An organic electroluminescent device
By using the first and second compounds of a specific structure in the hole injection layer of an organic electroluminescent device, the problems of reduced efficiency and short life in the prior art are solved, and devices with low voltage, high efficiency and long life are achieved performance.
Patent Information
- Application Number
- CN202111488167.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2021-02-06
- Filing Date
- 2021-12-08
- Publication Date
- 2025-02-25
- Estimated Expiration
- 2041-12-08
AI Technical Summary
Existing organic electroluminescent devices are less efficient at high brightness conditions and are difficult to achieve more saturated luminescence spectra, higher efficiency and longer device life.
The first organic layer containing the first compound having the structure of Formula 1 and the second compound having the structure of Formula 2 is used as the hole injection layer, and the performance of the device is improved by reasonably matching these two compounds.
The low voltage, high efficiency and long life characteristics of organic electroluminescent devices are achieved, providing better device performance.
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Figure CN114914372B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to an organic electronic device, in particular, to an organic electroluminescent device, more particularly, to an organic electroluminescent device comprising a first compound having a structure of Formula 1 and a second compound having a structure of Formula 2 in a first organic layer, and a display component comprising the organic electroluminescent device. Background Art
[0002] Organic electronic devices include but are not limited to the following categories: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light emitting devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51 (12): 913-915). Once a bias voltage is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and the anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.
[0004] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet light emission. The triplet generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet light emission from heavy metals containing complexes as emitters. Therefore, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from triplet to singlet. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
[0005] OLEDs can also be classified into small molecule and polymer OLEDs based on the form of the material used. Small molecules are any organic or organometallic material that is not a polymer. Small molecules can have a large molecular weight as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.
[0006] There are various OLED manufacturing methods. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution methods if the material can be dissolved or dispersed in a solvent.
[0007] The emission color of OLED can be achieved by the structural design of the luminescent material. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, it is expected to have a more saturated emission spectrum, higher efficiency and longer device life.
[0008] Organic electroluminescent devices convert electrical energy into light by applying voltage across the two ends of the device. Generally, an organic electroluminescent device includes an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the electroluminescent device includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (including a main material and a doping material), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. According to the different functions of the materials, the materials constituting the organic layer can be divided into hole injection materials, hole transport materials, electron blocking materials, main materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, hole blocking materials, and the like. When a bias is applied to the device, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Holes and electrons meet to form excitons, and the excitons recombine to emit light. Among them, the hole injection layer is one of the important functional layers that affect the performance of the organic electroluminescent device. The selection and matching of its materials can have an important impact on the performance of the organic electroluminescent device, such as driving voltage, efficiency, and life. Commercially, it is expected to obtain organic electroluminescent devices with low driving voltage, high efficiency, long service life and other characteristics. Therefore, the development of new hole injection layers is a very critical research field.
[0009] Most of the early OLED devices only have one layer of organic material between the anode and the light-emitting layer, which takes into account the functions of hole injection, hole transport and even electron blocking. This device structure is limited by a single hole transport material, and it is impossible to achieve a relatively ideal match of energy levels, so it is difficult to obtain very ideal performance. With the growing demand for device performance in the industry, the performance requirements for the hole transport area between the anode and the light-emitting layer are also increasing. Later, the hole transport material was further subdivided into two layers: the hole injection layer and the hole transport layer. At this time, a single triarylamine material is generally used as the hole injection layer. Common triarylamine materials are as follows:
[0010]
[0011] For example, US20160190447A1 discloses a spirobifluorene-triarylamine structure The document discloses an organic compound which can be used as a hole transport material in a hole transport layer, a hole injection layer or an exciton blocking layer, or as a matrix material for a fluorescent light emitter or a phosphorescent light emitter. However, the document does not focus on the effect of the combination of the compound and a P-type doping material on the device performance.
[0012] In the most advanced device structure in the industry, multiple organic layers are usually set between the anode and the light-emitting layer to realize the hole injection function, hole transport function and electron blocking function respectively. In order to obtain a better hole injection effect, a certain proportion of p-type doping materials are often doped into the hole transport material (such as aromatic amine compounds) in the hole injection layer. Common p-type doping materials are:
[0013]
[0014] For example, US20200087311 discloses a dehydrogenated benzobisoxazole, dehydrogenated benzodithiazole or dehydrogenated benzodiselenazole and similar structures. An organic compound, which can be used as a p-type doping material or hole injection material with a deep LUMO. This application only focuses on such p-type doping material itself, and does not pay attention to the impact of the combination of such p-type doping material and hole transport material on device performance.
[0015] This doped hole injection layer achieves the p-type doping effect through the strong electron capture ability of the p-type doping material, and can obtain effectively improved hole injection and conductive properties. In this doped hole injection layer, on the one hand, it is very important to research and develop better p-type doping materials and / or better hole transport materials; on the other hand, the matching of p-type doping materials and hole transport materials is more important, and mismatch often leads to a significant reduction in device performance. Therefore, the reasonable matching of p-type doping materials and hole transport materials is very critical. Summary of the invention
[0016] The present invention aims to provide a series of novel organic electroluminescent devices to solve at least some of the above problems. The novel organic electroluminescent device comprises an anode, a cathode and a first organic layer arranged between the anode and the cathode, wherein the first organic layer comprises at least a first compound having a structure of Formula 1 and a second compound having a structure of Formula 2. This novel material combination consisting of the first compound and the second compound can be used in a hole injection layer in an organic electroluminescent device, which can make the organic electroluminescent device have excellent characteristics of low voltage, high efficiency and long life, and can provide better device performance.
[0017] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0018] anode,
[0019] cathode,
[0020] and a first organic layer disposed between the anode and the cathode, wherein the first organic layer comprises at least a first compound and a second compound, wherein the first compound has a structure represented by Formula 1:
[0021]
[0022] In formula 1,
[0023] X and Y are selected, at each occurrence, identically or differently, from NR', CR"R"', O, S or Se;
[0024] Z1 and Z2 are each identically or differently selected from O, S or Se;
[0025] R, R', R" and R'" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, 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 aralkyl having 7-30 carbon atoms substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups 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, and combinations thereof;
[0026] Each R may be the same or different, and at least one of R, R', R", and R'" is a group having at least one electron withdrawing group;
[0027] Adjacent substituents in Formula 1 can be optionally linked to form a ring;
[0028] The second compound has a structure represented by Formula 2:
[0029]
[0030] In formula 2,
[0031] X1 to X8 are selected, at each occurrence, identically or differently, from C, CR1 or N; X9 to X 18 Each occurrence is identically or differently selected from CR1 or N;
[0032] Q is selected from C, Si or Ge;
[0033] L1 to L3 are identically or differently selected at each occurrence 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;
[0034] Ar1 and Ar2 are each identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
[0035] R1 is 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 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;
[0036] Adjacent substituents L1, L2, L3, R1, Ar1 and Ar2 can be optionally linked to form a ring.
[0037] According to another embodiment of the present invention, a display component is also disclosed, which includes the organic electroluminescent device described in the above embodiment.
[0038] According to another embodiment of the present invention, a compound combination is also disclosed, which comprises a first compound and a second compound, wherein the first compound has a structure represented by Formula 1:
[0039]
[0040] In formula 1,
[0041] X and Y are selected, at each occurrence, identically or differently, from NR', CR"R"', O, S or Se;
[0042] Z1 and Z2 are each identically or differently selected from O, S or Se;
[0043] R, R', R" and R'" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, 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 aralkyl having 7-30 carbon atoms substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups 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, and combinations thereof;
[0044] Each R may be the same or different, and at least one of R, R', R", and R'" is a group having at least one electron withdrawing group;
[0045] Adjacent substituents in Formula 1 can be optionally linked to form a ring;
[0046] The second compound has a structure represented by Formula 2:
[0047]
[0048] In formula 2,
[0049] X1 to X8 are selected, at each occurrence, identically or differently, from C, CR1 or N; X9 to X 18 Each occurrence is identically or differently selected from CR1 or N;
[0050] Q is selected from C, Si or Ge;
[0051] L1 to L3 are identically or differently selected at each occurrence 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;
[0052] Ar1 and Ar2 are each identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
[0053] R1 is 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 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;
[0054] Adjacent substituents L1, L2, L3, R1, Ar1 and Ar2 can be optionally linked to form a ring.
[0055] The novel organic electroluminescent device disclosed in the present invention comprises an anode, a cathode and a first organic layer arranged between the anode and the cathode, wherein the first organic layer comprises at least a first compound having a structure of Formula 1 and a second compound having a structure of Formula 2. The novel material combination consisting of the first compound and the second compound can be used in a hole injection layer in an organic electroluminescent device, and can make the organic electroluminescent device have excellent characteristics of low voltage, high efficiency and long life, and can provide better device performance. BRIEF DESCRIPTION OF THE DRAWINGS
[0056] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the organic electroluminescent device disclosed herein.
[0057] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the organic electroluminescent device disclosed herein. DETAILED DESCRIPTION
[0058] 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.
[0059] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.
[0060] 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.
[0061] 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.
[0062] 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.
[0063] 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.
[0064] The materials and structures described herein may also be used in other organic electronic devices listed above.
[0065] 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.
[0066] 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.
[0067] 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.
[0068] 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).
[0069] 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.
[0070] 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).
[0071] Definition of Substituent Terms
[0072] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.
[0073] 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.
[0074] 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.
[0075] 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.
[0076] 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.
[0077] 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.
[0078] 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.
[0079] 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.
[0080] 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.
[0081] 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.
[0082] 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.
[0083] 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,
[0084] 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.
[0085] 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.
[0086] 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.
[0087] 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.
[0088] 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.
[0089] 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.
[0090] 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.
[0091] 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.
[0092] In the compounds mentioned in the present disclosure, multiple substitution 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 multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.
[0093] 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.
[0094] 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:
[0095]
[0096] 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:
[0097]
[0098] 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:
[0099]
[0100] 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:
[0101]
[0102] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0103] anode,
[0104] cathode,
[0105] and a first organic layer disposed between the anode and the cathode, wherein the first organic layer comprises at least a first compound and a second compound, wherein the first compound has a structure represented by Formula 1:
[0106]
[0107] In formula 1,
[0108] X and Y are selected, at each occurrence, identically or differently, from NR', CR"R"', O, S or Se;
[0109] Z1 and Z2 are each identically or differently selected from O, S or Se;
[0110] R, R', R" and R'" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, 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 aralkyl having 7-30 carbon atoms substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups 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, and combinations thereof;
[0111] Each R may be the same or different, and at least one of R, R', R", and R'" is a group having at least one electron withdrawing group;
[0112] Adjacent substituents in Formula 1 can be optionally linked to form a ring;
[0113] The second compound has a structure represented by Formula 2:
[0114]
[0115] In formula 2,
[0116] X1 to X8 are selected, at each occurrence, identically or differently, from C, CR1 or N; X9 to X 18 Each occurrence is identically or differently selected from CR1 or N;
[0117] Q is selected from C, Si or Ge;
[0118] L1 to L3 are identically or differently selected at each occurrence 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;
[0119] Ar1 and Ar2 are each identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
[0120] R1 is 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 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;
[0121] Adjacent substituents L1, L2, L3, R1, Ar1 and Ar2 can be optionally linked to form a ring.
[0122] In this embodiment, the adjacent substituents in Formula 1 can be optionally connected to form a ring, which is intended to mean that in Formula 1, adjacent substituent groups, such as adjacent substituents R" and R'", adjacent substituents R and R", adjacent substituents R and R', adjacent substituents R and R'", and two adjacent substituents R, any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups may not be connected to form a ring.
[0123] Herein, L1, L2, L3, R1, Ar1 and Ar2 can be optionally connected to form a ring, which is intended to mean that in Formula 2, adjacent substituent groups, such as adjacent substituent R1, adjacent substituent R1 and L3, adjacent substituent L1 and L2, adjacent substituent L1 and L3, adjacent substituent L2 and L3, adjacent substituent Ar1 and Ar2, adjacent substituent Ar1 and L3, adjacent substituent Ar2 and L3, adjacent substituent Ar1 and R1, and adjacent substituent Ar2 and R1, any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups may not be connected to form a ring.
[0124] According to one embodiment of the present invention, in Formula 1, X and Y are identically or differently selected from CR"R"' or NR' each time they appear, and R', R" and R"' are groups having at least one electron withdrawing group.
[0125] According to one embodiment of the present invention, in Formula 1, R, R', R", and R'" are groups having at least one electron-withdrawing group.
[0126] According to one embodiment of the present invention, in Formula 1, X and Y are selected from O, S or Se the same or differently each time they appear, and at least one of R is a group having at least one electron withdrawing group.
[0127] According to one embodiment of the present invention, in Formula 1, each R is a group having at least one electron-withdrawing group.
[0128] According to one embodiment of the present invention, the Hammett constant of the electron-withdrawing base is ≥0.05, preferably ≥0.3, and more preferably ≥0.5.
[0129] The Hammett substituent constant value of the electron-withdrawing group of the present invention is ≥0.05, and the electron-withdrawing ability is relatively strong, which can significantly reduce the LUMO energy level of the compound, thereby achieving the effect of improving the charge mobility.
[0130] It should be noted that the Hammett substituent constant value includes the Hammett substituent para constant and / or meta constant. As long as one of the para constant and the meta constant satisfies greater than or equal to 0.05, it can be used as a preferred selected group of the present invention.
[0131] According to one embodiment of the present invention, the electron withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring group, and any of the following groups substituted by one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring group: having Alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 ring carbon atoms, heteroalkyl groups having 1 to 20 carbon atoms, aralkyl groups having 7 to 30 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, aryloxy groups having 6 to 30 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, alkynyl groups having 2 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, heteroaryl groups having 3 to 30 carbon atoms, alkylsilyl groups having 3 to 20 carbon atoms, arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
[0132] According to one embodiment of the present invention, the electron-withdrawing group is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pyrimidine, triazine, and combinations thereof.
[0133] According to one embodiment of the present invention, each occurrence of X and Y is identically or differently selected from the group consisting of the following structures:
[0134] O, S, Se,
[0135]
[0136] R2 is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, 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 groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups 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, and combinations thereof;
[0137] Preferably, R2 is selected, at each occurrence, identically or differently, from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidyl, triazine, and combinations thereof;
[0138] V and W are selected from CR in the same or different order at each occurrence. v R w , NR v , O, S or Se;
[0139] Ar is the same or different at each occurrence and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0140] A, R a , R b , R c , R d , R e , R f , R g , R h , R v and R wis selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, 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 groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups 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, and combinations thereof;
[0141] A is a group having at least one electron withdrawing group, and for any of the structures, when R a , R b , R c , R d , R e , R f , R g , R h , R v and R w When one or more of a , R b , R c , R d , R e , R f , R g , R h , R v and R w At least one of them is a group having at least one electron-withdrawing group; preferably, the group having at least one electron-withdrawing group is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazine, and combinations thereof.
[0142] In this embodiment, “*” indicates the position where X and Y are connected to the dehydrobenzodioxazole ring, dehydrobenzodithiazole ring or dehydrobenzodiselenazole ring in Formula 1.
[0143] According to one embodiment of the present invention, each occurrence of X and Y is identically or differently selected from the group consisting of the following structures:
[0144] O, S, Se,
[0145] In this embodiment, “*” indicates the position of X and Y that is connected to the dehydrobenzodioxazole ring, dehydrobenzodithiazole ring or dehydrobenzodiselenazole ring in Formula 1.
[0146] According to one embodiment of the present invention, wherein R appears each time and is selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, Unsubstituted heteroaryl groups having 3-30 carbon atoms, and any of the following groups substituted by one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl and phosphino groups: alkyl groups having 1-20 carbon atoms, cycloalkyl groups having 3-20 ring carbon atoms, alkoxy groups having 1-20 carbon atoms, alkenyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms, heteroaryl groups having 3-30 carbon atoms, and combinations thereof.
[0147] According to one embodiment of the present invention, each occurrence of R is identically or differently selected from the group consisting of: hydrogen, deuterium, methyl, isopropyl, NO2, SO2CH3, SCF3, C2F5, OC2F5, OCH3, diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, vinyl substituted with one or more of CN or CF3, substituted with CN or C A substituted ethynyl group among F3, dimethylphosphinoyl, diphenylphosphinoyl, F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, trifluoromethylphenyl, trifluoromethoxyphenyl, bis(trifluoromethyl)phenyl, bis(trifluoromethoxy)phenyl, 4-cyanotetrafluorophenyl, phenyl or biphenyl substituted by one or more of F, CN or CF3, tetrafluoropyridyl, pyrimidinyl, triazine, diphenylboryl, oxaboranthenyl, and combinations thereof.
[0148] According to one embodiment of the present invention, X and Y are
[0149] According to one embodiment of the present invention, each occurrence of R is identically or differently selected from the group consisting of the following structures:
[0150]
[0151]
[0152]
[0153] In this embodiment, It represents the position where the R group is connected to the dehydrobenzodioxazole ring, dehydrobenzodithiazole ring or dehydrobenzodiselenazole ring in Formula 1.
[0154] According to one embodiment of the present invention, in the first compound represented by Formula 1, two Rs are the same.
[0155] According to one embodiment of the present invention, the first compound is selected from the group consisting of Compound 1 to Compound 1356; Compound 1 to Compound 1356 have a structure represented by Formula 1-1:
[0156]
[0157] Wherein, two Z are the same, and the Z, X, Y, and R are respectively selected from atoms or groups shown in the following table:
[0158]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172]
[0173]
[0174] According to one embodiment of the present invention, the second compound has a structure represented by any one of Formula 2-1 to Formula 2-12:
[0175]
[0176]
[0177] X1 to X 18 Each occurrence is identically or differently selected from CR1;
[0178] L1 to L3 are identically or differently selected at each occurrence 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;
[0179] Ar1 and Ar2 are each identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
[0180] R1 is 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 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;
[0181] Adjacent substituents L1, L2, L3, R1, Ar1 and Ar2 can be optionally linked to form a ring.
[0182] According to one embodiment of the present invention, the second compound has a structure represented by Formula 2-1, Formula 2-2, Formula 2-3, Formula 2-4, Formula 2-6 or Formula 2-10.
[0183] According to one embodiment of the present invention, in Formula 2, X1 to X 18 At least one of them is N.
[0184] According to one embodiment of the present invention, the second compound has a structure represented by any one of Formula 2-13 to Formula 2-24:
[0185]
[0186] X1 to X 18 Each occurrence is identically or differently selected from CR1 or N;
[0187] L1 to L3 are identically or differently selected at each occurrence 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;
[0188] Ar1 and Ar2 are each identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
[0189] R1 is 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 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;
[0190] Adjacent substituents L1, L2, L3, R1, Ar1 and Ar2 can be optionally linked to form a ring.
[0191] According to one embodiment of the present invention, the second compound has a structure represented by Formula 2-13, Formula 2-14, Formula 2-15, Formula 2-16, Formula 2-18 or Formula 2-22.
[0192] According to one embodiment of the present invention, in Formula 2-13 to Formula 2-24, X1 to X 18 Each occurrence is identically or differently selected from CR1.
[0193] According to one embodiment of the present invention, in Formula 2-13 to Formula 2-24, X1 to X 18 At least one of them is selected from N.
[0194] In this embodiment, in Formula 2-13 to Formula 2-24, X1 to X 18 At least one of them is selected from N, which is intended to represent: In Formula 2-13, Formula 2-17 and Formula 2-21, X1 to X7, X9 to X 12 and X 15 To X 18 At least one of them is N; in Formula 2-14, Formula 2-18 and Formula 2-22, X1 to X6, X8 to X 12 and X 15 To X 18At least one of them is N; in Formula 2-15, Formula 2-19 and Formula 2-23, X1 to X5, X7 to X 12 and X 15 To X 18 At least one of them is N; and in Formula 2-16, Formula 2-20 and Formula 2-24, X1 to X4, X6 to X 12 and X 15 To X 18 At least one of them is N.
[0195] According to one embodiment of the present invention, wherein L1 to L3 are identically or differently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, or a combination thereof each time they appear.
[0196] According to one embodiment of the present invention, L1 to L3 are selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted silylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzoselenopheneylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted spirobifluorenylene, a substituted or unsubstituted anthraceneylene, a substituted or unsubstituted perylene, or a combination thereof.
[0197] According to one embodiment of the present invention, each time L1 to L3 appear, they are selected from the group consisting of:
[0198]
[0199]
[0200] In this embodiment, "*" indicates the position where L-1 to L-13 is bonded to the nitrogen in Formula 2, and the dotted line indicates the position where L-1 to L-13 is connected to any one of X1 to X8 in Formula 2, Ar1 or Ar2.
[0201] According to one embodiment of the present invention, Ar1 and Ar2 each time appear, identically or differently have a structure represented by any one of Formula 3-1 to Formula 3-4:
[0202]
[0203] Each occurrence of E is identical or different and is selected from O, S, Se, C(R4)2, Si(R4)2 or Ge(R4)2; when two R4 are present at the same time, the two R4 may be identical or different;
[0204] R3, when present each time, may be identical or different and may represent mono-, poly- or non-substituted;
[0205] R3 and R4 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 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 substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 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;
[0206] Adjacent substituents R3, R4 can be optionally linked to form a ring.
[0207] In this embodiment, adjacent substituents R3 and R4 can be optionally connected to form a ring, which is intended to indicate that adjacent substituent groups, for example, adjacent substituents R3 and R3, adjacent substituents R3 and R4, and adjacent substituents R4 and R4, any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.
[0208] In this embodiment, the dotted line indicates the position in the structure of Ar1 that is connected to L1; the dotted line also indicates the position in the structure of Ar2 that is connected to L2.
[0209] According to one embodiment of the present invention, R3 and R4 are selected from hydrogen, deuterium, halogen, 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, or a combination thereof, the same or different when they appear each time.
[0210] According to one embodiment of the present invention, wherein Ar1 and Ar2 are identically or differently selected from the group consisting of G1 to G37 each time they appear:
[0211]
[0212]
[0213] R4 is 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 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;
[0214] Adjacent substituents R4 can be optionally linked to form a ring.
[0215] In this embodiment, adjacent substituents R4 can be optionally connected to form a ring, which is intended to mean that any two adjacent substituents R4 can be connected to form a ring. Obviously, any two adjacent substituents R4 may not be connected to form a ring.
[0216] According to one embodiment of the present invention, wherein R4 is selected from hydrogen, deuterium, 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, or a combination thereof, the same or different each time it appears.
[0217] According to one embodiment of the present invention, R4 is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, fluorene, phenyl, biphenyl, naphthyl, or a combination thereof, the same or different each time it occurs.
[0218] According to one embodiment of the present invention, wherein R1 is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or a combination thereof, the same or different each time it appears.
[0219] According to one embodiment of the present invention, X1 to X 18 At least one or two of them are selected from CR1 at each occurrence, the same or different, and said R1 at each occurrence is selected from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.
[0220] According to one embodiment of the present invention, in Formula 2-1 to Formula 2-24, X9 to X 18 At least one or two of them are selected from CR1 at each occurrence, the same or different, and said R1 at each occurrence is selected from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.
[0221] According to one embodiment of the present invention, wherein R1 is selected from hydrogen, deuterium, fluorine, methyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, or a combination thereof, the same or different each time it occurs.
[0222] According to one embodiment of the present invention, the Ar1 and Ar2 in the second compound are connected to form a ring.
[0223] According to one embodiment of the present invention, L1 and L2 are single bonds.
[0224] According to one embodiment of the present invention, the second compound has a structure represented by Formula 2-25:
[0225]
[0226] X1 to X8 are selected, at each occurrence, identically or differently, from C, CR1 or N;
[0227] X9 to X 18Each occurrence is identically or differently selected from CR1 or N;
[0228] Q is selected from C, Si or Ge at each occurrence;
[0229] T is selected, identically or differently, at each occurrence from CR5', R5', O, S or NR5';
[0230] R5, when present each time, is identical or different and represents mono-substitution, poly-substitution or no substitution;
[0231] R5 and R5' 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 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 substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 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;
[0232] L3 is identically or differently selected at each occurrence 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;
[0233] Adjacent substituents R1, R5 and R5' can optionally be linked to form a ring.
[0234] In this embodiment, adjacent substituents R1, R5 and R5' can be optionally connected to form a ring, which is intended to mean that adjacent substituent groups, for example, adjacent substituents R1 and R1, adjacent substituents R5 and R5, adjacent substituents R5 and R5', and adjacent substituents R5' and R5', any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.
[0235] According to one embodiment of the present invention, wherein the second compound is selected from compound I-1 to compound I-7, compound I-12 to compound I-182, compound I-185 to compound I-229, compound I-232 to compound I-273, compound II-1 to compound II-7, compound II-9 to compound II-30, compound II-32 to compound II-35, compound II-39 to compound II-79, compound II-81 to compound II-95, compound II-97 to compound II-110, compound II-112 to compound II-208, compound II-210 to compound II-221, compound I I-225 to compound II-243, compound II-245 to compound II-273, compound II-275 to compound II-286, compound II-288, compound II-290 to compound II-308, compound II-310 to compound II-332, compound III-1 to compound III-7, compound III-12 to compound III-182, compound III-185 to compound III-229, compound III-232 to compound III-273, compound IV-1 to compound IV-7, compound IV-12 to compound IV-182, compound IV-185 to compound IV-2 29, compounds IV-232 to IV-273, compounds V-1 to V-7, compounds V-12 to V-182, compounds V-185 to V-229, compounds V-232 to V-273, compounds VI-1 to VI-7, compounds VI-12 to VI-182, compounds VI-185 to VI-229, compounds VI-232 to VI-273, compounds VII-1 to VII-7, compounds VII-12 to VII-182, compounds VII-185 to VII-229, compounds VII-232 to V II-273, compounds VIII-1 to VIII-7, compounds VIII-12 to VIII-182, compounds VIII-185 to VIII-229, compounds VIII-232 to VIII-273, compounds IX-1 to IX-7, compounds IX-12 to IX-182, compounds IX-185 to IX-229, compounds IX-232 to IX-273, compounds X-1 to X-7, compounds X-12 to X-182, compounds X-185 to X-229, or compounds X-232 to X-273;Among them, Compound I-1 to Compound I-7, Compound I-12 to Compound I-182, Compound I-185 to Compound I-229, Compound I-232 to Compound I-273 have a structure represented by Formula 2-13:;
[0236]
[0237] In formula 2-13, X1 to X7, X9 to X 12 and X 15 To X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table:
[0238]
[0239]
[0240]
[0241]
[0242] The compounds II-1 to II-7, II-9 to II-30, II-32 to II-35, II-39 to II-79, II-81 to II-95, II-97 to II-110, II-112 to II-208, II-210 to II-221, II-225 to II-243, II-245 to II-273, II-275 to II-286, II-288, II-290 to II-308, II-310 to II-332 are shown below:
[0243]
[0244]
[0245]
[0246]
[0247]
[0248]
[0249]
[0250]
[0251]
[0252]
[0253]
[0254]
[0255]
[0256]
[0257]
[0258]
[0259]
[0260]
[0261]
[0262]
[0263] In the structures of compounds II-1 to II-7, compounds II-9 to II-30, compounds II-32 to II-35, compounds II-39 to II-79, compounds II-81 to II-95, compounds II-97 to II-110, compounds II-112 to II-208, compounds II-210 to II-221, compounds II-225 to II-243, compounds II-245 to II-273, compounds II-275 to II-286, compounds II-288, compounds II-290 to II-308, compounds II-310 to II-332, Ph represents a phenyl group;
[0264] Among them, the compounds III-1 to III-7, compounds III-12 to III-182, compounds III-185 to III-229, and compounds III-232 to III-273 have a structure represented by Formula 2-15:
[0265]
[0266] In formula 2-15, X1 to X5, X7 to X 12 and X15 To X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table:
[0267]
[0268]
[0269]
[0270]
[0271] Among them, compounds IV-1 to IV-7, compounds IV-12 to IV-182, compounds IV-185 to IV-229, and compounds IV-232 to IV-273 have a structure represented by Formula 2-16:
[0272]
[0273] In formula 2-16, X1 to X4, X6 to X 12 and X 15 To X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table:
[0274]
[0275]
[0276]
[0277]
[0278] Among them, Compound V-1 to Compound V-7, Compound V-12 to Compound V-182, Compound V-185 to Compound V-229, and Compound V-232 to Compound V-273 have a structure represented by Formula 2-1:
[0279]
[0280] In Formula 2-1, X1 to X7, X9 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table:
[0281]
[0282]
[0283]
[0284]
[0285] Among them, compound VI-1 to compound VI-7, compound VI-12 to compound VI-182, compound VI-185 to compound VI-229, and compound VI-232 to compound VI-273 have a structure represented by Formula 2-2:
[0286]
[0287] In Formula 2-2, X1 to X6, X8 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table:
[0288]
[0289]
[0290]
[0291]
[0292] Among them, compound VII-1 to compound VII-7, compound VII-12 to compound VII-182, compound VII-185 to compound VII-229, compound VII-232 to compound VII-273 have a structure represented by Formula 2-3:
[0293]
[0294] In formula 2-3, X1 to X5, X7 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table:
[0295]
[0296]
[0297]
[0298]
[0299] Among them, compounds VIII-1 to VIII-7, compounds VIII-12 to VIII-182, compounds VIII-185 to VIII-229, and compounds VIII-232 to VIII-273 have a structure represented by Formula 2-4:
[0300]
[0301] In formula 2-4, X1 to X4, X6 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table:
[0302]
[0303]
[0304]
[0305]
[0306] Among them, compounds IX-1 to IX-7, compounds IX-12 to IX-182, compounds IX-185 to IX-229, and compounds IX-232 to IX-273 have a structure represented by Formula 2-6:
[0307]
[0308] In formula 2-6, X1 to X6, X8 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table:
[0309]
[0310]
[0311]
[0312]
[0313] Among them, Compound X-1 to Compound X-7, Compound X-12 to Compound X-182, Compound X-185 to Compound X-229, or Compound X-232 to Compound X-273 have a structure represented by Formula 2-10:
[0314]
[0315] In formula 2-10, X1 to X6, X8 to X18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table:
[0316]
[0317]
[0318]
[0319]
[0320] According to an embodiment of the present invention, the first organic layer is a hole injection layer, and the hole injection layer is in contact with an anode.
[0321] According to one embodiment of the present invention, in the first organic layer, the weight ratio of the first compound to the second compound is between 10000:1 and 1:10000; preferably, the weight ratio of the first compound to the second compound is between 100:1 and 1:10000; more preferably, the weight ratio of the first compound to the second compound is between 10:1 and 1:10000.
[0322] According to one embodiment of the present invention, in the first organic layer, the first compound accounts for 0.01% to 10% of the total weight of the first organic layer; or the first compound accounts for 0.01% to 5% of the total weight of the first organic layer; or the first compound accounts for 0.01% to 3% of the total weight of the first organic layer; or the first compound accounts for 0.01% to 2% of the total weight of the first organic layer; or the first compound accounts for 0.01% to 1.5% of the total weight of the first organic layer; or the first compound accounts for 0.01% to 1% of the total weight of the first organic layer.
[0323] According to one embodiment of the present invention, the organic electroluminescent device further comprises at least one light-emitting layer.
[0324] According to one embodiment of the present invention, the at least one light-emitting layer comprises at least one host material and at least one doping material.
[0325] According to an embodiment of the present invention, the maximum emission wavelength of the organic electroluminescent device is between 300-1200 nm.
[0326] According to an embodiment of the present invention, the organic electroluminescent device further comprises a second organic layer, and the second organic layer is disposed between the first organic layer and the at least one light-emitting layer.
[0327] According to one embodiment of the present invention, the second organic layer contains a compound, which contains any one or more chemical structural units selected from the following group: triarylamine, carbazole, fluorene, spirobifluorene, thiophene, furan, phenyl, oligophenylene vinylene, oligofluorene, and combinations thereof.
[0328] According to an embodiment of the present invention, the one compound in the second organic layer is the second compound.
[0329] According to an embodiment of the present invention, the organic electroluminescent device further comprises a third organic layer, and the third organic layer is disposed between the second organic layer and the light-emitting layer.
[0330] According to one embodiment of the present invention, the third organic layer contains another compound, and the other compound contains any one or more compounds of chemical structural units selected from the following groups: triarylamine, carbazole, fluorene, spirobifluorene, thiophene, furan, phenyl, oligophenylene vinylene, oligofluorene, and combinations thereof.
[0331] According to an embodiment of the present invention, the another compound in the third organic layer is the second compound.
[0332] According to an embodiment of the present invention, in the device, among all the organic layers disposed between the anode and the light-emitting layer, only the first organic layer is p-type doped.
[0333] According to an embodiment of the present invention, the thickness of the first organic layer is between 0.1 nm and 40 nm, and the thickness of the second organic layer is between 0.1 nm and 300 nm.
[0334] According to another embodiment of the present invention, a display component is disclosed, which includes an organic electroluminescent device. The specific structure of the organic electroluminescent device is as shown in any of the above embodiments.
[0335] According to another embodiment of the present invention, a compound combination is also disclosed, which comprises a first compound and a second compound, wherein the first compound has a structure represented by Formula 1:
[0336]
[0337] In formula 1,
[0338] X and Y are selected, at each occurrence, identically or differently, from NR', CR"R"', O, S or Se;
[0339] Z1 and Z2 are each identically or differently selected from O, S or Se;
[0340] R, R', R" and R'" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, 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 aralkyl having 7-30 carbon atoms substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups 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, and combinations thereof;
[0341] Each R may be the same or different, and at least one of R, R', R", and R'" is a group having at least one electron withdrawing group;
[0342] Adjacent substituents in Formula 1 can be optionally linked to form a ring;
[0343] The second compound has a structure represented by Formula 2:
[0344]
[0345] In formula 2,
[0346] X1 to X8 are selected, at each occurrence, identically or differently, from C, CR1 or N; X9 to X 18 Each occurrence is identically or differently selected from CR1 or N;
[0347] Q is selected from C, Si or Ge;
[0348] L1 to L3 are identically or differently selected at each occurrence 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;
[0349] Ar1 and Ar2 are each identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
[0350] R1 is 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 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;
[0351] Adjacent substituents L1, L2, L3, R1, Ar1 and Ar2 can be optionally linked to form a ring.
[0352] Combination with other materials
[0353] 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.
[0354] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compound combinations 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.
[0355] The device of the present invention may include charge injection and transport layers, such as a hole transport layer, an electron transport layer, and an electron injection layer; it may also include a light-emitting layer, the light-emitting layer includes at least one light-emitting dopant and at least one main compound, and the light-emitting dopant may be a fluorescent light-emitting dopant and / or a phosphorescent light-emitting dopant; it may also include a blocking layer, such as a hole blocking layer and an electron blocking layer.
[0356] Conventional hole transport materials in the prior art can be used in the hole transport layer. For example, the hole transport layer can typically but not limitedly include the following hole transport materials:
[0357]
[0358]
[0359] Conventional electron transport materials in the prior art may be used in the electron transport layer. For example, the electron transport layer may typically but not limitedly include the following electron transport materials:
[0360]
[0361]
[0362] Conventional luminescent materials and host materials in the prior art may be used in the luminescent layer. For example, the luminescent layer may typically but not limitedly include the following fluorescent luminescent materials and fluorescent host materials:
[0363]
[0364]
[0365]
[0366] The light-emitting layer may also typically but not limitedly include the following phosphorescent light-emitting materials and phosphorescent host materials:
[0367]
[0368]
[0369]
[0370]
[0371]
[0372]
[0373] Conventional electron blocking materials in the prior art may be used in the electron blocking layer. For example, the electron blocking layer may typically but not limitedly include the following electron blocking materials:
[0374]
[0375] The first compound and the second compound used in the present invention can be obtained by referring to the preparation method in the prior art, or can also be easily prepared by referring to patent applications such as publication number US20200087311A1, US20160190447A1, etc., which will not be repeated here. The preparation method of the electroluminescent device is not limited, and the preparation method of the following embodiment is only an example and should not be understood as a limitation. Those skilled in the art can reasonably improve the preparation method of the following embodiment based on the prior art. Exemplarily, the ratio of various materials in each organic layer is not particularly limited, and those skilled in the art can reasonably choose within a certain range based on the prior art. 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.), using methods familiar to those skilled in the art. Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, 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.
[0376] Device Embodiment
[0377] Example 1-1: Preparation of fluorescent organic electroluminescent device.
[0378] First, a 0.7 mm thick glass substrate with a pre-patterned The thick indium tin oxide (ITO) was used as the anode. After washing the substrate with deionized water and detergent, the ITO surface was treated with oxygen plasma and UV ozone. Subsequently, the substrate was dried in a glove box to remove moisture and loaded on a rack into a vacuum chamber. The organic layers specified below were placed in a vacuum of about 10 -6 Torr's case The anode layer was deposited sequentially by vacuum thermal evaporation at a rate of: first, compound II-130 and compound 70 were simultaneously deposited as a hole injection layer (HIL, 99:1, ), the evaporated compound II-130 was used as a hole transport layer (HTL, ), then, the compound EB1 is evaporated to serve as an electron blocking layer (EBL, ), on which compound BH and compound BD are simultaneously evaporated as a light-emitting layer (EML, 96:4, ), evaporate compound HB1 as a hole blocking layer (HBL, ), compound ET and Liq were co-deposited as electron transport layer (ETL, 40:60, ), evaporation Thick Liq is used as the electron injection layer (EIL). Finally, aluminum is evaporated as the cathode. ). The device was then transferred back to the glove box and encapsulated with a glass cover slip to complete the device.
[0379] Example 1-2: The preparation method is the same as that of Example 1-1, except that compound II-7 and compound 70 are evaporated as the hole injection layer (HIL, 99:1, ), and the evaporated compound II-7 is used as a hole transport layer (HTL, ).
[0380] Comparative Example 1-1: The preparation method is the same as that of Example 1-1, except that the compound HT and the compound 70 are evaporated as the hole injection layer (HIL, 99:1, ), and the evaporated compound HT is used as a hole transport layer (HTL, ).
[0381] Comparative Example 1-2: The preparation method is the same as that of Example 1-1, except that the compound II-130 and the compound PD-1 are evaporated as the hole injection layer (HIL, 99:1, ).
[0382] Comparative Example 1-3: The preparation method is the same as that of Example 1-2, except that the compound II-7 and the compound PD-1 are evaporated as the hole injection layer (HIL, 99:1, ).
[0383] Comparative Example 1-4: The preparation method is the same as that of Comparative Example 1-1, except that the evaporation of compound HT and compound PD-1 is used as the hole injection layer (HIL, 99:1, ).
[0384] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.
[0385] Table 1 Device structures of organic layers of Examples 1-1 to 1-2 and Comparative Examples 1-1 to 1-4
[0386]
[0387] The structure of the materials used in the device is shown below:
[0388]
[0389] Table 2 shows the device performance of Examples 1-1 to 1-2 and Comparative Examples 1-1 to 1-4. The color coordinates (CIE), voltage, and power efficiency (PE) are calculated at a current density of 10 mA / cm 2 The device life (LT95) is measured at 80mA / cm 2 The measured lifetime under constant current driving is the time at which the brightness decays to 95% of the initial brightness.
[0390] Table 2 Device performance of Examples 1-1 to 1-2 and Comparative Examples 1-1 to 1-4
[0391] Part Number CIEx CIE Voltage (V) PE(lm / W) LT95(h) Example 1-1 0.141 0.104 4.1 4.3 112 Example 1-2 0.140 0.105 4.0 4.8 85 Comparative Example 1-1 0.140 0.094 4.9 3.6 102 Comparative Example 1-2 0.141 0.110 10.5 2.2 3 Comparative Examples 1-3 0.141 0.105 8.4 3.0 1 Comparative Examples 1-4 0.140 0.094 12.8 1.7 19
[0392] It can be seen from the data in Table 2 that the color coordinates of the embodiment are substantially consistent with those of the comparative example.
[0393] Compared with Comparative Example 1-1, the voltage of Example 1-1 is reduced by 0.8V, the power efficiency is increased by 0.7lm / W, and the life is further significantly improved by nearly 10% on the high life level of Comparative Example 1-1, which is very rare. Compared with Comparative Example 1-2, the voltage of Example 1-1 is greatly reduced by 6.4V, the power efficiency is increased by 2.1lm / W, and the life is greatly increased by 36 times. Compared with Comparative Example 1-4, the voltage of Example 1-1 is greatly reduced by 8.7V, the power efficiency is increased by 2.6lm / W, and the life is greatly increased by 5 times.
[0394] Compared with Comparative Example 1-1, the voltage of Example 1-2 is reduced by 0.9V, the power efficiency is increased by 1.2lm / W, and although the lifespan is reduced compared with Comparative Example 1-1, the lifespan data of Example 1-2 is still at a very high level in the industry. Compared with Comparative Example 1-3, the voltage of Example 1-2 is greatly reduced by 4.4V, the power efficiency is increased by 1.8lm / W, and the lifespan is greatly increased by 84 times. Compared with Comparative Example 1-4, the voltage of Example 1-2 is greatly reduced by 8.8V, the power efficiency is increased by 3.1lm / W, and the lifespan is greatly increased by 3.5 times.
[0395] From the above comparison, it can be seen that when the combination of the first compound and the second compound selected by the present invention is used in a fluorescent organic electroluminescent device, the organic electroluminescent device can obtain a lower voltage, a higher efficiency and a longer life, which proves the excellent performance and broad application prospects of the combination of the first compound and the second compound selected by the present invention.
[0396] Example 2-1: Preparation of phosphorescent organic electroluminescent device.
[0397] First, a 0.7 mm thick glass substrate with a pre-patterned The thick indium tin oxide (ITO) was used as the anode. After washing the substrate with deionized water and detergent, the ITO surface was treated with oxygen plasma and UV ozone. Subsequently, the substrate was dried in a glove box to remove moisture and loaded on a rack into a vacuum chamber. The organic layers specified below were placed in a vacuum of about 10 -6 Torr's case The anode layer was deposited sequentially by vacuum thermal evaporation at a rate of: first, compound II-130 and compound 70 were simultaneously deposited as a hole injection layer (HIL, 99:1, ), the evaporated compound II-130 was used as a hole transport layer (HTL, ), then, the compound EB2 is evaporated to serve as an electron blocking layer (EBL, ), on which compound RH and compound RD are simultaneously evaporated as a light-emitting layer (EML, 98:2, ), evaporate compound HB2 as a hole blocking layer (HBL, ), compound ET and Liq were co-deposited as electron transport layer (ETL, 40:60, ), evaporation Thick Liq is used as the electron injection layer (EIL). Finally, aluminum is evaporated as the cathode. ). The device was then transferred back to the glove box and encapsulated with a glass cover slip to complete the device.
[0398] Example 2-2: The preparation method is the same as that of Example 2-1, except that compound II-7 and compound 70 are evaporated as the hole injection layer (HIL, 99:1, ), and the evaporated compound II-7 is used as a hole transport layer (HTL, ).
[0399] Comparative Example 2-1: The preparation method is the same as that of Example 2-1, except that the compound HT and the compound 70 are evaporated as the hole injection layer (HIL, 99:1, ), and the evaporated compound HT is used as a hole transport layer (HTL, ).
[0400] Comparative Example 2-2: The preparation method is the same as that of Example 2-1, except that the compound II-130 and the compound PD-1 are evaporated as the hole injection layer (HIL, 99:1, ).
[0401] Comparative Example 2-3: The preparation method is the same as that of Example 2-2, except that the compound II-7 and the compound PD-1 are evaporated as the hole injection layer (HIL, 99:1, ).
[0402] Comparative Example 2-4: The preparation method is the same as that of Comparative Example 2-1, except that the evaporation of compound HT and compound PD-1 is used as the hole injection layer (HIL, 99:1, ).
[0403] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.
[0404] Table 3 Device structures of organic layers of Examples 2-1 to 2-2 and Comparative Examples 2-1 to 2-4
[0405]
[0406]
[0407] The structure of the new material used in the device is shown below:
[0408]
[0409] Table 4 shows the device performance of Examples 2-1 to 2-2 and Comparative Examples 2-1 to 2-4. The color coordinates (CIE), voltage, and power efficiency (PE) are calculated at a current density of 10 mA / cm 2 The device life (LT95) is measured at 80mA / cm 2 The measured lifetime under constant current driving is the time at which the brightness decays to 95% of the initial brightness.
[0410] Table 4 Device performance of Examples 2-1 to 2-2 and Comparative Examples 2-1 to 2-4
[0411] Part Number CIEx CIE Voltage (V) PE(lm / W) LT95(h) Example 2-1 0.681 0.318 4.5 14.7 132 Example 2-2 0.680 0.318 4.3 15.2 131 Comparative Example 2-1 0.681 0.318 6.4 11.4 81 Comparative Example 2-2 0.679 0.319 14.6 6.8 20 Comparative Example 2-3 0.678 0.320 12.8 7.4 65 Comparative Examples 2-4 0.678 0.320 25.9 3.1 1
[0412] Compared with Comparative Example 2-1, the voltage of Example 2-1 is reduced by 1.9V, the power efficiency is increased by 3.3lm / W, and the life is increased by 0.6 times. Compared with Comparative Example 2-2, the voltage of Example 2-1 is greatly reduced by 10.1V, the power efficiency is increased by 7.9lm / W, and the life is greatly increased by 5.6 times. Compared with Comparative Example 2-4, the voltage of Example 2-1 is greatly reduced by 21.4V, the power efficiency is increased by 11.6lm / W, and the life is greatly increased by 131 times.
[0413] Compared with Comparative Example 2-1, the voltage of Example 2-2 is reduced by 2.1V, the power efficiency is increased by 3.8lm / W, and the life is increased by 0.6 times. Compared with Comparative Example 2-3, the voltage of Example 2-2 is greatly reduced by 8.5V, the power efficiency is increased by 7.8lm / W, and the life is increased by 1 times. Compared with Comparative Example 2-4, the voltage of Example 2-2 is greatly reduced by 21.6V, the power efficiency is increased by 12.1lm / W, and the life is greatly increased by 130 times.
[0414] From the above comparison, it can be seen that when the combination of the first compound and the second compound selected by the present invention is used in a phosphorescent organic electroluminescent device, the organic electroluminescent device can obtain a lower voltage, a higher efficiency and a longer life, which proves the excellent performance and broad application prospects of the combination of the first compound and the second compound selected by the present invention.
[0415] In summary, the material combination of the first compound and the second compound selected in the present invention can achieve the excellent effects of reducing voltage, improving efficiency, and greatly improving or maintaining a high level of device life, whether in fluorescent organic electroluminescent devices or phosphorescent organic electroluminescent devices, indicating broad application prospects in commercial applications.
[0416] 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 organic electroluminescent device, comprising: anode, cathode, and a first organic layer disposed between the anode and the cathode, wherein the first organic layer comprises at least a first compound and a second compound, wherein the first compound has a structure represented by Formula 1: In formula 1, X and Y are selected, at each occurrence, identically or differently, from NR', CR"R"', O, S or Se; Z1 and Z2 are each identically or differently selected from O, S or Se; R, R', R" and R'" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, cyano, isocyano, SCN, OCN, SF5, borane, phosphino, 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 aralkyl having 7-30 carbon atoms, substituted or unsubstituted Alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups 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, and combinations thereof; Each R may be the same or different, and at least one of R, R', R", and R'" is a group having at least one electron withdrawing group; Adjacent substituents in Formula 1 can be optionally linked to form a ring; The second compound has a structure represented by Formula 2: In formula 2, X1 to X8 are selected, at each occurrence, identically or differently, from C, CR1 or N; X9 to X 18 Each occurrence is identically or differently selected from CR1 or N; Q is selected from C, Si or Ge; L1 to L3 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar1 and Ar2 are each identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; R1 is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituents L1, L2, L3, R1, Ar1 and Ar2 can be optionally linked to form a ring; Substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, refers to alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, any one of which may be selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heterocyclic groups having 3-20 ring atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted aryl groups having 6-30 carbon atoms, unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilanyl groups having 6-20 carbon atoms, unsubstituted alkylgermanyl groups having 3-20 carbon atoms, unsubstituted arylgermanyl groups having 6-20 carbon atoms, unsubstituted amino groups having 0-20 carbon atoms, cyano groups, mercapto groups, and combinations thereof.
2. The organic electroluminescent device according to claim 1, wherein: In Formula 1, X and Y are identically or differently selected from CR"R"' or NR' at each occurrence, and R', R" and R"' are groups having at least one electron withdrawing group.
3. The organic electroluminescent device according to claim 1, wherein: In Formula 1, R, R', R", and R'" are groups having at least one electron withdrawing group.
4. The organic electroluminescent device according to claim 1, wherein: In Formula 1, X and Y are identically or differently selected from O, S or Se at each occurrence, and at least one of R is a group having at least one electron withdrawing group.
5. The organic electroluminescent device according to claim 1, wherein: In Formula 1, each R is a group having at least one electron withdrawing group.
6. The organic electroluminescent device according to claim 1, wherein: The Hammett constant of the electron-withdrawing basis is ≥ 0.
05.
7. The organic electroluminescent device according to claim 1, wherein: The electron withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, cyano, isocyano, SCN, OCN, SF5, borane, phosphino, azaaromatic ring group, and any of the following groups substituted by one or more of halogen, nitroso, nitro, cyano, isocyano, SCN, OCN, SF5, borane, phosphino, azaaromatic ring group: alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, heteroalkyl having 1-20 carbon atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, alkenyl having 2-20 carbon atoms, alkynyl having 2-20 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, alkylsilyl having 3-20 carbon atoms, arylsilyl having 6-20 carbon atoms, and combinations thereof.
8. The organic electroluminescent device according to claim 7, wherein: The electron withdrawing group is selected from the group consisting of F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pyrimidinyl, triazine, and combinations thereof.
9. The organic electroluminescent device according to claim 1, wherein X and Y are selected from the group consisting of the following structures in the same or different manner each time they appear: O, S, Se, R2 is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, cyano, isocyano, SCN, OCN, SF5, borane, phosphino, 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 aralkyl having 7-30 carbon atoms, substituted or unsubstituted arylalkyl having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof; V and W are selected from CR in the same or different order at each occurrence. v R w , NR v , O, S or Se; Ar is the same or different at each occurrence and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; A, R a , R b , R c , R d , R e , R f , R g , R h , R v and R w is selected, at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, cyano, isocyano, SCN, OCN, SF5, borane, phosphino, 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 alkyl having 1 to 2 0 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups 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, and its combination; A is a group having at least one electron withdrawing group, and for any of the structures, when R a , R b , R c , R d , R e , R f , R g , R h , R v and R w When one or more of a , R b , R c , R d , R e , R f , R g , R h , R v and R w At least one of them is a group having at least one electron-withdrawing group; the group having at least one electron-withdrawing group is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazine, and combinations thereof; "*" indicates the position of X and Y that is connected to the dehydrobenzodioxazole ring, dehydrobenzodithiazole ring or dehydrobenzodiselenazole ring in Formula 1.
10. The organic electroluminescent device according to claim 9, wherein X and Y each time appear, are identically or differently selected from the group consisting of the following structures: O, S, Se, "*" indicates the position of X and Y that is connected to the dehydrobenzodioxazole ring, dehydrobenzodithiazole ring or dehydrobenzodiselenazole ring in Formula 1.
11. The organic electroluminescent device according to claim 1, wherein: R is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, cyano, isocyano, SCN, OCN, SF5, borane, phosphino, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring ... -30 carbon atoms, heteroaryl groups, and any of the following groups substituted by one or more of halogen, nitroso, nitro, cyano, isocyano, SCN, OCN, SF5, borane and phosphineoxy: alkyl groups having 1-20 carbon atoms, cycloalkyl groups having 3-20 ring carbon atoms, alkoxy groups having 1-20 carbon atoms, alkenyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms, heteroaryl groups having 3-30 carbon atoms, and combinations thereof.
12. The organic electroluminescent device according to claim 11, wherein: R is selected, at each occurrence, the same or different, from the group consisting of hydrogen, deuterium, methyl, isopropyl, NO2, SO2CH3, SCF3, C2F5, OC2F5, OCH3, diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, vinyl substituted with one or more of CN or CF3, ethynyl substituted with one of CN or CF3, dimethylphosphinoyl, diphenylphosphinoyl, F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, trifluoromethylphenyl, trifluoromethoxyphenyl, bis(trifluoromethyl)phenyl, bis(trifluoromethoxy)phenyl, 4-cyanotetrafluorophenyl, phenyl or biphenyl substituted with one or more of F, CN or CF3, tetrafluoropyridyl, pyrimidinyl, triazine, diphenylboryl, oxaboranthenyl, and combinations thereof.
13. The organic electroluminescent device according to claim 10, wherein each occurrence of R is identically or differently selected from the group consisting of the following structures: It represents the position where the R group is connected to the dehydrobenzodioxazole ring, dehydrobenzodithiazole ring or dehydrobenzodiselenazole ring in Formula 1.
14. The organic electroluminescent device according to claim 13, wherein: In one first compound represented by Formula 1, two Rs are the same.
15. The organic electroluminescent device according to claim 13, wherein: The first compound is selected from the group consisting of Compound 1 to Compound 1356; Compound 1 to Compound 1356 have a structure represented by Formula 1-1: Wherein, two Z are the same, and the Z, X, Y, and R are respectively selected from atoms or groups shown in the following table:
16. The organic electroluminescent device according to claim 1, wherein: The second compound has a structure represented by any one of Formula 2-1 to Formula 2-12: X1 to X 18 Each occurrence is identically or differently selected from CR1; L1 to L3 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar1 and Ar2 are each identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; R1 is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituents L1, L2, L3, R1, Ar1 and Ar2 can be optionally linked to form a ring.
17. The organic electroluminescent device according to claim 16, wherein: The second compound has a structure represented by Formula 2-1, Formula 2-2, Formula 2-3, Formula 2-4, Formula 2-6, or Formula 2-10.
18. The organic electroluminescent device according to claim 1, wherein: The second compound has a structure represented by any one of Formula 2-13 to Formula 2-24: X1 to X 18 Each occurrence is identically or differently selected from CR1 or N; L1 to L3 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar1 and Ar2 are each identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; R1 is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituents L1, L2, L3, R1, Ar1 and Ar2 can be optionally linked to form a ring.
19. The organic electroluminescent device according to claim 18, wherein: The second compound has a structure represented by Formula 2-13, Formula 2-14, Formula 2-15, Formula 2-16, Formula 2-18, or Formula 2-22.
20. The organic electroluminescent device according to claim 18, wherein: The L1 to L3 are identically or differently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, or a combination thereof at each occurrence.
21. The organic electroluminescent device according to claim 20, wherein: L1 to L3 are selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted silylfluorenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzoselenopheneylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted spirobifluorenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted pyrenylene, or a combination thereof.
22. The organic electroluminescent device according to claim 20, wherein: L1 to L3 are selected, at each occurrence, identically or differently, from the group consisting of:
23. The organic electroluminescent device according to claim 22, wherein Ar1 and Ar2 each time appear, identically or differently have a structure represented by any one of Formula 3-1 to Formula 3-4: E is selected, identically or differently, at each occurrence from O, S, Se, C(R4)2, Si(R4)2 or Ge(R4)2; R3, when present at each occurrence, is identical or different and represents mono-, poly- or non-substituted; R3 and R4 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 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 cycloalkyl having 2 to 20 carbon atoms, alkenyl having carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituents R3 and R4 can be optionally linked to form a ring; The dotted line indicates the position in the structure of Ar1 that is connected to L1; the dotted line also indicates the position in the structure of Ar2 that is connected to L2.
24. The organic electroluminescent device according to claim 23, wherein: Ar1 and Ar2 are each identically or differently selected from the group consisting of G1 to G37: R4 is 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 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 cycloalkyl having 2 to 20 carbon atoms substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituents R4 can be optionally linked to form a ring.
25. The organic electroluminescent device according to claim 24, wherein: R4 is selected, at each occurrence, identically or differently, from hydrogen, deuterium, methyl, ethyl, isopropyl, fluorene, phenyl, biphenyl, naphthyl, or a combination thereof.
26. The organic electroluminescent device according to claim 1, wherein: R1 is selected, at each occurrence, identically or differently, from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.
27. The organic electroluminescent device according to claim 26, wherein: R1 is selected, at each occurrence, identically or differently, from hydrogen, deuterium, fluorine, methyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, or a combination thereof.
28. The organic electroluminescent device according to claim 1, wherein: The Ar1 and Ar2 in the second compound are connected to form a ring.
29. The organic electroluminescent device according to claim 28, wherein: L1 and L2 are single bonds.
30. The organic electroluminescent device according to claim 28, wherein: The second compound has a structure represented by Formula 2-25: X1 to X8 are selected, at each occurrence, identically or differently, from C, CR1 or N; X9 to X 18 Each occurrence is identically or differently selected from CR1 or N; Q is selected from C, Si or Ge at each occurrence; T is selected, identically or differently, at each occurrence from CR5', R5', O, S or NR5'; R5, when present each time, is identical or different and represents mono-substitution, poly-substitution or no substitution; R5 and R5' 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 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 cycloalkyl having 2 to 20 carbon atoms, alkenyl having carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; L3 is identically or differently selected at each occurrence 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; Adjacent substituents R1, R5 and R5' can optionally be linked to form a ring.
31. The organic electroluminescent device according to claim 24, wherein: The second compound is selected from compound I-1 to compound I-7, compound I-12 to compound I-182, compound I-185 to compound I-229, compound I-232 to compound I-273, compound II-1 to compound II-7, compound II-9 to compound II-30, compound II-32 to compound II-35, compound II-39 to compound II-79, compound II-81 to compound II-95, compound II-97 to compound II-110, compound II-112 to compound II-208, compound II-210 to compound II-221, compound II-225 to compound II -243, compound II-245 to compound II-273, compound II-275 to compound II-286, compound II-288, compound II-290 to compound II-308, compound II-310 to compound II-332, compound III-1 to compound III-7, compound III-12 to compound III-182, compound III-185 to compound III-229, compound III-232 to compound III-273, compound IV-1 to compound IV-7, compound IV-12 to compound IV-182, compound IV-185 to compound IV-229, compound I V-232 to compound IV-273, compound V-1 to compound V-7, compound V-12 to compound V-182, compound V-185 to compound V-229, compound V-232 to compound V-273, compound VI-1 to compound VI-7, compound VI-12 to compound VI-182, compound VI-185 to compound VI-229, compound VI-232 to compound VI-273, compound VII-1 to compound VII-7, compound VII-12 to compound VII-182, compound VII-185 to compound VII-229, compound VII-232 to compound VII- 273, compounds VIII-1 to VIII-7, compounds VIII-12 to VIII-182, compounds VIII-185 to VIII-229, compounds VIII-232 to VIII-273, compounds IX-1 to IX-7, compounds IX-12 to IX-182, compounds IX-185 to IX-229, compounds IX-232 to IX-273, compounds X-1 to X-7, compounds X-12 to X-182, compounds X-185 to X-229, or compounds X-232 to X-273; Among them, compounds I-1 to I-7, compounds I-12 to I-182, compounds I-185 to I-229, and compounds I-232 to I-273 have a structure represented by Formula 2-13: In formula 2-13, X1 to X7, X9 to X 12 and X 15 To X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table: The compounds II-1 to II-7, II-9 to II-30, II-32 to II-35, II-39 to II-79, II-81 to II-95, II-97 to II-110, II-112 to II-208, II-210 to II-221, II-225 to II-243, II-245 to II-273, II-275 to II-286, II-288, II-290 to II-308, II-310 to II-332 are shown below: In the structures of compounds II-1 to II-7, compounds II-9 to II-30, compounds II-32 to II-35, compounds II-39 to II-79, compounds II-81 to II-95, compounds II-97 to II-110, compounds II-112 to II-208, compounds II-210 to II-221, compounds II-225 to II-243, compounds II-245 to II-273, compounds II-275 to II-286, compounds II-288, compounds II-290 to II-308, compounds II-310 to II-332, Ph represents a phenyl group; Among them, compound III-1 to compound III-7, compound III-12 to compound III-182, compound III-185 to compound III-229, compound III-232 to compound III-273 have a structure represented by Formula 2-15: In formula 2-15, X1 to X5, X7 to X 12 and X 15 To X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table: Among them, compounds IV-1 to IV-7, compounds IV-12 to IV-182, compounds IV-185 to IV-229, and compounds IV-232 to IV-273 have a structure represented by Formula 2-16: In formula 2-16, X1 to X4, X6 to X 12 and X 15 To X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table: Among them, Compound V-1 to Compound V-7, Compound V-12 to Compound V-182, Compound V-185 to Compound V-229, and Compound V-232 to Compound V-273 have a structure represented by Formula 2-1: In Formula 2-1, X1 to X7, X9 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table: Among them, compound VI-1 to compound VI-7, compound VI-12 to compound VI-182, compound VI-185 to compound VI-229, and compound VI-232 to compound VI-273 have a structure represented by Formula 2-2: In Formula 2-2, X1 to X6, X8 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table: Among them, compound VII-1 to compound VII-7, compound VII-12 to compound VII-182, compound VII-185 to compound VII-229, compound VII-232 to compound VII-273 have a structure represented by Formula 2-3: In formula 2-3, X1 to X5, X7 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table: Among them, compounds VIII-1 to VIII-7, compounds VIII-12 to VIII-182, compounds VIII-185 to VIII-229, and compounds VIII-232 to VIII-273 have a structure represented by Formula 2-4: In formula 2-4, X1 to X4, X6 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table: Among them, compounds IX-1 to IX-7, compounds IX-12 to IX-182, compounds IX-185 to IX-229, and compounds IX-232 to IX-273 have a structure represented by Formula 2-6: In formula 2-6, X1 to X6, X8 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table: Among them, Compound X-1 to Compound X-7, Compound X-12 to Compound X-182, Compound X-185 to Compound X-229, or Compound X-232 to Compound X-273 have a structure represented by Formula 2-10: In formula 2-10, X1 to X6, X8 to X 18 All are CH, L1 and L2 are single bonds, and L3, Ar1 and Ar2 correspond to atoms or groups selected from the following table:
32. The organic electroluminescent device according to claim 1, wherein: The first organic layer is a hole injection layer, and the hole injection layer is in contact with the anode.
33. The organic electroluminescent device according to claim 32, wherein: The organic electroluminescent device further comprises at least one light-emitting layer.
34. The organic electroluminescent device according to claim 33, wherein: The organic electroluminescent device further comprises a second organic layer, and the second organic layer is disposed between the first organic layer and the at least one light-emitting layer.
35. The organic electroluminescent device according to claim 34, wherein: The second organic layer comprises a compound comprising any one or more chemical structural units selected from the group consisting of triarylamine, carbazole, fluorene, spirobifluorene, thiophene, furan, phenyl, oligophenylene vinylene, oligofluorene, and combinations thereof.
36. The organic electroluminescent device according to claim 34, wherein: The one compound in the second organic layer is the second compound.
37. The organic electroluminescent device according to claim 34, wherein: The organic electroluminescent device further comprises a third organic layer, which is disposed between the second organic layer and the light-emitting layer.
38. The organic electroluminescent device according to claim 37, wherein: The third organic layer comprises another compound, wherein the other compound comprises any one or more chemical structural units selected from the group consisting of triarylamine, carbazole, fluorene, spirobifluorene, thiophene, furan, phenyl, oligophenylene vinylene, oligofluorene, and combinations thereof.
39. The organic electroluminescent device according to claim 37, wherein: The another compound in the third organic layer is the second compound.
40. The organic electroluminescent device according to claim 34, wherein: The thickness of the first organic layer is between 0.1 nm and 40 nm, and the thickness of the second organic layer is between 0.1 nm and 300 nm.
41. A display component comprising the organic electroluminescent device according to any one of claims 1 to 40.
42. A compound combination comprising a first compound and a second compound, wherein the first compound has a structure represented by Formula 1: In formula 1, X and Y are selected, at each occurrence, identically or differently, from NR', CR"R"', O, S or Se; Z1 and Z2 are each identically or differently selected from O, S or Se; R, R', R" and R'" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, cyano, isocyano, SCN, OCN, SF5, borane, phosphino, 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 aralkyl having 7-30 carbon atoms, substituted or unsubstituted Alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups 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, and combinations thereof; Each R may be the same or different, and at least one of R, R', R", and R'" is a group having at least one electron withdrawing group; Adjacent substituents in Formula 1 can be optionally linked to form a ring; The second compound has a structure represented by Formula 2: In formula 2, X1 to X8 are selected, at each occurrence, identically or differently, from C, CR1 or N; X9 to X 18 Each occurrence is identically or differently selected from CR1 or N; Q is selected from C, Si or Ge; L1 to L3 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar1 and Ar2 are each identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; R1 is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituents L1, L2, L3, R1, Ar1 and Ar2 can be optionally linked to form a ring; Substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, refers to alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, any one of which may be selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heterocyclic groups having 3-20 ring atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted aryl groups having 6-30 carbon atoms, unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilanyl groups having 6-20 carbon atoms, unsubstituted alkylgermanyl groups having 3-20 carbon atoms, unsubstituted arylgermanyl groups having 6-20 carbon atoms, unsubstituted amino groups having 0-20 carbon atoms, cyano groups, mercapto groups, and combinations thereof.
Citation Information
Patent Citations
Isaac t
US1320161A
Very low voltage, high efficiency phosphorescent OLED in a p-i-n structure
US20030230980A1
Transparent electrodes
US20040174116A1
Organic electroluminescent materials and devices
US20150349273A1
Materials for organic electroluminescent devices
US20160190447A1