a thickness of Finally, evaporation 8-Hydroxyquinoline-lithium (Liq) with a thickness of 1000 nm was used as an electron injection layer (EIL), and a vapor deposition The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.
[0298] Device Example 2
[0299] The implementation method of Device Example 2 is the same as that of Device Example 1, except that Compound 2-21 is used instead of Compound 2-25 as the second host in the emission layer (EML).
[0300] Device Example 3
[0301] Device Example 3 is implemented in the same manner as Device Example 1, except that Compound 1-89 is used instead of Compound 1-107 as the first host in the emission layer (EML), and Compound 2-107 is used instead of Compound 2-25 as the second host (the weight ratio of Compound 1-89 to Compound 2-107 is 49:49).
[0302] Device Example 4
[0303] Device Example 4 was implemented in the same manner as Device Example 1, except that Compound 1-89 was used instead of Compound 2-25 as the second host in the emission layer (EML) (the weight ratio of Compound 1-107 to Compound 1-89 was 88:10).
[0304] Device Comparison Example 1
[0305] Device Comparative Example 1 was implemented in the same manner as Device Example 1, except that Compound 2-25 was used instead of Compound 1-107 and Compound 2-25 as a host in the emission layer (EML) (the weight ratio of Compound 2-25 to Compound RD was 98:2).
[0306] Device Comparison Example 2
[0307] The implementation of Comparative Device Example 2 is the same as Comparative Device Example 1, except that Compound 1-107 is used as a host instead of Compound 2-25 in the emission layer (EML).
[0308] Device Comparison Example 3
[0309] The implementation of Comparative Device Example 3 is the same as Comparative Device Example 1, except that Compound 2-21 is used as a host instead of Compound 2-25 in the emission layer (EML).
[0310] Device Comparison Example 4
[0311] The implementation of Comparative Device Example 4 is the same as Comparative Device Example 1, except that Compound 2-107 is used as a host instead of Compound 2-25 in the emission layer (EML).
[0312] The detailed device layer structure and thickness are shown in Table 1. For layers using more than one material, different compounds are doped in the weight ratios recorded.
[0313] Table 1 Device structures of device embodiments and comparative examples
[0314]
[0315]
[0316] The material structure used in the device is shown below:
[0317]
[0318]
[0319] At 80mA / cm 2 The device life (LT97) was tested at a constant current of 1.5 %. LT97 refers to the time required for the device brightness to decay to 97% of its initial brightness. These data are recorded and shown in Table 2.
[0320] Table 2 Device data
[0321]
[0322] discuss:
[0323] As shown in Table 2, the device life of Example 1 is 102 hours, which is 149% and 43.7% higher than that of Comparative Example 1 and Comparative Example 2, respectively; the device life of Example 2 is 136 hours, which is 91.5% and 223.8% higher than that of Comparative Example 2 and Comparative Example 3, respectively; the device life of Example 3 is 166 hours, which is 72.9% higher than that of Comparative Example 4; the device life of Example 4 is 124 hours, which is 74.6% higher than that of Comparative Example 2; these data prove that the combination of the first compound and the second compound selected in the present invention as the main material can greatly improve the device life and obtain more excellent device performance. It is fully proved that the compound combination of the first compound and the second compound selected in the present invention has very good application prospects.
[0324] 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 apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein 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 about why the present invention works are not intended to be restrictive.
Claims
1. An electroluminescent device, comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a first compound and a second compound; and the first compound is different from the second compound; The organic layer is a light-emitting layer, and the first compound and the second compound are host materials; The first compound has a structure of H1-L1-Ar1; and H1 has a structure represented by Formula 1: In Formula 1, A1, A2 and A3 are selected from N or CR at each occurrence, the same or different, and Ring A, Ring B and Ring C are selected from a carbocyclic ring having 5 to 30 carbon atoms or a heterocyclic ring having 3 to 30 carbon atoms at each occurrence; R x Each occurrence, identically or differently, indicates mono-, poly- or non-substitution; Adjacent substituents R, R x can optionally be linked to form a ring; L1 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; Ar1 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; The second compound has a structure of H2-L2-Ar2; The H2 has a structure represented by Formula 2; In formula 2, Each time Z1-Z3, Z6-Z8 appears, they are selected from CR z1 or N, Z4 and Z5 are selected from CR each time they appear, either identically or differently z2 , and the two substituents R in Z4 and Z5 z2 are connected to form a ring, and the ring has at least 7 ring atoms; Ar2 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; L2 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; R, R x , R z1 Each occurrence is identically or differently 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 heterocyclyl 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 An 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 amino group having 0 to 20 carbon atoms, a carboxylic acid group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, and combinations thereof; R z2 Each occurrence is identically or differently selected from the group consisting of: hydrogen, 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 heterocyclyl 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 substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, carboxyl groups, hydroxyl groups, mercapto groups, and combinations thereof; Adjacent substituent R z1 , R z2 Can optionally be linked to form a ring.
2. The electroluminescent device according to claim 1, wherein In Formula 1, the ring A, ring B and ring C are identically or differently selected from a 5-membered carbon ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms each time they occur.
3. The electroluminescent device according to claim 2, wherein the ring A, the ring B and the ring C are selected from a 5-membered carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring, the same or different when each ring A, the ring B and the ring C appear.
4. The electroluminescent device according to claim 1 or 2, wherein the H1 has a structure represented by Formula 1-a: in, A1 to A3 are selected from N or CR at each occurrence, the same or different, X1 to X 10 Each occurrence is selected from N or CR, either identically or differently x ; R, R x Each occurrence is identically or differently 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 heterocyclyl 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 An 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 amino group having 0 to 20 carbon atoms, a carboxylic acid group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, and combinations thereof; Adjacent substituents R, R x Can optionally be linked to form a ring.
5. The electroluminescent device according to claim 4, wherein R, R x Each occurrence is identically or differently 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 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 amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof.
6. The electroluminescent device of claim 1, wherein R and R x At least one of the following is selected from deuterium, 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.
7. The electroluminescent device of claim 6, wherein R and R x At least one of them is selected from deuterium, phenyl, biphenyl, or pyridyl.
8. The electroluminescent device according to claim 4, wherein the adjacent substituents R between A1 to A3 and the adjacent substituents R between X1 to X3 are x , the adjacent substituents R between X4 and X6 x , and X7 to X 10 Adjacent substituents R x , at least one of these adjacent substituent groups is connected to form a ring.
9. The electroluminescent device of claim 1, wherein said H1 is selected from the group consisting of: Optionally, the hydrogen in H-1 to H-139 can be partially or completely replaced by deuterium.
10. The electroluminescent device according to claim 1, wherein In the second compound, H2 has a structure represented by any one of Formula 2-1 to Formula 2-8: In Formula 2-1 to Formula 2-8, Each time Z1-Z3, Z6-Z8 appears, they are selected from CR z1 or N; Z h1 -Z h8 Each occurrence is the same or different selection from CR zh or N; Z m Selected from CR zm or N; Z n Selected from CR zn R zn , O, S or NR zn ; When Z n Selected from CR zn R zn When two R zn Can be the same or different; R z1 , R zh , R zm , R zn The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted substituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, carboxylic acid groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and its combination; Adjacent substituent R z1 , R zh , R zm , R zn Can optionally be linked to form a ring.
11. The electroluminescent device according to claim 10, wherein: In Formula 2-1 to Formula 2-8, R z1 , R zh , R zm , R zn each occurrence being identically or differently 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 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 amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituent R z1 , R zh , R zm , R zn Can optionally be linked to form a ring.
12. The electroluminescent device of claim 1, wherein the H2 is selected from the group consisting of H-1 to H-139 and the following structures: Optionally, the hydrogen in said H-1 to H-139 and said H2-1 to H2-53 can be partially or completely replaced by deuterium.
13. The electroluminescent device according to claim 1, wherein each of Ar1 and Ar2 has a structure represented by any one of the following structures, the same or different: in, Z is selected from O, S, CR z R z ,SiR z R z , NR z , B.R. z or PR z ; When there are two R z When two R z Can be the same or different; R Ar The same or different at each occurrence indicates mono-, poly- or no substitution; R z , R Ar each occurrence is identically or differently 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 6-30 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 amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituent R z , R Ar Can optionally be linked to form a ring.
14. The electroluminescent device according to claim 13, wherein Z is selected from O, S, CR z R z ,SiR z R z or NR z ; R z , R Ar Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
15. The electroluminescent device according to claim 14, wherein R z , R Ar Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, 9-phenylcarbazolyl, naphthylphenyl, phenylpyridinyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, silyfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, triphenylene, terphenyl, and combinations thereof.
16. The electroluminescent device according to claim 9 or 12, wherein Ar1 and Ar2 are selected from the following structures when they appear the same or differently: Optionally, hydrogen in the structures Ar-1 to Ar-53 can be partially or fully replaced by deuterium.
17. The electroluminescent device of claim 1, wherein each occurrence of L1, L2 is identically or differently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, and combinations thereof.
18. The electroluminescent device of claim 17, wherein each occurrence of L1 and L2 is identically or differently selected from the group consisting of a single bond, a phenylene group, a naphthylene group, a biphenylene group, a terphenylene group, a triphenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a pyridylene group, a thiophenylene group, and combinations thereof.
19. The electroluminescent device according to claim 16, wherein each occurrence of L1 and L2 is identically or differently selected from the group consisting of the following structures: "*" indicates the position in the structure of L-1 to L-27 connected to H1 or H2, represents the position in the structure of said L-1 to L-27 connected to said Ar1 or said Ar2; Optionally, hydrogen in the structures of L-1 to L-27 can be partially or completely replaced by deuterium.
20. The electroluminescent device of claim 19, wherein the first compound has a structure of H1-L1-Ar1, wherein H1 is selected from any one of the group consisting of H-1 to H-139, L1 is selected from any one of the group consisting of L-0 to L-27, and Ar1 is selected from any one of the group consisting of Ar-1 to Ar-53; optionally, hydrogen in the structure of the first compound can be partially or completely replaced by deuterium.
21. The electroluminescent device according to claim 20, wherein the first compound is selected from the group consisting of Compound 1-1 to Compound 1-322, wherein Compound 1-1 to Compound 1-322 have a structure of H1-L1-Ar1, wherein H1, L1 and Ar1 are respectively selected from the structures listed in the following table: Optionally, hydrogen in the above compounds 1-1 to 1-322 can be partially or completely replaced by deuterium.
22. An electroluminescent device as described in claim 19, wherein the second compound has a structure of H2-L2-Ar2, wherein H2 is selected from any one of the group consisting of H-1 to H-139, H2-1 to H2-53, wherein L2 is selected from any one of the group consisting of L-0 to L-27, and wherein Ar2 is selected from any one of the group consisting of Ar-1 to Ar-53; optionally, hydrogen in the structure of the second compound can be partially or completely replaced by deuterium.
23. The electroluminescent device according to claim 22, wherein the second compound is selected from the group consisting of Compound 1-1 to Compound 1-322, Compound 2-1 to Compound 2-316, and the Compound 2-1 to Compound 2-316 have a structure of H2-L2-Ar2, wherein H2, L2 and Ar2 are respectively selected from the structures listed in the following table: Optionally, hydrogen in the above-mentioned compounds 1-1 to 1-322 and compounds 2-1 to 2-316 can be partially or completely replaced by deuterium.
24. The electroluminescent device of claim 1, wherein the light-emitting layer further comprises at least one phosphorescent light-emitting material.
25. The electroluminescent device of claim 24, wherein: In the light-emitting layer, at least one phosphorescent material is a metal complex having M(L a ) m (L b ) n (L c ) q The general formula of M is selected from metals with a relative atomic mass greater than 40; L a , L b , L c are the first ligand, the second ligand and the third ligand coordinated with the M respectively; L a , L b , L c can optionally be linked to form a multidentate ligand; L a , L b , L c can be the same or different; m is 1, 2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of m, n, q 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, the two L b Can be the same or different; L a It has a structure as shown in Formula 3: in, Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring; 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; Ring D and Ring E via U a and U b condense; U a and U b is selected identically or differently at each occurrence from C or N; R d , R e Each occurrence of the same or different means mono-, poly- or no-substitution; Each time V1-V4 appears, they are selected from CR v or N; R d , R e , R v Each occurrence is identically or differently 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 heterocyclyl 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 an 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 amino group having 0 to 20 carbon atoms, a carboxylic acid group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, and combinations thereof; Adjacent substituent R d , R e , R v can optionally be linked into a ring; L b , L c Each occurrence is identically or differently selected from any one of the following structures: in, R a , R b and R c Each occurrence is identical or different, indicating mono-, poly-, or unsubstituted; X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each occurrence is identically or differently 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 Each occurrence is identically or differently 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 heterocyclyl 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 An 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 amino group having 0 to 20 carbon atoms, a carboxylic acid group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, and combinations thereof; The ligand L b , L c In the structure of a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.
26. The electroluminescent device of claim 24, wherein: In the light-emitting layer, at least one phosphorescent material is a metal complex having M(L a ) m (L b ) n The general formula of M is selected from metals with a relative atomic mass greater than 40; L a , L b are the first ligand and the second ligand coordinated with the M respectively; L a , L b can optionally be linked to form a multidentate ligand; 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 M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, the two L b Can be the same or different; L a It has a structure as shown in Formula 3: in, Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring; 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; Ring D and Ring E via U a and U b condense; U a and U b is selected identically or differently at each occurrence from C or N; R d , R e Each occurrence of the same or different means mono-, poly- or no-substitution; Each time V1-V4 appears, they are selected from CR v or N; R d , R e , R v Each occurrence is identically or differently 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 heterocyclyl 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 an 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 amino group having 0 to 20 carbon atoms, a carboxylic acid group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, and combinations thereof; Adjacent substituent R d , R e , R v can optionally be linked into a ring; Wherein the ligand L b Has the following structure: wherein R1 to R7 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 heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl 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 an 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 amino group having 0 to 20 carbon atoms, a carboxylic acid group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, and combinations thereof.
27. An electroluminescent device as claimed in claim 26, wherein at least one or two of R1-R3 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 one or two of R4-R6 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.
28. An electroluminescent device as described in claim 27, at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups with 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups with 2-20 carbon atoms, or combinations thereof at each occurrence, either identically or differently; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups with 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups with 2-20 carbon atoms at each occurrence, either identically or differently.
29. An electroluminescent device as claimed in claim 25 or 26, wherein the at least one phosphorescent light emitting material is an Ir complex, a Pt complex or an Os complex.
30. The electroluminescent device of claim 29, wherein the at least one phosphorescent material is an Ir complex having Ir(L a )(L b )(L c )、Ir(L a )2(L b )、Ir(L a )2(L c ) or Ir(L a )(L c )A structure shown in any one of 2.
31. A display assembly comprising the electroluminescent device according to any one of claims 1 to 30.
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