Organic electroluminescent materials and devices thereof

Abstract

Disclosed are an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound with a structure shown in a formula 1, can be used as a host material, a hole transport material or an electron blocking material in an organic electroluminescent device, and can provide better device performance, such as higher efficiency, especially longer service life. Also disclosed are an organic electroluminescent device comprising the compound and a compound composition comprising the compound.

Description

Technical Field

[0001] The present invention relates to compounds for organic electronic devices, such as organic light-emitting devices, and more particularly to a compound having a structure of formula 1, an organic electroluminescent device and a compound composition comprising the compound. Background Art

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

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

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

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

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

[0007] The emission color of OLED can be achieved by the structural design of the luminescent material. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, it is expected to have a more saturated emission spectrum, higher efficiency and longer device life.

[0008] CN111995530A discloses a compound for a covering layer having the following general formula structure, which also discloses It does not disclose or teach triarylamine compounds with a substituent group bonded to the 2-position of quinoline, nor does it teach the application of such compounds as other materials in organic electroluminescent devices.

[0009] There is still room for improvement in the many triarylamine-based organic semiconductor materials reported so far. In order to meet the industry's increasing demands, especially for higher device efficiency and longer device life performance, new materials still need further research and development. Summary of the invention

[0010] The present invention aims to provide a series of compounds having the structure of Formula 1 to solve at least part of the above problems. The compounds can be used as host materials, hole transport materials, or electron blocking materials in organic electroluminescent devices. These novel compounds can provide better device performance.

[0011] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:

[0012]

[0013] in,

[0014] X1 to X5 select CR the same or different each time it appears x ;

[0015] Y1 to Y5 select CR the same or different each time it appears y ;

[0016] R is selected from 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;

[0017] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0018] Ar1, Ar2 are selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms;

[0019] R x , R y, each occurrence being identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0020] In X1 to X5, the adjacent substituent R x can optionally be linked to form a ring;

[0021] In Y1 to Y5, the adjacent substituent R y Can optionally be linked to form a ring.

[0022] According to another embodiment of the present invention, an organic electroluminescent device is also disclosed, which includes an anode, a cathode, and an organic layer arranged between the anode and the cathode, wherein the organic layer contains a compound having formula 1, and the specific structure of the compound is shown in the above embodiment.

[0023] According to another embodiment of the present invention, a compound composition is also disclosed, which comprises the compound having the structure of Formula 1. The specific structure of the compound is shown in the above embodiment.

[0024] The novel compounds with the structure of Formula 1 disclosed in the present invention can be used as host materials, hole transport materials, or electron blocking materials in organic electroluminescent devices. These novel compounds can provide better device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0026] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound compositions disclosed herein. DETAILED DESCRIPTION

[0027] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An 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 can 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.

[0028] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0029] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0030] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0031] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0032] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.

[0033] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0034] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.

[0035] 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.

[0036] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

[0037] 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).

[0038] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.

[0039] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0040] Definition of Substituent Terms

[0041] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0042] Alkyl - as used herein, includes straight chain and branched alkyl. Alkyl can be an alkyl with 1 to 20 carbon atoms, preferably an alkyl with 1 to 12 carbon atoms, more preferably an alkyl with 1 to 6 carbon atoms. Examples of alkyl 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, alkyl can be optionally substituted.

[0043] Cycloalkyl - as used herein, includes cyclic alkyl. Cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, cycloalkyl can be optionally substituted.

[0044] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbons in an alkyl chain substituted with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom and a boron atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl may be optionally substituted.

[0045] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.

[0046] Alkynyl - as used herein, encompasses straight chain alkynyl. Alkynyl can be an alkynyl containing 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl can be optionally substituted.

[0047] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadrenyl. In addition, the aryl group may be optionally substituted.

[0048] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.

[0049] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group can be optionally substituted.

[0050] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.

[0051] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.

[0052] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0053] Alkylsilyl - as used herein, encompasses alkyl-substituted silicon groups. Alkylsilyl can be an alkylsilyl having 3-20 carbon atoms, preferably an alkylsilyl having 3 to 10 carbon atoms. The example of an alkylsilyl includes trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl can be optionally substituted.

[0054] Arylsilyl-as used herein, encompasses at least one aryl substituted silicon radical.Arylsilyl can be an arylsilyl with 6-30 carbon atoms, preferably an arylsilyl with 8 to 20 carbon atoms.The example of arylsilyl includes triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl.In addition, arylsilyl can be optionally substituted.

[0055] Alkylgermanyl - As used herein, alkyl-substituted germanium is encompassed. The alkylgermanyl may be an alkylgermanyl having 3-20 carbon atoms, preferably an alkylgermanyl having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyltert-butylgermanyl, methyldi-tert-butylgermanyl. In addition, the alkylgermanyl may be optionally substituted.

[0056] Arylgermanyl - as used herein, encompasses at least one aryl or heteroaryl substituted germanium. Arylgermanyl can be an arylgermanyl having 6-30 carbon atoms, preferably an arylgermanyl having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyltert-butylgermanyl. In addition, arylgermanyl can be optionally substituted.

[0057] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0058] 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 groups, substituted sulfinyl groups, substituted sulfonyl groups, substituted phosphino groups refer to any one of alkyl groups, cycloalkyl groups, heteroalkyl groups, heterocyclic groups, aralkyl groups, alkoxy groups, aryloxy groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, alkylgermanyl groups, arylgermanyl groups, amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, sulfinyl groups, sulfonyl groups and phosphino groups, which may be substituted by one or more of deuterium, halogen groups, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted alkyl groups having 1 to 20 carbon atoms, 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 aryl having 6-30 carbon atoms , 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, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0059] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0060] In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

[0061] In the compounds mentioned in the present disclosure, polysubstitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituent existing in multiple available substitution positions can be the same structure or different structures.

[0062] In the compounds mentioned in the present disclosure, unless clearly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged ring, condensed ring, etc.), as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0063] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0064]

[0065] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0066]

[0067] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to a further distant carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0068]

[0069] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0070]

[0071] According to one embodiment of the present invention, a compound having Formula 1 is disclosed:

[0072]

[0073] in,

[0074] X1 to X5 select CR the same or different each time it appears x ;

[0075] Y1 to Y5 select CR the same or different each time it appears y ;

[0076] R is selected from 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;

[0077] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0078] Ar1, Ar2 are selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms;

[0079] R x , R y, each occurrence being identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0080] In X1 to X5, the adjacent substituent R x can optionally be linked to form a ring;

[0081] In Y1 to Y5, the adjacent substituent R y Can optionally be linked to form a ring.

[0082] In this context, “the adjacent substituent R x "can optionally be linked to form a ring" is intended to mean that any two adjacent substituents R x Obviously, any adjacent substituents R x They can also not be connected to form a ring.

[0083] In this context, “the adjacent substituent R y "can optionally be linked to form a ring" is intended to mean that any two adjacent substituents R y Obviously, any adjacent substituents R y They can also not be connected to form a ring.

[0084] According to one embodiment of the present invention, each time Y2-Y4 appears, C or CR is selected the same or differently. y ; and one of Y2-Y4 is C and connected to L.

[0085] According to one embodiment of the present invention, Y3 is C and connected to L.

[0086] According to one embodiment of the present invention, R is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0087] According to one embodiment of the present invention, R is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted silanyl.

[0088] According to one embodiment of the present invention, R x , R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0089] According to one embodiment of the present invention, R x , R y is selected, at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, phenyl, pyridyl, vinyl, naphthyl, biphenyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, carbazolyl, yl, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof.

[0090] According to one embodiment of the present invention, at least one of Ar1 and Ar2 has a structure of Formula 1-1:

[0091]

[0092] In Formula 1-1, Z1-Z5 are selected from C, N or CR at each occurrence, the same or different Z , and one of Z1-Z5 is C and connected to Ar3;

[0093] Ar3 is selected, at each occurrence, identically or differently, from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms.

[0094] According to one embodiment of the present invention, Ar3 is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, the same or different each time it occurs.

[0095] According to one embodiment of the present invention, Ar1 and Ar2 are selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted silanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted spirosilanyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted adamantyl, substituted or unsubstituted cyclohexyl, or a combination thereof.

[0096] According to one embodiment of the present invention, Ar1 and Ar2 are selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted silanyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzoxazolyl, or a combination thereof.

[0097] According to one embodiment of the present invention, Ar1 and Ar2 are selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted silanyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzoxazolyl, or a combination thereof.

[0098] According to one embodiment of the present invention, Ar1 and Ar2 are selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, fluorenyl, silyl, yl, benzoxazolyl, or a combination thereof.

[0099] According to one embodiment of the present invention, L is selected from a single bond.

[0100] According to one embodiment of the present invention, the compound is selected from the group consisting of compound A-1 to compound A-266; the specific structures of compound A-1 to compound A-266 are shown in claim 7.

[0101] According to one embodiment of the present invention, an organic electroluminescent device is also disclosed, comprising:

[0102] anode,

[0103] cathode,

[0104] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having Formula 1, and the specific structure of the compound is as shown in any of the above embodiments.

[0105] According to one embodiment of the present invention, in the device, the organic layer is a light-emitting layer, a hole transport layer, or an electron blocking layer.

[0106] According to an embodiment of the present invention, in the device, the organic layer is a light-emitting layer, and the compound is a host material.

[0107] According to one embodiment of the present invention, in the device, the organic layer is a hole transport layer, and the compound is a hole transport material.

[0108] According to an embodiment of the present invention, in the device, the organic layer is an electron blocking layer, and the compound is an electron blocking material.

[0109] According to one embodiment of the present invention, the organic layer is a light-emitting layer, the compound is a host compound, and the light-emitting layer further comprises a second host compound, and the second host compound has a structure represented by Formula 2:

[0110]

[0111] In formula 2,

[0112] L 21 To L 23 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0113] Ar 21 To Ar 23 Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.

[0114] According to one embodiment of the present invention, the second compound has a structure shown in Formula 2-1:

[0115]

[0116] Each occurrence of T1-T6 is identically or differently selected from C, N or CR T , and one of T1-T6 is C and connected to L 23 connected;

[0117] L1 to L3 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0118] Ar 21 and Ar 22 is selected, at each occurrence, identically or differently, from 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;

[0119] R T The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0120] Adjacent substituent R T Can optionally be linked to form a ring.

[0121] In this context, “the adjacent substituent R T "can optionally be linked to form a ring" is intended to mean that any two adjacent substituents R T Obviously, any adjacent substituents R T They can also not be connected to form a ring.

[0122] According to one embodiment of the present invention, the second compound has a structure shown in Formula 2-1-1 or Formula 2-1-2:

[0123]

[0124] Wherein in formula 2-1-1, T1-T5 are selected from C, N or CR at each occurrence, the same or different T , T 11 -T 15 Each occurrence is selected from N or CR, either identically or differently T1 , and one of T1-T5 is C and connected to L 23 In formula 2-1-2, T1-T4 are selected from C, N or CR at each occurrence, either identically or differently. T , T 11 -T 14 Each occurrence is selected from N or CR, either identically or differently T1 , and one of T1-T4 is C and connected to L 23 connected;

[0125] Q is selected from O, S or Se;

[0126] L 21 To L 23 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0127] Ar 21 and Ar 22 is selected, at each occurrence, identically or differently, from 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;

[0128] R T , R T1The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0129] Adjacent substituent R T , R T1 Can optionally be linked to form a ring.

[0130] In this context, adjacent substituents R T , R T1 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R T Between the two substituents R T1 Between, the substituent R T and R T1 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0131] According to one embodiment of the present invention, in Formula 2-1-2, Q is selected from O or S.

[0132] According to one embodiment of the present invention, in formula 2-1-2, Q is O.

[0133] According to one embodiment of the present invention, in Formula 2-1-1, T1 to T5 are selected from C or CR each time they appear, the same or different. T , T 11 To T 15 Each occurrence is the same or different selection from CR T1 In formula 2-1-2, T1 to T4 are selected from C or CR each time they appear, either identically or differently. T , T11 To T 14 Each occurrence is the same or different selection from CR T1 .

[0134] According to one embodiment of the present invention, wherein the R T , R T1 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0135] According to one embodiment of the present invention, in Formula 2-1-1, at least one of T1 to T5 is selected from CR T , or T 11 To T 15 At least one of CR T1 In formula 2-1-2, at least one of T1 to T4 is selected from CR T , or T 11 To T 14 At least one of CR T1 ; and said R T , R T1 and is selected, identically or differently on each occurrence, from substituted or unsubstituted aryl having 6 to 30 carbon atoms.

[0136] According to one embodiment of the present invention, wherein the R T , R T1 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and combinations thereof.

[0137] According to one embodiment of the present invention, wherein the Ar 21 and Ar 22 At least one of them has a structure with two condensed rings or three condensed rings.

[0138] According to one embodiment of the present invention, wherein Ar 21 and Ar 22 Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, or a combination thereof.

[0139] According to one embodiment of the present invention, wherein Ar 21 and Ar 22is selected, at each occurrence, identically or differently, from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted indolocarbazolyl, or a combination thereof.

[0140] According to one embodiment of the present invention, L 21 To L 23 Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof.

[0141] According to one embodiment of the present invention, L 21 To L 23 Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, or a combination thereof.

[0142] According to one embodiment of the present invention, the compound is selected from the group consisting of compound B-1 to compound B-255; the specific structures of compound B-1 to compound B-255 are shown in claim 10.

[0143] According to one embodiment of the present invention, the organic layer is a light-emitting layer, the compound is a host compound; the light-emitting layer further comprises a first metal complex having M(L a ) m (L b ) n (L c ) q The general formula of

[0144] M is selected from metals with a relative atomic mass greater than 40;

[0145] L a , L b , L c are the first ligand, the second ligand and the third ligand coordinated with the M respectively; L a , L b , L can be optionally linked to form a multidentate ligand;

[0146] L a , L b , L ccan be the same or different; m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of m, n, q is equal to the oxidation state of the M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, the two L b can be the same or different; when q is 2, the two L c Can be the same or different;

[0147] L a It has a structure as shown in Formula 2:

[0148]

[0149] in,

[0150] Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0151] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0152] Ring D and Ring E via U a and U b condense;

[0153] U a and U b is selected identically or differently at each occurrence from C or N;

[0154] R d , R e Each occurrence of the same or different means mono-, poly- or no-substitution;

[0155] Each time V1-V4 appears, they are selected from CR v or N;

[0156] R d , R e , R vThe alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0157] Adjacent substituent R d , R e , R v can be optionally linked into a ring;

[0158] L b , L c Each occurrence is identically or differently selected from any one of the following structures:

[0159]

[0160] in,

[0161] R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0162] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0163] X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;

[0164] R a , R b , Rc , R N1 , R N2 , R C1 and R C2 The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0165] The ligand L b , L c In the structure of a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.

[0166] In this context, adjacent substituents R d , R e , R v can be optionally connected to form a ring, which is intended to indicate that when there is a substituent R d , Substituent R e , Substituent R v When adjacent substituent groups, such as adjacent substituents R d Between and adjacent substituents R e Between and adjacent substituents R v Between and adjacent substituents R d With R e Between and adjacent substituents R d With R v Between and adjacent substituents R e With R vAny one or more of these adjacent substituent groups can be linked to form a ring. d , Substituent R e , Substituent R v When the substituent groups are not linked to form a ring.

[0167] In this context, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and R C1 Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, the substituent R a and R N2 Between, the substituent R b and R N2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0168] According to one embodiment of the present invention, in the device, wherein, in Formula 2, R d , R e , R v At least one or two groups of adjacent substituents are connected to form a ring. For example, two substituents R d Connect to form a ring, or two substituents R e Connect to form a ring, or two substituents R vConnect to form a ring, or substituent R d With substituent R e Connected to form a ring, or substituent R d With substituent R v Connected to form a ring, or substituent R e With substituent R v Connected to form a ring, or two substituents R d When two substituents R are connected to form a ring e Connect to form a ring, or two substituents R d When two substituents R are connected to form a ring v Connect to form a ring, or two substituents R e When two substituents R are connected to form a ring v Connect to form a ring, substituent R e With substituent R v When the ring is formed, two substituents R v Ring, or substituent R d With substituent R v When the ring is formed, two substituents R v Ringing; R d , R e , R v A similar situation occurs when more groups of adjacent substituents are connected to form a ring.

[0169] According to one embodiment of the present invention, in the device, the phosphorescent light-emitting material is a metal complex having M(L a ) m (L b ) n The general formula of

[0170] The metal M is selected from metals with a relative atomic mass greater than 40;

[0171] L a , L b are the first ligand and the second ligand coordinated with the M respectively; L a , L b can optionally be linked to form a multidentate ligand;

[0172] m is 1, 2 or 3; n is 0, 1 or 2; the sum of m and n is equal to the oxidation state of M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, the two L b Can be the same or different;

[0173] L a It has a structure as shown in Formula 2:

[0174]

[0175] in,

[0176] Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0177] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0178] Ring D and Ring E via U a and U b condense;

[0179] U a and U b is selected identically or differently at each occurrence from C or N;

[0180] R d , R e Each occurrence of the same or different means mono-, poly- or no-substitution;

[0181] Each time V1-V4 appears, they are selected from CR v or N;

[0182] R d , R e , R v The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0183] Adjacent substituent R d , R e , R v can be optionally linked into a ring;

[0184] Wherein the ligand L bHas the following structure:

[0185]

[0186] wherein R1 to R7 are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms, The invention also includes but is not limited to alkenyl, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0187] According to one embodiment of the present invention, in the device, the ligand L b Has the following structure:

[0188]

[0189] Among them, at least one of R1-R3 is selected from 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, or a combination thereof; and / or at least one of R4-R6 is selected from 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, or a combination thereof.

[0190] According to one embodiment of the present invention, in the device, the ligand L b Has the following structure:

[0191]

[0192] Among them, at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof, the same or different at each occurrence; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof, the same or different at each occurrence.

[0193] According to one embodiment of the present invention, in the device, the ligand L b Has the following structure:

[0194]

[0195] wherein at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof, the same or different at each occurrence; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof, the same or different at each occurrence.

[0196] According to one embodiment of the present invention, the metal M is selected from Ir, Pt or Os.

[0197] According to one embodiment of the present invention, the phosphorescent material is an Ir complex having Ir(L a )(L b )(L c )、Ir(L a )2(L b )、Ir(L a )(L b )2、Ir(L a )2(L c ) or Ir(L a )(L c )A structure shown in any one of 2.

[0198] According to one embodiment of the present invention, wherein L a The compound has a structure as shown in Formula 2 and comprises at least one structural unit selected from the group consisting of a 6-membered and 6-membered aromatic ring, a 6-membered and 6-membered heteroaromatic ring, a 6-membered and 5-membered aromatic ring and a 6-membered and 5-membered heteroaromatic ring.

[0199] According to one embodiment of the present invention, wherein L a The compound has a structure as shown in Formula 2 and comprises at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.

[0200] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains a ligand L a , the L a Each occurrence is identically or differently selected from any one of the group consisting of:

[0201]

[0202]

[0203] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains a ligand L b , the L b Each occurrence is identically or differently selected from any one of the group consisting of:

[0204]

[0205]

[0206] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is selected from the group consisting of the following structures:

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229] According to another embodiment of the present invention, a compound composition is also disclosed, which comprises a compound represented by Formula 1, and the specific structure of the compound is shown in any of the aforementioned embodiments.

[0230] Combination with other materials

[0231] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0232] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of luminescent 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.

[0233] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.

[0234] Material synthesis example:

[0235] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0236] Synthesis Example 1: Synthesis of Compound A-24

[0237] Step 1: Synthesis of intermediate 3

[0238]

[0239] Under an oxygen atmosphere, intermediate 1 (25.0 g, 122.75 mmol), intermediate 2 (18.12 g, 135.02 mmol), palladium acetate (2.76 g, 12.27 mmol), and dimethyl sulfoxide (200 mL) were added to a three-necked flask and reacted at 110° C. for 16 h. After the reaction was completed, the mixture was extracted with ethyl acetate, the organic phase was washed with water, and the solvent was removed by concentration. The crude product was purified by column chromatography using PE / DCM=4 / 1 to obtain 6 g of white solid intermediate 3 (yield: 15.5%).

[0240] Step 2: Synthesis of Compound A-24

[0241]

[0242] Under nitrogen protection, intermediate 3 (2.7 g, 8.55 mmol), intermediate 4 (3.33 g, 8.98 mmol), bis(dibenzylideneacetone)palladium (96.95 mg, 0.17 mmol), 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (140.40 mg, 0.34 mmol), sodium tert-butoxide (1.64 g, 17.10 mmol), and xylene (100 mL) were added to a three-necked flask and reacted at 140° C. for 2 h. After the reaction was completed, the mixture was extracted with dichloromethane, the organic phase was washed with water, and the crude product obtained by concentrating the solvent was purified by column chromatography (PE / DCM=2 / 1) to obtain yellow solid compound A-24 (3.5 g, yield: 63%). The product was confirmed to be the target product with a molecular weight of 650.3.

[0243] Synthesis Example 2: Synthesis of Compound A-5

[0244]

[0245] Under nitrogen protection, intermediate 3 (1.50 g, 4.75 mmol), intermediate 5 (1.85 g, 4.99 mmol), bis(dibenzylideneacetone)palladium (53.86 mg, 0.095 mmol), 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (78.00 mg, 0.19 mmol), sodium tert-butoxide (0.91 g, 9.5 mmol), and xylene (100 mL) were added to a three-necked flask and reacted at 140° C. for 2 h. After the reaction was completed, the liquid was filtered, and the crude product was purified by column chromatography with (PE / DCM=1 / 1) to obtain a yellow solid compound A-5 (2.0 g, yield: 70%). The product was confirmed to be the target product with a molecular weight of 600.3.

[0246] 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.

[0247] Device Embodiment

[0248] First, the glass substrate with a 120nm thick indium tin oxide (ITO) anode was cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate was dried in a nitrogen-filled glove box to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -6 Torr's case The compound HT and the compound HI were co-evaporated to form a hole injection layer (HIL, weight ratio 97:3) with a thickness of Compound HT was used as a hole transport layer (HTL) with a thickness of Compound EB is used as an electron blocking layer (EBL) with a thickness of Then, the compound A-24 of the present invention as the first host, the compound B-227 as the second host, and the compound RD as the dopant were co-evaporated to form an emitting layer (EML, weight ratio 29.1:67.9:3) with a thickness of Compound HB was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron transport layer (ETL, weight ratio 40:60) with a thickness of Finally, evaporation 8-Hydroxyquinoline-lithium (Liq) was used as an electron injection layer (EIL) and evaporated The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.

[0249] Device Example 2

[0250] The implementation of Device Example 2 is the same as that of Device Example 1, except that the present compound A-5 is used as the host in the emission layer (EML) instead of the present compound A-24.

[0251] Device Comparison Example 1

[0252] The implementation of Comparative Device Example 1 is the same as that of Example 1, except that Compound C is used as a host in the emission layer (EML) instead of Compound A-24 of the present invention.

[0253] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.

[0254] Table 1 Device structures of device embodiments and comparative examples

[0255]

[0256]

[0257] The material structure used in the device is shown below:

[0258]

[0259] Table 2 lists the 2 The maximum emission wavelength (λ max ), current efficiency (CE), external quantum efficiency (EQE), power efficiency (PE) data and device lifetime (LT97). Device lifetime (LT97) refers to the time required for the device brightness to decay to 97% of its initial brightness.

[0260] Table 2 Device data

[0261] Device ID <![CDATA[λ max (nm)]]> CE[cd / A] EQE[%] PE[lm / W] LT97[h] Example 1 622 28.6 26.8 24.4 1152 Example 2 622 29.7 27.9 25.2 2072 Comparative Example 1 622 28.6 26.7 23.7 420

[0262] As can be seen from the data in Table 2, the maximum emission wavelength of device embodiments 1, 2 and comparative example 1 remain consistent; the only difference between embodiment 1 and comparative example 1 is that the 2-position of quinoline is replaced by an aryl group, and the device efficiency of comparative example 1 is already at a very high level, and it can still maintain a comparable or slightly improved level; more importantly, compared with comparative example 1, embodiment 1 can significantly improve the device life by 1.7 times. Embodiment 2 and embodiment 1 use different Ar1 / Ar2, and embodiment 2 can also achieve high efficiency and long life similar to embodiment 1; more importantly, compared with comparative example 1, embodiment 2, after the 2-position of quinoline is replaced by an aryl group, the device life is unexpectedly greatly improved by 3.9 times. This shows that the compounds of the present invention can make the hole transport in the device more stable, and can better recombine with the electrons in the device, thereby significantly improving the performance of the device.

[0263] Based on the above results, it can be seen that the compound having the structure of Formula 1 disclosed in the present invention can be used as a main material to improve the life of the device, and therefore has broad commercial development prospects and application value.

[0264] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

Claims

1. A compound having formula 1: in, X1-X5 selects CR the same or different each time it appears x ; Each time Y1-Y5 appears, choose C or CR, either the same or different. y ; and one of Y1-Y5 is C and connected to L; R is selected from 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; L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar1, Ar2 are selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms; R x , R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; In X1 to X5, the adjacent substituent R x can optionally be linked to form a ring; In Y1 to Y5, the adjacent substituent R y Can optionally be linked to form a ring.

2. The compound according to claim 1, wherein Each time Y2-Y4 appears, choose C or CR, either the same or different. y ; and one of Y2-Y4 is C and connected to L; Preferably, Y3 is C and is linked to L.

3. The compound according to claim 1, wherein Ar1, Ar2 are selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms; Preferably, Ar1, Ar2 are selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted silanyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzoxazolyl, or a combination thereof.

4. The compound according to claim 1, wherein R x , R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; the adjacent substituent R x , R y can optionally be linked to form a ring; Preferably, the R x , R y , each occurrence of which is selected, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, phenyl, pyridyl, vinyl, naphthyl, biphenyl, phenanthrenyl, triphenylene, dibenzofuranyl, dibenzothienyl, carbazolyl, yl, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, or a combination thereof.

5. The compound according to claim 1, wherein R is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof; Preferably, R is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted silanyl.

6. The compound of any one of claims 1 to 5, wherein L is selected from a single bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Preferably, wherein L is selected from a single bond, or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms; More preferably, L is selected from a single bond.

7. The compound of claim 1, wherein the compound is selected from the group consisting of Compound A-1 to Compound A-266: Optionally, hydrogen in the structures of Compound A-1 to Compound A-266 can be partially or completely replaced by deuterium.

8. An organic electroluminescent device, comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic layer is a light-emitting layer and the compound is a host compound; or the organic layer is a hole transport layer and the compound is a hole transport compound; or the organic layer is an electron blocking layer and the compound is an electron blocking compound; Preferably, the organic layer is a light-emitting layer, and the compound is a host material.

10. The organic electroluminescent device according to claim 8, wherein the organic layer is a light-emitting layer, the light-emitting layer further comprises a second compound, the second compound is a host material, and the second compound has a structure represented by Formula 2: in, L 21 To L 23 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar 21 To Ar 23 is selected, at each occurrence, identically or differently, from 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; Preferably, the second compound B-1 to compound B-255 are composed of the following: Optionally, hydrogen in the structures of Compound B-1 to Compound B-255 can be partially or completely replaced by deuterium.

11. The organic electroluminescent device according to claim 8, wherein the organic layer is a light-emitting layer, and the light-emitting layer further comprises at least one phosphorescent light-emitting material.

12. The organic electroluminescent device according to claim 11, wherein the phosphorescent material is a metal complex having M(L a ) m (L b ) n (L c ) q The general formula of M is selected from metals with a relative atomic mass greater than 40; L a , L b , L c are the first ligand, the second ligand and the third ligand coordinated with the M respectively; L a , L b , L can be optionally linked to form a multidentate ligand; L a , L b , L c can be the same or different; m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of m, n, q is equal to the oxidation state of the M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, the two L b can be the same or different; when q is 2, the two L c Can be the same or different; L a It has a structure as shown in Formula 3: in, Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring; Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring Ring D and Ring E via U a and U b condense; U a and U b is selected identically or differently at each occurrence from C or N; R d , R e Each occurrence of the same or different means mono-, poly- or no-substitution; Each time V1-V4 appears, they are selected from CR v or N; R d , R e , R v The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituent R d , R e , R v can be optionally linked into a ring; Ligand L b , L c Each occurrence is identically or differently selected from any one of the following structures: in, R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ; R a , R b , R c , R N1 , R N2 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be linked to form a ring; Wherein the ligand L b Each occurrence is identically or differently selected from the following structures: wherein R1 to R7 are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms, substituted or unsubstituted alkenyl having 6-30 carbon atoms, substituted or unsubstituted aryl having 3-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; Preferably, the phosphorescent material is an Ir complex, a Pt complex or an Os complex; More preferably, the phosphorescent material is an Ir complex having Ir(L a )(L b )(L c )、Ir(L a )2(L b )、Ir(L a )(L b )2、Ir(L a )2(L c ) or Ir(L a )(L c )A structure shown in any one of 2.

13. A compound composition comprising the compound according to any one of claims 1 to 7.

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