Organic electroluminescent material and device thereof

Abstract

Disclosed are a novel organic electroluminescent material and a device thereof. The novel organic electroluminescent material is a conjugated system compound represented by Formula 1 and containing two N-containing five-membered heterocyclic rings. The compound can be used as a charge transport material and a charge injection material in an organic electroluminescent device to improve the balance of electrons and holes in the device, and can greatly improve the performance of the organic electroluminescent device, bringing excellent device effects, such as reducing the device voltage, and improving the device efficiency and lifespan. Also disclosed are an organic electroluminescent device and a compound composition containing the organic electroluminescent material.

Description

Technical Field

[0001] The present invention relates to a novel organic electroluminescent material and a device thereof, and more particularly to an organic electroluminescent material having a structure of Formula 1, an organic electroluminescent device comprising the material, and a compound composition comprising the material. Background Art

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

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device that included an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12):913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.

[0004] OLEDs can be categorized into three different types based on their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet emission. Triplet states generated in the device are wasted through non-radiative decay channels. As a result, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metal complexes as the emitter. This allows for the harvesting of both singlet and triplet states, achieving an IQE of 100%. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, enabling 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 categorized based on the form of the materials used, into small molecule and polymer OLEDs. A small molecule is any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights as long as they have a precise structure. Dendrimers, with their well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

[0006] Various OLED manufacturing methods exist. Small molecule OLEDs are typically produced by vacuum thermal evaporation. Polymer OLEDs are produced using solution methods such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be produced using solution methods if the material can be dissolved or dispersed in a solvent.

[0007] Organic electroluminescent devices convert electrical energy into light by applying a voltage across the device. Typically, an organic electroluminescent device includes an anode, a cathode, and an organic layer between the anode and cathode. The organic layers of an organic electroluminescent device include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (containing a host material and a light-emitting material), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Depending on the function of the material, the materials that make up the organic layer can be divided into hole injection materials, hole transport materials, electron blocking materials, host materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials. When a bias is applied to the device, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. The holes and electrons meet to form excitons, which recombine to emit light. The hole injection layer is one of the important functional layers that affects the performance of the organic electroluminescent device. The selection and combination of its materials can have a significant impact on the performance of the organic electroluminescent device, such as driving voltage, efficiency, and lifespan. Commercially, it is expected to obtain organic electroluminescent devices with characteristics such as low driving voltage, high efficiency, and long service life. Therefore, the development of new hole injection layers is a very critical research field.

[0008] Early OLED devices mostly had only one layer of organic material between the anode and the light-emitting layer, which combined hole injection, hole transport, and even electron blocking functions. This device structure was limited by a single hole transport material, making it impossible to achieve an ideal energy level match, and therefore difficult to achieve very ideal performance. As the industry's demand for device performance grew, the performance requirements for the hole transport region between the anode and the light-emitting layer also increased. Later, the hole transport material was further subdivided into two layers: the hole injection layer and the hole transport layer. At this time, a single triarylamine material was generally used as the hole injection layer. Common triarylamine materials are as follows:

[0009]

[0010] The most advanced device structures in the industry currently typically have multiple organic layers between the anode and the light-emitting layer to achieve hole injection, hole transport, and electron blocking functions, respectively. To achieve better hole injection, the hole transport material (e.g., aromatic amine compounds) in the hole injection layer is often doped with a certain proportion of p-type dopant. Common p-type dopant materials include:

[0011]

[0012] Most commonly used p-type dopant materials currently suffer from various issues, making it difficult to simultaneously achieve excellent hole injection capability, high stability, and high film-forming properties. For example, F4TCNQ and F6TCNNQ, while offering excellent hole injection capability, suffer from low evaporation temperatures, which hinders deposition control, production performance reproducibility, and device thermal stability. Therefore, research and development of novel p-type dopant materials to address these challenges is urgent.

[0013] K.Suzuki, M.Tomura, S.Tanaka, Y.Yamashita, Tetrahedron Letter, 2000, 41, 8359-8364 discloses a compound having a bithiophene and bithiazole structure, wherein the structure of the specific compound is: However, this compound has a different skeleton structure from the compound claimed in the present application, and this document does not disclose or teach any application of this type of compound in organic electroluminescent devices.

[0014] K. Yui, Y. Aso, T. Otsubo, F. Ogura, J. Chem. Soc., Chem. Commun., 1987, 24, 1816–1817; K. Yui, Y. Aso, T. Otsubo, F. Ogura, Bull. Chem. Soc. Jpn., 1989, 62, 1539–1846; H. Ishida, K. Yui, Y. Aso, T. Otsubo, F. Ogura, Bull. Chem. Soc. Jpn., 1990, 63, 2828–2835; disclose a series of compounds having thiophene and bithiophene structures, among which specific examples include:

[0015] The above compounds are all structurally different from the compounds claimed in the present application, and these documents do not disclose or teach any application of such compounds.

[0016] Improving the performance of organic electroluminescent devices (OLEDs) to achieve higher device efficiency, such as higher external quantum efficiency and longer lifetime, and meet the ever-increasing demands for device performance remains a pressing challenge for researchers. The properties of charge transport materials have a crucial impact on device performance, so developing novel compounds with enhanced charge transfer capabilities and expanding the options for transport materials holds great promise for both industry and application. Summary of the Invention

[0017] The present invention aims to provide a series of novel organic electroluminescent materials and devices to address at least some of the aforementioned issues. The compounds described are compounds having the structure of Formula 1 and comprising a conjugated system of two nitrogen-containing five-membered heterocycles. They can be used as charge transport materials, charge injection materials, and similar materials in organic electroluminescent devices. These novel compounds possess strong charge transfer capabilities and can provide low-voltage, high-efficiency, and long-life organic electroluminescent devices, significantly improving their performance and promising broader application prospects.

[0018] According to one embodiment of the present invention, a compound is disclosed, which has a structure shown by Formula 1:

[0019]

[0020] in,

[0021] Y is selected from the group consisting of O, S, Se and NR at each occurrence, the same or different. N the group formed;

[0022] Ring Z is identically or differently selected at each occurrence from the group consisting of an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, and combinations thereof;

[0023] Each occurrence of R is the same or different and represents mono-, poly- or no substitution;

[0024] R, R N each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof;

[0025] R', R" are each identically or differently selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring group, and halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring group any of the following groups substituted by one or more of: alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, heteroalkyl having 1-20 carbon atoms, heterocyclyl having 3-20 ring atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, and combinations thereof;

[0026] Adjacent substituents R, R N , R', and R" can be optionally linked to form a ring.

[0027] According to another embodiment of the present invention, an organic electroluminescent device is disclosed, which comprises the compound described in the above embodiment.

[0028] According to another embodiment of the present invention, a compound composition is also disclosed, which comprises the compound described in the above embodiment.

[0029] The present invention discloses a series of conjugated system compounds having a structure of Formula 1 and comprising two nitrogen-containing five-membered heterocyclic rings. The compounds can be used as charge transport materials and charge injection materials in organic electroluminescent devices, thereby improving the balance of electrons and holes in the devices, significantly improving the performance of organic electroluminescent devices, and bringing excellent device effects, such as reducing device voltage and achieving increased device efficiency and lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0031] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound compositions disclosed herein. DETAILED DESCRIPTION

[0032] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0033] There are many more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated by reference in their entireties, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in their entireties. An example of an injection layer is provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety.

[0034] The above layered structure is provided by way of non-limiting example. 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 can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired emission spectrum.

[0035] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. The organic layer can include one or more layers.

[0036] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is shown schematically and non-limitingly. Figure 1 The difference is that an encapsulation layer 102 can also be included above cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as 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 No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0037] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0038] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0039] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, the cathode may be described as being "disposed on" the anode even if various organic layers are present between the cathode and the anode.

[0040] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0041] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is not believed to contribute to the photoactive properties of the emissive material, but the ancillary ligand may modify the properties of the photoactive ligand.

[0042] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0043] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but relies on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap so as to convert between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the inverse intersystem crossing (IRISC) rate is fast enough to minimize the non-radiative decay by the triplet, the fraction of backfilling the singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the electrically generated excitons.

[0044] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Typically, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0045] Definition of Substituent Terms

[0046] Halogen or halide - as used herein, includes fluorine, chlorine, bromine and iodine.

[0047] Alkyl - as used herein, includes straight chain and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.

[0048] Cycloalkyl - as used herein, includes cyclic alkyl groups. Cycloalkyl groups can be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably cycloalkyl groups 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, and the like. Of the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. In addition, the cycloalkyl group may be optionally substituted.

[0049] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbon atoms in the alkyl chain substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. The example of heteroalkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl can be optionally substituted.

[0050] Alkenyl - as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. Alkenyl groups can be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, alkenyl groups can be optionally substituted.

[0051] Alkynyl - as used herein, encompasses straight chain alkynyl groups. Alkynyl groups can be alkynyl groups comprising 2 to 20 carbon atoms, preferably alkynyl groups having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl groups can be optionally substituted.

[0052] Aryl or aromatic group or aromatic ring - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthren, fluorene, pyrene, 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'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl. In addition, the aryl group may be optionally substituted.

[0053] Heterocyclic group or heterocycle - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothiol. Additionally, heterocyclyl groups may be optionally substituted.

[0054] Heteroaryl or heteroaromatic ring - As used herein, non-fused and fused heteroaromatic groups may contain from 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Heteroaryl also refers to heteroaryl. The heteroaryl group may have 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group comprises an oxadiazole, an isocyanine ...

[0055] Alkoxy - as used herein, is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclyl are the same as those described above. The alkoxy group may 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, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. In addition, the alkoxy group may be optionally substituted.

[0056] Aryloxy - As used herein, it is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenyloxy. In addition, the aryloxy group may be optionally substituted.

[0057] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl.Alkyl group can be substituted alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl,

[0058] Alkylsilyl - As used herein, encompasses alkyl-substituted silicon groups. The alkylsilyl group may 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, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. Additionally, the alkylsilyl group may be optionally substituted.

[0059] Arylsilyl - As used herein, encompasses silicon groups substituted with at least one aryl group. The arylsilyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldibiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilyl group may be optionally substituted.

[0060] Alkylgermanyl - As used herein, alkyl-substituted germanium groups are encompassed. The alkylgermanyl group can be an alkylgermanyl group having 3 to 20 carbon atoms, preferably an alkylgermanyl group having 3 to 10 carbon atoms. Examples of alkylgermanyl groups include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyl-tert-butylgermanyl, and methyldi-tert-butylgermanyl. Additionally, the alkylgermanyl group can be optionally substituted.

[0061] Arylgermanyl - As used herein, encompasses germanium groups substituted with at least one aryl or heteroaryl group. The arylgermanyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylgermanyl groups include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, and diphenyltert-butylgermanyl. Additionally, the arylgermanyl group may be optionally substituted.

[0062] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., means that one or more CH groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives will readily occur to one of ordinary skill in the art, and all such analogs are intended to be included within the terminology described herein.

[0063] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid , substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphino group, refers to alkyl, cycloalkyl, heteroalkyl, heterocyclic group, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid group, ester group, sulfinyl, sulfonyl and phosphino group, any one of which may be selected from deuterium, halogen, unsubstituted alkyl group having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted alkyl having 6-30 carbon atoms aryl, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted alkylgermanyl having 3 to 20 carbon atoms, unsubstituted arylgermanyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0064] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attaching a fragment are considered equivalent.

[0065] In the compounds described herein, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in compounds may be preferred because it enhances device efficiency and stability.

[0066] In the compounds described herein, polysubstitution refers to a range including disubstitution up to the maximum number of available substitutions. When a substituent in a compound described herein represents polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its connected structure, and the substituents present at multiple available substitution positions can have the same structure or different structures.

[0067] In the compounds mentioned in the present disclosure, unless clearly defined, such as adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including the situation where adjacent substituents can be connected to form a ring, and also including the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged ring, condensed ring, etc.), as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0068] In the present invention, the number of ring atoms refers to the number of atoms that constitute the ring itself in a compound (e.g., a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) in which atoms are bonded to form a cyclic structure. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the number of ring atoms. The term "ring atoms" as used herein has the same meaning unless otherwise specified.

[0069] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, as can be exemplified by the following formula:

[0070]

[0071] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other via a chemical bond to form a ring, as can be exemplified by the following formula:

[0072]

[0073] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to further distant carbon atoms are linked to each other by a chemical bond to form a ring, as can be exemplified by the following formula:

[0074]

[0075] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to mean that the adjacent two substituents

[0076] Where one of the substituents represents hydrogen, the second substituent is bonded at the position where the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0077]

[0078] According to one embodiment of the present invention, a compound is disclosed, which has a structure shown in Formula 1:

[0079]

[0080] in,

[0081] Y is selected from the group consisting of O, S, Se and NR at each occurrence, the same or different. N the group formed;

[0082] Ring Z is identically or differently selected at each occurrence from the group consisting of an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, and combinations thereof;

[0083] Each occurrence of R is the same or different and represents mono-, poly- or no substitution;

[0084] R, R N each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof;

[0085] R', R" are each identically or differently selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring group, and halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring group any of the following groups substituted by one or more of: alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, heteroalkyl having 1-20 carbon atoms, heterocyclyl having 3-20 ring atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, and combinations thereof;

[0086] Adjacent substituents R, R N , R', and R" can be optionally linked to form a ring.

[0087] In this context, “adjacent substituents R, R N , R', R" can be optionally linked to form a ring" is intended to mean that adjacent substituent groups, for example, between two substituents R, substituents R and R N Between the substituents R' and R", any one or more of these substituent groups can be connected to form a ring. Obviously, none of these substituents can be connected to form a ring. According to one embodiment of the present invention, when ring Z is selected from a heteroaromatic ring having 3-30 carbon atoms, the heteroaromatic ring does not include pyridine, pyridazine, pyrimidine, thiazole, oxazole, imidazole, pyrazine, triazine, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and aza analogs thereof.

[0088] According to one embodiment of the present invention, when ring Z is selected from a heteroaromatic ring having 3-30 carbon atoms, the heteroaromatic ring is preferably: thiophene, furan, selenophene, pyrrole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indole, carbazole.

[0089] According to one embodiment of the present invention, when R, R N When selected from substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, the heteroaryl group does not include pyridine, pyridazine, pyrimidine, thiazole, oxazole, imidazole, pyrazine, triazine, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and aza analogs thereof.

[0090] According to one embodiment of the present invention, when R, R NWhen the heteroaryl group is selected from substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, the heteroaryl group is preferably thiophene, furan, selenophene, pyrrole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indole, or carbazole.

[0091] According to one embodiment of the present invention, R, R N Each occurrence of is the same or different and is selected from groups that do not contain an electron withdrawing group.

[0092] According to one embodiment of the present invention, R, R N Not selected from electron withdrawing groups.

[0093] According to one embodiment of the present invention, the Hammett constant of the electron-withdrawing base is ≥0.05, preferably ≥0.3, and more preferably ≥0.5.

[0094] According to one embodiment of the present invention, the electron-withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, nitrogen heteroaromatic ring group, and any of the following groups substituted by one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, nitrogen heteroaromatic ring group: having 1-20 carbon atoms The present invention also includes an alkyl group having 3-20 ring carbon atoms, a cycloalkyl group having 3-20 carbon atoms, a heteroalkyl group having 1-20 carbon atoms, a heterocyclyl group having 3-20 ring atoms, an aralkyl group having 7-30 carbon atoms, an alkoxy group having 1-20 carbon atoms, an aryloxy group having 6-30 carbon atoms, an alkenyl group having 2-20 carbon atoms, an alkynyl group having 2-20 carbon atoms, an aryl group having 6-30 carbon atoms, a heteroaryl group having 3-30 carbon atoms, an alkylsilyl group having 3-20 carbon atoms, an arylsilyl group having 6-20 carbon atoms, and combinations thereof.

[0095] According to one embodiment of the present invention, wherein each occurrence of Y is identically or differently selected from O, S or Se.

[0096] According to one embodiment of the present invention, wherein said Y is selected from O or S the same or differently each time it occurs.

[0097] According to one embodiment of the present invention, wherein said Y is O.

[0098] According to one embodiment of the present invention, each occurrence of Y is the same or different and is selected from NR N , and R NEach occurrence is identically or differently selected from the group consisting of: substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0099] According to one embodiment of the present invention, R N Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and combinations thereof.

[0100] According to one embodiment of the present invention, wherein ring Z is identically or differently selected from the group consisting of: an aromatic ring having 6 to 20 carbon atoms, a heteroaromatic ring having 6 to 20 carbon atoms, and a combination thereof.

[0101] According to one embodiment of the present invention, wherein each occurrence of ring Z is identically or differently selected from an aromatic ring having 6 to 20 carbon atoms.

[0102] According to one embodiment of the present invention, wherein each occurrence of ring Z is identically or differently selected from a benzene ring, a biphenyl ring, a terphenyl ring, a triphenylene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a pyrene ring, Ring and perylene ring.

[0103] According to one embodiment of the present invention, at least one of R is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof.

[0104] According to one embodiment of the present invention, at least one of R is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0105] According to one embodiment of the present invention, each occurrence of R is identically or differently selected from hydrogen or an electron-donating group.

[0106] According to one embodiment of the present invention, wherein R is selected from hydrogen, deuterium, unsubstituted or substituted with at least one electron-donating group at each occurrence: an alkyl group having 1-20 carbon atoms, a cycloalkyl group having 3-20 ring carbon atoms, a heteroalkyl group having 1-20 carbon atoms, an aralkyl group having 7-30 carbon atoms, an alkoxy group having 1-20 carbon atoms, an aryl group having 6-30 carbon atoms, a heteroaryl group having 3-30 carbon atoms, and combinations thereof.

[0107] According to one embodiment of the present invention, the Hammett constant of the electron-donating group is <0.05, preferably <0.03, and more preferably <0.

[0108] It should be noted that the Hammett substituent constant value includes the Hammett substituent para constant and / or meta constant. As long as one of the para constant and the meta constant is less than 0.05, further less than 0.03, and further less than 0, it can be used as a preferred electron donating group in the present invention.

[0109] According to one embodiment of the present invention, the electron-donating group is the same or different each time it appears and is selected from the group consisting of: an alkyl group having 1-20 carbon atoms, a cycloalkyl group having 3-20 ring carbon atoms, a heteroalkyl group having 1-20 carbon atoms, a heterocyclyl group having 3-20 ring atoms, an aralkyl group having 7-30 carbon atoms, an alkoxy group having 1-20 carbon atoms, an aryloxy group having 6-30 carbon atoms, an aryl group having 6-30 carbon atoms, a heteroaryl group having 3-30 carbon atoms and containing only at least one of O atoms, S atoms, and Se atoms, and combinations thereof.

[0110] According to one embodiment of the present invention, the electron-donating group is the same or different each time it appears and is selected from the group consisting of: an alkyl group having 1-20 carbon atoms, a cycloalkyl group having 3-20 ring carbon atoms, an aralkyl group having 7-30 carbon atoms, an aryl group having 6-30 carbon atoms, and combinations thereof.

[0111] According to one embodiment of the present invention, at least one of R' and R" is a group having at least one electron-withdrawing group.

[0112] According to one embodiment of the present invention, each of R' and R" is a group having at least one electron-withdrawing group.

[0113] According to one embodiment of the present invention, R', R" are selected from the group consisting of the following structures at each occurrence, the same or different: halogen, nitro, ester, cyano, isocyano, SCN, OCN, sulfinyl, sulfonyl, phosphino, nitrogen heteroaromatic ring group, and any of the following groups substituted by one or more of halogen, nitro, ester, cyano, isocyano, SCN, OCN, sulfinyl, sulfonyl, phosphino, nitrogen heteroaromatic ring group: alkyl having 1-20 carbon atoms, heterocyclic group having 3-20 ring atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0114] According to one embodiment of the present invention, wherein R', R" are selected from the group consisting of: halogen, cyano, SCN, and any of the following groups substituted by one or more of halogen, cyano, SCN: alkyl having 1 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0115] According to one embodiment of the present invention, wherein R', R" each time appear, the same or different are selected from the group consisting of: fluorine, cyano, SCN, trifluoromethyl, 2,3,5,6-tetrafluoro-4-cyanophenyl, 2,3,5,6-tetrafluoropyridyl, cyanophenyl, fluorophenyl, and combinations thereof.

[0116] According to one embodiment of the present invention, each occurrence of R', R" is identical or different and is selected from the group consisting of the following structures:

[0117]

[0118] “*” represents the connection position of R′ and R″ having the above structure and Formula 1.

[0119] According to one embodiment of the present invention, R', R" are selected from “*” represents the connection position of R′ and R″ having the above structure and Formula 1.

[0120] According to one embodiment of the present invention, R N In formula 1 Each occurrence is identically or differently selected from the group consisting of:

[0121]

[0122]

[0123] In the above structure, Ph represents a phenyl group;

[0124] “﹋” represents the structure above. The connection position with the five-membered conjugated heterocycle containing N in Formula 1, "﹋" also represents when Y is selected from NR N When the R having the above structure N The connection position with N.

[0125] According to one embodiment of the present invention, in a compound represented by Formula 1, two ring Zs are the same, and two Rs are the same.

[0126] According to one embodiment of the present invention, the compound is selected from the group consisting of Compound I-1 to Compound I-204; the specific structures of Compound I-1 to Compound I-204 are shown in Claim 11.

[0127] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:

[0128] anode,

[0129] cathode,

[0130] An organic layer is disposed between the anode and the cathode, wherein the organic layer comprises the compound described in any one of the preceding embodiments.

[0131] According to one embodiment of the present invention, the organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer is formed solely from the compound.

[0132] According to one embodiment of the present invention, the organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer further comprises at least one hole transport material; wherein the molar doping ratio of the compound to the hole transport material is from 10000:1 to 1:10000.

[0133] According to one embodiment of the present invention, the organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer further comprises at least one hole transport material; the molar doping ratio of the compound to the hole transport material is from 10:1 to 1:100.

[0134] According to one embodiment of the present invention, the organic electroluminescent device comprises at least two light-emitting units, the organic layer is a charge generation layer and is arranged between the at least two light-emitting units, wherein the charge generation layer comprises a p-type charge generation layer and an n-type charge generation layer; preferably, the p-type charge generation layer comprises the compound.

[0135] According to one embodiment of the present invention, the p-type charge generation layer further comprises at least one hole transport material, wherein the molar doping ratio of the compound to the hole transport material is 10,000:1 to 1:10,000.

[0136] According to one embodiment of the present invention, the p-type charge generation layer further comprises at least one hole transport material, wherein the molar doping ratio of the compound to the hole transport material is 10:1 to 1:100.

[0137] According to one embodiment of the present invention, the hole transport material is selected from the group consisting of the following compounds: compounds having triarylamine units, spirobifluorene compounds, pentacene compounds, oligothiophene compounds, oligophenyl compounds, oligophenylene vinyl compounds, oligofluorene compounds, porphyrin complexes, metal phthalocyanine complexes, and combinations thereof.

[0138] According to one embodiment of the present invention, the charge generation layer further comprises a buffer layer disposed between the p-type charge generation layer and the n-type charge generation layer, and the buffer layer comprises the compound.

[0139] According to one embodiment of the present invention, the organic electroluminescent device is prepared by a vacuum evaporation method.

[0140] According to one embodiment of the present invention, a compound composition is also disclosed, which comprises the compound described in any of the aforementioned embodiments.

[0141] Combination with other materials

[0142] The materials described herein for use in specific layers of organic light-emitting devices can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. Patent Application No. US2016 / 0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0143] The materials described herein as being useful in specific layers of an organic light-emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. patent application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0144] The device of the present invention may include charge injection and transport layers, such as a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer; it may also include a light-emitting layer, which includes at least one light-emitting dopant and at least one host compound, and the light-emitting dopant may be a fluorescent light-emitting dopant and / or a phosphorescent light-emitting dopant; it may also include a blocking layer, such as a hole blocking layer and an electron blocking layer.

[0145] There is no limitation on the preparation method of the organic electroluminescent device, and the preparation method of the following embodiment is only an example and should not be understood as a limitation. Those skilled in the art can make reasonable improvements to the preparation method of the following embodiment based on the existing technology. For example, the ratio of various materials in each organic layer is not particularly limited, and those skilled in the art can reasonably select within a certain range based on the existing technology. In the embodiment of the device, the characteristics of the device are also tested using conventional equipment in the field (including but not limited to the vapor deposition machine produced by Angstrom Engineering, the optical testing system and life testing system produced by Suzhou Fusida, the ellipsometer produced by Beijing Liangtuo, etc.) using methods familiar to those skilled in the art. Since those skilled in the art are aware of the use of the above-mentioned equipment, testing methods and other related contents, they can obtain the inherent data of the sample with certainty and without being affected. Therefore, the above-mentioned related contents will not be elaborated in this patent.

[0146] The measured LUMO energy levels obtained in this paper were determined by cyclic voltammetry (CV) to determine the electrochemical properties of the compounds. A CorrTest CS120 electrochemical workstation, manufactured by Wuhan Kosit Instrument Co., Ltd., was used. A three-electrode working system was used: a platinum disk electrode as the working electrode, an Ag / AgNO3 electrode as the reference electrode, and a platinum wire electrode as the auxiliary electrode. Anhydrous DCM was used as the solvent, and 0.1 mol / L tetrabutylammonium hexafluorophosphate was used as the supporting electrolyte. The target compound was prepared into 10 -3mol / L solution, nitrogen was bubbled into the solution for 10 min to remove oxygen before testing. Instrument parameters were set as follows: scan rate 100 mV / s, potential interval 0.5 mV, and test window 1 V to -0.5 V.

[0147] The calculated LUMO energy levels obtained in this paper were obtained by DFT calculation [GAUSS-09, B3LYP / 6-311G(d)] method.

[0148] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more equipment conventional in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kosite's electrochemical workstation, Anhui Beiyi Ke's sublimator, etc.), and is tested for structure confirmation and characteristics using methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested using equipment conventional in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical testing system, life test system, Beijing Liangtuo's ellipsometer, etc.), and are tested using methods well known to those skilled in the art. Since those skilled in the art are aware of the use of the above-mentioned equipment, testing methods and other related content, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related content is no longer expanded in this patent.

[0149] Material Synthesis Example

[0150] The preparation method of the compound of the present invention is not limited. The following compounds are typically but not limitedly exemplified, and their synthesis routes and preparation methods are as follows.

[0151] Synthesis Example 1: Synthesis of Compound I-1

[0152] Step 1: Synthesis of [Intermediate 1-b]

[0153]

[0154] Under nitrogen, 1-a (2.2 g, 7.6 mmol) was added to THF (50 mL), cooled to -72°C (ethanol / dry ice), and a 1.0 M LiHMDS solution (35 mL) was slowly added dropwise. The temperature was then slowly raised to -30°C and allowed to react for 0.5 h. ZnCl2 (2.0 M, 17 mL) was added dropwise at -30°C, and the temperature was slowly raised to 0°C for 10 min. Elemental solid iodine (7.8 g, 31 mmol) was added to the reaction solution and allowed to react at 0°C for 2 h. After completion of the reaction, the product was quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried over anhydrous Na2SO4, filtered, and concentrated. 1-b was obtained by silica gel column chromatography (eluent: DCM / PE = 1 / 2) as a white solid (4.0 g, 97% yield).

[0155] Step 2: Synthesis of [Intermediate 1-c]

[0156]

[0157] Under a nitrogen atmosphere, malononitrile (4.52 g, 68.4 mmol) was added to anhydrous DMF (160 mL). NaH (2.80 g, 70.0 mmol, 60% content) was added portionwise at 0°C and stirred for 30 minutes. 1-b (8.8 g, 16.3 mmol) and Pd(PPh4)3 (1.88 g, 1.63 mmol) were then added, and the temperature was raised to 90°C for 24 hours. After complete conversion, the product was poured into ice water and the pH was adjusted to <1 with 2N dilute hydrochloric acid. A large amount of yellow solid precipitated, which was filtered and washed with plenty of water and petroleum ether. The solid product was dissolved in acetone, concentrated, and filtered to obtain a yellow solid. The solid was washed three times with dichloromethane and finally filtered to obtain 1-c (4.4 g, 65% yield) as a yellow solid.

[0158] Step 3: Synthesis of Compound I-1

[0159]

[0160] Under a nitrogen atmosphere, 1-c (4.4 g, 10.6 mmol) was added to DCM (600 mL). The temperature was lowered to 0°C, and PIFA ([bis(trifluoroacetoxy)iodo]benzene) (9.3 g, 21.6 mmol) was added portionwise. The mixture was stirred at room temperature for 3 days, and the solution turned purple-black. The solution was concentrated, filtered, and washed twice with DCM / PE (1:1) (50 mL) to obtain compound I-1 (2.9 g, 66% yield) as a black solid. The product was confirmed to be the desired product with a molecular weight of 414.1.

[0161] The LUMO of compound I-1 was measured by cyclic voltammetry in DCM and was -4.70 eV. The LUMO of compound I-1 was calculated by DFT and was -4.83 eV.-4 The product was heated and sublimed at 300°C for 2 h under vacuum conditions of 0.5 Pa to obtain a black solid compound I-1.

[0162] Synthesis Example 2: Synthesis of Compound I-2

[0163] Step 1: Synthesis of [Intermediate 2-b]

[0164]

[0165] Under a nitrogen atmosphere, 2-a (4.7 g, 14.9 mmol) was added to THF (500 mL). The temperature was lowered to -72°C (ethanol / dry ice), and a 1.0 M LiHMDS solution (32 mL) was slowly added dropwise. The temperature was then slowly raised to -30°C and the reaction continued for 2 h. Elemental solid iodine (15.1 g, 59.4 mmol) was added to the reaction solution, and the reaction was allowed to warm to room temperature for 1 h. After completion, the reaction was quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried over anhydrous Na2SO4, filtered, and concentrated. The product 2-b (6.5 g, 77% yield) was isolated by silica gel column chromatography (DCM / PE = 2 / 1 as eluent) to afford a white solid.

[0166] Step 2: Synthesis of [Intermediate 2-c]

[0167]

[0168] Under a nitrogen atmosphere, malononitrile (4.57 g, 68.6 mmol) was added to anhydrous DMF (300 mL). NaH (2.75 g, 68.6 mmol, 60% content) was added portionwise at 0°C and stirred for 30 minutes. 2-b (6.5 g, 11.4 mmol) and Pd(PPh4)3 (1.32 g, 1.14 mmol) were added, and the temperature was raised to 90°C for 24 hours. After complete conversion, the mixture was poured into ice water and the pH was adjusted to <1 with 2N dilute hydrochloric acid. A large amount of yellow solid precipitated, which was filtered and washed with a small amount of water and petroleum ether. The solid product was dissolved in acetone, the solvent was removed by rotary evaporation, and the mixture was dried. The mixture was then washed twice with acetonitrile and dichloromethane, filtered, and washed three times with dichloromethane (20 mL) to obtain a beige solid 2-c (3.5 g, 69% yield).

[0169] Step 3: Synthesis of compound I-2

[0170]

[0171] Under a nitrogen atmosphere, 2-c (3.5 g, 7.88 mmol) was added to DCM (1000 mL), cooled to 0°C, and PIFA (6.77 g, 15.75 mmol) was added portionwise. The mixture was stirred at room temperature for 2 days, and the solution turned purple-black. The solution was concentrated and filtered to obtain a black solid. The solid was washed twice with DCM / PE = 1:1 (20 mL) and finally dried to obtain a black solid I-2 (2.6 g, 74% yield). The product was confirmed to be the target product with a molecular weight of 442.1. The LUMO of compound I-2 was measured by cyclic voltammetry in DCM and calculated by DFT to be -4.70 eV.

[0172] Synthesis Example 3: Synthesis of Compound I-3

[0173] Step 1: Synthesis of [Intermediate 3-b]

[0174]

[0175] Under a nitrogen atmosphere, 3-a (13.8 g, 34.5 mmol) was added to THF (350 mL), cooled to -72°C (ethanol / dry ice), and a 1.0 M LiHMDS solution (140 mL) was slowly added dropwise. The temperature was then slowly raised to -30°C and allowed to react for 0.5 h. A 2.0 M ZnCl solution (70 mL) was added dropwise at -30°C, and the temperature was slowly raised to 0°C for 10 min. Elemental solid iodine (35.5 g, 140 mmol) was added to the reaction solution and allowed to react at 0°C for 2 h. After completion of the reaction, the product was quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried over anhydrous Na2SO4, filtered, and the solvent was evaporated. The product 3-b (21.3 g, 95% yield) was isolated by silica gel column chromatography (DCM / PE = 2 / 1 as eluent) to afford the product as a white solid.

[0176] Step 2: Synthesis of [Intermediate 3-c]

[0177]

[0178] Under a nitrogen atmosphere, malononitrile (11.6 g, 176 mmol) was added to anhydrous DMF (260 mL). K₂CO₃ (15.6 g, 113 mmol) was added portionwise at 0°C and stirred for 30 minutes. Then, 3-b (18.7 g, 28.7 mmol) and Pd(PPh₄)₃ (3.44 g, 2.98 mmol) were added, and the temperature was raised to 90°C for 24 hours. After complete conversion, the mixture was poured into ice water and the pH was adjusted to <1 with 2N dilute hydrochloric acid. A large amount of yellow solid precipitated, which was filtered and washed with copious amounts of water and petroleum ether. The solid product was dissolved in acetone, the solvent was removed by rotary evaporation, and the mixture was dried. The product was then washed with acetonitrile and dichloromethane, filtered, and washed three times with dichloromethane (20 mL). Finally, 3-c (8.9 g, 59% yield) was obtained as a yellow solid by filtration.

[0179] Step 3: Synthesis of Compound I-3

[0180]

[0181] Under nitrogen atmosphere, 3-c (8.9 g, 16.9 mmol) was added to DCM (1000 mL), cooled to 0 ° C, and PIFA (14.5 g, 33.7 mmol) was added in batches. The mixture was stirred at room temperature for 3 days and the solution turned purple-black. Most of the solvent was removed by rotary evaporation, filtered, and washed twice with DCM / PE = 1:1 (100 mL). Finally, it was dried to obtain a black solid I-3 (6.8 g, 77% yield). The product was confirmed to be the target product with a molecular weight of 526.2. The LUMO of compound I-3 was measured by cyclic voltammetry in DCM = -4.71 eV, and the LUMO of compound I-3 was calculated by DFT = -4.72 eV. At 4.9*10 -4 Pa under vacuum conditions and heated at a constant temperature of 280 ° C for 3 h to obtain the product black solid compound I-3.

[0182] Synthesis Example 4: Synthesis of Compound I-7

[0183] Step 1: Synthesis of [Intermediate 4-b]

[0184]

[0185] Under a nitrogen atmosphere, 4-a (11.5 g, 33.0 mmol) was added to THF (220 mL). The temperature was lowered to -72°C (ethanol / dry ice), and a 1.0 M LiHMDS solution (150 mL) was slowly added dropwise. The temperature was then slowly raised to -30°C and the reaction continued for 0.5 h. A 2.0 M ZnCl solution (75 mL) was added dropwise at -30°C, and the temperature was slowly raised to 0°C for 10 min. Elemental solid iodine (33.6 g, 132 mmol) was added to the reaction solution, and the temperature was returned to room temperature. The reaction was continued at room temperature for 2 h. After the reaction was complete, the product was quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried over anhydrous Na2SO4, filtered, and the solvent was evaporated. The product 4-b (17.0 g, 86% yield) was isolated by silica gel column chromatography (DCM / PE = 1 / 2 as eluent).

[0186] Step 2: Synthesis of [Intermediate 4-c]

[0187]

[0188] Under a nitrogen atmosphere, malononitrile (11.9 g, 180 mmol) was added to anhydrous DMF (300 mL). K₂CO₃ (24.8 g, 180 mmol) was added portionwise at 0°C and stirred for 20 minutes. 5-b (18.0 g, 30.0 mmol) and Pd(PPh₄)₃ (3.50 g, 3.03 mmol) were added, and the temperature was raised to 90°C for 24 hours. After complete conversion, the product was poured into ice water and the pH was adjusted to <1 with 2N dilute hydrochloric acid. A large amount of yellow solid precipitated, which was filtered and washed with a small amount of water and petroleum ether. The solid product was dissolved in THF, the solvent was removed by rotary evaporation, and the product was dried. The product was washed with acetonitrile and tetrahydrofuran, filtered, and washed three times with dichloromethane (20 mL) to obtain 4-c (7.0 g, 50% yield) as a yellow solid.

[0189] Step 3: Synthesis of compound I-7

[0190]

[0191] Under a nitrogen atmosphere, 4-c (7.0 g, 14.7 mmol) was added to DCM (800 mL), cooled to 0°C, and PIFA (12.6 g, 19.4 mmol) was added portionwise. The mixture was stirred at room temperature for 2 days, and the solution turned purple-black. After removing most of the solvent by rotary evaporation, the mixture was filtered to obtain a black solid. The solid was washed twice with DCM / PE = 1:1 (20 mL) and finally dried to obtain a black solid I-7 (6.6 g, 94% yield). The product was confirmed to be the target product with a molecular weight of 474.1. The LUMO of compound I-7 was measured by cyclic voltammetry in DCM and the LUMO of compound I-7 was -4.73 eV. DFT calculations showed that the LUMO of compound I-7 was -4.72 eV.

[0192] Comparative Synthesis Example 1: Synthesis of Compound S

[0193] Step 1: Synthesis of [Intermediate 5-b]

[0194]

[0195] 5-a (15.0 g, 47.2 mmol) was added to ethanol (400 mL), followed by p-toluenesulfonic acid monohydrate (2.06 g, 10.8 mmol) and NIS (N-iodosuccinimide) (32.5 g, 14.4 mmol). The reaction was then allowed to proceed at room temperature for 12 hours. Upon completion, a solid product was obtained. The product was then dissolved in DCM and concentrated. Silica gel column chromatography (DCM / PE = 1 / 5 as eluent) afforded the product 5-b (15.8 g, 59% yield) as a white solid.

[0196] Step 2: Synthesis of Compound S

[0197]

[0198] Under a nitrogen atmosphere, malononitrile (8.7 g, 132 mmol) was added to anhydrous DMF (120 mL). NaH (4.95 g, 123 mmol, 60% content) was added portionwise at 0°C and stirred for 30 minutes. Then, 5-b (7.5 g, 13.2 mmol) and Pd(PPh4)3 (1.8 g, 1.5 mmol) were added, and the temperature was raised to 90°C for 36 hours. After complete conversion, the mixture was poured into ice water and the pH was adjusted to <1 with 2N dilute hydrochloric acid. A large amount of solid precipitated, which was filtered and washed with DCM. The solid product was washed with water, extracted with DCM, and dried over anhydrous sodium sulfate. PIFA (10.2 g, 23.7 mmol) was added to the filtered filtrate, and the reaction was stirred at room temperature for 3 hours. The reaction yielded a dark purple-red solution. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (DCM / PE = 1 / 1 as eluent) to afford Compound S (2.0 g, 34% yield) as a black solid. The product was confirmed to be the target product with a molecular weight of 444.1. The LUMO of compound S was measured by cyclic voltammetry in DCM as -4.29 eV, and the LUMO of compound S was calculated by DFT as -4.33 eV. -4 Pa under vacuum conditions and heated at a constant temperature of 270 ° C for 2 h to obtain the product black solid compound S.

[0199] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0200] Device Examples

[0201] Device Example 1: Preparation of an organic electroluminescent device 100, such as Figure 1 shown.

[0202] First, a 0.7 mm thick glass substrate 101 is used, on which a pre-patterned The anode 110 is made of a thick indium tin oxide (ITO). After washing the substrate with deionized water and detergent, the ITO surface is treated with oxygen plasma and UV ozone. Subsequently, the substrate is dried in a glove box to remove moisture and placed on a rack and transferred to a vacuum chamber. The organic layers specified below are placed in a vacuum of about 10 -6 Torr's case The anode layer was deposited sequentially by vacuum thermal evaporation at a rate of: first, compound HT and compound I-1 were simultaneously deposited as a hole injection layer (HIL, 80:20, )120, the evaporated compound HT is used as a hole transport layer (HTL, )130, evaporated compound EB as electron blocking layer (EBL, )140, then, compound BH and compound BD are simultaneously evaporated as the light-emitting layer (EML, 96:4, )150, evaporate compound HB as hole blocking layer (HBL, )160, compound ET and Liq co-deposited as electron transport layer (ETL, 40:60, )170, evaporation Thickness of Liq as electron injection layer (EIL) 180. Finally, the metal aluminum is evaporated as cathode (Cathode, ) 190. The device was then transferred back to the glove box and encapsulated with a glass cover slip to complete the device.

[0203] Example 2: The preparation method is the same as that of Example 1, except that compound HT and compound I-3 are evaporated as the hole injection layer (HIL, 80:20, ).

[0204] Comparative Example 1: The preparation method is the same as that of Example 1, except that the compound HT and compound S are evaporated as the hole injection layer (HIL, 80:20, ).

[0205] The detailed device layer structures and thicknesses are shown in Table 1. For layers using more than one material, the different compounds are doped in the weight ratios listed.

[0206] Table 1 Device structure of the organic layer of Examples 1-2 and Comparative Example 1

[0207]

[0208] The structure of the materials used in the device is shown below:

[0209]

[0210]

[0211] Table 2 summarizes the device performance of Examples 1, 2 and Comparative Example 1. The color coordinates (CIE), voltage (V), current efficiency (CE), external quantum efficiency (EQE) and life LT95 (h) are obtained at a current density of 10 mA / cm 2 Measured below.

[0212] Table 2 Device performance of Examples 1-2 and Comparative Example 1

[0213]

[0214] Table 2 shows the test results of organic electroluminescent devices containing different combinations of p-type conductive doping materials and hole transport material compounds HT. From the color coordinates, it can be seen that the color coordinates of the examples shown are basically consistent with those of the comparative examples.

[0215] Compared with Comparative Example 1, the voltage of Example 1 is reduced by 5.58V, a decrease of 55%; compared with Comparative Example 1, the current efficiency and external quantum efficiency of Example 1 are greatly improved, among which the current efficiency is increased by 48% and the external quantum efficiency is increased by 53%; the life of Example 1 is also significantly improved compared with Comparative Example 1, by 167%.

[0216] Compared with Comparative Example 1, the voltage of Example 2 was reduced by 4.08 V, a 40% decrease. Compared with Comparative Example 1, both the current efficiency and external quantum efficiency of Example 2 were significantly improved, with the current efficiency increasing by 51% and the external quantum efficiency increasing by 55%. The lifetime of Example 2 was significantly improved by 27 times compared with Comparative Example 1. It can be seen that Compound I-3 used in Example 2 is based on Compound I-1 used in Example 1, but with further substitution on Ring Z. It exhibits even more outstanding charge transfer capability, and the organic electroluminescent device prepared therefrom has achieved significant improvements in overall performance, particularly a significant increase in device lifetime.

[0217] From the above comparison, it can be seen that the conjugated system compound containing two N-containing five-membered heterocycles having the structure of Formula 1 disclosed in the present invention has better charge transfer ability than the compound having the conjugated bithiophene structure selected in Comparative Example 1. The organic electroluminescent device prepared therefrom achieves a reduction in voltage and a significant increase in efficiency, and has an excellent device life. Therefore, it is proved that the compound of the present invention has an unparalleled advantage in hole transport and has broad commercial prospects. It can be used to prepare organic semiconductor devices and is suitable for different types of organic electronic devices, including but not limited to fluorescent OLEDs, phosphorescent OLEDs, white OLEDs, stacked OLEDs, OTFTs, OPVs, etc.

[0218] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be restrictive.

Claims

1. A compound having a structure shown in Formula 1: in, Y is selected, identically or differently, at each occurrence from O or S; Ring Z is selected, identically or differently, at each occurrence from: aromatic rings having 6 to 20 carbon atoms; R, when present at each occurrence, is identical or different and represents mono-, poly- or unsubstituted; R is selected at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, and combinations thereof; R', R" is selected from: cyano; The substituted alkyl and substituted alkoxy groups refer to alkyl and alkoxy groups, any one of which may be substituted with one or more deuterium, unsubstituted alkyl groups having 1 to 12 carbon atoms, unsubstituted alkoxy groups having 1 to 6 carbon atoms, and combinations thereof.

2. The compound of claim 1, wherein Y is O.

3. The compound as claimed in claim 1, wherein each occurrence of ring Z is identically or differently selected from: an aromatic ring having 6 to 12 carbon atoms.

4. The compound as claimed in claim 1, wherein the ring Z is selected from a benzene ring, a biphenyl ring, a terphenyl ring, a triphenylene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a pyrene ring, Ring and perylene ring.

5. The compound of claim 1, wherein at least one of R is selected from a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a combination thereof.

6. The compound as claimed in claim 1, wherein at least one of R is selected from a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms.

7. The compound of claim 1, wherein R is selected, identically or differently, at each occurrence, from hydrogen, deuterium, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and combinations thereof, which are unsubstituted or substituted with at least one electron-donating group.

8. The compound of claim 1, wherein R is selected, identically or differently, at each occurrence from hydrogen or an electron donating group.

9. The compound of claim 7 or 8, wherein the electron donating group is the same or different at each occurrence and is selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and combinations thereof.

10. The compound according to claim 7 or 8, wherein the electron donating group is the same or different each time it occurs and is selected from: an alkyl group having 1 to 12 carbon atoms.

11. The compound of claim 1, wherein R represents mono- or poly-substitution the same or differently at each occurrence; R represents deuterium, alkyl having 1 to 6 carbon atoms, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, and combinations thereof the same or differently at each occurrence.

12. The compound of claim 1, wherein R represents mono- or poly-substitution, identically or differently, at each occurrence; R represents deuterium, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, and combinations thereof, identically or differently at each occurrence.

13. The compound of claim 1, wherein R represents mono- or poly-substitution the same or differently at each occurrence; R represents deuterium, substituted or unsubstituted alkyl having 1-12 carbon atoms, and combinations thereof the same or differently at each occurrence.

14. The compound as claimed in claim 1, wherein in Formula 1 Each occurrence is identically or differently selected from the group consisting of: in Represents the above structure The connection position with the N-containing five-membered conjugated heterocycle in Formula 1.

15. The compound of claim 14, wherein the compound is selected from any one of the structures shown by the following compounds, wherein the compound has a structure of Formula 1-1: In formula 1-1, two Ys are the same, and B represents the structure The two Bs are the same, and R', R", Y and B correspond to atoms or groups selected from the following table, wherein R', R" are selected from "*" represents the connection position of R', R" having the above structure and formula 1-1:

16. An organic electroluminescent device, comprising: anode, cathode, An organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 to 15.

17. The organic electroluminescent device according to claim 16, wherein: The organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer is formed of the compound alone.

18. The organic electroluminescent device according to claim 16, wherein: The organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer further comprises at least one hole transport material; wherein the molar doping ratio of the compound to the hole transport material is from 10000:1 to 1:10000.

19. The organic electroluminescent device according to claim 16, wherein: The organic electroluminescent device comprises at least two light-emitting units, the organic layer is a charge generation layer and is disposed between the at least two light-emitting units, wherein the charge generation layer comprises a p-type charge generation layer and an n-type charge generation layer.

20. The organic electroluminescent device according to claim 19, wherein: The p-type charge generation layer includes the compound.

21. The organic electroluminescent device according to claim 20, wherein: The p-type charge generation layer further comprises at least one hole transport material, wherein a molar doping ratio of the compound to the hole transport material is 10000:1 to 1:10000.

22. The organic electroluminescent device according to claim 18 or 21, wherein: The hole transport material is selected from the group consisting of the following compounds: compounds having triarylamine units, spirobifluorene compounds, pentacene compounds, oligothiophene compounds, oligophenyl compounds, oligophenylene vinyl compounds, oligofluorene compounds, porphyrin complexes, metal phthalocyanine complexes, and combinations thereof.

23. The organic electroluminescent device according to claim 19, wherein: The charge generation layer further includes a buffer layer disposed between the p-type charge generation layer and the n-type charge generation layer, and the buffer layer includes the compound.

24. A compound composition comprising the compound of any one of claims 1-15.

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