An organic compound, an organic electroluminescent material and its application

Abstract

The present invention provides an organic compound, an organic electroluminescent material and its application. The organic compound has the structure shown in the following formula I. The organic compound provided by the present invention can be used as a hole transport layer and / or a luminescence assisting layer material, which can effectively transport holes and block electrons, improve the exciton utilization rate; has a suitable hole mobility, a relatively high Tg, good thermal stability, and the molecule has appropriate torsion and steric hindrance, making the material not easy to crystallize; can be used in the hole transport layer and / or the luminescence assisting layer of an organic light-emitting device, reduce the driving voltage of the device, and improve the luminescence efficiency and lifespan of the device.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic optoelectronic materials, and particularly relates to an organic compound, an organic electroluminescent material and its application. Background Art

[0002] An organic light-emitting device (OLED device) is a light-emitting device based on organic light-emitting materials, which has attracted wide attention due to its many advantages such as high-efficiency light emission, simple manufacturing process, and large-area flexibility.

[0003] At present, OLED devices have basically met the requirements of small and medium-sized displays and are widely used in flat panel displays and lighting fields such as instruments, high-end smartphones, and televisions. In addition to the necessary light-emitting layer, an OLED device contains any one or at least two combinations of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron buffer layer, an electron transport layer, an electron buffer layer or an electron injection layer, which are used to regulate the injection and transport of electrons and holes.

[0004] Existing hole transport materials have several technical problems: First, the poor solubility of the materials will lead to poor cleaning effect of the evaporated film during mass production; Second, the slow mobility of the materials will lead to too high overall voltage of the device; Third, the too fast mobility of the materials, especially the too fast lateral mobility of the materials, will lead to crosstalk between adjacent pixels; Fourth, the too deep LUMO energy level of the materials cannot effectively block the electron migration that may cross the light-emitting layer; Fifth, the low triplet energy level of the materials cannot effectively block the excitons in the light-emitting layer, resulting in low light-emitting efficiency of the device.

[0005] In order to solve the light-emitting problem in the hole transport layer, the method of using a light-emitting auxiliary layer between the hole transport layer and the light-emitting layer has been continuously studied. The auxiliary organic layer helps to improve the injection efficiency of carriers (holes and electrons) between the interfaces of each layer, balance the transport of carriers between each layer, and thus improve the brightness and efficiency of the device.

[0006] The research on organic electroluminescent materials has been widely carried out in the academic and industrial fields. However, so far, organic layer materials for stable and efficient organic electrical components have not been fully developed, and the industrialization process of this technology still faces many key problems. Therefore, developing new materials has always been an urgent problem for those skilled in the art. Summary of the Invention

[0007] Aiming at the deficiencies of the existing technology, the purpose of the present invention is to provide an organic compound, an organic electroluminescent material and its application. The organic compound provided by the present invention, as an organic electroluminescent compound, can be used as a hole transport layer and / or a light-emitting auxiliary layer material, which can reduce the driving voltage of the device and improve the light-emitting efficiency and lifespan of the device.

[0008] To achieve the object of the present invention, the following technical solutions are adopted in the present invention:

[0009] In a first aspect, the present invention provides an organic compound having a structure shown in the following formula I:

[0010]

[0011] Wherein, L1, L2, and L3 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 (such as C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) arylene group, a substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) heteroarylene group;

[0012] R is selected from any one of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C30 straight-chain or branched-chain alkyl group, a substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) cycloalkyl group, a substituted or unsubstituted C6-C60 (such as C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.) aryl group, a substituted or unsubstituted C3-C60 (such as C3, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl group.

[0013] The organic compound provided by the present invention can be used as a hole transport layer and / or a luminescence assisting layer material, which can effectively transport holes and block electrons, improving the exciton utilization rate; it has a suitable hole mobility, a relatively high Tg, good thermal stability, and the molecule has appropriate twists and steric hindrances, making the material not easy to crystallize; it can be used in the hole transport layer and / or the luminescence assisting layer of an organic light-emitting device, reducing the driving voltage of the device and improving the light-emitting efficiency and lifespan of the device.

[0014] In the present invention, the substituents in the substituted arylene, substituted heteroarylene, substituted straight-chain or branched alkyl, substituted cycloalkyl, substituted aryl, and substituted heteroaryl are each independently selected from deuterium, halogen, cyano, C1-C30 (such as C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight-chain or branched alkyl, C3-C30 (such as C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) cycloalkyl, C6-C60 (such as C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.) aryl, or C3-C60 (such as C3, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl, or any combination of at least two of them.

[0015] Preferably, the substituents in the substituted arylene, substituted heteroarylene, substituted straight-chain or branched alkyl, substituted cycloalkyl, substituted aryl, and substituted heteroaryl are each independently selected from deuterium, halogen, cyano, methyl, phenyl, naphthyl, dibenzofuran, dibenzothiophene, dimethylfluorenyl, or any combination of at least two of them.

[0016] In the present invention, the organic compound is selected from any one of the following formulas I-1 to I-4:

[0017]

[0018] Among them, the L1, L2, L3, and R have the same defined ranges as described in Formula I above.

[0019] In the present invention, the L1, L2, and L3 are each independently selected from a single bond or a phenylene group.

[0020] In the present invention, the R is selected from any one of hydrogen, deuterium, halogen, phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted benzonaphthofuranyl, and substituted or unsubstituted benzonaphthothiophenyl.

[0021] Preferably, the substituents in the substituted biphenyl, substituted terphenyl, substituted naphthyl, substituted phenanthryl, substituted anthryl, substituted pyridyl, substituted dibenzofuranyl, substituted dibenzothiophenyl, substituted carbazolyl, substituted dimethylfluorenyl, substituted diphenylfluorenyl, substituted spirobifluorenyl, substituted benzocarbazolyl, substituted benzonaphthofuranyl, and substituted benzonaphthothiophenyl are selected from any one or a combination of at least two of deuterium, halogen, cyano, methyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.

[0022] Preferably, the dimethylfluorenyl is selected from any one of the following structures:

[0023]

[0024] Among them, represents the connection site of the group;

[0025] Preferably, the diphenylfluorenyl is selected from any one of the following structures:

[0026]

[0027] Among them, represents the connection site of the group.

[0028] Preferably, the carbazolyl is selected from any one of the following structures:

[0029]

[0030] Among them, represents the connection site of the group.

[0031] In the present invention, the organic compound includes any one of M1 - M39 as follows:

[0032]

[0033]

[0034]

[0035] In a second aspect, the present invention provides an organic electroluminescent material, which includes the organic compound as described in the first aspect.

[0036] In a third aspect, the present invention provides an organic electroluminescent device, which includes an anode, a cathode, and an organic thin film layer located between the anode and the cathode. The organic thin film layer includes the organic compound as described in the first aspect or the organic electroluminescent material as described in the second aspect.

[0037] In the present invention, the organic thin film layer includes any one or a combination of at least two of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron buffer layer, an electron transport layer, an electron buffer layer, or an electron injection layer.

[0038] Preferably, the hole transport layer includes the organic compound as described in the first aspect.

[0039] Preferably, the light-emitting auxiliary layer includes the organic compound as described in the first aspect.

[0040] In a fourth aspect, the present invention provides an electronic device, which includes the organic electroluminescent device as described in the third aspect.

[0041] Preferably, the electronic device includes any one of an optical fiber, a lighting device, an electrophotographic photoreceptor, a photoelectric converter, an organic solar cell, a switching element, an organic light-emitting field effect transistor, an image sensor, or a dye laser.

[0042] Compared with the prior art, the present invention has the following beneficial effects:

[0043] The organic compound provided by the present invention can be used as a hole transport layer and / or a light-emitting auxiliary layer material, which can effectively transport holes and block electrons, improving the exciton utilization rate; it has a suitable hole mobility, a relatively high Tg, good thermal stability, and the molecules have appropriate twists and steric hindrances, making the material not easily crystallize; it can be used in the hole transport layer and / or the light-emitting auxiliary layer of an organic light-emitting device, reducing the driving voltage of the device and improving the light-emitting efficiency and lifespan of the device.

[0044] Term Explanation

[0045] Definition of Device Terms

[0046] As used in the present invention, the term "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device and can be included, as needed, in any layer constituting the organic electroluminescent device.

[0047] As used in the present invention, the term "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent element and can contain at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, an electron blocking material, a luminescence assisting material, a luminescent layer material (including a host material and a doping material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0048] The organic electroluminescent material disclosed in the present invention can contain at least one compound represented by Formula I. Although not limited thereto, the compound having the structure shown in Formula 1 can be included in the hole transport layer, and / or the compound having the structure shown in Formula I can be included in the luminescence assisting layer, and is not limited thereto.

[0049] Hereinafter, each layer of the organic electroluminescent element composed of the compound of Formula 1 of the present invention will be described.

[0050] Substrate

[0051] An organic EL element is usually fabricated on a light-transmissive substrate. The light-transmissive substrate is a substrate for supporting the organic EL element, and the transmittance of light in the visible region of wavelengths 400 - 700 nm is preferably 50% or more, and a smooth substrate is further preferably used.

[0052] Examples of such a light-transmissive substrate include a glass plate, a synthetic resin plate, etc. Examples of the glass plate include plates formed of soda-lime glass, barium- and strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz, etc. In addition, examples of the synthetic resin plate include plates of polycarbonate resin, acrylic resin, polyethylene terephthalate resin, polyether sulfide resin, polysulfone resin, etc.

[0053] Anode

[0054] The anode serves to inject holes into the hole transport layer or the light-emitting layer, and it is effective to have a work function of 4 eV or more (preferably 4.45 eV or more). Specific examples of the anode material include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, etc., as well as their alloys, the metal oxides such as tin oxide and indium oxide used in ITO substrates and NESA substrates, and organic conductive resins such as polythiophene or polypyrrole.

[0055] Cathode

[0056] As the cathode, a cathode using a metal, alloy, conductive compound, or a mixture thereof with a small work function (less than 4 eV) as the electrode material can be used. Specific examples of such electrode materials include magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, etc., as well as their alloys, and there is no particular limitation on them. As representative examples of such alloys, magnesium / silver, magnesium / indium, lithium / aluminum, etc. can be cited, and there is no particular limitation on them. The ratio of the alloy is controlled by the temperature, atmosphere, degree of vacuum, etc. of the evaporation source, and an appropriate ratio is selected. The anode and the cathode can also be formed by two or more layers as needed.

[0057] Light-emitting layer

[0058] The light-emitting layer has functions of both carrier injection, carrier transport, and light emission. The light-emitting layer material includes a host material and a guest material, and the guest material includes a phosphorescent guest material, a fluorescent guest material, a TADF guest material, etc.

[0059] Hole injection layer / hole transport layer

[0060] The hole injection layer / hole transport layer is a layer that helps inject holes into the light-emitting layer and transport the holes to the light-emitting region. It has a large hole mobility and an ionization energy that is usually as small as 5.7 eV or less. As such a hole injection layer / hole transport layer, a material that transports holes to the light-emitting layer at a lower electric field strength is preferred. More preferably, the hole mobility is, for example, 10 4 -10 6 V / cm electric field is 10 -4 cm 2 / V·s or more. Examples of materials known as hole transport layer materials include bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-di(naphthalen-1-yl)-N,N'-biphenylbenzidine (NPB), or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), etc.

[0061] Light-emitting auxiliary layer

[0062] The light-emitting auxiliary layer is used to reduce the potential barrier for hole transfer to the light-emitting layer, and also helps to block electrons, preventing electrons from spilling out of the light-emitting layer into the hole transport layer, thereby improving the light-emitting efficiency.

[0063] Electron buffer layer

[0064] The electron buffer layer helps to block holes in the light-emitting layer and also helps to transport electrons to the light-emitting layer to promote the combination of electrons and holes in the light-emitting layer, thereby improving the light-emitting efficiency.

[0065] Electron injection layer / electron transport layer

[0066] The electron injection layer / electron transport layer is a layer that helps to inject electrons into the light-emitting layer and transport electrons to the light-emitting region, with a large electron mobility. The adhesion improvement layer is an electron injection layer containing a material with particularly good adhesion to the cathode.

[0067] Specific examples of the materials used in the electron injection layer include, but are not particularly limited to, LiF, Liq, Li2O, BaO, NaCl, CsF, etc.

[0068] The functions of the OLED can be achieved by combining the various layers described above, or some layers can be completely omitted. 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 sub-layers. For example, the light-emitting layer can have two different light-emitting materials to achieve the desired emission spectrum.

[0069] To form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc. can be used. The organic electroluminescent compounds of the present disclosure can be formed into a film by co-evaporation or mixture evaporation methods.

[0070] The product is applied in optoelectronics, medicine, biotechnology, optical fibers, lighting devices, electrophotographic photoreceptors, photoelectric converters, organic solar cells, switching elements, organic light-emitting field-effect transistors, image sensors, or dye lasers.

[0071] Definition of substituent terms

[0072] As used in the present invention, the term "halogen" can include fluorine, chlorine, bromine, or iodine.

[0073] As used in the present invention, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 30 carbon atoms, including but not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0074] As used in this invention, the term "C3-C30 cycloalkyl" refers to a monocyclic hydrocarbon or polycyclic hydrocarbon derived from a hydrocarbon having 1 to 30 ring backbone carbon atoms, and the cycloalkane may include cyclopropyl, cyclobutyl, adamantyl, etc.

[0075] In this invention, aryl and arylene include monocyclic, polycyclic or fused-ring aryl, and the rings may be interrupted by short non-aromatic units and may contain spiro structures, including but not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, fluorenyl, spirobifluorenyl, etc.

[0076] In this invention, heteroaryl and heteroarylene include monocyclic, polycyclic or fused-ring heteroaryl, and the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen and sulfur. It includes but not limited to furyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and their derivatives, etc.

[0077] As used in this invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position is not limited to a specific position as long as the hydrogen at this position can be replaced by a substituent. When there are two or more substituents, the two or more substituents may be the same or different.

[0078] As used in this invention, unless otherwise specified, a hydrogen atom includes protium, deuterium and tritium.

[0079] In this invention, in the definition of a group, a range of carbon atom numbers is defined, and the number of carbon atoms is any integer within the defined range. For example, C6-C60 aryl means that the number of carbon atoms of the aryl can be any integer within the range of 6-60, such as 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55 or 60, etc.

[0080] In the present invention, "combination" means that one or more members in the applicable list are combined to form a known or chemically stable arrangement that can be envisioned by those of ordinary skill in the art from the list. For example, an alkyl group and deuterium can be combined to form a partially or fully deuterated alkyl group; for another example, a halogen, an alkyl group, and an aryl group can be combined to form a haloarylalkyl group. In some embodiments, the combination of substituents includes the combination of 2 - 4 groups; in other embodiments, the combination of substituents includes the combination of 2 - 3 groups; in still other embodiments, the combination of substituents includes the combination of 2 groups. Description of the Drawings

[0081] Figure 1 It is a schematic structural diagram of an organic electroluminescent device;

[0082] Where 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a light-emitting auxiliary layer, 6 is a light-emitting layer, 7 is an electron transport layer, 8 is an electron injection layer, and 9 is a cathode.

[0083] The simple layered structure illustrated in the drawings is provided by way of non-limiting examples. It should be understood that the embodiments of the present disclosure can be used in combination with various other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be obtained by combining the described layers in different ways, or certain layers can be completely omitted based on design, performance, and cost factors. Other layers not specifically described can also be included, and materials other than the specifically described materials can be used. Although many of the embodiments provided herein describe various materials as including a single material, it should be understood that combinations of materials can be used. In addition, the layers can have various sub-layers. The names given to the various layers herein are not intended to be strictly restrictive. Detailed Description of the Embodiments

[0084] The technical solution of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0085] In the following embodiments, the synthesis method of the organic compound is the Buchwald-Hartwig reaction; the test instrument is an SQD2 quadrupole mass spectrometer with an APCI source.

[0086] Example 1

[0087] This example provides an organic compound M3, and the preparation method of this organic compound includes the following steps:

[0088]

[0089] Under N2 protection, add raw material 1 (10 mmol), raw material 2 (10 mmol), sodium tert-butoxide (15 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.2 mmol), (8% eq) S-phos (0.8 mmol) and 80 mL of toluene into a 250 mL two-necked flask, and then reflux and stir. After cooling to room temperature, extract the organic layer with ethyl acetate and H2O; the extracted organic layer is dried over MgSO4 and filtered. The filtrate is concentrated under reduced pressure and purified by silica gel column chromatography (DCM / hexane), and then recrystallized and purified using a mixed solvent of DCM / acetone to obtain compound 3 (5.97 g, yield 83%).

[0090] MS(APCI) m / z [M+H] + : 720.62.

[0091] Example 2

[0092] This example provides an organic compound M4, which is only different from Example 1 in that raw material 2 is replaced with an equimolar amount of raw material 3, and other steps are the same as those in Example 1, to obtain compound M4 (6.31 g, yield 78%). The reaction formula is as follows:

[0093]

[0094] MS(APCI) m / z [M+H] + : 810.55.

[0095] Example 3

[0096] This example provides an organic compound M9, which is only different from Example 1 in that raw material 2 is replaced with an equimolar amount of raw material 4, and other steps are the same as those in Example 1, to obtain compound M9 (6.36 g, yield 80%). The reaction formula is as follows:

[0097]

[0098] MS(APCI) m / z [M+H] + : 796.49.

[0099] Example 4

[0100] This example provides an organic compound M19, which is only different from Example 1 in that raw material 1 is replaced with an equimolar amount of raw material 5, and raw material 2 is replaced with an equimolar amount of raw material 6, and other steps are the same as those in Example 1, to obtain compound M19 (6.60 g, yield 80%). The reaction formula is as follows:

[0101]

[0102] MS(APCI) m / z [M+H] + : 826.77.

[0103] Example 5

[0104] This example provides an organic compound M31. The preparation method of this organic compound includes the following steps:

[0105]

[0106] Synthesis of Intermediate 1: In a 250 mL three-necked flask, add raw material 1 (10 mmol), raw material 7 (10 mmol), 60 mL of toluene, 20 mL of ethanol, 20 mL of water, palladium tetrakis(triphenylphosphine) (0.4 mmol), and potassium carbonate (20 mmol). Heat to 80 °C and react for 5 h. After the reaction is completed, cool to room temperature, and extract the organic layer with ethyl acetate and H2O. The extracted organic layer is dried over MgSO4 and filtered. The filtrate is concentrated under reduced pressure and purified by silica column chromatography (DCM / hexane) to obtain Intermediate 1 (1.95 g, yield 43%);

[0107] The synthesis of compound M31 is the same as that of compound M3, except that raw material 1 is replaced with an equimolar amount of Intermediate 1 to obtain compound M31 (5.96 g, yield 75%).

[0108] MS(APCI) m / z [M+H] + : 796.49.

[0109] Example 6

[0110] This example provides an organic compound M33, which is different from Example 1 only in that raw material 2 is replaced with an equimolar amount of raw material 8, and the other steps are the same as in Example 1, to obtain compound M33 (5.57 g, yield 77%). The reaction formula is as follows:

[0111]

[0112] MS(APCI) m / z [M+H] + : 725.48.

[0113] Example 7

[0114] This example provides an organic compound M37. The reaction formula is as follows:

[0115]

[0116] The synthesis of intermediate 2 is the same as that of compound M3, except that raw material 1 is replaced with an equimolar amount of raw material 10, and raw material 2 is replaced with an equimolar amount of raw material 9, to obtain intermediate 2 (2.77 g, yield 45%);

[0117] The synthesis of compound M37 is the same as that of compound M3, except that raw material 2 is replaced with an equimolar amount of intermediate 2, to obtain compound M37 (6.62 g, yield 69%).

[0118] MS(APCI) m / z [M+H] + : 960.48.

[0119] The synthesis of compounds M1-M2, M5-M8, M10-M18, M20-M30, M32, M34-M36, M38-M39 is the same as that of compounds M3, M4, M9, M19, M31, M33 or M37.

[0120] Application Examples 1-7 and Comparative Application Example 1

[0121] The following Application Examples 1-7 and Comparative Application Example 1 respectively provide an OLED, as Figure 1 shown, the organic light-emitting device includes a substrate (indium tin oxide (ITO) coated glass substrate) 1, an anode 2, a hole injection layer (HIL) 3, a hole transport layer 4 (HTL-1), a light-emitting auxiliary layer (HTL-2) 5, a light-emitting layer (EML) 6, an electron transport layer (ETL) 7, an electron injection layer (EIL) 8, and a cathode 9 stacked in sequence;

[0122] The materials used are as follows:

[0123]

[0124]

[0125] The preparation steps of the OLED device are as follows:

[0126] (1) Substrate cleaning:

[0127] The glass substrate 1 coated with the ITO transparent electrode is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: 10 wt% ethylene glycol solvent, 1 wt% triethanolamine), rinsed in deionized water, ultrasonically degreased in an acetone-ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until all moisture is removed, and then cleaned with ultraviolet light and ozone;

[0128] (2) Evaporation:

[0129] Place the glass substrate 1 with the anode 2 above in a vacuum chamber, evacuate to 1×10-6 to 2×10 -4 Pa, the hole injection layer 3 material is vacuum-evaporated on the above-mentioned anode layer film by co-evaporation, where the evaporation rates of PD and NPB are adjusted according to the mass ratio, the total evaporation rate is 0.1 nm / s, and the evaporation thickness is 10 nm;

[0130] (3) The hole transport layer 4 is evaporated on the hole injection layer 3, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 60 nm;

[0131] (4) The light-emitting auxiliary layer 5 is evaporated on the hole transport layer 4, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 20 nm;

[0132] (5) The light-emitting layer 6 is evaporated on the light-emitting auxiliary layer 5, the host material and the guest material of the light-emitting layer are vacuum-evaporated by co-evaporation, the evaporation rates of the host material and the guest material are adjusted according to the mass ratio, the total evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 30 nm;

[0133] (6) An electron transport layer 7 is vacuum-evaporated on the light-emitting layer 6, the evaporation rates are adjusted according to the mass ratio of the compound ET and LiQ, the total evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 30 nm;

[0134] (7) An electron injection layer 8 is vacuum-evaporated on the electron transport layer 7, the evaporation rate is 0.05 nm / s, and the total evaporation film thickness is 1 nm;

[0135] (8) The cathode 9 is evaporated on the electron injection layer 8, for metal Al, the total evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 100 nm.

[0136] The compositions of the OLED devices in Application Examples 1-7 and Comparative Application Example 1 are as follows:

[0137]

[0138] Test Example

[0139] Device performance test:

[0140] Instrument: The characteristics such as current, voltage, brightness, and emission spectrum of the device are synchronously tested by a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0141] The test conditions for Application Examples 1-7 and Comparative Application Example 1 of the device are as follows:

[0142] Optoelectronic characteristic test conditions: The current density is 10 mA / cm 2 ;

[0143] Lifetime test: The current density is 50 mA / cm2 Record the time (in hours) when the device brightness drops to 95% of the original brightness;

[0144] The test results are shown in Table 1 below:

[0145] Table 1

[0146]

[0147] As can be seen from the data in Table 1, the organic compound provided by the present invention can be used in the hole transport layer and / or the light-emitting auxiliary layer of the organic light-emitting device, which can reduce the device driving voltage, improve the light-emitting efficiency and lifespan of the device.

[0148] The applicant declares that the present invention uses the above embodiments to illustrate the process method of the present invention, but the present invention is not limited to the above process steps, that is, it does not mean that the present invention must rely on the above process steps to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent substitution of the raw materials selected for the present invention, the addition of auxiliary components, and the selection of specific methods, etc., all fall within the protection scope and the disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that, The organic compound has a structure shown in the following Formula I: Wherein, L1 and L2 are each independently selected from any one of a single bond or a phenylene group; L3 is a single bond; The R is selected from any one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted benzonaphthofuranyl group, and a substituted or unsubstituted benzonaphthothiophenyl group; The substituents of the substituted phenyl group, substituted biphenyl group, substituted terphenyl group, substituted naphthyl group, substituted phenanthryl group, substituted anthryl group, substituted pyridyl group, substituted dibenzofuranyl group, substituted dibenzothiophenyl group, substituted carbazolyl group, substituted dimethylfluorenyl group, substituted diphenylfluorenyl group, substituted spirobifluorenyl group, substituted benzocarbazolyl group, substituted benzonaphthofuranyl group, and substituted benzonaphthothiophenyl group are selected from deuterium or a phenyl group.

2. The organic compound according to claim 1, wherein, The organic compound is selected from any one of the following Formulas I-1 to I-4: Wherein, L1, L2, L3, and R have the same defined ranges as described in Claim 1.

3. The organic compound according to claim 1, wherein The dimethylfluorenyl group is selected from any one of the following structures: Among them, represents the connection site of the group.

4. The organic compound according to claim 1, wherein The diphenylfluorenyl group is selected from any one of the following structures: Among them, represents the connection site of the group.

5. The organic compound according to claim 1, characterized in that, The organic compound includes any one of the following M1-M39:

6. An organic electroluminescent material, characterized in that, The organic electroluminescent material includes the organic compound as described in any one of Claims 1-5.

7. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic thin film layer located between the anode and the cathode, and the organic thin film layer includes the organic compound as described in any one of Claims 1-5 or the organic electroluminescent material as described in Claim 6.

8. The organic electroluminescent device according to claim 7, characterized in that, The organic thin film layer includes any one or a combination of at least two of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron buffer layer, an electron transport layer, an electron buffer layer, or an electron injection layer.

9. The organic electroluminescent device according to claim 8, wherein, The hole transport layer includes the organic compound as described in any one of Claims 1-4.

10. The organic electroluminescent device according to claim 8, characterized in that, The light-emitting auxiliary layer includes the organic compound as described in any one of Claims 1-5.

11. An electronic device, characterized in that, The electronic device includes the organic electroluminescent device as described in any one of Claims 7-10.

12. The electronic device according to claim 11, wherein The electronic device includes any one of an optical fiber, a lighting device, an electrophotographic photoreceptor, a photoelectric converter, an organic solar cell, a switching element, an organic light-emitting field effect transistor, an image sensor, or a dye laser.

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