Organic electroluminescent device, display assembly and electronic device thereof
By combining organic materials with specific structures, the material matching of blue-green or blue OLED devices is optimized, solving the problems of low efficiency and charge accumulation, improving the power efficiency and charge distribution of the devices, and improving the capacitance performance.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- BEIJING SUMMER SPROUT TECH CO LTD
- Filing Date
- 2024-11-29
- Publication Date
- 2026-06-05
AI Technical Summary
Existing blue-green or blue OLED devices suffer from low efficiency and insufficient stability. Charge accumulation leads to high capacitance, affecting device response time and refresh rate. Improved material combinations are needed to enhance overall performance.
A first organic layer is formed by combining a first organic material with a specific Formula 1 structure with a second organic material that emits green, blue-green, or blue light (λmax-PL≤524nm) to optimize carrier transport and charge distribution.
It improves device power efficiency, reduces charge per unit area, improves charge accumulation, and enhances overall device performance.
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Figure CN122161285A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to organic electroluminescent devices. More particularly, it relates to an organic electroluminescent device comprising a first organic material having a structure of Formula 1 and a second organic material having a PL peak wavelength satisfying specific conditions, as well as a display assembly and electronic device comprising the organic electroluminescent device. Background Technology
[0002] Organic light-emitting diodes (OLEDs) consist of a cathode, an anode, and a series of organic light-emitting materials stacked between the cathode and anode. They convert electrical energy into light by applying a voltage across the cathode and anode, offering advantages such as wide viewing angle, high contrast, and faster response time. In 1987, Tang and Van Slyke of Eastman Kodak reported an organic light-emitting device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as the electron transport and light-emitting layers (Applied Physics Letters, 1987, 51(12): 913-915). When a voltage was applied across the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs).
[0003] Due to its advantages such as low cost, low power consumption, high brightness, wide viewing angle, and thinness, OLED has been widely used in the display and lighting fields after decades of development. Among the red, green, and blue primary color emitting materials of OLEDs, research on red and green OLEDs is relatively mature, while research on blue or blue-green OLEDs is relatively lagging behind. Low efficiency and insufficient stability are technical challenges that urgently need to be overcome for blue-green or blue OLEDs. In addition, the capacitance of the device, as a key factor affecting the response time and refresh rate of OLED displays at low grayscale levels, has also become one of the key performance parameters of concern to industry professionals. In OLED devices, capacitance is closely related to charge accumulation. For example... Figure 2 The CV characteristic curve of the device is shown in the figure. When the voltage is lower than the starting voltage (V t When the charge accumulation is small, the capacitance is the geometric capacitance C. geo As the applied voltage increases, charge is gradually injected into the device and accumulates, resulting in an increase in capacitance. When the voltage reaches V... Cmax When the capacitance reaches its maximum value C, max At this point, the charge accumulation per unit area reaches saturation. If the voltage continues to increase, electrons begin to recombine with holes, leading to charge consumption, a gradual decrease in capacitance, and a corresponding reduction in charge. Using the amount of charge per unit area can help to more intuitively understand the relationship between capacitance change and charge injection, thus providing a quantitative basis for device performance optimization.
[0004] Currently, commercially available OLED devices typically consist of a cathode, an anode, and a series of organic functional layers positioned between the cathode and anode, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emissive layer (EML), and an electron injection layer (EIL). To obtain devices with superior overall performance, common improvement methods include developing novel device structures or researching new compounds. Furthermore, the combination of different materials within the organic layers significantly impacts device performance. Material combinations with better performance matching can balance charge carriers within the device, facilitating charge transport. Therefore, focusing on the interplay and interaction of organic materials and developing novel material combinations applicable to specific organic functional layers is crucial.
[0005] The applicant's prior patent application CN117624245A discloses a method including formula 1 Metal complexes with structural ligands and their application in electroluminescent devices. This application focuses on the properties of metal complexes with specific structures and the effects they can bring when applied to devices. However, it does not focus on / teach the different effects that can be brought about by the combination of different materials in the organic layer of the device, especially it does not teach what kind of host material with a special structure should be selected when combined with luminescent materials that meet specific wavelength conditions, so as to improve the charge accumulation in the device and further improve the power efficiency of the device.
[0006] As the industry's demands for device performance continue to rise, in addition to the development of new materials, how to obtain devices with superior overall performance, especially improving the efficiency of blue-green light or blue light materials in devices while improving charge accumulation, reducing device capacitance, increasing device refresh rate, and providing users with a better visual experience, has become an urgent problem for researchers in the industry. Summary of the Invention
[0007] This invention aims to provide a novel organic electroluminescent device to solve at least some of the aforementioned problems. The novel organic electroluminescent device includes a cathode, an anode, and a first organic layer disposed between the cathode and the anode. The first organic layer comprises a first organic material having a structure of Formula 1, and the peak wavelength of the PL (photoluminescence) spectrum satisfies a specific condition (λ). max-PL The novel organic electroluminescent device of the present invention utilizes a first organic material having a specific formula 1 structure in conjunction with green light, blue-green light, or blue light (λ). max-PLThe application of a second organic material (≤524nm) further improves the device power efficiency (PE), reduces the charge per unit area (uQ) in the device, improves the charge accumulation in the device, reduces the device capacitance, and helps to improve the overall performance of the device.
[0008] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0009] anode,
[0010] cathode,
[0011] and a first organic layer disposed between the anode and the cathode; the first organic layer comprises a first organic material and a second organic material; the second organic material is a metal complex, and the λ of the second organic material... max-PL ≤524nm;
[0012] The first organic material has a structure represented by Formula 1:
[0013]
[0014] in,
[0015] V is selected from O, S, or Se;
[0016] V1-V8 are selected from C and CR each time they appear, either identically or differently. v Or, at least one of N, V5-V8 is selected from C and is linked to the triazine structure in Formula 1;
[0017] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0018] Each time ring A appears, it is selected from an aromatic ring having 6-30 carbon atoms, a heteroaromatic ring having 3-30 carbon atoms, or a combination thereof, either the same or different.
[0019] R a Each occurrence of the same or different R indicates mono- or poly-substitution; when multiple Rs exist... a At that time, the R a Same or different;
[0020] R a and R vEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0021] R a At least one of them is selected from cyano;
[0022] Adjacent substituent R v They can be arbitrarily connected to form a loop;
[0023] Adjacent substituent R a They can be arbitrarily connected to form a ring.
[0024] According to another embodiment of the present invention, a display component is also disclosed, which includes the organic electroluminescent device described in any of the foregoing embodiments.
[0025] According to another embodiment of the present invention, an electronic device is also disclosed, which includes the organic electroluminescent device described in any of the foregoing embodiments or the display component described in the foregoing embodiments.
[0026] The novel organic electroluminescent device disclosed in this invention utilizes a first organic material having a specific formula 1 structure and λ max-PL The application of a second organic material with a wavelength of ≤524nm further improves the power efficiency (PE) of the device, reduces the charge per unit area (uQ) in the device, improves the charge accumulation in the device, and enhances the overall performance of the device. Attached Figure Description
[0027] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the compounds and combinations of compounds disclosed herein.
[0028] Figure 2 This is an example graph of the capacitance-voltage (CV) characteristic curve of an organic electroluminescent device. Detailed Implementation
[0029] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be manufactured by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference. The OLED may further be provided with an encapsulation layer, not shown, to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.
[0030] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.
[0031] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.
[0032] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.
[0033] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.
[0034] The materials and structures described in this article can also be used in other organic electronic devices listed above.
[0035] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.
[0036] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.
[0037] In OLED devices, the movement, distribution, and accumulation of charge within the device can be analyzed by studying the device's capacitance-voltage (CV) characteristics. For example... Figure 2 This is an example graph showing the capacitance-voltage (CV) characteristic curve of a device. For example... Figure 2 As shown, depending on the applied bias voltage, the study of charge dynamics in the device can be simply divided into the following four cases:
[0038] 1) When the applied voltage V0 is less than the starting voltage V t At that time, i.e., V0 <V t Charge carriers (holes) cannot enter the device, and the device behaves like an insulator connected between the anode and cathode. Therefore, in this case, the capacitance of the device is a constant, and this capacitance is called the geometric capacitance C of the device. geo ;
[0039] 2) When the applied voltage V0 is greater than the starting voltage V t But less than voltage V Cmax When, i.e., V t <V0<V Cmax Holes begin to be injected into the device, and as holes accumulate inside the device, the capacitance of the device gradually increases.
[0040] 3) As the applied voltage V0 continues to increase, the capacitance of the device also continues to increase until the applied voltage V0 equals the device voltage V. Cmax That is, V0 = V Cmax The device capacitance reaches its maximum value C. max ;
[0041] 4) When the applied voltage V0 is greater than the voltage V Cmax After that, V0 > V CmaxElectrons begin to be injected into the device, followed by a recombination process of holes and electrons. As the accumulated charge carriers in the device are consumed, the capacitance of the device gradually decreases.
[0042] As used in this article, unless otherwise specified, "capacitance C" refers to the internal capacitance of the device. max "" refers to the device's maximum capacitance, also known as the maximum internal capacitance. It represents the peak value that the device's capacitance can reach at a specific frequency as the test voltage increases. Figure 2 As shown in the figure. Generally, the display industry pays more attention to the capacitance of OLED devices in the range of 100-1000Hz, and the most commonly used capacitance data is the capacitance data under the condition of 500Hz. Therefore, this article also conducts the CV curve test of the device under the condition of 500Hz.
[0043] Generally speaking, the starting voltage V of the device t The voltage at which charge carriers begin to be injected into the device (i.e., the voltage at which charge carriers begin to be injected) is greater than -1V. In this application, "charge Q" is defined as the voltage from -1V to V. Cmax The integral over capacitor C (e.g.) Figure 2 The gray area (shown in the image) represents the total charge accumulation within the device. The unit of charge Q is nanocoulomb (nC); the larger the Q, the greater the charge accumulation within the device.
[0044] As used in this article, "charge per unit area uQ" refers to the amount of charge accumulated per unit area of the device, that is, the total amount of charge per unit area, and the unit is nC / cm². 2 Specifically, uQ refers to the total amount of charge accumulated inside the device during voltage changes (from -1V to V). Cmax uQ is the ratio of the integrated area of capacitor C to the effective light-emitting area of the device. uQ is an important parameter of device performance, reflecting the charge distribution within the device and its charge injection and accumulation capabilities. In OLED devices, the amount of charge accumulation affects device performance, such as brightness and efficiency. The specific testing method for uQ of the device of this invention is described below.
[0045] As used herein, "effective light-emitting area" refers to the area in an organic electroluminescent device where, in a direction perpendicular to the light-emitting surface, the anode is in direct contact with the organic layer and simultaneously the organic layer is in direct contact with the cathode. As mentioned above, the effective light-emitting area of the device embodiments and comparative examples provided herein is 0.04 cm². 2 .
[0046] As used in this article, the second organic material's "λ" max-PL"λ" refers to the maximum emission wavelength (peak wavelength) of the photoluminescence (PL) spectrum of the second organic material. The λ of the second organic material used in this invention... max-PL The specific testing methods are described below.
[0047] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.
[0048] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0049] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.
[0050] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).
[0051] Definition of the term "substituent group"
[0052] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.
[0053] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.
[0054] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.
[0055] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.
[0056] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.
[0057] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.
[0058] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fenene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methyldiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.
[0059] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.
[0060] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.
[0061] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.
[0062] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.
[0063] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.
[0064] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.
[0065] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.
[0066] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.
[0067] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.
[0068] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.
[0069] In this disclosure, unless otherwise defined, the term "substituted alkyl," "substituted cycloalkyl," "substituted heteroalkyl," "substituted heterocyclic," "substituted aralkyl," "substituted alkoxy," "substituted aryloxy," "substituted alkenyl," "substituted alkynyl," "substituted aryl," "substituted heteroaryl," "substituted alkylsilyl," "substituted arylsilyl," "substituted alkylgermanium," "substituted arylgermanium," "substituted amino," "substituted acyl," "substituted carbonyl," and "substituted carboxylic acid" are used interchangeably. Substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester group, sulfinyl, sulfonyl, and phosphinyl. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having... Cycloalkyl groups with 3-20 carbon atoms, unsubstituted heteroalkyl groups with 1-20 carbon atoms, unsubstituted heterocyclic groups with 3-20 carbon atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, and unsubstituted aryl groups with 6-30 carbon atoms. Unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof having 0-20 carbon atoms.
[0070] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.
[0071] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.
[0072] In the compounds mentioned in this disclosure, polysubstituted means including disubstituted, up to the maximum range of available substitutions. When a substituent in a compound mentioned in this disclosure represents polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.
[0073] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.
[0074] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:
[0075]
[0076] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:
[0077]
[0078] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:
[0079]
[0080] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:
[0081]
[0082] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0083] anode,
[0084] cathode,
[0085] and a first organic layer disposed between the anode and the cathode; the first organic layer comprises a first organic material and a second organic material; the second organic material is a metal complex, and the λ of the second organic material... max-PL ≤524nm;
[0086] The first organic material has a structure represented by Formula 1:
[0087]
[0088] in,
[0089] V is selected from O, S, or Se;
[0090] V1-V8 are selected from C and CR each time they appear, either identically or differently. v Or, at least one of N, V5-V8 is selected from C and is linked to the triazine structure in Formula 1;
[0091] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0092] Each time ring A appears, it is selected from an aromatic ring having 6-30 carbon atoms, a heteroaromatic ring having 3-30 carbon atoms, or a combination thereof, either the same or different.
[0093] R a Each occurrence of the same or different R indicates mono- or poly-substitution; when multiple Rs exist... a At that time, the R a Same or different;
[0094] R a and R vEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0095] R a At least one of them is selected from cyano;
[0096] Adjacent substituent R v They can be arbitrarily connected to form a loop;
[0097] Adjacent substituent R a They can be arbitrarily connected to form a ring.
[0098] In this paper, "adjacent substituent R" v "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R v Any one or more of the substituents in the formed group can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0099] In this paper, "adjacent substituent R" a "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R a Any one or more of the substituents in the resulting group can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0100] In this embodiment, at least one of V5-V8 is selected from C and is linked to the triazine structure in Formula 1. This means that at least one of V5-V8 is selected from C and is linked to the triazine structure in Formula 1 (i.e., The structure (where * indicates a connection position) is connected.
[0101] According to one embodiment of the present invention, V7 is selected from C and has a triazine structure in Formula 1 (i.e., The structure (where * indicates a connection position) is connected.
[0102] According to one embodiment of the present invention, at least one of V1-V4 is selected from CR. v The R v Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.
[0103] According to one embodiment of the present invention, V4 is selected from CR v The R v Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, either identically or differently.
[0104] According to one embodiment of the present invention, V4 is selected from CR v The R v Each time it appears, it is selected from substituted or unsubstituted phenyl groups, either the same or different.
[0105] According to one embodiment of the present invention, the first organic material has a structure represented by Formula 1-1:
[0106]
[0107] in,
[0108] V is selected from O, S, or Se;
[0109] V1-V3, V5-V6, and V8 are selected from CR each time they appear, either identically or differently. v Or N;
[0110] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0111] When ring A1 and ring A2 appear in the same or different ways, they are selected from aromatic rings having 6-30 carbon atoms, heteroaromatic rings having 3-30 carbon atoms, or combinations thereof;
[0112] R a1 and R b Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.
[0113] R a2 Each occurrence, whether identical or different, indicates single or multiple substitution;
[0114] When there are multiple R a1 R a2 R b At that time, the R a1 R a2 R b Same or different;
[0115] R a1 R a2 R v and R b Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0116] R a2 At least one of them is selected from cyano;
[0117] Adjacent substituent R v R b They can be arbitrarily connected to form a loop;
[0118] Adjacent substituent R a1 R a2 They can be arbitrarily connected to form a ring.
[0119] In this paper, "adjacent substituent R" v R b "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R v Between the two substituents R b Between, substituent R v and R bBetween these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0120] In this paper, "adjacent substituent R" a1 R a2 "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R a1 Between the two substituents R a2 Between, substituent R a1 and R a2 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0121] According to one embodiment of the present invention, V is selected from O or S.
[0122] According to one embodiment of the present invention, V is selected from O.
[0123] According to one embodiment of the present invention, V1-V8 are selected from C or CR each time they appear, either identically or differently. v .
[0124] According to one embodiment of the present invention, ring A1 and / or ring A2 are selected from aromatic rings having 6-12 carbon atoms or heteroaromatic rings having 3-12 carbon atoms each time they appear.
[0125] According to one embodiment of the present invention, wherein the ring A1 and / or ring A2 are selected from benzene rings or 6-membered heteroaromatic rings each time they appear.
[0126] According to one embodiment of the present invention, R a1 R a2 R v and R b Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
[0127] According to one embodiment of the present invention, R a1 R a2 R v and R bEach time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, cyano, and combinations thereof.
[0128] According to one embodiment of the present invention, R a1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, and combinations thereof.
[0129] According to one embodiment of the present invention, R a1 Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and combinations thereof.
[0130] According to one embodiment of the invention, Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.
[0131] According to one embodiment of the invention, Ar, each time it appears, is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and combinations thereof.
[0132] According to one embodiment of the present invention, the first organic material is selected from the group consisting of compounds A-1 to A-112, wherein the specific structures of compounds A-1 to A-112 are as described in claim 6.
[0133] According to one embodiment of the present invention, the hydrogen in compounds A-1 to A-112 may be partially or completely replaced by deuterium.
[0134] According to one embodiment of the present invention, wherein the second organic material λ max-PL Satisfies: 500nm≤λ max-PL ≤522nm.
[0135] According to one embodiment of the present invention, wherein the second organic material λ max-PL Satisfies: 510nm≤λ max-PL ≤520nm.
[0136] According to one embodiment of the present invention, wherein the second organic material λ max-PL Satisfies: 513nm≤λ max-PL ≤518nm.
[0137] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the second organic material is ≤40 nm.
[0138] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the second organic material is ≤35 nm.
[0139] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the second organic material is ≤32 nm.
[0140] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the second organic material is 25 nm ≤ FWHM ≤ 32 nm.
[0141] According to one embodiment of the present invention, the second organic material is a metal complex comprising a metal M and a ligand L coordinated to the metal M. a L a It has the structure represented by Equation 2:
[0142]
[0143] in,
[0144] Metal M is selected from metals with a relative atomic mass greater than 40;
[0145] G1 and G2 are selected from single bonds, O or S, either the same or different each time they appear;
[0146] Ring C y Each occurrence is selected, either identically or differently, from aromatic rings having 6-24 ring atoms, heteroaromatic rings having 5-24 ring atoms, or combinations thereof; ring C y Connected to metal M via G1;
[0147] Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different.
[0148] X1-X4 are selected from C or CR each time they appear, either identically or differently. x Furthermore, two of X1-X4 are selected from C, one of which is connected to Y1, and the other is connected to G2.
[0149] X5-X8 are selected from CR each time they appear, either the same or different. x Or N;
[0150] Y1 and Y2 are selected from C or N each time they appear, either in the same or different ways.
[0151] R y Each occurrence of the same or different R indicates monosubstitution, polysubstitution, or no substitution; when multiple Rs exist... y At that time, the R y Same or different;
[0152] R x R y R' is selected from the group consisting of, in the same or different manner each time it appears: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0153] Adjacent substituent R y They can be arbitrarily connected to form a loop;
[0154] Adjacent substituents R', R x They can be arbitrarily connected to form a ring.
[0155] In this paper, "adjacent substituent R" y "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R y Any one or more of the substituents in the resulting group can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0156] In this paper, "adjacent substituents R', R x "Optionally connected to form a ring" is intended to indicate that adjacent substituent groups, for example, between two substituents R', and between two substituents R', are... x Between, substituents R' and R x Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0157] According to one embodiment of the present invention, at least one of X1-X4 is selected from CR x The R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
[0158] According to an embodiment of the present invention, the first metal complex has M(L) a ) m (L b ) n (L c ) q The general formula;
[0159] L a L b and L c These are the first, second, and third ligands coordinated with metal M, respectively, and L c and the L a or L b Are they the same or different; among them, L a L b and L c They can be selectively linked to form multidentate ligands;
[0160] m is selected from 1, 2, or 3; n is selected from 0, 1, or 2; q is selected from 0, 1, or 2; m + n + q equals the oxidation state of metal M; when m is greater than or equal to 2, multiple L a Same or different; when n equals 2, the two L bSame or different; when q equals 2, the two L c Same or different;
[0161] L b L c Each occurrence may be selected from any of the following structures, either identically or differently:
[0162]
[0163] in,
[0164] R1, R2, and R3 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution;
[0165] X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;
[0166] X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;
[0167] R1, R2, R3, R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted groups having 6-30 carbon atoms. Aryloxy groups, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0168] The ligand L b L c In the structure, adjacent substituents R1, R2, R3, R N1 RN2 R C1 and R C2 They can be arbitrarily connected to form a ring.
[0169] In this embodiment, adjacent substituents R1, R2, R3, R N1 R N2 R C1 and R C2 They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, between two substituents R1, between two substituents R2, between two substituents R3, between substituents R1 and R2, between substituents R1 and R3, between substituents R2 and R3, between substituents R1 and R2. N1 Between, substituents R2 and R N1 Between, substituents R1 and R C1 Between, substituents R1 and R C2 Between, substituents R2 and R C1 Between, substituents R2 and R C2 Between, substituents R1 and R N2 Between, substituents R2 and R N2 Between, and R C1 and R C2 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0170] For example, Adjacent substituents R1 and R2 can optionally connect to form a ring, wherein when R1 is optionally connected to form a ring, It can form including but not limited to The structure. Obviously, these substituents can also not be connected to each other to form a ring.
[0171] According to one embodiment of the present invention, the second organic material has M(L) a ) m (L b ) n It has a general formula and a structure represented by Equation 2:
[0172]
[0173] in,
[0174] Metal M is selected from metals with a relative atomic mass greater than 40;
[0175] L a and L b These are the first and second ligands that coordinate with metal M, respectively; where L a and L bThey can be selectively linked to form multidentate ligands;
[0176] m is selected from 1 or 2, n is selected from 1 or 2, and m + n equals the oxidation state of metal M; when m is 2, the two L a Same or different; when n is 2, the two L b Same or different;
[0177] Ring C u , Ring C w and ring C y Each time it appears, it is selected from the same or different aromatic rings having 6-24 ring atoms, heteroaromatic rings having 5-24 ring atoms, or combinations thereof;
[0178] G1, G2, G3, and G4 are selected from single bonds, O, or S each time they appear, either the same or different.
[0179] Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different.
[0180] X1-X4 are selected from C, CR each time they appear, either identically or differently. x or CR n Furthermore, two of X1-X4 are selected from C, one of which is connected to Y1, and the other is connected to G2; and at least one of X1-X4 is selected from CR. n ;
[0181] X5-X8 are selected from CR each time they appear, either the same or different. x Or N;
[0182] Y1 and Y2 are selected from C or N each time they appear, either in the same or different ways.
[0183] R y R u and R w Each occurrence of the same or different R indicates monosubstitution, polysubstitution, or no substitution; when multiple Rs exist... y At that time, the R y Same or different; when multiple R exist u At that time, the R u Same or different; when multiple R exist w At that time, the R w Same or different;
[0184] R nEach time it appears, it is selected from the group consisting of the same or different groups of the following: halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
[0185] R x R y R u R w R' is selected from the group consisting of, in the same or different manner each time it appears: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0186] Adjacent substituent R u R w They can be arbitrarily connected to form a loop;
[0187] Adjacent substituent R y They can be arbitrarily connected to form a loop;
[0188] Adjacent substituents R', R x They can be arbitrarily connected to form a ring.
[0189] In this paper, "adjacent substituent R" y "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R y Any one or more of the substituents in the resulting group can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0190] In this paper, "adjacent substituents R', R x "Optionally connected to form a ring" is intended to indicate that adjacent substituent groups, for example, between two substituents R', and between two substituents R', are... x Between, substituents R' and R x Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0191] In this paper, "adjacent substituent R" u R w "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R u Between the two substituents R w Between, substituent R u and R w Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0192] According to an embodiment of the present invention, in formula 2 or formula 2-1 The structure is selected from any of the following structures each time it appears, either identically or differently:
[0193]
[0194] in,
[0195] R y Each occurrence of the same or different R indicates monosubstituted, polysubstituted, or unsubstituted; when multiple Rs exist in any structure y At that time, the R y Same or different;
[0196] R yEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0197] Adjacent substituent R y They can be arbitrarily connected to form a loop;
[0198] Here, "#" indicates the position connected to G1. Indicates the position connected to X1, X2, X3, or X4.
[0199] According to one embodiment of the present invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt each time it appears.
[0200] According to one embodiment of the present invention, the metal M is selected from Pt or Ir each time it appears.
[0201] According to one embodiment of the present invention, the metal complex has Ir(L) a ) m (L b ) 3-m The general formula structure, and the structure represented by Equation 3:
[0202]
[0203] in,
[0204] m is selected from 1 or 2; when m is selected from 1, the two L b Same or different; when m is selected from 2, the two L a Same or different;
[0205] Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist simultaneously, the two R' are either the same or different.
[0206] X3, X5-X8 are selected from CR each time they appear, either identically or differently. x Or N;
[0207] R y R u and R w Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0208] R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, and combinations thereof.
[0209] R', R x R y R u and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0210] Adjacent substituent R u R w They can be arbitrarily connected to form a loop;
[0211] Adjacent substituent R y They can be arbitrarily connected to form a loop;
[0212] Adjacent substituents R', R x They can be arbitrarily connected to form a ring.
[0213] In this paper, "adjacent substituent R" y "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R y Any one or more of the substituents in the resulting group can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0214] In this paper, "adjacent substituents R', R x "Optionally connected to form a ring" is intended to indicate that adjacent substituent groups, for example, between two substituents R', and between two substituents R', are... x Between, substituents R' and R x Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0215] In this paper, "adjacent substituent R" u R w "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R u Between the two substituents R w Between, substituent R u and R w Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0216] According to one embodiment of the invention, Z is selected from O or S each time it appears, either the same or different.
[0217] According to one embodiment of the present invention, Z is selected from O.
[0218] According to one embodiment of the present invention, R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 6 carbon atoms, and combinations thereof.
[0219] According to one embodiment of the present invention, R nEach time it appears, it is selected from the group consisting of the following, either identically or differently: substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, and combinations thereof.
[0220] According to one embodiment of the present invention, R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.
[0221] According to one embodiment of the present invention, at least one of X5-X8 is selected from CR. x And the R x Selected from cyano or fluorine.
[0222] According to one embodiment of the present invention, X7 or X8 is selected from CR x And the R x Selected from cyano or fluorine.
[0223] According to one embodiment of the present invention, X7 is selected from CR x And the R x Selected from cyano.
[0224] According to one embodiment of the present invention, at least two of X5-X8 are selected from CR x One of the Rs x Selected from cyano or fluorine, another of the R x Selected from deuterium, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.
[0225] According to one embodiment of the present invention, X7 is selected from CR x Wherein R x Selected from cyano or fluorine, X8 is selected from CR x The R x Selected from deuterium, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.
[0226] According to one embodiment of the present invention, X7 is selected from CR x And the R x Selected from cyano or fluorine, and X8 selected from CR x And the R x Selected from deuterium, substituted or unsubstituted aryl groups having 6-12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-12 carbon atoms, and combinations thereof.
[0227] According to one embodiment of the present invention, R yEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
[0228] According to one embodiment of the present invention, R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, and combinations thereof.
[0229] According to one embodiment of the present invention, at least one R y Each time it appears, it is selected from the group consisting of the same or different groups of: deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, and combinations thereof.
[0230] According to one embodiment of the present invention, R u and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted 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 alkylgermanium groups having 3-20 carbon atoms, and combinations thereof.
[0231] According to one embodiment of the present invention, R u and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, and combinations thereof.
[0232] According to one embodiment of the present invention, R u and R w Each time it appears, it is selected from hydrogen or deuterium, either the same or different.
[0233] According to one embodiment of the present invention, the second organic material is selected from the group consisting of metal complex 1 to metal complex 69, the specific structures of said metal complex 1 to metal complex 69 being as described in claim 19.
[0234] According to one embodiment of the present invention, the first organic layer further comprises a third organic material, the third organic material comprising at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, aromatic amine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
[0235] According to one embodiment of the present invention, the first organic layer further comprises a third organic material, the third organic material comprising at least one chemical group selected from the group consisting of: benzene, aromatic amine, carbazole, indolecarbazole, fluorene, dibenzothiophene, dibenzofuran, and combinations thereof.
[0236] According to one embodiment of the present invention, the third organic material has a structure represented by formula 3-1 or formula 4-1:
[0237]
[0238] in,
[0239] G is selected from C(R) each time it appears, either identically or differently. g )2, NR g O or S;
[0240] L T Each occurrence is the same or different of a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.
[0241] T is selected from C and CR each time it appears, either identically or differently. t Or N;
[0242] R t R gEach time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;
[0243] Ar3 and Ar4, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;
[0244] Adjacent substituent R t R g They can be arbitrarily connected to form a ring.
[0245] In this paper, "adjacent substituent R" t R g "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R t Between the two substituents R g Between, substituent R t and R g Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0246] According to one embodiment of the present invention, the third organic material has a structure represented by one of formulas 3-a to 3-j, and 4-a to 4-f:
[0247]
[0248] in,
[0249] T is selected from CR each time it appears, either the same or different.t Or N;
[0250] G is selected from C(R) each time it appears, either identically or differently. g )2, NR g O or S; when multiple Rs exist simultaneously g At that time, multiple R g Same or different;
[0251] L T Each occurrence is the same or different of a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.
[0252] Ar3 and Ar4, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0253] R t and R g Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;
[0254] Adjacent substituent R t R g They can be arbitrarily connected to form a ring.
[0255] According to one embodiment of the present invention, in formulas 3-a to 3-j and 4-a to 4-f, T is selected from CR each time it appears, either identically or differently. t Or N, and at least one of them T is selected from N, for example, one T or two T are selected from N.
[0256] According to one embodiment of the present invention, the third organic material is selected from the group consisting of compounds PH-1 to PH-114:
[0257]
[0258]
[0259]
[0260]
[0261]
[0262]
[0263]
[0264]
[0265]
[0266]
[0267]
[0268] In the above compounds PH-1 to PH-114, hydrogen can be partially or completely replaced by deuterium.
[0269] According to one embodiment of the present invention, the first organic layer is a light-emitting layer.
[0270] According to one embodiment of the present invention, the first organic layer is a light-emitting layer, wherein the second organic material in the light-emitting layer is a metal complex, and the metal complex is doped in the first organic material and the third organic material, wherein the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.
[0271] According to another embodiment of the present invention, the metal complex accounts for 3%-13% of the total weight of the light-emitting layer.
[0272] According to one embodiment of the present invention, the organic electroluminescent device further includes a hole injection layer. The hole injection layer can be a single-material functional layer or a functional layer containing multiple materials. The most commonly used multiple materials are hole transport materials doped with a certain proportion of p-type conductive doped materials. Common p-type doped materials include:
[0273]
[0274] According to another embodiment of the present invention, a display component is also disclosed, which includes the organic electroluminescent device described in any of the above embodiments.
[0275] According to another embodiment of the present invention, an electronic device is also disclosed, which includes the organic electroluminescent device described in any of the above embodiments, or includes the display component described in the above embodiments.
[0276] Combination with other materials
[0277] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.
[0278] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, blocking layers, implantation layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.
[0279] The first and second organic materials used in this invention can be readily obtained by referring to the preparation methods in the prior art or the applicant's earlier applications. For example, the first organic material of this invention can be prepared by referring to CN116162083A, and the second organic material can be prepared by referring to CN117624245A, CN111518139ACN2023107843394. Their preparation methods will not be elaborated here. The documents listed above are merely exemplary, and those skilled in the art can easily obtain other documents.
[0280] The testing method for the PL spectral correlation data of the second organic material of this invention is as follows: A fluorescence spectrophotometer (model F98) manufactured by Shanghai Prism Technology Co., Ltd. was used to determine the maximum emission wavelength (λ) of the PL spectrum of the material under test. max-PL The data included the peak width at half maximum (FWHM). Specifically, the sample was prepared with HPLC-grade toluene to a concentration of 1×10⁻⁶. -6 A mol / L solution was prepared by purging nitrogen gas to remove oxygen for 5 minutes, then excited with light at a wavelength of 500 nm at room temperature (298 K) and its emission spectrum was measured. The full width at half maximum (FWHM) and peak wavelength (λ) of the PL of the metal complexes 42 and 64 used in this invention were directly read from the spectrum. max-PL The data is shown in Table 1:
[0281] Table 1 PL spectral data of the second organic material
[0282] Second organic material FWHM(nm) max-PL (nm) Metal complex 42 28.5 515 Metal complex 64 29.1 515
[0283] Besides the inherent properties of organic materials, the combination of different materials within a device also has a crucial impact on device performance. Selecting a combination of materials with better performance matching can further improve device performance. In their research on green / blue-green / blue light-emitting devices, the inventors discovered that when a first organic material with a specific structure (Formula 1) is selected and the peak wavelength is within a specific range (λ... max-PL When green, blue-green, or blue light (≤524nm) light is combined with other organic materials, the overall performance of the device can be further improved, especially in terms of power efficiency (PE), reduced charge per unit area (uQ), and improved charge accumulation, which is beneficial to enhancing the overall performance of the device. Several specific device examples will be provided below for detailed explanation.
[0284] Device Examples
[0285] The fabrication method of the organic electroluminescent device is not limited. In the device embodiments, the device characteristics are tested using conventional equipment in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) and methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the sample definitively and unaffected, the above-mentioned related content will not be elaborated in this patent. The fabrication method of the following device embodiments is only an example and should not be construed as a limitation. Those skilled in the art can reasonably improve the fabrication method of the following device embodiments based on the prior art. For example, the proportion of various materials in the light-emitting layer is not particularly limited. Those skilled in the art can reasonably select within a certain range based on the prior art. For example, based on the total weight of the light-emitting layer materials, the main material can account for 80%-99%, and the light-emitting material can account for 1%-20%; or the main material can account for 90%-99%, and the light-emitting material can account for 1%-10%; or the main material can account for 94%-99%, and the light-emitting material can account for 1%-6%. In addition, the main material can be one or two materials, wherein the ratio of the two main materials to the main material can be 99:1 to 1:99; or, the ratio can be 80:20 to 20:80; or, the ratio can be 60:40 to 40:60.
[0286] Device Example 1: Fabrication of an organic electroluminescent device.
[0287] First, a 0.7mm thick glass substrate is used, on which a pre-patterned design is applied. Thick indium tin oxide (ITO) was used as the anode. The substrate was washed with deionized water and detergent, and then treated with oxygen plasma and UV ozone. Subsequently, the substrate was dried in a glove box to remove moisture and then placed on a support frame into a vacuum chamber. The organic layer specified below was applied at a vacuum degree of approximately 10... -6 Torr The deposition rate was achieved sequentially on the anode layer via vacuum thermal evaporation. First, compounds HT and HT1 were simultaneously deposited as a hole injection layer (HIL, weight ratio 97:3, thickness...). The vapor-deposited compound HT is used as a hole transport layer (HTL, thickness). Next, compound PH-1 is vapor-deposited as an electron blocking layer (EBL, thickness). Then, compound PH-1, compound A-5 (first organic material), and metal complex 42 (second organic material) are simultaneously vapor-deposited as the light-emitting layer, i.e., the first organic layer of the present invention (EML, weight ratio 55.2:36.8:8, thickness). Subsequently, compound HB was deposited on the EML for a hole blocking layer (HBL, thickness). Compounds ET and Liq were co-deposited as an electron transport layer (ETL, weight ratio 40:60, thickness...). ), vapor deposition Liq was used as the electron injection layer (EIL), and finally, metallic aluminum was deposited as the cathode. The device is then transferred back to the glove box and sealed with a glass cover to complete the device.
[0288] Device Example 2
[0289] The preparation method of device embodiment 2 is the same as that of device embodiment 1, except that compound A-55 is used instead of compound A-5 as the first organic material in the light-emitting layer.
[0290] Device Example 3
[0291] The preparation method of device example 3 is the same as that of device example 1, except that compound A-84 is used instead of compound A-5 as the first organic material in the light-emitting layer.
[0292] Device Example 4
[0293] The preparation method of device embodiment 4 is the same as that of device embodiment 1, except that compound A-2 is used instead of compound A-5 as the first organic material in the light-emitting layer, and metal complex 64 is used instead of metal complex 42 as the second organic material.
[0294] Device Comparison Example 1
[0295] The preparation method of Comparative Example 1 is the same as that of Example 1, except that compound C-1 is used instead of compound A-5 in the light-emitting layer.
[0296] Device Comparison Example 2
[0297] The fabrication method of Comparative Example 2 is the same as that of Comparative Example 1, except that metal complex 64 is used instead of metal complex 42 in the light-emitting layer.
[0298] The structure and thickness of the light-emitting layer of the device are shown in Table 2 below. The layers use more than one material and are obtained by doping different compounds in the stated weight ratios.
[0299] Table 2. Device light-emitting layer structures of Examples 1-4 and Comparative Examples 1-2
[0300]
[0301]
[0302] The structure of the materials used in the device is shown below:
[0303]
[0304] Table 3 summarizes the device performance of Examples 1 to 4 and Comparative Examples 1 to 2. The color coordinates CIE(x,y) and power efficiency (PE, lm / W) are given at a current density of 15 mA / cm². 2 The capacitance uQ per unit area was measured using an impedance analyzer (Keysight E4990A). A DC bias voltage of -4V to 5V was applied to the electrodes of the device, while a 100mV sinusoidal AC voltage signal was simultaneously superimposed. Tests were performed at an AC voltage frequency of 500Hz, and the CV curve of the device was measured. The capacitance was measured by applying voltages from -1V to V... Cmax The total charge Q accumulated inside the device is obtained by integrating the capacitance C. The relationship between the total charge Q and the effective light-emitting area of the device (0.04 cm²) is then calculated. 2 The ratio of the charge per unit area (uQ) of the device was used to obtain the charge per unit area. These data were recorded and shown in Table 3.
[0305] Table 3 Device data for Examples 1 to 4 and Comparative Examples 1 to 2
[0306]
[0307] discuss:
[0308] As shown in Tables 2 and 3, the second organic material used in Device Examples 1-4 and Comparative Examples 1-2 of this invention all employs the maximum emission wavelength λ of the PL spectrum. max-PL Blue-green light materials with a wavelength of ≤524nm. Table 3 shows that the color coordinates of Examples 1-4 and Comparative Examples 1-2 are basically the same, meaning the device colors are essentially equivalent.
[0309] A comparison reveals that the only difference between Examples 1 to 3 and Comparative Example 1 lies in whether the first organic layer of the device utilizes the first organic material of the present invention with a specific formula 1 structure combined with a second organic material whose maximum emission wavelength in the PL spectrum meets specific conditions. Table 3 shows that, compared to Comparative Example 1, which uses a combination of a non-inventive first organic material (compound C-1) and a second organic material, the device of the present invention, using a first organic material with a specific formula 1 structure (compound A-5) and λ... max-PLExample 1, which utilizes a second organic material (metal complex 42) under specific conditions, exhibits superior device performance, such as a further increase in PE and a decrease in uQ. Specifically, PE is increased by 15%, and uQ is reduced by 55%. Similarly, in device examples 2-3, two first organic materials with the same framework of Formula 1 but different structures are used in combination with the second organic material of the present invention. Data shows that Examples 2 and 3 also demonstrate excellent overall performance, achieving increases in PE and decreases in uQ compared to Comparative Example 1, with PE increases ranging from 15% to 18% and uQ decreases ranging from 54% to 64%.
[0310] The difference between Example 4 and Comparative Example 2 lies solely in whether the first organic material of the present invention, having a specific formula 1 structure, is used in combination with a second organic material whose maximum emission wavelength in the PL spectrum meets specific conditions. Table 3 shows that, compared to Comparative Example 2, the first organic material (compound A-2) of the present invention, having a specific formula 1 structure, and a second organic material whose maximum emission wavelength in the PL spectrum meets specific conditions, are more effective in this application. max-PL Devices combining a second organic material (metal complex 64) under specific conditions exhibit superior overall performance: PE is increased by 16% and uQ is reduced by 51%.
[0311] The above data shows that by selecting the first organic material of the present invention with a specific structure of Formula 1 and combining it with green / blue-green / blue light materials whose maximum emission wavelength of the PL spectrum meets specific conditions, a breakthrough improvement in device performance can be achieved. In particular, while improving the power efficiency of the device, it also further improves the charge accumulation in the device and reduces the device capacitance, which has broad prospects for commercial applications.
[0312] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.
Claims
1. An organic electroluminescent device, comprising: anode, cathode, And a first organic layer disposed between the anode and the cathode; The first organic layer comprises a first organic material and a second organic material; The second organic material is a metal complex, and the λ of the second organic material max-PL ≤524nm; The first organic material has a structure represented by Formula 1: in, V is selected from O, S, or Se; V1-V8 are selected from C and CR each time they appear, either identically or differently. v Or, at least one of N, V5-V8 is selected from C and is linked to the triazine structure in Formula 1; Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Each time ring A appears, it is selected from an aromatic ring having 6-30 carbon atoms, a heteroaromatic ring having 3-30 carbon atoms, or a combination thereof, either the same or different. R a Each occurrence of the same or different R indicates mono- or poly-substitution; when multiple Rs exist... a At that time, the R a Same or different; R a and R v Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; R a At least one of them is selected from cyano; Adjacent substituent R v They can be arbitrarily connected to form a loop; Adjacent substituent R a They can be arbitrarily connected to form a ring.
2. The organic electroluminescent device as described in claim 1, wherein, The first organic material has a structure represented by formula 1-1: in, V is selected from O, S, or Se; preferably, V is selected from O or S; more preferably, V is selected from O; V1-V3, V5-V6, and V8 are selected from CR each time they appear, either identically or differently. v Or N; Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; When ring A1 and ring A2 appear in the same or different ways, they are selected from aromatic rings having 6-30 carbon atoms, heteroaromatic rings having 3-30 carbon atoms, or combinations thereof; R a1 and R b Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted. R a2 Each occurrence, whether identical or different, indicates single or multiple substitution; R a1 R a2 R v and R b Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; R a2 At least one of them is selected from cyano; Adjacent substituent R v R b They can be arbitrarily connected to form a loop; Adjacent substituent R a1 R a2 They can be arbitrarily connected to form a ring.
3. The organic electroluminescent device as described in claim 1 or 2, wherein, V1-V8 are selected from C or CR each time they appear, either identically or differently. v ; Preferably, R a1 R a2 R v and R b Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, cyano groups, and combinations thereof. More preferably, R a1 R a2 R v and R b Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, cyano, and combinations thereof.
4. The organic electroluminescent device as described in claim 2, wherein, When ring A1 and / or ring A2 appear, they are selected from aromatic rings having 6-12 carbon atoms or heteroaromatic rings having 3-12 carbon atoms, either the same or different each time. Preferably, the rings A1 and / or A2 are selected from benzene rings or 6-membered heteroaromatic rings each time they appear.
5. An organic electroluminescent device as described in claim 1 or 2, wherein, Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof; Preferably, Ar, each time it appears, is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and combinations thereof.
6. The organic electroluminescent device as described in claim 1, wherein, The first organic material is selected from the group consisting of compounds A-1 to A-130, and the specific structures of compounds A-1 to A-130 are shown below: Optionally, the hydrogen in compounds A-1 to A-130 may be partially or completely replaced by deuterium.
7. The organic electroluminescent device according to any one of claims 1-6, wherein, The second organic material λ max-PL Satisfies: 500nm≤λ max-PL ≤522nm; preferably, the λ of the second organic material max-PL Satisfies: 510nm≤λ max-PL ≤520nm.
8. The organic electroluminescent device as described in claim 1 or 7, wherein, The full width at half maximum (FWHM) of the second organic material is ≤40nm, preferably ≤35nm, and more preferably ≤32nm.
9. The organic electroluminescent device as described in claim 1, 7, or 8, wherein, The second organic material is a metal complex, which comprises a metal M and a ligand L coordinated to the metal M. a L a It has a structure represented by Equation 2: in, Metal M is selected from metals with a relative atomic mass greater than 40; G1 and G2 are selected from single bonds, O or S, either the same or different each time they appear; Ring C y Each occurrence is selected, either identically or differently, from aromatic rings having 6-24 ring atoms, heteroaromatic rings having 5-24 ring atoms, or combinations thereof; ring C y Connected to metal M via G1; Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different. X1-X4 are selected from C or CR each time they appear, either identically or differently. x Furthermore, two of X1-X4 are selected from C, one of which is connected to Y1, and the other is connected to G2. X5-X8 are selected from CR each time they appear, either the same or different. x Or N; Y1 and Y2 are selected from C or N each time they appear, either in the same or different ways. R y Each occurrence of the same or different R indicates monosubstitution, polysubstitution, or no substitution; when multiple Rs exist... y At that time, the R y Same or different; R x R y R' is selected from the group consisting of, in the same or different manner each time it appears: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R y They can be arbitrarily connected to form a loop; Adjacent substituents R', R x They can be arbitrarily connected to form a loop; Preferably, at least one of X1-X4 is selected from CR x The R x It is selected from halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, cyano groups, and combinations thereof.
10. The organic electroluminescent device as claimed in claim 1, wherein, The second organic material has M(L) a ) m (L b ) n It has a general formula and a structure represented by Equation 2-1: in, Metal M is selected from metals with a relative atomic mass greater than 40; preferably, metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt each time it appears; more preferably, metal M is selected from Pt or Ir each time it appears. L a and L b These are the first and second ligands that coordinate with metal M, respectively; where L a and L b They can be selectively linked to form multidentate ligands; m is selected from 1 or 2, n is selected from 1 or 2, and m + n equals the oxidation state of metal M; when m is 2, the two L a Same or different; when n is 2, the two L b Same or different; Ring C u , Ring C w and ring C y Each time it appears, it is selected from the same or different aromatic rings having 6-24 ring atoms, heteroaromatic rings having 5-24 ring atoms, or combinations thereof; G1, G2, G3, and G4 are selected from single bonds, O, or S each time they appear, either the same or different. Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different. X1-X4 are selected from C, CR each time they appear, either identically or differently. x or CR n Furthermore, two of X1-X4 are selected from C, one of which is connected to Y1, and the other is connected to G2; and at least one of X1-X4 is selected from CR. n ; X5-X8 are selected from CR each time they appear, either the same or different. x Or N; Y1 and Y2 are selected from C or N each time they appear, either in the same or different ways. R y R u and R w Each occurrence of the same or different R indicates monosubstitution, polysubstitution, or no substitution; when multiple Rs exist... y At that time, the R y Same or different; when multiple R exist u At that time, the R u Same or different; when multiple R exist w At that time, the R w Same or different; R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof. R x R y R u R w R' is selected from the group consisting of, in the same or different manner each time it appears: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R u R w They can be arbitrarily connected to form a loop; Adjacent substituent R y They can be arbitrarily connected to form a loop; Adjacent substituents R', R x They can be arbitrarily connected to form a ring.
11. The organic electroluminescent device as claimed in claim 9 or 10, wherein, In Equations 2 and 2-1 The structure is selected from any of the following structures each time it appears, either identically or differently: in, R y Each occurrence of the same or different R indicates monosubstituted, polysubstituted, or unsubstituted; when multiple Rs exist in any structure y At that time, the R y Same or different; R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R y They can be arbitrarily connected to form a loop; Here, "#" indicates the position connected to G1. Indicates the position connected to X1, X2, X3, or X4.
12. The organic electroluminescent device as claimed in claim 1, wherein, The second organic material has Ir(L) a ) m (L b ) 3-m The general formula structure, and the structure represented by Equation 3: in, m is selected from 1 or 2; when m is selected from 1, the two L b Same or different; when m is selected from 2, the two L a Same or different; Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist simultaneously, the two R' are either the same or different. X3, X5-X8 are selected from CR each time they appear, either identically or differently. x Or N; R y R u and R w Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, and combinations thereof. R', R x R y R u and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R u R w They can be arbitrarily connected to form a loop; Adjacent substituent R y They can be arbitrarily connected to form a loop; Adjacent substituents R', R x They can be arbitrarily connected to form a ring.
13. The organic electroluminescent device according to any one of claims 9-12, wherein, Z is selected from O or S each time it appears, either the same or different; preferably, Z is selected from O.
14. The organic electroluminescent device according to any one of claims 10-12, wherein, R n Each time it appears, it is selected from the group consisting of the following, either the same or different: fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 6 carbon atoms, and combinations thereof. Preferably, R n Each time it appears, it is selected from the group consisting of the following, either identically or differently: substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, and combinations thereof; More preferably, R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.
15. The organic electroluminescent device according to any one of claims 9-14, wherein, At least one of X5-X8 is selected from CR. x And the R x Selected from cyano or fluorine; Preferably, X7 or X8 is selected from CR. x And the R x Selected from cyano or fluorine; More preferably, the X7 is selected from CR x And the R x Selected from cyano.
16. The organic electroluminescent device according to any one of claims 9-15, wherein, At least two of the X5-X8 models are selected from CR. x One of the R mentioned x Selected from cyano or fluorine, another of the R x Selected from deuterium, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; Preferably, X7 is selected from CR x And the R x Selected from cyano or fluorine, and X8 selected from CR x And the R x Selected from deuterium, substituted or unsubstituted aryl groups having 6-12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-12 carbon atoms, and Its combination.
17. The organic electroluminescent device according to any one of claims 9-16, wherein, R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof. Preferably, R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, and combinations thereof. More preferably, at least one R y Each time it appears, it is selected from the group consisting of the same or different groups of: deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, and combinations thereof.
18. The organic electroluminescent device according to any one of claims 10-17, wherein, R u and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted 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 alkylgermanium groups having 3-20 carbon atoms, and combinations thereof; Preferably, R u and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, and combinations thereof. More preferably, R u and R w Each time it appears, it is selected from hydrogen or deuterium, either the same or different.
19. The organic electroluminescent device as claimed in claim 1, wherein, The second organic material is selected from the group consisting of metal complex 1 to metal complex 69, and the specific structures of metal complex 1 to metal complex 69 are shown below:
20. The organic electroluminescent device as claimed in claim 1, wherein, The first organic layer further comprises a third organic material, the third organic material comprising at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, aromatic amine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof; Preferably, the first organic layer is a light-emitting layer, the first organic material and the third organic material are the main materials, and the second organic material is a phosphorescent material.
21. A display component comprising an organic electroluminescent device as described in any one of claims 1-20.
22. An electronic component comprising an organic electroluminescent device as described in any one of claims 1-20, or a display component as described in claim 21.