Organic compound, organic electroluminescent element and electronic equipment

Abstract

According to the organic compound, the organic electroluminescent element and the electronic equipment provided by the invention, tetramethylhydrophenanthrene is introduced into the arylamine compound, and aryl or heteroaryl cooperates with tetramethylhydrophenanthrene to adjust the energy level of arylamine, so that the hole mobility is improved, the hole transport performance is improved, and the luminous efficiency of the device is improved; the driving voltage, the luminous efficiency and the service life of the organic light-emitting device prepared from the organic compound disclosed by the invention are well improved. The organic compound has a structure represented by a formula (1), and in the formula (1), L1 to L3 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group; ar1-Ar3 are respectively and independently selected from hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C6-C60 aryl group, and substituted or unsubstituted C3-C60 heteroaryl group; r1 to R4 are respectively and independently selected from a substituted or unsubstituted alkyl group of C1 to C10 and a substituted or unsubstituted aryl group of C6 to C60.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescence technology, and more specifically, relates to an organic compound, an organic electroluminescent element, and an electronic device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are self-emissive display devices based on organic light-emitting materials. Unlike existing liquid crystal displays (LCDs), they do not require a backlight and are thin, making them suitable for flexible devices (flexible light-emitting display devices). OLEDs utilizing organic light emission typically have an anode, a cathode, and an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is usually composed of a multilayer structure made of various materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer.

[0003] A light-emitting auxiliary layer is typically added between the hole transport layer and the light-emitting layer to improve lifetime and efficiency. The light-emitting auxiliary layer can also assist the hole transport layer, reducing the potential barrier between the hole transport layer and the light-emitting layer, thereby lowering the driving voltage of the organic electroluminescent device, further increasing hole utilization, and thus improving the device's luminous efficiency and lifetime.

[0004] Research on organic electroluminescent materials has been extensively conducted in academia and industry, but so far, a stable and efficient organic layer material for organic electroluminescent devices that fully meets the requirements has not yet been developed. Therefore, developing higher-performance organic functional materials to reduce driving voltage, improve device luminous efficiency, and extend device lifetime has significant practical application value. Summary of the Invention

[0005] In view of the above-mentioned defects or improvement needs of the prior art, the present invention provides an organic compound that can be used as a high-performance light-emitting auxiliary layer material, which can significantly improve the performance of organic electroluminescent devices.

[0006] The technical solution adopted by the present invention to solve its technical problem is: an organic compound having the structure shown in formula (1),

[0007]

[0008] Among them, L1-L3 are each independently selected from single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene;

[0009] Ar1-Ar3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0010] R1-R4 are each independently selected from substituted or unsubstituted C1-C10 alkyl groups and substituted or unsubstituted C6-C60 aryl groups;

[0011] The substituents in the "substituted or unsubstituted" designation are each independently selected from deuterium, halogen, cyano, silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0012] The heteroatoms in the heteroaryl, heterocyclic alkyl, heterocyclic alkenyl, and heteroaryl groups are each independently at least one of N, O, S, Si, and P.

[0013] Furthermore, in an optional embodiment of the present invention, the organic compound has the structure shown in formula (2) or formula (3):

[0014]

[0015] Among them, L1-L3 are each independently selected from single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene;

[0016] Ar1-Ar3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0017] R1-R4 are each independently selected from substituted or unsubstituted C1-C10 alkyl groups and substituted or unsubstituted C6-C60 aryl groups.

[0018] Preferably, R1-R4 are each independently selected from substituted or unsubstituted C1-C10 alkyl groups;

[0019] More preferably, R1-R4 are each independently selected from methyl groups.

[0020] Furthermore, in an optional embodiment of the invention, the organic compound has the structure shown in formula (4) or formula 5:

[0021]

[0022] Among them, L1-L2 are each independently selected from single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene;

[0023] Ar1-Ar3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0024] R1-R4 are each independently selected from substituted or unsubstituted C1-C10 alkyl groups.

[0025] Preferably, L1-L2 are each independently selected from single-bonded, substituted or unsubstituted C6-C60 arylene groups.

[0026] More preferably, L1-L2 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted biphenylnaphthylene, and substituted or unsubstituted binaphthylphenylene.

[0027] Preferably, Ar1-Ar3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthyl, substituted or unsubstituted indene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted biphenyl Naphthyl, substituted or unsubstituted binaphthylphenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorene, substituted or unsubstituted spirodifluorene, and any combination of two or more of the above groups.

[0028] Furthermore, in an optional embodiment of the invention, each of R1-R4 is independently selected from substituted or unsubstituted methyl groups.

[0029] Furthermore, in an optional embodiment of the invention, each of L1-L2 is independently selected from single-bonded, substituted, or substituted groups, including:

[0030]

[0031] Preferably, each of L1-L2 is independently selected from single-bonded, substituted, or substituted groups, including:

[0032]

[0033] Furthermore, in an optional embodiment of the invention, each of Ar1-Ar3 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted groups, including:

[0034]

[0035] Furthermore, in an optional embodiment of the invention, the Ar3 is selected from substituted or unsubstituted groups of the following:

[0036]

[0037]

[0038] The present invention also provides a formulation comprising at least one of the above-described organic compounds and at least one solvent.

[0039] The present invention also provides an organic electroluminescent element, comprising:

[0040] First electrode;

[0041] The second electrode is configured to face the first electrode; and

[0042] One or more organic material layers, including a light-emitting layer, are disposed between the first electrode and the second electrode.

[0043] One or more layers of the organic material layer contain the organic compounds described in this invention.

[0044] Specifically, in one embodiment of the present invention, a hole transport layer is included between the first electrode and the light-emitting layer, and a light-emitting auxiliary layer is included between the hole transport layer and the light-emitting layer, the light-emitting auxiliary layer comprising the organic compound described in the present invention.

[0045] The present invention also provides an electronic device, which includes a display device and a lighting device, and is provided with the above-described organic electroluminescent element.

[0046] In summary, compared with the prior art, the above-described technical solutions conceived by this invention can achieve the following beneficial effects:

[0047] 1. The organic compounds of the present invention, by introducing tetramethylphenanthrene into an aromatic amine compound and by using aryl or heteroaryl groups to synergistically regulate the energy level of the aromatic amine, improve hole mobility, enhance hole transport performance, and improve the luminous efficiency of the device, the organic light-emitting devices prepared by the organic compounds of the present invention have good improvements in driving voltage, luminous efficiency and lifetime. Attached Figure Description

[0048] Figure 1This is a schematic diagram of the device structure of an organic electroluminescent element according to an embodiment of the present invention, wherein a first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a light-emitting auxiliary layer 4, a light-emitting layer 5, an electron transport layer 6, and a second electrode layer 7 are present. Detailed Implementation

[0049] Exemplary embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, these exemplary embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the exemplary embodiments are described below only by reference to the accompanying drawings to illustrate aspects. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Expressions such as “at least one” modify the entire list of elements when preceding or following the list of elements, but do not modify individual elements of the list.

[0050] It will be understood that when an element is referred to as being "on" another element, it may be in direct contact with the other element or there may be an intermediate element between them. Conversely, when an element is referred to as being "directly on" another element, there is no intermediate element.

[0051] It will be further understood that the terms “comprising” or “including” as used in this specification indicate the presence of the stated features, regions, integrals, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, regions, integrals, steps, operations, elements, components, and / or sets thereof.

[0052] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having meanings consistent with their meanings in the relevant field and in the context of this disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0053] As used herein, “about” or “approximately” includes the stated value and means within an acceptable range of deviation from the specific value, as determined by a person skilled in the art taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., limitations of the measurement system). For example, “about” may mean a deviation relative to the stated value within one or more standard deviations, or within ±30%, 20%, 10%, or 5%.

[0054] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of protection of the present invention. Furthermore, it should be understood that after reading the disclosure of this invention, those skilled in the art can make various modifications or alterations to the present invention, and these equivalent forms also fall within the scope of protection defined by this invention.

[0055] Unless otherwise specified, the experimental methods used in the following examples are conventional methods; unless otherwise specified, the reagents and materials used in the following examples are commercially available.

[0056] Terminology Explanation

[0057] As used in this invention, the term "halogen group" may include fluorine, chlorine, bromine or iodine.

[0058] As used in this invention, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 10 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0059] As used herein, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic nonaromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, etc.

[0060] As used in this invention, the term "C2-C10 heterocycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic ring having 2 to 10 carbon atoms, wherein the ring contains at least one heteroatom selected from O, S, N, P, and Si.

[0061] As used herein, the term "alkoxy" refers to a straight-chain, branched, or cyclic chain. The number of carbon atoms in an alkoxy group is not particularly limited, but it is preferred to have 1 to 10 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, and benzyloxy.

[0062] As used in this invention, the term "cycloalkenyl" refers to an unsaturated carbon ring that is not aromatic.

[0063] As used in this invention, the term "heterocyclic alkenyl" refers to an unsaturated heterocycle that is not aromatic.

[0064] As used herein, the term "C6-C60 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such an aryl group may have two or more rings simply side-attached to or fused together with each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthracene, pyrene, triphenylene, fluoranthyl, dimethyl-9,9-dimethylfluorene, 9,9-diphenylfluorene, spirodifluorene, etc.

[0065] As used in this invention, the term "arylene" refers to a divalent aryl group derived by removing a hydrogen atom from an "aryl" group, for example, a phenyl group by removing a hydrogen atom to form a phenylene group, or a naphthyl group by removing a hydrogen atom to form a naphthylene group.

[0066] As used in this invention, the term "C3-C60 heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom, such as N, O, S, P, B, or Si. Furthermore, such a heteroaryl can be in the form in which two or more rings are simply side-attached to each other, fused together, or fused with an aryl group. Examples of such heteroaryl groups include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indoleazinyl, indoleyl, indolepyridinyl, purineyl, phenanthrolinel, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thiophene, benzofuranyl, benzothiophene, benzothiazolyl, benzoimidazolyl, benzooxazolyl, carbazole, dibenzofuranyl, dibenzothiophene, etc., but the present invention is not limited thereto.

[0067] As used in this invention, the term "hybrid aryl" refers to a divalent heteroaryl derived by removing a hydrogen atom from a "heteroaryl", for example, a pyridyl group by removing a hydrogen atom to form a pyridyl group.

[0068] As used in this invention, the expression "Z group with XY carbon atoms" or "Z group with C(XY)" means the number of carbon atoms in the Z group when it is unsubstituted, excluding the number of carbon atoms in the substituents when substituted. For example, an aryl group with C6-C60 means that when unsubstituted, the number of carbon atoms in the aryl group is any integer from 6 to 60. That is, when unsubstituted, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...60.

[0069] As used in this invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The substitution can occur at any position where the hydrogen atom is substituted. That is, the position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. For example, a carbazolyl group, unless otherwise specified in this specification, includes any of the following groups, but is not limited thereto.

[0070]

[0071] This indicates the substitution position. "Unsubstituted" means that hydrogen atoms are retained, in which case hydrogen atoms include protium, deuterium, and tritium.

[0072] When two or more substituents are present, the two or more substituents can be the same or different.

[0073] As used in this invention, the term "terphenyl" includes

[0074] As used in this invention, hydrogen atoms include protium, deuterium, and tritium. The compounds of this invention may contain naturally occurring deuterium atoms, or deuterium atoms may be introduced by deuterating part or all of the starting material compound. If deuterium atoms are introduced from the starting material, the deuteration rate may be 100%, less than 100%, less than 95%, less than 90%, or less than 80%, or may be more than 1%, more than 5%, or more than 10%. If the deuteration rate is not 100%, it represents a mixture of deuterated and undeuterated compounds, or a mixture of fully deuterated and incompletely deuterated compounds, or a mixture of fully deuterated, undeuterated, and incompletely deuterated compounds.

[0075] As used in this invention, terms such as 1, 2, A, B, etc. are used. These terms are only used to distinguish constituent elements and do not limit the nature or order of the constituent elements corresponding to the terms.

[0076] Organic electroluminescent elements

[0077] The organic electroluminescent element of the present invention uses a previously disclosed structure, comprising an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer comprising a light-emitting layer, and at least one layer of the organic layer comprising the compound of the present invention.

[0078] The organic layer also includes, but is not limited to, one or more of the following: hole injection layer, hole transport layer, electron blocking layer, hole blocking layer, electron transport layer, and electron injection layer.

[0079] The light-emitting element of the present invention can be fluorescent, phosphorescent, or a combination thereof. The light-emitting element can be a single light-emitting element or a series connection of multiple light-emitting units.

[0080] The following are examples of simple light-emitting elements, but are not limited to them.

[0081] (1) Hole transport layer / fluorescent layer / electron transport layer;

[0082] (2) Hole transport layer / phosphorescent emissive layer / electron transport layer;

[0083] (3) Hole transport layer / first fluorescent luminescent layer / second fluorescent luminescent layer / electron transport layer;

[0084] (4) Hole transport layer / first phosphorescent layer / second phosphorescent layer / electron transport layer;

[0085] (5) Hole transport layer / fluorescent layer / spacer layer / phosphorescent layer / electron transport layer;

[0086] (6) Hole transport layer / electron blocking layer / fluorescent layer / electron transport layer;

[0087] (7) Hole transport layer / electron blocking layer / fluorescent layer / hole blocking layer / electron transport layer;

[0088] (8) Hole transport layer / electron blocking layer / phosphorescent layer / electron transport layer;

[0089] (9) Hole transport layer / electron blocking layer / phosphorescent layer / hole blocking layer / electron transport layer;

[0090] (10) Hole injection layer / hole transport layer / phosphorescent layer / electron transport layer / electron injection layer;

[0091] (11) Hole injection layer / hole transport layer / fluorescent layer / electron transport layer / electron injection layer;

[0092] (12) Hole injection layer / hole transport layer / electron blocking layer / phosphorescent layer / electron transport layer / electron injection layer;

[0093] (13) Hole injection layer / hole transport layer / electron blocking layer / fluorescent layer / electron transport layer / electron injection layer;

[0094] ...

[0095] Some functional layers in the above device structure may or may not exist, such as the electron injection layer may not be used.

[0096] Each of the aforementioned phosphorescent / fluorescent emitting layers can emit light in a different color.

[0097] As a series-connected organic electroluminescent element, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can also be called a charge generation layer, electron extraction layer, or connecting layer. For example, when stacking fluorescent and phosphorescent light-emitting layers, an intermediate layer is placed between the fluorescent and phosphorescent light-emitting layers to prevent excitons generated by the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer, or to adjust the balance of charge carriers.

[0098] When an organic light-emitting device comprises multiple layers of organic materials, the organic material layers can be formed from the same material or different materials.

[0099] The organic electroluminescent element described in this specification can be manufactured using materials and methods known in the art, except that one or more organic material layers are made using the compounds described in this invention.

[0100] As cathode materials, materials with low work functions are typically used to facilitate electron injection into organic material layers.

[0101] The hole injection layer is a layer in which holes from the electrodes are injected and it has the ability to transport holes.

[0102] Hole transport materials are layers that receive holes from a hole injection layer and transport the holes to a light-emitting layer. Hole transport materials, when appropriate, can receive holes from an anode or hole injection layer and transfer the holes to a light-emitting layer, and have a high hole mobility.

[0103] A luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively, and combine the holes and electrons to emit light in the visible light region. The luminescent layer material consists of a host material and dopant materials.

[0104] An electron transport material is a layer that receives electrons from an electron injection layer and transports them to a light-emitting layer. It is also a material with high electron mobility that can receive electrons from a cathode and transfer them to a light-emitting layer.

[0105] An electron injection layer is a layer into which electrons from the electrodes are injected.

[0106] The hole blocking layer is a layer that prevents holes from reaching the cathode.

[0107] An electron blocking layer is a layer that prevents electrons from reaching the anode.

[0108] Depending on the materials used, the organic light-emitting device described in this specification can be a top-emitting device, a bottom-emitting device, or a dual-emitting device.

[0109] The charge generation layer is the intermediate layer located between the anode and cathode in a series-connected device, and it is the layer that generates holes and electrons by utilizing charge separation. The charge generation layer is usually formed by a P-type layer on the cathode side and an N-type layer on the anode side, which can effectively separate charges and efficiently transport charge carriers.

[0110] The core of this invention is to provide an organic compound having the structure shown in formula (1).

[0111]

[0112] Among them, L1-L3 are each independently selected from single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene;

[0113] Ar1-Ar3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0114] R1-R4 are each independently selected from substituted or unsubstituted C1-C10 alkyl groups and substituted or unsubstituted C6-C60 aryl groups;

[0115] The substituents in the "substituted or unsubstituted" designation are each independently selected from deuterium, halogen, cyano, silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0116] The heteroatoms in the heteroaryl, heterocyclic alkyl, heterocyclic alkenyl, and heteroaryl groups are each independently at least one of N, O, S, Si, and P.

[0117] Specifically, the organic compound is selected from the following structures:

[0118]

[0119]

[0120]

[0121]

[0122] Those skilled in the art can synthesize the compounds of the present invention by referring to the following synthesis methods and known synthetic techniques. For example, one general synthetic formula of the present invention is as follows: 1.

[0124] 2.

[0126] 3.

[0128] 4.

[0130] 5.

[0132]

[0133] In the above general formula, unless the product synthesized in other steps is required, there is no order of the synthesis steps; in reactions 1 and 2, the halogen substituted on the compound is not limited to Br, other halogens (Cl, I, etc.) are also acceptable and can be selected according to the available raw materials;

[0134] In the above general formula, the definitions of L1-L3 and Ar1-Ar3 refer to the definitions in the invention description.

[0135] The method of this invention is merely exemplary. Compounds synthesized using commercial raw materials or existing techniques that replace the reactants in the general formula are also included within the scope of this application.

[0136] The specific synthesis embodiment of this application is as follows:

[0137] Example 1: Preparation of compound 1-1

[0138]

[0139] Step 1: Under nitrogen atmosphere, compound 2-bromo-9,10-phenanthrenequinone (4.35 g, 15.07 mmol) was added to anhydrous diethyl ether (300 mL), melted, and then methyl magnesium bromide (7.52 g, 63.03 mmol) was slowly added at -78 °C. The temperature was lowered to room temperature and stirred. After the reaction was complete, the mixture was extracted with dichloromethane, and the extract was dried over anhydrous magnesium sulfate and concentrated. Compound 1-1-1 (4.29 g, 90%) was separated by silica gel chromatography.

[0140] LC-MS (APCI): 316.57 [M+H] +

[0141] Step 2: Under nitrogen atmosphere, 1-1-1 (6.31 g, 20 mmol) was dissolved in tetrahydrofuran (200 mL). Butyllithium (13.2 mL, 1.6 mol / L) was slowly added dropwise at -40 °C, and the mixture was stirred for half an hour. Triisopropylboronic acid ester (3.95 g, 21 mmol) was added dropwise at -40 °C. After stirring at -40 °C for 1 hour, the mixture was stirred at room temperature for 4 hours. Dilute hydrochloric acid (5%) was added and stirred for 2 hours. The mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4 and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and n-hexane as the developing solvent to obtain pure compound 1-1-2 (4.76 g, 85% yield).

[0142] LC-MS (APCI): 281.17 [M+H] +

[0143] Step 3: Under nitrogen atmosphere, compounds 1-1-3 (6.41 g, 37.9 mmol) and 1-1-4 (8.83 g, 37.9 mmol) were completely dissolved in 110 mL of xylene. NaOt-Bu (4.17 g, 43.4 mmol) and bis(tri-tert-butylphosphine)palladium (0.16 g, 3.1 mmol) were added, followed by heating and stirring for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4 and concentrated by filtration. Compound 1-1-5 (9.76 g, 80% yield) was purified by column chromatography using ethyl acetate and n-hexane as the developing solvent.

[0144] LC-MS (APCI): 322.08 [M+H] +

[0145] Step 4: Under nitrogen atmosphere, 1-1-6 (3.14 g, 20.1 mmol) was dissolved in tetrahydrofuran (200 mL). Butyllithium (13.2 mL, 1.6 mol / L) was slowly added dropwise at -40 °C with stirring for half an hour. Then, triisopropylborate (3.95 g, 21.0 mmol) was added dropwise at -40 °C with stirring for 1 hour. The mixture was then stirred at room temperature for 4 hours, followed by the addition of dilute hydrochloric acid (5%) and stirring for 2 hours. After the reaction was complete, the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4 and concentrated by filtration. Using ethyl acetate and n-hexane as the developing solvent, pure compound 1-1-7 (2.32 g, 95% yield) was purified by column chromatography.

[0146] LC-MS (APCI): 122.81 [M+H] +

[0147] Step 5: Under nitrogen atmosphere, compound 1-1-8 (13.36 g, 42.2 mmol) and compound 1-1-7 (5.40 g, 44.3 mmol) were added to a four-necked flask, followed by toluene (70 mL), ethanol (30 mL), water (30 mL), potassium carbonate (11.61 g, 84.2 mmol), and tetrakis(triphenylphosphine)palladium (0.97 g, 8.4 mmol). The mixture was heated and stirred for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, washed with water, dried over MgSO4, and concentrated by filtration. Compound 1-1-9 (6.76 g, yield: 60%) was purified by column chromatography using ethyl acetate and n-hexane as the developing solvent.

[0148] LC-MS (APCI): 268.45 [M+H] +

[0149] Step 6: Under nitrogen atmosphere, compounds 1-1-9 (8.78 g, 32.8 mmol) and 1-1-5 (10.29 g, 32.0 mmol) were completely dissolved in 105 mL of xylene. NaOt-Bu (4.17 g, 43.4 mmol) and bis(tri-tert-butylphosphine)palladium (0.16 g, 3.1 mmol) were added, followed by heating and stirring for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4 and concentrated by filtration. Compound 1-1-10 (11.71 g, 72% yield) was purified by column chromatography using ethyl acetate and n-hexane as the developing solvent.

[0150] LC-MS (APCI): 509.45 [M+H] +

[0151] Step 7: Under nitrogen atmosphere, compound 1-1-10 (17.88 g, 35.2 mmol) and compound 1-1-2 (10.37 g, 37.0 mmol) were added to a three-necked flask, along with toluene (70 mL), ethanol (30 mL), water (30 mL), potassium carbonate (11.61 g, 84.2 mmol), and tetraphenylphosphine palladium (0.97 g).

[0152] After adding 8.4 mmol, the mixture was heated and stirred for 3 hours. After the reaction was completed, it was cooled to room temperature, washed with water, and the organic layer was dried over MgSO4 and then filtered and concentrated. Compound 1-1 (17.44 g, yield: 70%) was purified by column chromatography using ethyl acetate and n-hexane as the developing solvent.

[0153] LC-MS (APCI): 708.12 [M+H] +

[0154] Example 2: Preparation of compounds 1-3

[0155]

[0156] Prepared using the same synthetic method as in Example 1 of the above compound, but replacing compound 1-1-4 with compound 1-3-4, the compound of structural formula 1-3 can be synthesized (18.41 g, yield 69%, yield of the synthesis of 1-3-10 and 1-1-2 reaction) according to the above synthetic route.

[0157] LC-MS (APCI): 759.65 [M+H] +

[0158] Example 3: Preparation of compounds 1-12

[0159]

[0160] Prepared using the same synthetic method as in Example 1 of the above compound, but replacing compound 1-1-4 with compound 1-12-4, the compound of structural formula 1-12 (19.31 g, yield 76%, yield of the reaction of 1-3-10 and 1-1-2) can be synthesized by following the above synthetic route.

[0161] LC-MS (APCI): 722.57 [M+H] +

[0162] Example 4: Preparation of compounds 1-16

[0163]

[0164] Prepared using the same synthetic method as in Example 1 of the above compounds, but with compound 1-1-7 replaced by compound 1-16-7, the compound of structural formula 1-16 can be synthesized (21.35 g, yield 76%, yield of the synthesis of 1-16-10 and 1-1-2 reaction) according to the above synthetic route.

[0165] LC-MS (APCI): 799.36 [M+H] +

[0166] Example 5: Preparation of compounds 1-23

[0167]

[0168] Prepared using the same synthetic method as in Example 1 of the above compounds, but with compound 1-1-7 replaced by compound 1-23-7, the compound of structural formula 1-23 can be synthesized (18.86 g, yield 65%, yield of the synthesis of 1-23-10 and 1-1-2 reaction) by following the above synthetic route.

[0169] LC-MS (APCI): 825.48 [M+H] +

[0170] Example 6: Preparation of compounds 1-36

[0171]

[0172] Prepared using the same synthetic method as in Example 1 of the above compounds, but with compound 1-1-4 replaced by compound 1-36-4 and compound 1-1-9 replaced by compound 1-36-9, the compound with structural formula 1-36 (22.67 g, yield 74%, yield of the reaction of 1-14-10 and 1-1-2) can be synthesized by following the above synthetic route.

[0173] LC-MS (APCI): 871.21 [M+H] +

[0174] Those skilled in the art can synthesize the compounds of the present invention by referring to the above-described synthesis methods and known synthetic methods. Other structures can also be obtained by referring to the above-described synthesis methods and conventional synthetic techniques in the art.

[0175] The following application examples further illustrate the use of the compounds described in this invention in the preparation of organic electroluminescent devices.

[0176] Application Example 1:

[0177] This embodiment provides an organic electroluminescent device, such as... Figure 1 As shown, it includes a first electrode layer 1 (anode), a hole injection layer 2, a hole transport layer 3, a light-emitting auxiliary layer 4, a light-emitting layer 5, an electron transport layer 6, and a second electrode layer 7 (cathode).

[0178] Comparative Example 1

[0179] The specific device structure is as follows:

[0180] ITO / HATCN(5nm) / HT(60nm) / EB(5nm) / GH+GD(3wt%)(20nm) / ET(15nm) / Al(100nm).

[0181] HATCN is deposited on an ITO substrate to form a thickness of [missing information]. The first hole injection layer (HIL) is formed by evaporating HT on the first hole injection layer to form a thickness of [missing information]. A hole transport layer (HTL) is formed by evaporating EB on the hole transport layer to form a thickness of [thickness missing]. The light-emitting auxiliary layer (EBL) is formed by evaporating GH+GD (3wt%) on the light-emitting auxiliary layer to form a thickness of [missing information]. The light-emitting layer (EML) is sequentially deposited with a thickness of [thickness value missing]. Electron transport layer (ETL), vapor-deposited Al (thickness of) This forms a cathode, thereby creating an organic electroluminescent device.

[0182] The structural formulas of the materials in each layer of the device are as follows:

[0183]

[0184]

[0185] Comparative Example 2

[0186] The organic electroluminescent device of Comparative Example 2 was prepared using the same method as in the embodiment of Comparative Example 1 above, except that the light-emitting auxiliary layer (EBL) was replaced by compound EB-1 instead of compound EB in the embodiment of Comparative Example 1.

[0187] Device Example 1

[0188] The organic electroluminescent device of Device Example 1 was prepared using the same method as in the embodiment of Comparative Example 1 above, except that the light-emitting auxiliary layer (EBL) was replaced by compound 1-1 instead of compound EB in the embodiment of Comparative Example 1.

[0189] Device Example 2

[0190] The organic electroluminescent device of Device Example 2 was prepared using the same method as in Comparative Example 1 above, except that the light-emitting auxiliary layer (EBL) was replaced by compounds 1-3 instead of compound EB.

[0191] Device Example 3

[0192] The organic electroluminescent device of Device Example 3 was prepared using the same method as in Comparative Example 1 above, except that the light-emitting auxiliary layer (EBL) was replaced by compound 1-12 instead of EB.

[0193] Device Example 4

[0194] The organic electroluminescent device of Device Example 4 was prepared using the same method as in Comparative Example 1 above, except that the light-emitting auxiliary layer (EBL) was replaced by compound EB with compound 1-16.

[0195] Device Example 5

[0196] The organic electroluminescent device of Device Example 5 was prepared using the same method as in the embodiment of Comparative Example 1 above, except that the light-emitting auxiliary layer (EBL) was replaced by compound 1-23 instead of compound EB in the embodiment of Comparative Example 1.

[0197] Device Example 6

[0198] The organic electroluminescent device of Device Example 6 was prepared using the same method as in Comparative Example 1 above, except that the light-emitting auxiliary layer (EBL) was replaced by compound EB with compound 1-36.

[0199] Evaluation of organic electroluminescent devices

[0200] Lifetime testing method: A voltage is applied to the obtained organic electroluminescent element to achieve a current density of 30 mA / cm². 2 The time (LT95, in hours) until the brightness becomes 95% of the initial brightness was measured, with the lifetime of Comparative Example 1 being 100%, to obtain the relative lifetime values ​​of each comparative example and embodiment.

[0201] Drive voltage at current density of 15mA / cm 2 The following tests were conducted, with the driving voltage of Comparative Example 1 set to 100%, to obtain the relative values ​​of the driving voltages for each comparative example and embodiment.

[0202] Current efficiency at a current density of 15 mA / cm 2 The following tests were conducted, with the current efficiency of Comparative Example 1 set at 100%, to obtain the relative values ​​of current efficiency for each comparative example and embodiment. The test results are shown in Table 1.

[0203] Table 1

[0204] Light-emitting auxiliary layer Drive voltage, % Current efficiency, % Lifespan LT95%, Comparative Example 1 EB 100 100 100 Comparative Example 2 EB-1 98 102 91 Example 1 1-1 99 107 108 Example 2 1-3 99 105 114 Example 3 1-12 98 106 104 Example 4 1-16 100 108 111 Example 5 1-23 99 106 109 Example 6 1-36 98 109 110

[0205] As can be seen from the results shown in Table 1 above, the application of the organic compounds of the present invention in the light-emitting auxiliary layer significantly improves both luminous efficiency and lifetime compared to Comparative Examples 1 and 2. Therefore, the compounds of the present invention are suitable for preparing high-performance organic electroluminescent devices.

[0206] Those skilled in the art will readily understand that the above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, and improvements made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in formula (1). Among them, L1-L3 are each independently selected from single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; Ar1-Ar3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; R1-R4 are each independently selected from substituted or unsubstituted C1-C10 alkyl groups and substituted or unsubstituted C6-C60 aryl groups; The substituents in "substituted or unsubstituted" are each independently selected from deuterium, halogen, cyano, silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl. The heteroatoms in the heteroaryl, heterocyclic alkyl, heterocyclic alkenyl, and heteroaryl groups are each independently at least one of N, O, S, Si, and P.

2. An organic compound according to claim 1, characterized in that, The organic compound has the structure shown in formula (2): Among them, L1-L3 are each independently selected from single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; Ar1-Ar3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; R1-R4 are each independently selected from substituted or unsubstituted C1-C10 alkyl groups and substituted or unsubstituted C6-C60 aryl groups.

3. An organic compound according to claim 1, characterized in that, The organic compound has the structure shown in formula (3): Among them, L1-L2 are each independently selected from single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; Ar1-Ar3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; R1-R4 are each independently selected from substituted or unsubstituted C1-C10 alkyl groups.

4. An organic compound according to any one of claims 1-3, characterized in that, Each of R1-R4 is independently selected from substituted or unsubstituted methyl groups.

5. An organic compound according to any one of claims 1-3, characterized in that, Each of L1-L2 is independently selected from single-bonded, substituted, or substituted groups as follows:

6. An organic compound according to any one of claims 1-3, characterized in that, Each of Ar1-Ar3 is independently selected from the following groups, either substituted or unsubstituted:

7. An organic compound according to any one of claims 1-3, characterized in that, The organic compound is selected from the following structures:

8. An organic electroluminescent element, characterized in that, The organic electroluminescent element includes: First electrode; The second electrode is configured to face the first electrode; and One or more organic material layers, including a light-emitting layer, are disposed between the first electrode and the second electrode. One or more layers of the organic material layer contain an organic compound according to any one of claims 1-7.

9. An organic electroluminescent element according to claim 8, characterized in that, The organic material layer includes a light-emitting auxiliary layer, which contains an organic compound according to any one of claims 1-7.

10. An electronic device, characterized in that, The electronic device includes the organic electroluminescent element according to claim 9.

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