An electroluminescent device
The reduction in efficiency of existing OLED devices is solved by using a novel material combination of the first compound with the H-L1-E structure and the second compound of the general formula of M(La)m(Lb)n(Lc)q in OLED devices. and the problem of difficulty in achieving deep red luminescence has achieved efficient and long-lived crimson and even near-infrared luminescence, expanding its application potential.
Patent Information
- Application Number
- CN202110464195.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2021-04-30
- Publication Date
- 2025-02-14
- Estimated Expiration
- 2041-04-30
AI Technical Summary
The efficiency of existing phosphorescence OLED devices is rapidly reduced under high brightness, and it is difficult to achieve dark red and even near infrared luminescence, which limits its application in the fields of display, biomedical and vehicle lighting.
A novel material combination consisting of a first compound having a H-L1-E structure and a second compound having the general formula of M(La)m(Lb)n(Lc)q is used for the luminescent layer of an electroluminescent device. Achieve deep red luminescence and significantly reduce driving voltage, improving device efficiency and life.
It achieves high efficiency and long life under high brightness conditions, can provide deeper red and near-infrared spectra, expanding the potential of OLED devices in a variety of application fields.
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Figure CN115275029B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to electronic devices, such as electroluminescent devices. More particularly, to an organic layer comprising a HL 1 -E structure and having M(L a ) m (L b ) n (L c ) q An electroluminescent device comprising a novel material combination of the second compound of the general formula, and the device has at least one maximum emission wavelength greater than 630 nm. 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] With the increasing application of OLED, new and higher requirements are put forward for deep red luminescent materials with wavelengths greater than 630nm and long wavelength luminescent materials in near infrared. For example, in the display industry, the ultra-high-definition display color gamut standard BT.2020 issued by the International Telecommunication Union's Radio Communication Sector (ITU-R) has proposed a wider color gamut standard, which requires the development of luminescent materials with deeper red than the current commercial materials. In the fields of biomedicine, specific long-wavelength luminescence is also required for detection and treatment. The new tumor therapy - photodynamic therapy uses 630nm laser radiation to mark tumor tissue to achieve the effect of accurately destroying cancerous tissue. Red light with a wavelength of 660nm can be absorbed by chlorophyll a to promote photosynthesis. Deep red light (730nm) can control the entire process of plants from germination to nutritional growth to flowering. Therefore, the irradiation of specific wavelengths of light is very important for the industrial production of cash crops. In the field of automotive lighting, the latest OLED taillights also use deep red materials. Other near-infrared luminescent materials play an important role in special fields such as detection, sensing, optical communication, and night vision. Therefore, the development of deep red and even near-infrared luminescent materials and their electroluminescent devices has important practical significance. Currently, phosphorescent devices have been widely used in display panels and other fields, but deep red devices are often less efficient. In addition to the properties of the material itself, the combination of phosphorescent luminescent materials and host materials is directly related to the luminescent performance of the device. Therefore, the selection and optimization of the combination of phosphorescent luminescent materials and host materials is an important part of the relevant research in the industry. Summary of the invention
[0009] The present invention aims to provide a novel electroluminescent device to solve at least part of the above problems. The organic layer of the electroluminescent device comprises a 1 -E structure and having M(L a ) m (L b ) n (L c ) q The novel material combination is composed of a second compound of the general formula of , and the device has at least one maximum emission wavelength greater than 630 nm. The novel material combination can be used in the light-emitting layer of an electroluminescent device, and the novel material combination can achieve deep red light emission in the device, and can significantly reduce the driving voltage of the device while significantly improving the efficiency and / or life of the device, and can provide better device performance.
[0010] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0011] anode,
[0012] cathode,
[0013] 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 device has at least one maximum emission wavelength greater than 630 nm;
[0014] The first compound has HL 1 -E, wherein H has a structure represented by formula A:
[0015]
[0016] In formula A,
[0017] Z 1 -Z 3 , Z 6 -Z 8 Each occurrence is the same or different selection from CR z1 or N, Z 4 With Z 5 Each occurrence is the same or different selection from CR z2 , and Z 4 With Z 5 The two substituents R z2 Connect to form a ring;
[0018] L 1 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;
[0019] E 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;
[0020] R z1The 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 aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0021] 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl, 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 alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0022] Adjacent substituent R z1 , R z2 can optionally be linked to form a ring;
[0023] The second compound is a metal complex having M(L a ) m (L b )n (L c ) q The general formula is: M is selected from metals with a relative atomic mass greater than 40; L a , L b and L c are respectively the first ligand, the second ligand and the third ligand coordinated with the metal M; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to the oxidation state of the metal M; when m is equal to 2 or 3, multiple L a can be the same or different; when n is equal to 2, the two L b can be the same or different; when q is equal to 2, the two L c Can be the same or different;
[0024] L a , L b and L c can optionally be linked to form a multidentate ligand;
[0025] Among them, the L a Each occurrence is identically or differently selected from the structure represented by any one of Formula 1-1 to Formula 1-14:
[0026]
[0027] in,
[0028] X 1 -X 6 Each occurrence is the same or different selection from CR x or N;
[0029] Y 1 -Y 6 Each time it appears, it is selected from C, CR y or N;
[0030] W 1 , W 2 Each occurrence is the same or different selection from CR w R w ,SiR w R w ,GeR w R w , NR w , P.R. w , C=O, O, S or Se; when there are two R w When two R w Can be the same or different;
[0031] L b and L cEach occurrence is identically or differently selected from any one of the group consisting of:
[0032]
[0033] R i , R ii and R iii Each occurrence of the same or different means mono-, poly- or no-substitution;
[0034] X a Selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;
[0035] X b and X c Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;
[0036] G.R i , R ii , R iii , R N1 , R N2 , R C1 , R C2 , R x , R y and R w 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0037] Adjacent substituents G, Rx , R y and R w can optionally be linked to form a ring;
[0038] Adjacent substituent R i , R ii , R iii , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.
[0039] According to another embodiment of the present invention, a display assembly is disclosed, which includes the electroluminescent device shown in the above embodiment.
[0040] The organic layer of the electroluminescent device disclosed in the present invention comprises a 1 -E structure and having M(L a ) m (L b ) n (L c ) q The novel material combination is composed of a second compound of the general formula of , and the device has at least one maximum emission wavelength greater than 630nm. The novel material combination can be used in the light-emitting layer of an electroluminescent device. The novel material combination can realize deep red light emission in the device, and can significantly reduce the driving voltage of the device while significantly improving the efficiency and / or life of the device, and can provide better device performance. BRIEF DESCRIPTION OF THE DRAWINGS
[0041] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the electroluminescent device disclosed herein.
[0042] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the electroluminescent device disclosed herein. DETAILED DESCRIPTION
[0043] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1An 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.
[0044] 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 one doped with F at a molar ratio of 50:1. 4
[0013] An example of an n-doped electron transport layer is BPhen doped with Li at a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety.
[0013] An example of an n-doped electron transport layer is BPhen doped with Li at a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety.
[0013] 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 a metal such as Mg:Ag and 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.
[0045] 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.
[0046] 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.
[0047] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The 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.
[0048] 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.
[0049] The materials and structures described herein may also be used in other organic electronic devices listed above.
[0050] 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.
[0051] 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.
[0052] 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.
[0053] 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).
[0054] 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.
[0055] 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).
[0056] Definition of Substituent Terms
[0057] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.
[0058] 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.
[0059] 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.
[0060] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbons in an alkyl chain substituted with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom and a boron atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl may be optionally substituted.
[0061] 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.
[0062] 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.
[0063] 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.
[0064] 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.
[0065] 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 substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group may be optionally substituted.
[0066] 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.
[0067] 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.
[0068] 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,
[0069] 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.
[0070] 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.
[0071] Alkylgermanyl - As used herein, alkyl substituted germanyl is contemplated. The alkylgermanyl may be an alkylgermanyl having 3-20 carbon atoms, preferably an alkylgermanyl having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyltert-butylgermanyl, methyldi-tert-butylgermanyl. In addition, the alkylgermanyl may be optionally substituted.
[0072] Arylgermanyl - as used herein, encompasses germanyl substituted with at least one aryl or heteroaryl group. The arylgermanyl may be an arylgermanyl having 6 to 30 carbon atoms, preferably an arylgermanyl having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyltert-butylgermanyl. In addition, the arylgermanyl may be optionally substituted.
[0073] 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.
[0074] 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 alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid , substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, refers to alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any one of which may be selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted cycloalkyl having 6-30 carbon atoms, unsubstituted cycloalkyl having 2-2 ... Aryl, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermanyl having 3-20 carbon atoms, unsubstituted arylgermanyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.
[0075] 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.
[0076] 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.
[0077] 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.
[0078] In the compounds mentioned in the present disclosure, unless clearly 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 (including spirocyclic, bridged ring, condensed ring, etc.), 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.
[0079] 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:
[0080]
[0081] 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:
[0082]
[0083] 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 a further distant carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0084]
[0085] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the two adjacent substituents 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:
[0086]
[0087] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0088] anode,
[0089] cathode,
[0090] 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 device has at least one maximum emission wavelength greater than 630 nm;
[0091] The first compound has HL 1 -E, wherein H has a structure represented by formula A:
[0092]
[0093] In formula A,
[0094] Z 1 -Z 3 , Z 6 -Z 8 Each occurrence is the same or different selection from CR z1 or N, Z 4 With Z 5 Each occurrence is the same or different selection from CR z2 , and Z 4 With Z 5 The two substituents R z2 Connect to form a ring;
[0095] L 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] E 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;
[0097] R z1The 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 aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0098] 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl, 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 alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0099] Adjacent substituent R z1 , R z2 can optionally be linked to form a ring;
[0100] The second compound is a metal complex having M(L a ) m (L b )n (L c ) q The general formula is: M is selected from metals with a relative atomic mass greater than 40; L a , L b and L c are respectively the first ligand, the second ligand and the third ligand coordinated with the metal M; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to the oxidation state of the metal M; when m is equal to 2 or 3, multiple L a can be the same or different; when n is equal to 2, the two L b can be the same or different; when q is equal to 2, the two L c Can be the same or different;
[0101] L a , L b and L c can optionally be linked to form a multidentate ligand;
[0102] Among them, the L a Each occurrence is identically or differently selected from the structure represented by any one of Formula 1-1 to Formula 1-14:
[0103]
[0104] in,
[0105] X 1 -X 6 Each occurrence is the same or different selection from CR x or N;
[0106] Y 1 -Y 6 Each time it appears, it is selected from C, CR y or N;
[0107] W 1 , W 2 Each occurrence is the same or different selection from CR w R w ,SiR w R w ,GeR w R w , NR w , P.R. w , C=O, O, S or Se; when there are two R w When two R w Can be the same or different;
[0108] L b and L cEach occurrence is identically or differently selected from any one of the group consisting of:
[0109]
[0110] R i , R ii and R iii Each occurrence of the same or different means mono-, poly- or no-substitution;
[0111] X a Selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;
[0112] X b and X c Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;
[0113] G.R i , R ii , R iii , R N1 , R N2 , R C1 , R C2 , R x , R y and R w 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0114] Adjacent substituents G, Rx , R y and R w can optionally be linked to form a ring;
[0115] Adjacent substituent R i , R ii , R iii , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.
[0116] In this article, the device has at least one maximum emission wavelength greater than 630nm, which is intended to mean that the electroluminescent device of the present invention may have only one maximum emission wavelength (e.g., a red light device) or may have multiple maximum emission wavelengths (e.g., a white light device), wherein at least one maximum emission wavelength is greater than 630nm. Preferably, the electroluminescent device of the present invention has at least one maximum emission wavelength greater than 635nm, or at least one maximum emission wavelength greater than 640nm, or at least one maximum emission wavelength greater than 650nm, or at least one maximum emission wavelength greater than 670nm.
[0117] In this embodiment, the adjacent substituent R z1 , R z2 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, Z 1 -Z 3 The adjacent substituent R z1 Between, Z 6 -Z 8 The adjacent substituent R z1 Between, Z 3 The substituent R z1 With Z 4 The substituent R z2 Between, Z 3 The substituent R z1 With Z 5 The substituent R z2 Between, Z 6 The substituent R z1 With Z 4 The substituent R z2 Between, and Z 6 The substituent R z1 With Z 5 The substituent R 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.
[0118] In this embodiment, La , L b and L c can be optionally linked to form a multidentate ligand, and is intended to represent L a , L b and L c Any two or three of L can be linked to form a tetradentate ligand or a hexadentate ligand. a , L b and L c It is also possible that none of them are connected so as not to form a multidentate ligand.
[0119] In this context, adjacent substituents G, R x , R y and R w can be optionally connected to form a ring, and is intended to indicate that in the L a Adjacent substituent groups in the structure of x Between adjacent substituents R y Between adjacent substituents R w Between adjacent substituents G and R y Between adjacent substituents G and R w Between, and adjacent substituents R x With R y Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituents may be connected to form a ring. In particular, in formula 1-1, adjacent substituents R x With R y They are not connected to form an oxygen heterocycle.
[0120] In this embodiment, the adjacent substituent R i , R ii , R iii , R N1 , R N2 , R C1 and R C2 can be optionally connected to form a ring, and is intended to indicate that in the L b , L c Adjacent substituent groups in the structure of i Between adjacent substituents R ii Between adjacent substituents R iii Between adjacent substituents R i With R ii Between adjacent substituents R ii With R iii Between adjacent substituents R i With R iii Between adjacent substituents R i With RN1 Between adjacent substituents R i With R C1 Between adjacent substituents R i With R C2 Between adjacent substituents R ii With R N1 Between adjacent substituents R iii With R N1 Between adjacent substituents R ii With R C1 Between adjacent substituents R ii With R C2 Between adjacent substituents R i With R N2 Between adjacent substituents R ii With R N2 Between, and adjacent substituents R C1 With 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.
[0121] According to one embodiment of the present invention, in Formula A, Z 4 With Z 5 The two substituents R z2 The rings are connected to form a ring having at least 6 ring atoms.
[0122] According to one embodiment of the present invention, in Formula A, Z 4 With Z 5 The two substituents R z2 The rings are connected to form a ring having at least 7 ring atoms.
[0123] According to one embodiment of the present invention, in the first compound, H has a structure represented by any one of Formula A-1 to Formula A-8:
[0124]
[0125] In Formula A-1 to Formula A-8,
[0126] Z 1 -Z 3 , Z 6 -Z 8 Each occurrence is the same or different selection from CR z1 or N;
[0127] Z h1 -Z h9 Each occurrence is the same or different selection from CR zh or N;
[0128] Z m Selected from CR zm or N;
[0129] 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;
[0130] 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 aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0131] Adjacent substituent R z1 , R zh , R zm , R zn Can optionally be linked to form a ring.
[0132] In this context, adjacent substituents R z1 , R zh , R zm , R zn can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, Z 1 -Z 3 The adjacent substituent R z1 Between, Z 6-Z 8 The adjacent substituent R z1 Between adjacent substituents R zh Between adjacent substituents R zh and R zm Between adjacent substituents R zn Between, and adjacent to, 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.
[0133] According to one embodiment of the present invention, in Formula A-1 to Formula A-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;
[0134] Adjacent substituent R z1 , R zh , R zm , R zn Can optionally be linked to form a ring.
[0135] According to one embodiment of the present invention, in the first compound, H has a structure represented by any one of Formula A-1 to Formula A-8:
[0136]
[0137] In Formula A-1 to Formula A-8,
[0138] Z 1 -Z 3 , Z 6 -Z 8 Each occurrence is the same or different selection from CR z1 ;
[0139] Z h1 -Z h9Each occurrence is the same or different selection from CR zh or N;
[0140] Z m Selected from N;
[0141] Z n Select from O, S or NR zn ;
[0142] R z1 , R zh , 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 aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0143] Adjacent substituent R z1 , R zh , R zn Can optionally be linked to form a ring.
[0144] In this context, adjacent substituents R z1 , R zh , R zn can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, Z 1 -Z 3 The adjacent substituent R z1 Between, Z 6 -Z 8 The adjacent substituent R z1 Between adjacent substituents R zh Between adjacent substituents R zn Between, and adjacent substituents R zh and R znAny 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.
[0145] According to one embodiment of the present invention, in the first compound, H has a structure represented by any one of Formula A-1 to Formula A-8:
[0146]
[0147] In Formula A-1 to Formula A-8,
[0148] Z 1 -Z 3 , Z 6 -Z 8 Each occurrence is the same or different selection from CR z1 ;
[0149] Z h1 -Z h9 Each occurrence is the same or different selection from CR zh or N;
[0150] Z m Selected from N;
[0151] Z n Select from O, S or NR zn ;
[0152] 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;
[0153] Adjacent substituent R z1 , R zh , R zn Can optionally be linked to form a ring.
[0154] According to one embodiment of the present invention, in the first compound, H is selected from the group consisting of the following structures:
[0155]
[0156]
[0157]
[0158] In this embodiment, "*" indicates that the structure of H is different from that of L. 1 The location of the connection.
[0159] According to one embodiment of the present invention, the hydrogen in the structures of H-1 to H-76 can be partially or completely replaced by deuterium.
[0160] According to one embodiment of the present invention, in the first compound, E has a structure represented by Formula Ea or Formula Eb:
[0161]
[0162] In Formula Ea and Formula Eb,
[0163] E 1 -E 14 Each time it appears, it is selected from C, CR e or N;
[0164] R e 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 aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0165] Adjacent substituent R e Can optionally be linked to form a ring.
[0166] In this embodiment, " " indicates that the structure of E is consistent with L1 The location of the link.
[0167] In this embodiment, in Formula Ea, E 1 -E 6 One of them is C, and the C and L 1 connection; in formula Eb, E 7 -E 14 One of them is C, and the C and L 1 connect.
[0168] In this embodiment, the adjacent substituent R e can be optionally connected to form a ring, which is intended to indicate that any adjacent substituents R e Obviously, any adjacent substituents R e They can also not be connected to form a ring.
[0169] According to one embodiment of the present invention, in the formula Ea, E 1 -E 6 At least two of them are N; in the formula Eb, E 7 -E 14 At least 2 of them are N.
[0170] According to one embodiment of the present invention, in the formula Ea, E 1 -E 6 3 of them are N; in the formula Eb, E 7 -E 10 2 of them are N.
[0171] According to one embodiment of the present invention, in the first compound, E has a structure represented by any one of Formula E-1 to Formula E-10:
[0172]
[0173] R A Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0174] V is selected from O, S or Se;
[0175] R AThe 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 aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0176] Adjacent substituent R A Can optionally be linked to form a ring.
[0177] In this context, adjacent substituents R A can be optionally connected to form a ring, which is intended to indicate that any adjacent substituents R A Obviously, any adjacent substituents R A They can also not be connected to form a ring.
[0178] In this embodiment, Indicates that the structure of E and L 1 The location of the link.
[0179] According to one embodiment of the present invention, in the first compound, E has a structure represented by any one of Formula E-11 to Formula E-21:
[0180]
[0181] R A Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0182] V is selected from O, S or Se;
[0183] R Aeach 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 heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, cyano, hydroxyl, mercapto, and combinations thereof;
[0184] Adjacent substituent R A Can optionally be linked to form a ring.
[0185] In this embodiment, " " indicates that the structure of E is consistent with L 1 The location of the link.
[0186] According to one embodiment of the present invention, in Formula E-1 to Formula E-21, the R A Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof;
[0187] Adjacent substituent R A Can optionally be linked to form a ring.
[0188] According to one embodiment of the present invention, in Formula E-1 to Formula E-21, the R A each occurrence being identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuterated methyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl, phenylpyridyl, and combinations thereof;
[0189] Adjacent substituent R A Can optionally be linked to form a ring.
[0190] According to one embodiment of the present invention, in Formula E-1 to Formula E-21, there is at least one R A , and the R A Each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof;
[0191] Adjacent substituent R A Can optionally be linked to form a ring.
[0192] According to one embodiment of the present invention, in Formula E-1 to Formula E-21, there is at least one R A , and the R A Each occurrence is identically or differently selected from the group consisting of deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof;
[0193] Adjacent substituent R A Can optionally be linked to form a ring.
[0194] According to one embodiment of the present invention, in Formula E-1 to Formula E-21, there is at least one R A , and the R A Each occurrence is identically or differently selected from the group consisting of: deuterium, fluorine, cyano, methyl, trideuterated methyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl, phenylpyridyl, and combinations thereof;
[0195] Adjacent substituent R A Can optionally be linked to form a ring.
[0196] According to one embodiment of the present invention, in the first compound, E is selected from the group consisting of the following structures:
[0197]
[0198]
[0199] Indicates that the structure of E and L 1 The location of the link.
[0200] According to one embodiment of the present invention, wherein the L 1 is 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 pyridylene group, a dibenzothienylene group, a dibenzofuranylene group and a thienylene group.
[0201] According to one embodiment of the present invention, wherein the L 1 Selected from the group consisting of:
[0202]
[0203] "*" indicates the L 1 The position to which the H is connected in the structure of Indicates the L 1 The position in the structure where the E is linked.
[0204] According to one embodiment of the present invention, the hydrogen in the structures of L-1 to L-22 can be partially or completely replaced by deuterium.
[0205] According to one embodiment of the present invention, the first compound has HL 1 -E structure, the H is selected from any one of the group consisting of H-1 to H-76, the L 1 Any one selected from the group consisting of L-0 to L-22, and E selected from the group consisting of E-1 to E-38. Optionally, hydrogen in the structure of the first compound can be partially or completely replaced by deuterium.
[0206] According to one embodiment of the present invention, the first compound is selected from the group consisting of Compound 1-1 to Compound 1-249, and the specific structures of Compound 1-1 to Compound 1-249 are shown in Claim 12.
[0207] According to one embodiment of the present invention, the hydrogen in the compounds 1-1 to 1-249 can be partially or completely replaced by deuterium.
[0208] According to one embodiment of the present invention, in Formula 1-1 to Formula 1-14, X 1 -X 6 Each occurrence is the same or different selection from CR x , Y 1 -Y 6 Each occurrence is selected from C or CR, either identically or differently y .
[0209] In this embodiment, in Formula 1-1 to Formula 1-14, Y 1 -Y 6Each occurrence is selected from C or CR, either identically or differently y , is intended to indicate that: in Formulas 1-1 to 1-10, 1-12 to 1-14, Y 1 -Y 5 Each occurrence is the same or different selection from CR y ; In formula 1-11, Y 1 -Y 4 Each occurrence is selected from C or CR, either identically or differently y , Y 5 -Y 6 Each occurrence is the same or different selection from CR y .
[0210] According to one embodiment of the present invention, in Formula 1-1 to Formula 1-14, X 1 -X 6 At least one of is selected from N.
[0211] According to one embodiment of the present invention, in Formula 1-1 to Formula 1-14, X 1 To X 3 At least one of them is N.
[0212] According to one embodiment of the present invention, in Formula 1-1 to Formula 1-14, X 1 or X 2 is N.
[0213] According to one embodiment of the present invention, in Formula 1-1 to Formula 1-14, Y 1 -Y 6 There are at least two adjacent substituents R y Connect to form a ring.
[0214] According to one embodiment of the present invention, wherein the L a Each occurrence is identically or differently selected from the structure represented by any one of Formula 1-1, Formula 1-2, Formula 1-4 to Formula 1-10, and Formula 1-12.
[0215] According to one embodiment of the present invention, wherein the L a Each occurrence is identical or different and is selected from the structure represented by formula 1-1, wherein the adjacent substituents R x can be optionally linked to form a ring, with adjacent substituents R y Can optionally be linked to form a ring.
[0216] In this embodiment, the adjacent substituent R x can be optionally linked to form a ring, with adjacent substituents R ycan be optionally connected to form a ring, which is intended to indicate that: in the structure represented by formula 1-1, any adjacent substituent R x They can be connected to form a ring, and any adjacent substituents R y They can be connected to form a ring, and the substituent R x and R y Obviously, the adjacent substituents R x They may not be connected to form a ring, and adjacent substituents R y They may not be connected to form a ring.
[0217] According to one embodiment of the present invention, wherein the L a Each occurrence is identically or differently selected from the structure represented by any one of Formula 1-1, Formula 1-2 and Formula 1-6.
[0218] According to one embodiment of the present invention, wherein the L a Each time it appears, the same or different one is selected from the group consisting of Formula 1-1-1 to Formula 1-1-4, Formula 1-2-1 to Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1, Formula 1-7-2, Formula 1-8-1, Formula 1-9-1 to Formula 1-9-3, Formula 1-10-1 to Formula 1-10-3, and Formula 1-12-1 to Formula 1-12-3:
[0219]
[0220]
[0221] in,
[0222] X 1 -X 6 Each occurrence is the same or different selection from CR x or N;
[0223] Y 1 -Y 6 Each occurrence is the same or different selection from CR y or N;
[0224] B 1 -B 4 Each occurrence is the same or different selection from CR b or N;
[0225] W 1 and W 2 Each occurrence is the same or different selection from CR w R w ,SiR w R w ,GeRw R w , NR w , P.R. w , C=O, O, S or Se; when there are two R w When two R w Can be the same or different;
[0226] G.R x , R y , R w , R b , R n3 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0227] and,
[0228] In the above formula 1-1-1, formula 1-2-4, formula 1-2-5, formula 1-5-1 to formula 1-5-4, formula 1-6-1, formula 1-6-2, formula 1-7-1, and formula 1-7-2, X 3 -X n At least one of the following is selected from CR x , the X n Corresponding to the X 3 -X 6 The one with the largest sequence number in any of the formulas 1-1-1, 1-2-4, 1-2-5, 1-5-1 to 1-5-4, 1-6-1, 1-6-2, 1-7-1, and 1-7-2, and the R xeach occurrence being identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 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 arylsilanyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, cyano, isocyano, and combinations thereof;
[0229] In the formula 1-6-1 and the formula 1-7-1, G is selected from the group consisting of NRR, OR and SR at each occurrence, the same or different; R is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof at each occurrence;
[0230] Adjacent substituents G, R x , R y , R b , R w , R n3 , R can be optionally linked to form a ring.
[0231] In this embodiment, the adjacent substituents G, R x , R y , R b , R w , R n3 , R can be optionally linked to form a ring, which is intended to represent adjacent groups of substituents, for example, adjacent substituents R x Between adjacent substituents R y Between adjacent substituents R x and R y Between adjacent substituents R x and R b Between adjacent substituents R y and R b Between adjacent substituents R w and R b Between adjacent substituents Rw Between adjacent substituents R x and R n3 Between adjacent substituents R y and R n3 Between adjacent substituents R x and R w Between adjacent substituents R y and R w Between adjacent substituents R Between adjacent substituents R w Between G, the adjacent substituent R y and G, and the adjacent substituent R b 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.
[0232] Herein, in Formula 1-1-1, Formula 1-2-4, Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1, and Formula 1-7-2, X 3 -X n At least one of the following is selected from CR x , the X n Corresponding to the X 3 -X 6 The one with the largest sequence number in any of the formulas 1-1-1, 1-2-4, 1-2-5, 1-5-1 to 1-5-4, 1-6-1, 1-6-2, 1-7-1, and 1-7-2; for example, for formula 1-1-1, the X n Corresponding to the X 3 -X 6 The largest number X in formula 1-1-1 6 , that is, in formula 1-1-1, X 3 -X 6 At least one of CR x For another example, for Formula 1-5-1, the X n Corresponding to the X 3 -X 6 The largest number X in formula 1-5-1 4 , that is, X in formula 1-5-1 3 -X 4 At least one of CR x For another example, for Formula 1-6-1, the X n Corresponding to the X 3 -X 6 The largest number X in formula 1-6-1 5 , that is, X in formula 1-6-13 -X 5 At least one of CR x For another example, for Formula 1-7-1, the X n Corresponding to the X 3 -X 6 The largest number X in formula 1-7-1 3 , that is, X in formula 1-7-1 3 Selected from CR x .
[0233] According to an embodiment of the present invention, in Formula 1-1-1, Formula 1-2-4, Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1, and Formula 1-7-2, X 3 -X n At least one of the following is selected from CR x , the X n Corresponding to the X 3 -X 6 The one with the largest sequence number in any of the formulas 1-1-1, 1-2-4, 1-2-5, 1-5-1 to 1-5-4, 1-6-1, 1-6-2, 1-7-1, and 1-7-2, and the R x Each occurrence is identically or differently selected from the group consisting of halogen, cyano, alkyl having 1 to 20 carbon atoms substituted by at least one cyano or halogen, cycloalkyl having 3 to 20 ring carbon atoms substituted by at least one cyano or halogen, aralkyl having 7 to 30 carbon atoms substituted by at least one cyano or halogen, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilanyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, and combinations thereof.
[0234] According to one embodiment of the present invention, in Formula 1-6-1 and Formula 1-7-1, G is selected from the group consisting of NRR, OR and SR each time it appears, the same or different; R is selected from the group consisting of deuterium, 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.
[0235] According to an embodiment of the present invention, in Formula 1-1-1, Formula 1-2-4, Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1, and Formula 1-7-2, X 3 -X n At least one of the following is selected from CR x , the X n Corresponding to the X 3 -X 6 The one with the largest sequence number in any of the formulas 1-1-1, 1-2-4, 1-2-5, 1-5-1 to 1-5-4, 1-6-1, 1-6-2, 1-7-1, and 1-7-2, and the R x each occurrence is identically or differently selected from the group consisting of: fluoro, cyano, trifluoromethyl, cyanomethyl, 2,2,2-trifluoroethyl, 2-cyanoisopropyl, 3,3,3-trifluoro-2,2-dimethylpropyl, phenyl, 4-isopropylphenyl, 2,4,6-triisopropylphenyl, pyridyl, 2-isopropylpyridin-5-yl, 2-isopropylpyridin-6-yl, 2-isopropylpyrimidin-4-yl, 2-isopropylpyrimidin-5-yl, 5-isopropyl Pyrimidin-2-yl, 5-isopropylpyrazin-2-yl, 3,5-di-tert-butyltriazinyl, trimethylsilyl, triethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, triphenylsilyl, 1-methylsiletan-1-yl, 1-methylsilolan-1-yl, trimethylgermanyl, phenyldimethylgermanyl, and combinations thereof;
[0236] In the formula 1-6-1 and formula 1-7-1, G is selected from dimethylamino, diethylamino, diisopropylamino, methylphenylamino, N-pyrrolidino, N-morpholino, methoxy, ethoxy, isopropoxy, phenoxy, methyl sulfide or phenyl sulfide each time it appears.
[0237] According to one embodiment of the present invention, in Formula 1-1 to Formula 1-14, X 1 -X 6 At least one or two of them are selected from CR in the same or different order each time they appear. x , and / or Y 1 -Y 6 At least one or two of them are selected from CR in the same or different order each time they appear. y ; said R x , R yeach occurrence is identically or differently selected from the group consisting of: 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl 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 alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
[0238] According to one embodiment of the present invention, in Formula 1-1, Formula 1-3, Formula 1-6, Formula 1-9, Formula 1-10, and Formula 1-14, X 4 Each occurrence is the same or different selection from CR x , in Formula 1-2, Formula 1-11 to Formula 1-13, X 2 Each occurrence is the same or different selection from CR x In formula 1-4, formula 1-5, formula 1-7, and formula 1-8, X 3 Each occurrence is the same or different selection from CR x ; and / or in Formula 1-1 to Formula 1-14, Y 1 and / or Y 3 Each occurrence is the same or different selection from CR y ; said R x , R yeach occurrence is identically or differently selected from the group consisting of: 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl 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 alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
[0239] According to one embodiment of the present invention, in Formula 1-1, Formula 1-3, Formula 1-6, Formula 1-9, Formula 1-10, and Formula 1-14, X 4 Each occurrence is the same or different selection from CR x , in Formula 1-2, Formula 1-11 to Formula 1-13, X 2 Each occurrence is the same or different selection from CR x In formula 1-4, formula 1-5, formula 1-7, and formula 1-8, X 3 Each occurrence is the same or different selection from CR x ; and / or in Formula 1-1 to Formula 1-14, Y 1 and / or Y 3 Each occurrence is the same or different selection from CR y ; said R x , R yEach occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 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, cyano, isocyano, hydroxyl, mercapto, and combinations thereof.
[0240] According to one embodiment of the present invention, in Formula 1-1, Formula 1-3, Formula 1-6, Formula 1-9, Formula 1-10, and Formula 1-14, X 4 Each occurrence is the same or different selection from CR x , in Formula 1-2, Formula 1-11 to Formula 1-13, X 2 Each occurrence is the same or different selection from CR x In formula 1-4, formula 1-5, formula 1-7, and formula 1-8, X 3 Each occurrence is the same or different selection from CR x ; and / or in Formula 1-1 to Formula 1-14, Y 1 and / or Y 3 Each occurrence is the same or different selection from CR y ; said R x , R y each occurrence is identically or differently selected from the group consisting of: deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, cyano, trifluoromethyl, cyanomethyl, 2,2,2-trifluoroethyl, 2-cyanoisopropyl, 3,3,3-trifluoro-2,2-dimethylpropyl, phenyl, 4-isopropylphenyl, 2,4,6-triisopropylphenyl, pyridyl, 2-isopropylpyridin-5-yl, 2-isopropylpyridin-6-yl, 2-isopropylpyrimidin-4-yl , 2-isopropylpyrimidin-5-yl, 5-isopropylpyrimidin-2-yl, 5-isopropylpyrazin-2-yl, 3,5-di-tert-butyltriazinyl, trimethylsilyl, triethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, triphenylsilyl, 1-methylsiletan-1-yl, 1-methylsilolan-1-yl, and combinations thereof.
[0241] According to one embodiment of the present invention, W 1 is selected identically or differently on each occurrence from C═O, O or S.
[0242] According to one embodiment of the present invention, L a Each time it appears, choose the same or different one from L a1 To L a673 The group consisting of L a1 To L a673 For the specific structure, please refer to claim 20.
[0243] According to one embodiment of the present invention, wherein the L a1 To L a673 The hydrogen in the structure may be partially or completely replaced by deuterium.
[0244] According to one embodiment of the present invention, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.
[0245] According to one embodiment of the present invention, M is selected from Ir or Pt.
[0246] According to one embodiment of the present invention, M is Ir.
[0247] According to one embodiment of the present invention, wherein the L b Has the following structure:
[0248]
[0249] R 1 –R 7 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 aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted 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, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0250] Adjacent substituent R 1 , R 2 , R 3 , R 4 , R 5 , R6 , R 7 Can optionally be linked to form a ring.
[0251] In this context, adjacent substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 can be optionally linked to form a ring, which is intended to indicate adjacent groups of substituents, for example, adjacent substituents R 1 and R 2 , the adjacent substituent R 2 and R 3 , the adjacent substituent R 1 and R 3 , the adjacent substituent R 4 and R 5 , the adjacent substituent R 5 and R 6 , the adjacent substituent R 4 and R 6 , the adjacent substituent R 1 and R 7 , the adjacent substituent R 2 and R 7 , the adjacent substituent R 3 and R 7 , the adjacent substituent R 4 and R 7 , the adjacent substituent R 5 and R 7 , and the adjacent substituent R 6 and R 7 , any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring.
[0252] According to one embodiment of the present invention, L b Each occurrence is identically or differently selected from the following structures:
[0253]
[0254] Where R 1 -R 3 At least one of them is selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, or a combination thereof; and / or R 4 -R 6At least one of the above is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.
[0255] According to one embodiment of the present invention, L b Each occurrence is identically or differently selected from the following structures:
[0256]
[0257] Where R 1 -R 3 At least two of them 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 R 4 -R 6 At least one of the above is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.
[0258] According to one embodiment of the present invention, L b Each occurrence is identically or differently selected from the following structures:
[0259]
[0260] Where R 1 -R 3 At least two of them are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and / or R 4 -R 6 At least two of them are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
[0261] According to one embodiment of the present invention, the second compound has the following structure:
[0262]
[0263] m is 1 or 2;
[0264] R 1 –R 7The 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 aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted 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, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0265] Adjacent substituent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 Can optionally be linked to form a ring.
[0266] According to one embodiment of the present invention, the second compound has the following structure:
[0267]
[0268] m is 1 or 2;
[0269] R 1 -R 3 At least one or two of them are selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, or a combination thereof; and / or R 4 -R 6 At least one of them is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof;
[0270] Adjacent substituent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 Can optionally be linked to form a ring.
[0271] According to one embodiment of the present invention, the second compound has the following structure:
[0272]
[0273] m is 1 or 2;
[0274] R 1 -R 3 At least two of them are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and / or R 4 -R 6 At least two of them are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof;
[0275] Adjacent substituent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 Can optionally be linked to form a ring.
[0276] According to one embodiment of the present invention, L b Each time it appears, choose the same or different one from L b1 To L b322 The group consisting of L b1 To L b322 For the specific structure, please refer to claim 23.
[0277] According to one embodiment of the present invention, L c Each time it appears, choose the same or different one from L c1 To L c180 The group consisting of L c1 To L c180 For the specific structure, please refer to claim 23.
[0278] According to one embodiment of the present invention, the second compound is an Ir complex having a a )(L b )(L c )、Ir(L a ) 2 (L b )、Ir(L a ) 2(L c ) and Ir(L a )(L c ) 2 When the second compound has Ir(L a )(L b )(L c ) structure, the L a Choose from L a1 To L a673 Any one of the group consisting of b Choose from L b1 To L b322 Any one of the group consisting of c Choose from L c1 To L c180 When the second compound has Ir(L a ) 2 (L b ) structure, the L a Choose from L a1 To L a673 Any one or any two of the group consisting of b Choose from L b1 To L b322 When the second compound has Ir(L a ) 2 (L c ) structure, the L a Choose from L a1 To L a673 Any one or any two of the group consisting of c Choose from L c1 To L c180 When the second compound has Ir(L a )(L c ) 2 When the structure of L a Choose from L a1 To L a673 Any one of the group consisting of c Choose from L c1 To L c180 Any one or any two of the group consisting of.
[0279] According to one embodiment of the present invention, the second compound is selected from the group consisting of Compound 1 to Compound 330, and the specific structures of Compound 1 to Compound 330 are shown in Claim 24.
[0280] According to one embodiment of the present invention, the organic layer is a light-emitting layer, the first compound is a host material, and the second compound is a light-emitting material.
[0281] According to an embodiment of the present invention, the device emits red light or white light.
[0282] According to an embodiment of the present invention, the device has at least one maximum emission wavelength greater than 635 nm.
[0283] According to an embodiment of the present invention, the device has at least one maximum emission wavelength greater than 640 nm.
[0284] According to another embodiment of the present invention, a display assembly is disclosed, which includes the electroluminescent device shown in any of the above embodiments.
[0285] Combination with other materials
[0286] 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.
[0287] The materials described herein as specific layers that can be used in an organic light-emitting device can be used in combination with a variety of other materials present in the device. For example, the combination of the first compound and the second compound disclosed herein can be used in combination with a variety of light-emitting dopants, 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.
[0288] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.
[0289] The first compound used in the present invention can be purchased or obtained by referring to the preparation method in the prior art, or can also be easily prepared by referring to the patent applications with publication numbers / application numbers of US20180337340A1, CN111868210A, CN202010285016.7, CN202010268985.1, CN202010285026.0, CN202010720191.4, and CN202010825242.X. The second compound used in the present invention can be purchased or obtained by referring to the preparation method in the prior art, for example, it can be easily prepared by referring to the patent applications with publication numbers / application numbers of CN109956977A, CN111909212A, CN202011219604.7, and CN202110348602.6, or can also be prepared by referring to the following examples.
[0290] Material synthesis example:
[0291] The preparation method of the second compound selected in the present invention is not limited, and the following compound is typically but not limitedly exemplified, and its synthesis route and preparation method are as follows:
[0292] Synthesis Example 1: Synthesis of Compound 313
[0293] Step 1: Synthesis of intermediate 3
[0294]
[0295] Intermediate 1 (9.10 g, 62.69 mmol), intermediate 2 (23.30 g, 81.50 mmol), cuprous iodide (0.60 g, 3.13 mmol), N, N-dimethylglycine hydrochloride (DMG.HCl, 0.44 g, 3.13 mmol), potassium carbonate (21.66 g, 156.73 mmol) were dissolved in N, N-dimethylformamide (100 mL), and then the reaction was heated to 100 ° C and stirred for 20 hours under nitrogen protection, and cooled to room temperature. Then ethyl acetate was added to the reaction system, the liquid was separated, the aqueous phase was extracted with ethyl acetate, the organic phase was combined, dried, and the solvent was removed in vacuo to obtain a crude product, which was separated by silica gel column chromatography (eluent ethyl acetate: petroleum ether = 1:10, v / v) to obtain intermediate 3 (16.00 g, yield 73%).
[0296] Step 2: Synthesis of intermediate 4
[0297]
[0298] Dissolve the intermediate 3 (4.00 g, 11.42 mmol) in 40 mL of ultra-dry tetrahydrofuran, slowly add n-butyl lithium (12.56 mmol, 2M / L, 6.3 mL) solution at -76 ° C in a nitrogen atmosphere, and stir for 2.5 hours. After the reaction of the raw materials is complete, add water to quench the reaction, warm to 0 ° C, add iodine (3.50 g, 13.7 mmol), DBU (1,8-diazabicyclo [5.4.0] undec-7-ene, 4.35 g, 28.55 mmol), stir at room temperature for 3 hours, and filter to obtain a crude product. Column chromatography separation (PE: EA = 50: 1) can obtain a yellow liquid intermediate 4 (2.77 g, yield 90%).
[0299] Step 3: Synthesis of Iridium Dimer
[0300]
[0301] A mixture of intermediate 4 (3.97 g, 14.75 mmol), iridium trichloride trihydrate (1.30 g, 3.69 mmol), 2-ethoxyethanol (48 mL) and water (16 mL) was refluxed under a nitrogen atmosphere for 40 hours. After cooling to room temperature, 3.10 g of iridium dimer was obtained by filtration, which was directly used in the next step without further purification.
[0302] Step 4: Synthesis of compound 313
[0303]
[0304] The iridium dimer obtained in step 3, intermediate 5 (2.09 g, 9.23 mmol) and potassium carbonate (2.55 g, 18.45 mmol) were added to a reaction tube containing 20 mL of dichloromethane and heated to 60°C under nitrogen protection for 24 hours. It was then poured into a funnel filled with diatomaceous earth and filtered, and the filter cake was washed with ethanol. Dichloromethane was added to the filter cake and the filtrate was collected. Ethanol was then added and the resulting solution was concentrated, but not concentrated to dryness. After filtration, 1.35 g of product compound 313 was obtained, and the total yield of the two steps was 38.3%. The structure of the product was confirmed by LC-MS to be the target product, with a molecular weight of 954.3.
[0305] Synthesis Example 2: Synthesis of Compound 309
[0306] Step 1: Synthesis of iridium dimer
[0307]
[0308] A mixture of intermediate 6 (1.5 g, 6.80 mmol), iridium trichloride trihydrate (0.60 g, 1.70 mmol), 2-ethoxyethanol (18 mL) and water (6 mL) was refluxed under a nitrogen atmosphere for 40 hours. After cooling to room temperature, 0.80 g of iridium dimer was obtained by filtration and used directly in the next step without further purification.
[0309] Step 2: Synthesis of compound 309
[0310]
[0311] The iridium dimer obtained in step 1, intermediate 5 (0.36 g, 1.50 mmol) and potassium carbonate (0.83 g, 6.00 mmol) were added to a reaction tube containing 20 mL of dichloromethane and heated to 60°C under nitrogen protection for 40 hours. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the filter cake and the filtrate was collected. Ethanol was then added and the resulting solution was concentrated, but not concentrated to dryness. After filtration, 0.36 g of product compound 309 was obtained, and the total yield of the two steps was 25.0%. The structure of the product was confirmed by LC-MS to be the target product with a molecular weight of 854.3.
[0312] Synthesis Example 3: Synthesis of Compound 156
[0313] Step 1: Synthesis of iridium dimer
[0314]
[0315] A mixture of intermediate 7 (1.5 g, 4.2 mmol), iridium trichloride trihydrate (427 mg, 1.2 mmol), 2-ethoxy alcohol (12 mL) and water (4 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next step without further purification.
[0316] Step 2: Synthesis of compound 156
[0317]
[0318] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (580 mg, 2.4 mmol) and potassium carbonate (0.83 g, 6.04 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 40 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 940 mg of compound 156 was obtained with a yield of 66%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1166.5.
[0319] Synthesis Example 4: Synthesis of Compound 319
[0320] Step 1: Synthesis of intermediate 9
[0321]
[0322] The intermediate 8 (2g, 6.97mmol) was dissolved in 20mL THF, the reaction system was replaced with nitrogen three times, the reaction bottle was placed in a dry ice-ethanol system and cooled to -72°C, n-BuLi (3.34mL, 8.36mmol, 2.5M) was slowly added dropwise to the system, and the reaction was kept at low temperature for 1.5 hours after the addition was completed, and then trimethylgermanium bromide (1.65g, 8.71mmol) was added dropwise to the system, and the temperature was slowly restored to room temperature after the addition was completed, and the reaction was allowed to proceed overnight. After TLC detection, water was added to quench the reaction, the THF layer was separated, the aqueous phase was extracted three times with EA, the organic phases were combined, dried, rotary evaporated, and purified by column chromatography to obtain a colorless oily liquid intermediate 9 (1.7g, yield 69.7%).
[0323] Step 2: Synthesis of iridium dimer:
[0324]
[0325] A mixture of intermediate 9 (1.4 g, 3.99 mmol), iridium trichloride trihydrate (0.40 g, 1.14 mmol), 2-ethoxyethanol (15 mL) and water (5 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the solid was filtered and washed several times with methanol and dried to give an iridium dimer (0.68 g, 63%), which was used directly in the next step without further purification.
[0326] Step 3: Synthesis of compound 319
[0327]
[0328] The iridium dimer obtained in step 2 (0.68 g, 0.36 mmol), 3,7-diethyl-3-methylnonane-4,6-dione (0.33 g, 1.46 mmol), K 2 CO 3 A mixture of (0.50g, 3.6mmol) and 2-ethoxyethanol (20mL) was stirred at 50°C for 24 hours. After the reaction was complete, the reaction system was naturally cooled to room temperature, and the precipitate was filtered through diatomaceous earth and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, a red crude product was obtained. The crude product was dissolved in 20mL of DCM, and 32mL of MeOH was slowly added thereto. After the addition was completed, it was stirred at room temperature for 1 hour, and a solid precipitated and filtered to obtain compound 319 (0.58g, 0.52mmol). The structure of the compound was confirmed as the target product by LC-MS, and the molecular weight was 1118.3.
[0329] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other second compound structures of the present invention by improving it.
[0330] The preparation method of the electroluminescent device is not limited. The preparation method of the following embodiment is only an example and should not be construed as limiting. A person skilled in the art can reasonably improve the preparation method of the following embodiment based on the prior art. For example, the ratio of various materials in the light-emitting layer is not particularly limited. A person 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 main material can account for 80%-99%, and the light-emitting material can account for 1%-20%; or the main material can account for 90%-98%, and the light-emitting material can account for 2%-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, and the ellipsometer produced by Beijing Liangtuo, etc.) by 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, they can obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents will not be elaborated in this patent.
[0331] Device Example 1.1
[0332] First, the glass substrate with a 120nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then 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 Compound HI is used as a hole injection layer (HIL) with a thickness of 100 nm. Compound HT was used as a hole transport layer (HTL) with a thickness of Compound EB is used as electron blocking layer (EBL) with a thickness of Then, the compound 115 as a dopant material was co-doped with the compound 1-34 as a host material (weight ratio of 2:98) to form an emission layer (EML) with a thickness of Compound HB is used as a hole blocking layer (HBL) with a thickness of On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) (weight ratio is 40:60) are co-deposited as an electron transport layer (ETL) with a thickness of Finally, 1 nm thick Liq was deposited as an electron injection layer and 120 nm Al was deposited as a cathode. The device was then transferred back to the glove box and encapsulated with a glass cover and a moisture absorber to complete the device.
[0333] Device Example 1.2
[0334] The implementation of Device Example 1.2 is the same as that of Device Example 1.1, except that Compound 1-35 is used as the host material instead of Compound 1-34 in the light-emitting layer.
[0335] Device Example 1.3
[0336] The implementation of Device Example 1.3 is the same as that of Device Example 1.1, except that Compound 1-39 is used as the host material instead of Compound 1-34 in the light-emitting layer.
[0337] Device Comparison Example 1
[0338] The implementation of Comparative Device Example 1 is the same as that of Device Example 1.1, except that Compound H1 is used as the host material in the light-emitting layer instead of Compound 1-34.
[0339] Device Example 2.1
[0340] Device Example 2.1 is carried out in the same manner as Device Example 1.1, except that Compound 91 is used instead of Compound 115 as the dopant material in the light-emitting layer.
[0341] Device Example 2.2
[0342] The implementation of Device Example 2.2 is the same as that of Device Example 2.1, except that Compound 1-17 is used as the host material instead of Compound 1-34 in the light-emitting layer.
[0343] Device Example 2.3
[0344] The implementation of Device Example 2.3 is the same as that of Device Example 2.1, except that Compound 1-39 is used as the host material instead of Compound 1-34 in the light-emitting layer.
[0345] Device Example 2.4
[0346] The implementation of Device Example 2.4 is the same as that of Device Example 2.1, except that Compound 1-35 is used as the host material instead of Compound 1-34 in the light-emitting layer.
[0347] Device Comparison Example 2
[0348] The implementation of Comparative Device Example 2 is the same as that of Device Example 2.1, except that Compound H1 is used as the host material in the light-emitting layer instead of Compound 1-34.
[0349] Device Example 3
[0350] The implementation of Device Example 3 is the same as that of Device Example 2.2, except that Compound 132 is used instead of Compound 91 as the dopant material in the light-emitting layer.
[0351] Device Comparison Example 3
[0352] The implementation of Comparative Device Example 3 is the same as that of Example 3, except that Compound H1 is used as a host material in the light-emitting layer instead of Compound 1-17.
[0353] Device Example 4
[0354] Device Example 4 was carried out in the same manner as Device Example 1.1, except that Compound 313 was used instead of Compound 115 as the dopant material in the light-emitting layer.
[0355] Device Comparison Example 4
[0356] The implementation of device comparative example 4 is the same as that of device example 4, except that compound H1 is used as a host material instead of compound 1-34 in the light-emitting layer.
[0357] Device Example 5
[0358] The implementation of Device Example 5 is the same as that of Device Example 1.1, except that Compound 309 is used instead of Compound 115 as the dopant material in the light-emitting layer.
[0359] Device Comparison Example 5
[0360] The implementation of Comparative Device Example 5 is the same as that of Example 5, except that Compound H1 is used as a host material in the light-emitting layer instead of Compound 1-34.
[0361] Device Example 6
[0362] The implementation of Device Example 6 is the same as that of Device Example 1.1, except that Compound 175 is used instead of Compound 115 as the dopant material in the light-emitting layer.
[0363] Device Comparison Example 6
[0364] The implementation of Comparative Device Example 6 is the same as that of Example 6, except that Compound H1 is used as a host material in the light-emitting layer instead of Compound 1-34.
[0365] Device Example 7
[0366] The implementation method of Device Example 7 is the same as that of Device Example 2.2, except that Compound 156 is used instead of Compound 91 as the dopant material in the light-emitting layer.
[0367] Device Example 8
[0368] The implementation of Device Example 8 is the same as that of Device Example 2.1, except that Compound 319 is used instead of Compound 91 as the dopant material in the light-emitting layer.
[0369] Device Example 9
[0370] The implementation of Device Example 9 is the same as that of Device Example 2.1, except that Compound 329 is used instead of Compound 91 as the dopant material in the light-emitting layer.
[0371] Device Example 10
[0372] The implementation of Device Example 10 is the same as that of Device Example 2.1, except that Compound 326 is used instead of Compound 91 as the dopant material in the light-emitting layer.
[0373] Device Comparison Example 7
[0374] The implementation of Comparative Device Example 7 is the same as that of Example 7, except that Compound H1 is used as a host material in the light-emitting layer instead of Compound 1-17.
[0375] Device Comparison Example 8
[0376] The implementation of Comparative Device Example 8 is the same as that of Device Example 2.2, except that Compound RD-A is used instead of Compound 91 as the dopant material in the light-emitting layer.
[0377] Device Comparison Example 9
[0378] The implementation of Comparative Device Example 9 is the same as that of Device Example 2.1, except that Compound RD-A is used instead of Compound 91 as the dopant material in the light-emitting layer.
[0379] Device Comparative Example 10
[0380] The implementation of Comparative Device Example 10 is the same as that of Device Example 2.4, except that Compound RD-A is used instead of Compound 91 as the dopant material in the light-emitting layer.
[0381] The device layer structure and thickness are shown in the table below. Where more than one material is used, different compounds are doped in the weight ratios recorded.
[0382] Table 1 Device structures of device embodiments and comparative examples
[0383]
[0384]
[0385]
[0386] The structure of the materials used in the device is shown below:
[0387]
[0388]
[0389] At 15mA / cm 2 The maximum emission wavelength λ of Examples 1.1 to 1.3 and Comparative Example 1 was measured at a current density of max (nm), voltage and external quantum efficiency (EQE). In order to more intuitively show the comparison of data, the voltage and external quantum efficiency data of Comparative Example 1 are set to 1.00, and the voltage and external quantum efficiency of other examples are converted relative to the corresponding data of Comparative Example 1. The relevant data and conversion results are shown in Table 2.
[0390] Table 2 Device data
[0391] Part Number <![CDATA[λ max (nm)]]> Voltage EQE Example 1.1 640 0.81 1.08 Example 1.2 640 0.76 1.07 Example 1.3 640 0.85 1.09 Comparative Example 1 638 1.00 1.00
[0392] At 15mA / cm 2 The maximum emission wavelength λ of Examples 2.1 to 2.4 and Comparative Example 2 was measured at a current density of max (nm), voltage and external quantum efficiency (EQE) at 80mA / cm 2 The lifespans (LT97) of Examples 2.1 to 2.4 and Comparative Example 2 were measured at a current density of . In order to more intuitively show the comparison of data, the voltage, external quantum efficiency and lifespan of Comparative Example 2 were all set to 1.00, and the voltage, external quantum efficiency and lifespan of other examples were converted relative to the corresponding data of Comparative Example 2. The relevant data and conversion results are shown in Table 3.
[0393] Table 3 Device data
[0394] Part Number <![CDATA[λ max (nm)]]> Voltage EQE LT97 Example 2.1 654 0.91 1.13 1.68 Example 2.2 654 0.93 1.21 1.73 Example 2.3 654 0.94 1.19 1.23 Example 2.4 654 0.87 1.24 1.73 Comparative Example 2 653 1.00 1.00 1.00
[0395] At 15mA / cm 2 The maximum emission wavelength λ of Example 3 and Comparative Example 3 was measured at a current density of max (nm), voltage and external quantum efficiency (EQE) at 80mA / cm 2 The lifespans (LT97) of Example 3 and Comparative Example 3 were measured at a current density of . In order to more intuitively show the comparison of data, the voltage, external quantum efficiency and lifespan of Comparative Example 3 were all set to 1.00, and the voltage, external quantum efficiency and lifespan of Example 3 were converted relative to the corresponding data of Comparative Example 3. The relevant data and conversion results are shown in Table 4.
[0396] Table 4 Device data
[0397] Part Number <![CDATA[λ max (nm)]]> Voltage EQE LT97 Example 3 688 0.79 1.22 2.10 Comparative Example 3 682 1.00 1.00 1.00
[0398] At 15mA / cm 2 The maximum emission wavelength λ of Example 4 and Comparative Example 4 was measured at a current density of max(nm), voltage and external quantum efficiency (EQE). In order to more intuitively show the comparison of data, the voltage and external quantum efficiency of Comparative Example 4 are both set to 1.00, and the voltage and external quantum efficiency of Example 4 are converted relative to the corresponding data of Comparative Example 4. The relevant data and conversion results are shown in Table 5.
[0399] Table 5 Device data
[0400] Part Number <![CDATA[λ max (nm)]]> Voltage EQE Example 4 690 0.61 2.04 Comparative Example 4 688 1.00 1.00
[0401] At 15mA / cm 2 The maximum emission wavelength λ of Example 5 and Comparative Example 5 was measured at a current density of max (nm), voltage and external quantum efficiency (EQE). In order to more intuitively show the comparison of data, the voltage and external quantum efficiency of Comparative Example 5 are both set to 1.00, and the voltage and external quantum efficiency of Example 5 are converted relative to the corresponding data of Comparative Example 5. The relevant data and conversion results are shown in Table 6.
[0402] Table 6 Device data
[0403] Part Number <![CDATA[λ max (nm)]]> Voltage EQE Example 5 645 0.56 1.46 Comparative Example 5 643 1.00 1.00
[0404] At 15mA / cm 2 The maximum emission wavelength λ of Example 6 and Comparative Example 6 was measured at a current density of max (nm), voltage and external quantum efficiency (EQE). In order to more intuitively show the comparison of data, the voltage and external quantum efficiency of Comparative Example 6 are both set to 1.00, and the voltage and external quantum efficiency of Example 6 are converted relative to the corresponding data of Comparative Example 6. The relevant data and conversion results are shown in Table 7.
[0405] Table 7 Device data
[0406] Part Number <![CDATA[λ max (nm)]]> Voltage EQE Example 6 637 0.62 2.59 Comparative Example 6 635 1.00 1.00
[0407] It can be seen from the data in Tables 2 to 7 that the devices using the first compound and the second compound in the present invention can achieve deep red light emission above 630nm, and the maximum emission wavelength of the devices in the embodiments are red-shifted relative to the comparative examples, achieving deeper red light emission. In addition, more importantly, in terms of device performance, the first compound and the second compound selected in the present invention can also significantly improve device performance, such as device efficiency, voltage and / or life: Compared with Comparative Example 1, the external quantum efficiency of Examples 1.1 to 1.3 is increased by 8%, 7%, and 9%, respectively, and the voltage is greatly reduced by 19%, 24%, and 15%, respectively; Compared with Comparative Example 2, the external quantum efficiency of Examples 2.1 to 2.4 is greatly increased by 13%, 21%, 19% and 24%, respectively, the voltage is reduced by 9%, 7%, 6% and 13%, respectively, and the life is greatly increased by 68%, 73%, respectively. , 23% and 73%; compared with Comparative Example 3, the external quantum efficiency of Example 3 is increased by 22%, and the voltage is reduced by 21%. More importantly, the life of Example 3 is greatly improved by 2.1 times compared with Comparative Example 3; the voltage of Example 4 is greatly reduced by 39% compared with Comparative Example 4, and a more significant improvement occurs in the external quantum efficiency, which doubles the improvement; relative to Comparative Example 5, the external quantum efficiency of Example 5 is greatly improved by 46%, while the voltage is greatly reduced by 44%; compared with Comparative Example 6, the voltage of Example 6 is greatly reduced by 38%, and the external quantum efficiency is greatly improved, which is nearly 1.6 times that of Comparative Example 6.
[0408] From the above specific data comparison, it can be clearly seen that the combination of the first compound and the second compound selected by the present invention can generally red-shift the maximum emission wavelength of the device, obtain deeper red light emission, and more importantly, significantly reduce the driving voltage of the device under deep red color, and significantly improve the external quantum efficiency and / or life of the device. The maximum improvement of EQE in the embodiment reached nearly 1.6 times, and the maximum reduction of driving voltage reached 44%. These results prove the great advantages of the electroluminescent device of the present invention using the combination of the first compound and the second compound.
[0409] At 15mA / cm 2 The maximum emission wavelength λ of Example 7 and Comparative Example 7 was measured at a current density of max (nm) and voltage. At 80mA / cm 2 The life (LT97) measured at a current density of . In order to more intuitively show the comparison of data, the voltage and life data of Comparative Example 7 are set to 1.00, and the voltage and life of Example 7 are converted relative to the corresponding data of Comparative Example 7. The relevant data and conversion results are shown in Table 8.
[0410] Table 8 Device data
[0411] Part Number <![CDATA[λ max (nm)]]> Voltage LT97 Example 7 673 0.80 2.00 Comparative Example 7 671 1.00 1.00
[0412] Compared with Comparative Example 7, the maximum emission wavelength of Example 7 is red-shifted by 2 nm, and more importantly, the device life of Example 7 is doubled, and the driving voltage is reduced by 20%, which once again proves the excellent performance of the first compound and the second compound selected by the present invention in the deep red device.
[0413] At 15mA / cm 2 The external quantum efficiencies (EQE) of Example 1.1, Example 2.1, Example 6, Examples 8 to 10, and Comparative Example 9 were measured at a current density of . In order to more intuitively show the comparison of the data, the external quantum efficiency of Comparative Example 9 was set to 1.00, and the external quantum efficiencies of other examples were converted relative to the corresponding data of Comparative Example 9. The relevant data and conversion results are shown in Table 9.
[0414] Table 9 Device data
[0415]
[0416]
[0417] At 15mA / cm 2 The external quantum efficiency (EQE) of Example 1.2, Example 2.4 and Comparative Example 10 was measured at a current density of . In order to more intuitively show the comparison of data, the external quantum efficiency of Comparative Example 10 was set to 1.00, and the external quantum efficiencies of other examples were converted relative to the corresponding data of Comparative Example 10. The relevant data and conversion results are shown in Table 10.
[0418] Table 10 Device data
[0419]
[0420] At 15mA / cm 2 The external quantum efficiency (EQE) of Example 2.2, Example 3, Example 7 and Comparative Example 8 was measured at a current density of . In order to more intuitively show the comparison of data, the external quantum efficiency of Comparative Example 8 was set to 1.00, and the external quantum efficiency of other examples was converted relative to the corresponding data of Comparative Example 8. The relevant data and conversion results are shown in Table 11.
[0421] Table 11 Device data
[0422]
[0423] The light-emitting layers of Comparative Examples 8-10 use a combination of the first compound selected in the present invention and the dopant material compound RD-A. From the data comparison of Tables 9-11, it can be seen that when the first compound selected in the present invention is used in combination with the second compound, the device can achieve deep red emission, and the maximum emission wavelength of the device has a very large red shift relative to the comparative example (the lowest is 65nm, Example 9 Vs. Comparative Example 9). More importantly, in terms of device performance, the device efficiency of the embodiment has been greatly improved compared to the comparative example, generally more than doubled compared to the comparative example, and the highest even reached 5.27 times that of the comparative example; once again proving the excellent performance of the first compound and the second compound selected in the present invention in deep red devices.
[0424] In summary, the combination of the first compound and the second compound selected in the present invention can achieve deep red light emission greater than 630nm, and can show excellent device performance in the device, and can significantly reduce the driving voltage of the device while significantly improving the efficiency and / or life of the device. It is proved that the combination of the first compound and the second compound selected in the present invention has excellent application prospects.
[0425] 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 device has at least one maximum emission wavelength greater than 630 nm; The organic layer is a light-emitting layer, the first compound is a host material, and the second compound is a light-emitting material; The first compound has a structure of H-L1-E, and H has a structure represented by formula A: In formula A, 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 having at least 7 ring atoms; 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; E 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; R z1 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 aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl, 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 alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituent R z1 , R z2 can optionally be linked to form a ring; The second compound is a metal complex having M(L a ) m (L b ) n The general formula is: M is selected from metals with a relative atomic mass greater than 40; L a , L b are respectively the first ligand and the second ligand coordinated with the metal M; m is selected from 1 or 2, n is selected from 1 or 2, and m+n is equal to the oxidation state of the metal M; when m is equal to 2, multiple L a can be the same or different; when n is equal to 2, the two L b Can be the same or different; L a , L b can optionally be linked to form a multidentate ligand; Among them, the L a Each occurrence is identically or differently selected from the structure represented by any one of Formulae 1-1-1 to 1-1-4, Formulae 1-2-1 to 1-2-5, Formulae 1-4 to 1-10, and Formula 1-12: in, X1-X6 are selected from CR in the same or different way each time they appear x or N; B1-B4 are selected from CR in the same or different way each time they appear b or N; Y1-Y5 are selected from CR y or N; W1, W2 are selected from O, S or Se at each occurrence, the same or different; L b Selected from: X b and X c Selected from O; G.R i , R ii , R iii , R x , R y , and R b 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Furthermore, in Formula 1-1-1, Formula 1-2-4, and Formula 1-2-5, X3-X n At least one of the following is selected from CR x , the X n The corresponding X3-X6 has the largest sequence number in any one of the formulas 1-1-1, 1-2-4, and 1-2-5, and the R x each occurrence is identically or differently selected from the group consisting of halogen, cyano, alkyl having 1 to 20 carbon atoms substituted by at least one cyano or halogen, cycloalkyl having 3 to 20 ring carbon atoms substituted by at least one cyano or halogen, aralkyl having 7 to 30 carbon atoms substituted by at least one cyano or halogen, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilanyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, and combinations thereof; Adjacent substituents G, R x , R y , and R b can optionally be linked to form a ring; Adjacent substituent R i , R ii , R iii Can optionally be linked to form a ring.
2. The electroluminescent device according to claim 1, wherein In the first compound, H has a structure represented by any one of Formula A-1 to Formula A-8: In Formula A-1 to Formula A-8, Each time Z1-Z3, Z6-Z8 appears, they are selected from CR z1 or N; Z h1 -Z h9 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 aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituent R z1 , R zh , R zm , R zn Can optionally be linked to form a ring.
3. The electroluminescent device according to claim 2, wherein: The H has a structure represented by Formula A-1 or Formula A-6, wherein R z1 , R zh 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 Can optionally be linked to form a ring.
4. The electroluminescent device of claim 1, wherein the H is selected from the group consisting of: 5 . The electroluminescent device according to claim 4 , wherein hydrogen in the structures H-1 to H-76 can be partially or completely substituted by deuterium.
6. The electroluminescent device according to claim 1, wherein In the first compound, the E has a structure represented by Formula Ea or Formula Eb: In Formula Ea and Formula Eb, E1-E 14 Each time it appears, it is selected from C, CR e or N; R e 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 aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituent R e Can optionally be linked to form a ring.
7. The electroluminescent device according to claim 6, wherein in formula Ea, at least two of E1-E6 are N; and in formula Eb Middle, E7-E 14 At least 2 of them are N.
8. The electroluminescent device according to claim 7, wherein in formula Ea, three of E1-E6 are N; and in formula Eb, E7-E 10 Two of them are N.
9. The electroluminescent device according to claim 1, wherein: In the first compound, E has a structure represented by any one of Formula E-1 to Formula E-10: In Formula E-1 to Formula E-10, R A Each occurrence of the same or different means mono-, poly- or no-substitution; V is selected from O, S or Se; R A 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 aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituent R A Can optionally be linked to form a ring.
10. The electroluminescent device according to claim 9, wherein E has a structure represented by any one of Formula E-11 to Formula E-21: R A Each occurrence of the same or different means mono-, poly- or no-substitution; V is selected from O, S or Se; R A 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 heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, cyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituent R A Can optionally be linked to form a ring.
11. The electroluminescent device according to claim 10, wherein: In Formula E-1 to Formula E-21, the R A Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; Adjacent substituent R A Can optionally be linked to form a ring.
12. The electroluminescent device according to claim 11, wherein R A Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuterated methyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl, phenylpyridyl, and combinations thereof.
13. The electroluminescent device according to claim 10 or 11, wherein: In Formula E-1 to Formula E-21, there is at least one R A , and the R A Each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; Adjacent substituent R A Can optionally be linked to form a ring.
14. The electroluminescent device according to claim 13, wherein the at least one R A Each occurrence is identically or differently selected from the group consisting of deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1-20 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 the at least one R A Each occurrence is identically or differently selected from the group consisting of: deuterium, fluorine, cyano, methyl, trideuterated methyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl, phenylpyridyl, and combinations thereof.
16. The electroluminescent device according to claim 4, wherein: In the first compound, the E is selected from the group consisting of the following structures: It indicates the position of the E structure at which the E is linked to the L1.
17. The electroluminescent device of claim 1, wherein: The L1 is 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 pyridylene group, a dibenzothienylene group, a dibenzofuranylene group and a thienylene group.
18. The electroluminescent device of claim 17, wherein: The hydrogen in the phenylene, naphthylene, biphenylene, terphenylene, triphenylene, pyridylene, dibenzothienylene, dibenzofuranylene and thienylene groups may be partially or completely replaced by deuterium.
19. The electroluminescent device of claim 16, wherein L1 is selected from the group consisting of: "*" indicates the position in the structure of L1 that is connected to the formula H, It indicates the position of the structure of L1 that is linked to the E.
20. The electroluminescent device according to claim 19, wherein the hydrogen in the structures of L-1 to L-22 can be partially or completely replaced by deuterium.
21. The electroluminescent device of claim 19, wherein: The first compound has a structure of H-L1-E, wherein H is selected from any one of the group consisting of H-1 to H-76, L1 is selected from any one of the group consisting of L-0 to L-22, and E is selected from any one of the group consisting of E-1 to E-38.
22. The electroluminescent device according to claim 21, wherein hydrogen in the structure of the first compound can be partially or completely replaced by deuterium.
23. The electroluminescent device of claim 21, wherein the first compound is selected from the group consisting of:
24. The electroluminescent device according to claim 23, wherein hydrogen in the structures of Compounds 1-1 to 1-249 can be partially or completely replaced by deuterium.
25. The electroluminescent device of claim 1, wherein: In Formula 1-1 to Formula 1-14, X1-X6 are selected from CR x , Y1-Y6 are selected from C or CR at each occurrence, the same or different y .
26. The electroluminescent device of claim 1, wherein: In Formulae 1-1 to 1-14, at least one of X1 to X6 is selected from N.
27. The electroluminescent device of claim 26, wherein at least one of X1 to X3 is N.
28. The electroluminescent device of claim 27, wherein X1 or X2 is N.
29. The electroluminescent device of claim 1, wherein: In Formulae 1-1-1 to 1-1-4, 1-2-1 to 1-2-5, 1-4 to 1-10, and 1-12, at least two adjacent substituents R are present in Y1-Y5. y Connect to form a ring.
30. The electroluminescent device of claim 1, wherein: The L a Each time it appears, the same or different one is selected from the group consisting of Formula 1-1-1 to Formula 1-1-4, Formula 1-2-1 to Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1, Formula 1-7-2, Formula 1-8-1, Formula 1-9-1 to Formula 1-9-2, Formula 1-10-1 to Formula 1-10-2, and Formula 1-12-1 to Formula 1-12-2: in, X1-X6 are selected from CR in the same or different way each time they appear x or N; Y1-Y5 are selected from CR y or N; B1-B4 are selected from CR in the same or different way each time they appear b or N; W1 and W2 are selected from O, S or Se at each occurrence, the same or different; G.R x , R y , R b 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; and, In the formula 1-6-1 and the formula 1-7-1, G is selected from the group consisting of NRR, OR and SR at each occurrence, the same or different; R is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof at each occurrence; Adjacent substituents G, R x , R y , R b , R can be optionally linked to form a ring.
31. The electroluminescent device according to claim 30, wherein in Formula 1-1-1, Formula 1-2-4, Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1, Formula 1-7-2, X3-X n At least one of the following is selected from CR x , the X n The X3-X6 corresponding to the largest sequence number in any of the formulas 1-1-1, 1-2-4, 1-2-5, 1-5-1 to 1-5-4, 1-6-1, 1-6-2, 1-7-1, and 1-7-2, and the R x each occurrence is identically or differently selected from the group consisting of halogen, cyano, alkyl having 1 to 20 carbon atoms substituted by at least one cyano or halogen, cycloalkyl having 3 to 20 ring carbon atoms substituted by at least one cyano or halogen, aralkyl having 7 to 30 carbon atoms substituted by at least one cyano or halogen, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilanyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, and combinations thereof; In the formula 1-6-1 and formula 1-7-1, G is selected from the group consisting of NRR, OR and SR at each occurrence, the same or different; R is selected from the group consisting of deuterium, 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.
32. The electroluminescent device as claimed in claim 31, wherein in Formula 1-1-1, Formula 1-2-4, Formula 1-2-5, Formula 1-5-1 to Formula 1-5-4, Formula 1-6-1, Formula 1-6-2, Formula 1-7-1, Formula 1-7-2, X3-X n At least one of the following is selected from CR x , the X n The X3-X6 corresponding to the largest sequence number in any of the formulas 1-1-1, 1-2-4, 1-2-5, 1-5-1 to 1-5-4, 1-6-1, 1-6-2, 1-7-1, and 1-7-2, and the R x each occurrence is identically or differently selected from the group consisting of: fluoro, cyano, trifluoromethyl, cyanomethyl, 2,2,2-trifluoroethyl, 2-cyanoisopropyl, 3,3,3-trifluoro-2,2-dimethylpropyl, phenyl, 4-isopropylphenyl, 2,4,6-triisopropylphenyl, pyridyl, 2-isopropylpyridin-5-yl, 2-isopropylpyridin-6-yl, 2-isopropylpyrimidin-4-yl, 2-isopropylpyrimidin-5-yl, 5-isopropyl Pyrimidin-2-yl, 5-isopropylpyrazin-2-yl, 3,5-di-tert-butyltriazinyl, trimethylsilyl, triethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, triphenylsilyl, 1-methylsiletan-1-yl, 1-methylsilolan-1-yl, trimethylgermanyl, phenyldimethylgermanyl, and combinations thereof; In the formula 1-6-1 and formula 1-7-1, the G is selected from dimethylamino, diethylamino, diisopropylamino, methylphenylamino, N-pyrrolidino, N-morpholino, methoxy, ethoxy, isopropoxy, phenoxy, methyl sulfide or phenyl sulfide the same or different each time it appears.
33. The electroluminescent device of claim 1, wherein: In Formulas 1-1-1 to 1-1-4, 1-2-1 to 1-2-5, 1-4 to 1-10, and 1-12, at least one or two of X1 to X6 are selected from CR x , and / or at least one or two of Y1-Y6 are selected from CR y ; said R x , R y each occurrence is identically or differently selected from the group consisting of: 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 aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl 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 alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
34. The electroluminescent device as claimed in claim 33, wherein in Formulas 1-1-1 to 1-1-4, 1-2-1 to 1-2-5, 1-6, 1-9 and 1-10, X4 is selected from CR x In Formula 1-2, Formula 1-11 to Formula 1-13, X2 is selected from CR x In formula 1-4, formula 1-5, formula 1-7, and formula 1-8, X3 is selected from CR x ; and / or in Formula 1-1 to Formula 1-14, Y1 and / or Y3 are selected from CR at each occurrence, the same or different y .
35. The electroluminescent device according to claim 34, wherein R x , R y Each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 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, cyano, isocyano, hydroxyl, mercapto, and combinations thereof.
36. The electroluminescent device of claim 1, wherein: W1 is selected from O or S identically or differently on each occurrence.
37. The electroluminescent device of claim 1, wherein: L a Each occurrence is identically or differently selected from the group consisting of: Wherein, TMS in the above structure is trimethylsilyl.
38. The electroluminescent device according to claim 37, wherein L a1 To L a106 , L a139 To L a182 , L a185 To L a190 , L a199 To L a204 , L a211 To L a232 , L a263 To L a451 , L a462 To L a464 , L a466 To L a468 , L a470 To L a472 , L a474 To L a476 , L a481 To L a524 , L a529 To L a672 The hydrogen in the structure may be partially or completely replaced by deuterium.
39. The electroluminescent device of claim 1, wherein: The metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.
40. The electroluminescent device of claim 39, wherein M is selected from Ir or Pt.
41. The electroluminescent device of claim 40, wherein M is Ir.
42. The electroluminescent device of claim 1, wherein: The L b Has the following structure: R1-R7 are selected, at each occurrence, identically or differently, 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl 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, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituents R1, R2, R3, R4, R5, R6, R7 can be optionally linked to form a ring.
43. An electroluminescent device as described in claim 42, at least one or 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; and / or at least one of R4-R6 is 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.
44. An electroluminescent device as described in claim 43, 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; 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.
45. The electroluminescent device of claim 37, wherein: L b Each occurrence is identically or differently selected from the group consisting of:
46. The electroluminescent device of claim 45, wherein: The second compound is an Ir complex and has a a )2(L b ) shown in the structure; said L a Choose from L a1 To L a106 , L a139 To L a182 , L a185 To L a190 , L a199 To L a204 , L a211 To L a232 , L a263 To L a451 , L a462 To L a464 , L a466 To L a468 , L a470 To L a472 , L a474 To L a476 , L a481 To L a524 , L a529 To L a672 Any one or any two of the group consisting of b Choose from L b1 To L b322 Any one of the groups.
47. The electroluminescent device of claim 46, wherein the second compound is selected from the group consisting of Compound 1 to Compound 330, Compound 1 to Compound 38, Compound 43 to Compound 126, Compound 131 to Compound 214, Compound 219 to Compound 302, Compound 304, Compound 306 to Compound 330, having Ir(L a )2(L b ) in which two L a Same, L a and L b The corresponding structures are selected from the following table:
48. The electroluminescent device of claim 1, wherein: The device emits red light or white light.
49. The electroluminescent device of claim 48, said device having at least one maximum emission wavelength greater than 635 nm.
50. The electroluminescent device of claim 49, said device having at least one maximum emission wavelength greater than 640 nm.
51. A display component comprising the electroluminescent device of claim 1.
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