Organic light-emitting device

Abstract

Disclosed is an organic electroluminescent device. The organic electroluminescent device comprises an anode, a cathode, a first organic layer and a second organic layer, wherein the first organic layer and the second organic layer are arranged between the anode and the cathode; the first organic layer includes a first organic material represented by Formula 1, and the second organic layer includes a second organic material represented by Formula 2. The first organic material may be used as a hole transport material in an organic electroluminescent device, and the second organic material may be used as an electron blocking material in an organic electroluminescent device. The electroluminescent device can maintain low voltage and high efficiency or further improve the efficiency, especially the service life of the device can be greatly prolonged unexpectedly, and the device has very excellent comprehensive performance. An electronic assembly is also disclosed.

Description

TECHNICAL FIELD

[0001] The present application relates to organic electronic devices, in particular to an organic electroluminescent device. More particularly, to an organic electroluminescent device comprising a first organic layer comprising a first organic material and a second organic layer comprising a second organic material, and to an electronic assembly comprising said organic electroluminescent device. BACKGROUND

[0002] Organic electronic devices include, but are not limited to, the following kinds: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.

[0003] In 1987, Tang and Van Slyke at Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole-transport layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transport and light-emitting layers (Applied Physics Letters, 1987, 51(12): 913-915). Upon biasing the device, green light emitted from the device. This invention laid the foundation for the development of modern organic light emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are self-emissive solid state devices, they offer great potential for display and lighting applications. In addition, the intrinsic properties of organic materials, such as their flexibility, can make them well suited for special applications, such as fabrication on flexible substrates.

[0004] OLEDs can be categorized into three different types according to their light emission mechanism. OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It only uses singlet emission. The triplet states generated in the device are wasted through a nonradiative decay channel. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metals containing complexes as emitters. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs have directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small molecule and polymer OLEDs according to the form of materials used. Small molecules refer to any organic or organometallic materials that are not polymers. The molecular weight of small molecules can be large as long as they have precise structures. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant light-emitting groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

[0006] There are various OLED manufacturing methods. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution methods if the materials can be dissolved or dispersed in solvents.

[0007] The emission color of OLEDs can be achieved by the design of the light-emitting material structure. OLEDs can include one light-emitting layer or multiple light-emitting layers to achieve the desired spectrum. Green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays usually use a hybrid strategy, using blue fluorescent and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, it is desirable to have more saturated emission spectrum, higher efficiency, and longer device lifetime.

[0008] KR20170100698A discloses a light emitting diode having a structure in which a first electrode, a second electrode, and a light emitting layer are sequentially stacked on a substrate, and the light emitting layer includes a first light emitting layer and a second light emitting layer, and the first light emitting layer includes a first host and a first dopant, and the second light emitting layer includes a second host and a second dopant. Compounds of the structure, and specific compounds of the structure are disclosed: This patent application focuses on the properties of the compounds themselves, and the compounds are applied as hole transport materials in electroluminescent devices. This patent application does not disclose or teach the influence of the compounds on the performance of the devices when used in combination with specific hole transport materials as electron blocking materials.

[0009] The previous patent application CN118108751A of the present inventors discloses a compound having the structure , wherein Ar1 has the structure represented by , and discloses specific compounds , etc. This patent application does not disclose or teach the influence of the compounds on the performance of the devices when used in combination with specific hole transport materials.

[0010] CN103108859A discloses a compound having the structure , and discloses specific compounds , etc. This patent application focuses on the properties of the compounds themselves, and the amine fragment in the compounds is connected to the 2-position of the spirobifluorene fragment. This application does not disclose or teach compounds with other specific connection positions between the spirobifluorene fragment and the amine fragment, nor does it disclose or teach the influence of the compounds on the performance of the devices when used in combination with specific electron blocking materials as hole transport materials.

[0011] In order to improve the overall performance of OLED devices, such as reducing voltage, improving efficiency and lifetime, etc., on the one hand, it is very important to develop new organic materials with better performance, and on the other hand, the matching between organic materials is also very important. Therefore, it is also a technical problem to be solved by researchers in the field to continuously develop more matched material combinations so that they can be applied to specific organic functional layers to obtain more excellent device performance. SUMMARY

[0012] The present application aims to provide a new electroluminescent device containing a first organic material in a first organic layer and a second organic material in a second organic layer to solve at least part of the above problems. The first organic material has a structure represented by formula 1, and the second organic material has a structure represented by formula 2. The first organic material can be used as a hole transport material in an organic electroluminescent device, and the second organic material can be used as an electron blocking material in an organic electroluminescent device. The electroluminescent device can maintain low voltage, maintain high efficiency or further improve efficiency, while significantly improving device lifetime, providing better overall device performance.

[0013] According to one embodiment of the present application, an organic electroluminescent device is disclosed, comprising:

[0014] anode,

[0015] cathode,

[0016] And a first organic layer and a second organic layer disposed between the anode and the cathode,

[0017] Wherein, the first organic layer contains a first organic material, and the second organic layer contains a second organic material;

[0018] The first organic material has a structure represented by Formula 1:

[0019]

[0020] L1, L2 and L3, each time appearing, are selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0021] Ar1 and Ar2, 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;

[0022] R1 and R2 appearing the same or different each time indicate monosubstitution, polysubstitution, or no substitution;

[0023] R1 and R2, each time appearing, are 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... 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;

[0024] Adjacent substituents L1, L2, L3, R1, R2, Ar1, and Ar2 can optionally be linked to form a ring;

[0025] The second organic material has a structure represented by Formula 2:

[0026]

[0027] R a R b R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0028] R a R b R c 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;

[0029] Ar a and Ar b Each time it appears, it is selected from the same or different groups of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted anthrayl, substituted or unsubstituted pyrene, or combinations thereof;

[0030] L a L b Lc Each time it appears, it is selected from the same or different single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted phenanthroline, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted pyreneylene, or combinations thereof;

[0031] Adjacent substituent R a R b R c They can be arbitrarily connected to form a ring.

[0032] According to another embodiment of the present invention, an electronic component comprising an organic electroluminescent device is also disclosed, wherein the specific structure of the organic electroluminescent device is as shown in the foregoing embodiment.

[0033] The novel organic electroluminescent device disclosed in this invention comprises an anode, a cathode, and a first organic layer and a second organic layer disposed between the anode and the cathode. The first organic layer comprises a first organic material having a specific structure represented by Formula 1, and the second organic layer comprises a second organic material having a specific structure represented by Formula 2. The first organic material can be used as a hole transport material in the organic electroluminescent device, and the second organic material can be used as an electron blocking material in the organic electroluminescent device. The electroluminescent device can maintain low voltage, maintain high efficiency or further improve efficiency, and in particular, can achieve an unexpectedly significant increase in device lifetime, exhibiting excellent overall device performance. Attached Figure Description

[0034] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the organic electroluminescent devices disclosed herein.

[0035] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the organic electroluminescent devices disclosed herein. Detailed Implementation

[0036] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1An 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 fabricated 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1 The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 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 on the outside of 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.

[0041] 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.

[0042] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0043] 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.

[0044] 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.

[0045] In this invention, materials are described as "same" or "different," for example, "the third organic material is the same as or different from the first organic material." "Same" means that two or more materials have the same chemical structural formula, or that the difference between two or more materials lies solely in the substitution of hydrogen with deuterium in their chemical structural formulas. Conversely, "different" means that the organic materials used have different chemical structural formulas (i.e., the difference in chemical structural formulas is not only in the substitution of hydrogen with deuterium in their molecular formulas).

[0046] As used herein, "P-type conductive dopant" refers to a dopant with oxidizing ability, which has a strong electron-withdrawing ability and is an electron acceptor.

[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-TThese 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, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, 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 and a second organic layer disposed between the anode and the cathode,

[0086] Wherein, the first organic layer contains a first organic material, and the second organic layer contains a second organic material;

[0087] The first organic material has a structure represented by Formula 1:

[0088]

[0089] L1, L2 and L3, each time appearing, are selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0090] Ar1 and Ar2, 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;

[0091] R1 and R2 appearing the same or different each time indicate monosubstitution, polysubstitution, or no substitution;

[0092] R1 and R2, each time appearing, are 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... 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;

[0093] Adjacent substituents L1, L2, L3, R1, R2, Ar1, and Ar2 can optionally be linked to form a ring;

[0094] The second organic material has a structure represented by Formula 2:

[0095]

[0096] R a R b R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0097] R a R b R cEach 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;

[0098] Ar a and Ar b Each time it appears, it is selected from the same or different groups of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted anthrayl, substituted or unsubstituted pyrene, or combinations thereof;

[0099] L a L b L c Each time it appears, it is selected from the same or different single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted phenanthroline, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted pyreneylene, or combinations thereof;

[0100] Adjacent substituent R a R b R c They can be arbitrarily connected to form a ring.

[0101] In this document, adjacent substituents L1, L2, L3, R1, R2, Ar1, and Ar2 can optionally be linked to form a ring, intended to indicate that, in Formula 1, any one or more of the following adjacent substituent groups, such as adjacent substituents R1, R2, R1 and R2, R1 and L3, L1 and L2, L1 and L3, L2 and L3, Ar1 and Ar2, Ar1 and R1, and Ar2 and R1, can be linked to form a ring. It is obvious that these adjacent substituent groups may also not be linked to form a ring.

[0102] In this paper, "adjacent substituent R" a R b R c "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two adjacent substituents R a Between two adjacent substituents R b Between two adjacent substituents R c 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.

[0103] According to one embodiment of the present invention, in Formula 1, L1, L2 and L3 are selected, each time they appear, from single bonds, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0104] According to one embodiment of the present invention, in Formula 1, L1, L2 and L3, each time they appear, are selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorene, substituted or unsubstituted silylfluorene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted phenanthroline, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted pyreneyl, or combinations thereof.

[0105] According to one embodiment of the present invention, in Formula 1, L1, L2 and L3, each time they appear, are selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzoselenylene, or combinations thereof.

[0106] According to one embodiment of the present invention, in Formula 1, R1 and R2 are selected from the group consisting of 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, and combinations thereof.

[0107] According to one embodiment of the present invention, in Formula 1, R1 and R2 are selected, in the same or different ways, from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenyl, substituted or unsubstituted phenanthryl, or combinations thereof.

[0108] According to one embodiment of the present invention, in Formula 1, R1 and R2 are selected from hydrogen, deuterium, methyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or combinations thereof, each time they appear in the same or different forms.

[0109] According to one embodiment of the present invention, in Formula 1, Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0110] According to one embodiment of the present invention, in Formula 1, Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted pyreneyl, or combinations thereof.

[0111] According to one embodiment of the present invention, in Formula 1, Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or combinations thereof.

[0112] According to one embodiment of the present invention, in Formula 1, at least one of Ar1 and Ar2 is selected from substituted or unsubstituted fluorene groups.

[0113] According to one embodiment of the present invention, the first organic material is selected from the group consisting of compounds 1-1 to 1-67:

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] According to one embodiment of the present invention, the hydrogen in the structures of compounds 1-1 to 1-67 can be partially or completely replaced by deuterium.

[0120] According to an embodiment of the present invention, in formula 2, R a R b R c 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.

[0121] According to an embodiment of the present invention, in formula 2, R a R b R c Each time it appears, it is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenyl, substituted or unsubstituted phenanthryl, or combinations thereof.

[0122] According to an embodiment of the present invention, in formula 2, R a R b R c Each time it appears, it is selected from hydrogen, deuterium, methyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or combinations thereof, either identically or differently.

[0123] According to an embodiment of the present invention, in formula 2, Ar a and Ar b Each time it appears, it is selected from the same or different groups of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or combinations thereof.

[0124] According to an embodiment of the present invention, in formula 2, L a L b L c Each time it appears, it is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, or combinations thereof.

[0125] According to an embodiment of the present invention, in formula 2, L a L b L c Each time it appears, it is selected from single-bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, either identically or differently.

[0126] According to an embodiment of the present invention, in formula 2, R c Indicates single substitution, and the R c It is selected from deuterium, 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 aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0127] According to one embodiment of the present invention, the second organic material has a structure represented by Formula 2-1:

[0128]

[0129] In Equation 2-1,

[0130] R aR b Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0131] R a 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;

[0132] R c Selected from deuterium, 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 aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0133] Ar a and Ar b Each time it appears, it is selected from the same or different groups of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted anthrayl, substituted or unsubstituted pyrene, or combinations thereof;

[0134] L a L b L cEach time it appears, it is selected from the same or different groups of single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted phenanthylene, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted pyreneylene, or combinations thereof.

[0135] According to one embodiment of the present invention, the second organic material has a structure represented by Formula 2-2:

[0136]

[0137] In Equation 2-2,

[0138] R a R b Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0139] R a R b R c 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;

[0140] Ar a and Ar cEach time it appears, it is selected from the same or different groups of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted anthrayl, substituted or unsubstituted pyrene, or combinations thereof;

[0141] Z1-Z5 are selected from C or CR each time they appear, either identically or differently. z And one of Z1-Z5 is selected from C and is associated with Ar c Connection; the R z 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;

[0142] And there is at least one R z Each time it appears, it is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof.

[0143] According to an embodiment of the present invention, in formula 2-2, at least one R zIt is selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, or combinations thereof.

[0144] According to an embodiment of the present invention, in formula 2-2, Z2 is selected from CR z And the R z It is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, or combinations thereof.

[0145] According to one embodiment of the present invention, in formula 2-2, Z3 is selected from C and combined with Ar. c connect.

[0146] According to an embodiment of the present invention, in formula 2-2, R c It is selected from deuterium, 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 aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0147] According to one embodiment of the present invention, the second organic material is selected from the group consisting of compounds H1 to H60:

[0148]

[0149]

[0150]

[0151]

[0152] According to one embodiment of the present invention, the hydrogen in the structure of compounds H1 to H60 can be partially or completely replaced by deuterium.

[0153] According to one embodiment of the present invention, the first organic layer is disposed between the second organic layer and the anode.

[0154] According to one embodiment of the present invention, the first organic layer and the second organic layer are in direct contact.

[0155] According to one embodiment of the present invention, the first organic layer is a hole transport layer and the second organic layer is an electron blocking layer.

[0156] According to one embodiment of the present invention, the first organic layer is composed of a first organic material.

[0157] According to one embodiment of the present invention, a third organic layer is included between the first organic layer and the anode, the third organic layer being a hole injection layer.

[0158] According to one embodiment of the present invention, the third organic layer comprises a third organic material, which may be the same as or different from the first organic material.

[0159] According to one embodiment of the present invention, the third organic material is the same as the first organic material.

[0160] According to one embodiment of the present invention, the third organic layer further includes a fourth organic material, wherein the fourth organic material is a p-type conductive dopant.

[0161] According to one embodiment of the present invention, the thickness of the first organic layer is between 5 nm and 150 nm.

[0162] According to one embodiment of the present invention, the thickness of the first organic layer is between 15 nm and 120 nm.

[0163] According to one embodiment of the present invention, the thickness of the first organic layer is between 25 nm and 100 nm.

[0164] According to one embodiment of the present invention, the thickness of the second organic layer is between 1 nm and 100 nm.

[0165] According to one embodiment of the present invention, the thickness of the second organic layer is between 3 nm and 50 nm.

[0166] According to one embodiment of the present invention, the thickness of the second organic layer is between 5 nm and 30 nm.

[0167] According to one embodiment of the present invention, the organic electroluminescent device further comprises a light-emitting layer.

[0168] According to one embodiment of the present invention, the light-emitting layer comprises at least one phosphorescent material.

[0169] According to one embodiment of the present invention, an electronic component is disclosed, which includes the organic electroluminescent device described in any of the foregoing embodiments.

[0170] Combination with other materials

[0171] 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.

[0172] 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 organic materials disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, barrier 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.

[0173] 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 further in this patent. The fabrication method of the following device embodiments is merely an example and should not be construed as limiting. Those skilled in the art can make reasonable improvements to the fabrication method of the following device embodiments based on the prior art.

[0174] Device Examples

[0175] Example 1: Fabrication of organic electroluminescent devices.

[0176] First, a 0.7mm thick glass substrate is used, on which a pre-patterned indium tin oxide (ITO) substrate is formed. As the anode, the substrate was washed with deionized water and detergent, and then the ITO surface was treated with oxygen plasma and UV ozone. The substrate was then dried in a glove box to remove moisture and placed on a support before being transferred to 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 via vacuum thermal evaporation. First, compounds 1-32 and PD were simultaneously deposited as a hole injection layer (HIL, weight ratio 97:3). Compound 1-32 was deposited on the hole injection layer as a hole transport layer (HTL). Next, compound H51 was deposited on the hole transport layer as an electron blocking layer (EBL). Subsequently, compounds RH and RD were co-deposited as the luminescent layer (EML, weight ratio 97:3). Compounds ET and Liq were co-deposited as an electron transport layer (ETL, weight ratio 40:60). Evaporation Liq was used as the electron injection layer (EIL), and finally, metallic aluminum (Al) was deposited. As a cathode, the device is then returned to the glove box and sealed with a glass cover to complete the device.

[0177] Example 2: The preparation method is the same as in Example 1, except that compound H3 is used instead of compound H51 as the electron blocking layer.

[0178] Example 3: The preparation method is the same as in Example 1, except that compound H1 is used instead of compound H51 as the electron blocking layer.

[0179] Example 4: The preparation method is the same as in Example 1, except that compound H7 is used instead of compound H51 as the electron blocking layer.

[0180] Example 5: The preparation method is the same as in Example 2, except that compounds 1-3 and PD are used instead of compounds 1-32 and PD as the hole injection layer, and compound 1-3 is used instead of compound 1-32 as the hole transport layer.

[0181] Comparative Example 1: The preparation method was the same as in Example 1, except that compound EB-1 was used instead of compound H51 as the electron blocking layer.

[0182] Comparative Example 2: The preparation method is the same as in Example 4, except that compound HT-1 and compound PD are used instead of compounds 1-32 and compound PD as hole injection layers, and compound HT-1 is used instead of compounds 1-32 as hole transport layers.

[0183] Comparative Example 3: The preparation method is the same as in Example 1, except that compound HT-2 and compound PD are used instead of compound 1-32 and compound PD as hole injection layer, and compound HT-2 is used instead of compound 1-32 as hole transport layer.

[0184] Comparative Example 4: The preparation method is the same as in Example 4, except that compound HT-2 and compound PD are used instead of compound 1-32 and compound PD as hole injection layer, and compound HT-2 is used instead of compound 1-32 as hole transport layer.

[0185] The detailed device layer structure and thickness are shown in Table 1 below. The layers used are made of more than one material, and are obtained by doping different compounds in the weight ratios specified herein.

[0186] Table 1. Partial device structures of Examples 1-5 and Comparative Examples 1-4

[0187]

[0188]

[0189] The material structure used in the device is as follows:

[0190]

[0191]

[0192] Table 2 summarizes the device performance of Examples 1-5 and Comparative Examples 1-4. Among them, color coordinates (CIE) are... x CIE y The voltage and external quantum efficiency (EQE) are measured at a constant current density of 10 mA / cm². 2 The device lifetime (LT95) was measured at a constant current density of 80 mA / cm². 2 The following measurements were taken.

[0193] Table 2 Device data for Examples 1-5 and Comparative Examples 1-4

[0194]

[0195] discuss:

[0196] As can be seen from the data in Table 2, the color coordinates of Examples 1-5 are consistent with those of Comparative Examples 1-4.

[0197] Example 1 uses a combination of a first organic material 1-32 having a specific structure represented by Formula 1 and a second organic material H51 having a specific structure represented by Formula 2. Comparative Example 1 uses a combination of the first organic material 1-32 and compound EB-1. The only difference between compound EB-1 and the second organic material H51 selected in this invention is the connecting group on the N atom, but the device performance is significantly different. Compared with Comparative Example 1, Example 1 has a substantially comparable low voltage and high EQE. More importantly, the lifetime of Example 1 is unexpectedly and significantly improved by 4.6 times. Comparative Example 3 uses a commonly used compound HT-2 and the second organic material H51. Compared with Comparative Example 3, Example 1 has a comparable low voltage and a further 10% improvement in EQE. More importantly, the lifetime is significantly improved by 5.0 times, which is a very unexpected performance improvement. These data demonstrate the unique advantages of the combination of the first organic material with a specific structure and the second organic material with a specific structure in this invention.

[0198] Examples 2-4, using a first organic material with a specific structure represented by Formula 1 combined with different second organic materials, all exhibited excellent overall device performance. While maintaining low voltage and high EQE, the lifetime was unexpectedly and significantly improved. Compared with Comparative Example 1, the lifetime of Examples 2-4 was improved by 5.2 times, 5.2 times, and 4.5 times, respectively. This indicates that the combination of different second organic materials with specific structures and the first organic material with specific structures in this invention can maintain low voltage and high EQE, while achieving an unexpectedly significant improvement in lifetime, thus enhancing the overall device performance.

[0199] Example 4 uses a combination of a first organic material 1-32 having a specific structure represented by Formula 1 and a second organic material H7 having a specific structure represented by Formula 2. Comparative Example 2 uses a commercially available compound HT-1 combined with the second organic material H7. Both compound HT-1 and the compound 1-32 selected in this invention have a spirodifluorene-triarylamine structure, differing only in the connection position between spirodifluorene and triarylamine; however, their device performances differ significantly. As shown in Table 2, Comparative Example 2 already exhibits high device performance in the industry. At this level, the voltage and EQE of Example 4 are essentially equivalent, with a lifetime increase of 52.5%, which is quite unexpected. Comparative Example 4 uses a commonly used compound HT-2 combined with the second organic material H7. Compared to Comparative Example 4, Example 4 has essentially equivalent low voltage and high EQE, and more importantly, a lifetime increase of 4.8 times, which is also quite unexpected. The above data shows that the first organic material with a specific structure represented by Formula 1 selected in this invention has significantly improved device performance when combined with the second organic material with a structure represented by Formula 2 selected in this invention, compared with the hole transport materials commonly used in the prior art. In particular, it can achieve a significant increase in lifetime.

[0200] Example 5, using different combinations of the first organic materials 1-3 and the second organic material H3 with a specific structure represented by Formula 2, also exhibited excellent overall device performance, maintaining low voltage and high EQE while achieving a lifetime of up to 300 hours. This further demonstrates the unique advantages of combining the first organic material with a specific structure and the second organic material with a specific structure as described in this invention.

[0201] In summary, the combination of the first organic material with a specific structure represented by Formula 1 and the second organic material with a specific structure represented by Formula 2, selected in this invention, when applied to organic electroluminescent devices, can better balance the charge carriers in the device, which is beneficial to charge transport in the device. This results in the device having superior overall performance, maintaining low voltage while maintaining high efficiency or further improving efficiency. In particular, it can achieve an unexpectedly large increase in lifetime, comprehensively improving the overall performance of the device and having broad application prospects.

[0202] 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: an anode, a cathode, and a first organic layer and a second organic layer disposed between the anode and the cathode, wherein the first organic layer comprises a first organic material and the second organic layer comprises a second organic material; the first organic material has a structure represented by Formula 1: L1, L2, and L3 are the same or different at each occurrence selected from a single bond, a substituted or unsubstituted arylene having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof; Ar1and Ar2are the same or different at each occurrence selected from a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or a combination thereof; R1and R2represent mono-substitution, multi-substitution, or no substitution at each occurrence; R1and R2are the same or different at each occurrence selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, a substituted or unsubstituted heterocyclyl having 3-20 ring atoms, a substituted or unsubstituted aralkyl having 7-30 carbon atoms, a substituted or unsubstituted alkoxy having 1-20 carbon atoms, a substituted or unsubstituted aryloxy having 6-30 carbon atoms, a substituted or unsubstituted alkenyl having 2-20 carbon atoms, a substituted or unsubstituted alkynyl having 2-20 carbon atoms, a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, a substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, a substituted or unsubstituted arylsilane having 6-20 carbon atoms, a substituted or unsubstituted alkylgermanium having 3-20 carbon atoms, a substituted or unsubstituted arylgermanium having 6-20 carbon atoms, a substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and a combination thereof; adjacent substituents L1, L2, L3, R1, R2, Ar1, and Ar2may be optionally linked to form a ring; the second organic material has a structure represented by Formula 2: R a , R b , R c each occurrence, identically or differently, represents mono-, poly- or no substitution; R a , R b , R c are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having from 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having from 1-20 carbon atoms, a substituted or unsubstituted heterocyclyl having from 3-20 ring atoms, a substituted or unsubstituted aralkyl having from 7-30 carbon atoms, a substituted or unsubstituted alkoxy having from 1-20 carbon atoms, a substituted or unsubstituted aryloxy having from 6-30 carbon atoms, a substituted or unsubstituted alkenyl having from 2-20 carbon atoms, a substituted or unsubstituted alkynyl having from 2-20 carbon atoms, a substituted or unsubstituted aryl having from 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having from 3-30 carbon atoms, a substituted or unsubstituted alkylsilicon having from 3-20 carbon atoms, a substituted or unsubstituted arylsilane having from 6-20 carbon atoms, a substituted or unsubstituted alkyl germanium having from 3-20 carbon atoms, a substituted or unsubstituted aryl germanium having from 6-20 carbon atoms, a substituted or unsubstituted amino having from 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; Ar a and Ar b is, at each occurrence, selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, or a combination thereof; L a , L b , L c is, at each occurrence, independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted diphenylene furan, substituted or unsubstituted diphenylene thienyl, substituted or unsubstituted diphenylene selenolene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted anthracenylene, substituted or unsubstituted pyrenylene, or a combination thereof; adjacent substituents R a , R b , R c may optionally be joined to form a ring.

2. The organic electroluminescent device of claim 1, in Formula 1, the L1, L2, and L3 are the same or different at each occurrence selected from a single bond, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof; Preferably, each occurrence of L1, L2and L3is the same or different selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzoselenophenylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triphenylylene, substituted or unsubstituted pyridinylene, substituted or unsubstituted anthracenylene, substituted or unsubstituted pyrenylene, or a combination thereof; More preferably, each occurrence of L1, L2and L3is the same or different selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzoselenophenylene, or a combination thereof.

3. The organic electroluminescent device of claim 1, in formula 1, each occurrence of R1, R2is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and a combination thereof; Preferably, each occurrence of R1, R2is the same or different selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted phenanthryl, or a combination thereof; More preferably, each occurrence of R1, R2is the same or different selected from hydrogen, deuterium, methyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or a combination thereof.

4. The organic electroluminescent device of claim 1, in formula 1, each occurrence of Ar1and Ar2is the same or different selected from substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, or a combination thereof; Preferably, each occurrence of said Ar1and Ar2is the same or different selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silafluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, or a combination thereof; More preferably, each occurrence of said Ar1and Ar2is the same or different selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or a combination thereof.

5. The organic electroluminescent device according to claim 1, wherein The first organic material is selected from the group consisting of Compound 1-1 to Compound 1-67: Optionally, the hydrogen in the structure of said Compound 1-1 to Compound 1-67 can be partially or entirely replaced with deuterium.

6. The organic electroluminescent device according to claim 1, in formula 2, R a , R b , R c is selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, and a combination thereof; Preferably, R a R b R c Each time it appears, it is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted phenanthryl, or combinations thereof; More preferably, R a , R b , R c is, at each occurrence, selected from the group consisting of hydrogen, deuterium, methyl, t-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or a combination thereof.

7. The organic electroluminescent device according to claim 1, in formula 2, Ar a and Ar b is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or a combination thereof.

8. The organic electroluminescent device according to claim 1, in formula 2, L a , L b , L c is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted diphenanthrolene, a substituted or unsubstituted dibenzothiophenylene, or a combination thereof; Preferably, L a L b L c Each time it appears, it is selected from single-bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, either identically or differently.

9. The organic electroluminescent device according to claim 1, wherein The second organic material is selected from the group consisting of Compound H1 to Compound H60: Optionally, the hydrogen in the structure of said Compound H1 to Compound H60 can be partially or entirely replaced with deuterium.

10. The organic electroluminescent device according to claim 1, wherein The first organic layer is a hole transport layer, and the second organic layer is an electron blocking layer.

11. The organic electroluminescent device according to claim 1, wherein A third organic layer is comprised between the first organic layer and the anode, the third organic layer being a hole injection layer.

12. The organic electroluminescent device according to claim 11, wherein The third organic layer comprises a third organic material, which is the same or different from the first organic material; Preferably, the third organic material is the same as the first organic material.

13. An electronic assembly comprising the organic electroluminescent device of any one of claims 1-12.

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