Novel compound and organic electroluminescent device comprising same

Abstract

The invention provides an organic compound, belongs to the technical field of organic light-emitting materials, and also relates to an application of the compound in an organic light-emitting device. The organic compound is characterized in that the compound has a structure shown in a formula (1): # imgabs0 #, the organic electroluminescent element comprises a first electrode, a second electrode and one or more organic layers between the first electrode and the second electrode, and at least one organic layer contains the organic compound provided by the invention.

Description

Technical Field

[0001] The present invention provides an organic compound, belonging to the technical field of organic light-emitting materials. The present invention also relates to the application of the compound in an organic electroluminescent device. Background Art

[0002] An organic light-emitting diode is a self-luminous display device based on an organic electroluminescent material. Different from existing liquid crystal display devices, it has the characteristics of not requiring a backlight source and being thin, and is a technology suitable for flexible device devices (flexible light-emitting display devices). An organic electroluminescent device using the organic light-emitting phenomenon usually has a structure including an anode, a cathode, and an organic layer therebetween. In order to improve the efficiency and stability of the organic electroluminescent device, the organic layer is usually composed of a multi-layer structure formed of various different substances. For example, it is composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like.

[0003] A light-emitting auxiliary layer is usually added between the hole transport layer and the light-emitting layer to improve the lifetime and efficiency. The light-emitting auxiliary layer mainly functions to assist the hole transport layer, can reduce the potential barrier between the hole transport layer and the light-emitting layer, reduce the driving voltage of the organic electroluminescent device, further increase the utilization rate of holes, and thus improve the light-emitting efficiency and lifetime of the device.

[0004] The research on organic electroluminescent materials has been widely carried out in the academic and industrial fields. However, so far, an organic layer material for a stable and efficient organic electroluminescent element has not been fully developed. Therefore, it is the general trend of the industrialization process of developing higher-performance organic functional materials. Summary of the Invention

[0005] The purpose of the present invention is to provide an organic compound, especially a light-emitting auxiliary layer material. The compound is applied to an organic electroluminescent device, can improve the light-emitting efficiency of the device, and reduce the driving voltage.

[0006] An organic compound, characterized in that the compound has the structure shown in formula (1):

[0007]

[0008] wherein, a is selected from an integer of 0-2, and when a is selected from 0, does not exist,

[0009] L 1 -L 3 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group,

[0010] Ar 1- Ar 3 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl.

[0011] When substituted in the "substituted or unsubstituted", the substituents are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0012] The heteroatoms of the heteroaryl are selected from one or more of oxygen, sulfur, and nitrogen.

[0013] Preferably, the compound has the structures shown in formula (2) and formula (3):

[0014]

[0015] More preferably, the compound has the structures shown in formula (4) and formula (5):

[0016]

[0017] Preferably, the L 1 -L 3 Each is independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluoranthenylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted perylenylene, substituted or unsubstituted triphenylene, substituted or unsubstituted ylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted 9,9-dimethylfluorenylene, substituted or unsubstituted 9,9-diphenylfluorenylene, substituted or unsubstituted spirobifluorenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolylene.

[0018] More preferably, the L 1 is selected from a single bond.

[0019] More preferably, the L 2 and L 3Each is independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted 9,9-dimethylfluorenylene, a substituted or unsubstituted 9,9-diphenylfluorenylene, a substituted or unsubstituted spirobifluorenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene.

[0020] Preferably, the Ar 1 -Ar 3 Each is independently selected from hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted perylenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted group, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted 9,9-dimethylfluorenyl, a substituted or unsubstituted 9,9-diphenylfluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazolyl.

[0021] More preferably, the Ar 1 is selected from a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted 9,9-dimethylfluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl.

[0022] More preferably, the Ar 2 and Ar 3 Each is independently selected from hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted 9,9-dimethylfluorenyl, a substituted or unsubstituted 9,9-diphenylfluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl.

[0023] Preferably, when the "substituted or unsubstituted" is substituted, the substituents are each independently selected from deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, fluoranthenyl, triphenylenyl, group, dibenzofuranyl, dibenzothiophenyl, or a combination of one or more thereof.

[0024] In a specific embodiment of the present invention, the organic compound is selected from any one of the following compounds numbered 1-1 to 1-36 and 2-1 to 2-36:

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032] Use of the compound according to the present invention as an organic electroluminescent material.

[0033] An organic electroluminescent element, comprising a substrate, an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode, wherein the light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, and the hole transport region contains the compound according to the present invention.

[0034] Preferably, the hole transport region includes at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. The light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer, and the light-emitting auxiliary layer contains the organic compound according to the present invention.

[0035] An electronic device, comprising: one or more of a display, a monitor, and a lighting device, including the organic electroluminescent element according to the present invention; and a control unit for driving the above display device.

[0036] The beneficial effects of the present invention are:

[0037] The organic compound of the present invention is applied to the light-emitting auxiliary layer, which can reduce the potential barrier between the hole transport layer and the light-emitting layer, improve the hole migration speed, improve the hole transport performance, and reduce the driving voltage of the organic electroluminescent device. The prepared device has good improvements in light-emitting efficiency and lifespan. Description of the Drawings

[0038] Figure 1 It is a schematic structural diagram of the organic electroluminescent element described in Application Example 1, wherein 1 is the anode, 2 is the hole injection layer, 3 is the hole transport layer, 4 is the light-emitting auxiliary layer, 5 is the light-emitting layer, 6 is the electron transport layer, and 7 is the cathode. Detailed Embodiments

[0039] To more fully describe the present invention to those skilled in the art, embodiments of the present invention are provided. The scope of the present invention is not limited to the following embodiments. These embodiments can make the present invention more thorough and complete, and fully convey the concept of the present invention to those skilled in the art.

[0040] The present disclosure can be more easily understood by reference to the following specific embodiments and the examples included therein. Before disclosing and describing the compounds, devices, and / or methods of the present invention, it should be understood that, unless otherwise specified, they are not limited to specific synthetic methods or specific reagents, as these can vary. It should also be understood that the terms used in the present invention are only for describing specific aspects and are not intended to be limiting. Although any methods and materials similar or equivalent to those described in the present invention can be used in this practice or test, exemplary methods and materials are now described.

[0041] Unless otherwise specified, the experimental methods used in the following examples are all conventional methods; unless otherwise specified, the reagents, materials, etc. used in the following examples can all be obtained from commercial sources.

[0042] As used in the present invention, the term "halogen" can include fluorine, chlorine, bromine, or iodine.

[0043] As used in the present invention, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 10 carbon atoms, and examples thereof include but are not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0044] As used in the present invention, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyls include but are not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantane, etc.

[0045] As used in the present invention, the term "C2-C10 heterocycloalkyl" has a monovalent substituent of a monocyclic or polycyclic ring having 2 to 10 carbon atoms, and the ring contains at least one heteroatom selected from O, S, N, P, Si.

[0046] As used in the present invention, the term "alkoxy" refers to a straight-chain, branched-chain, or cyclic chain. The number of carbon atoms in the alkoxy is not particularly limited herein, but the alkoxy preferably has 1 to 10 carbon atoms. Specific examples thereof include but are not limited to methoxy, ethoxy, n-propoxy, isopropoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, benzyloxy.

[0047] As used in the present invention, the term "aryl having 6 to 60 carbon atoms" 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 aryl may have a form in which two or more of the rings are simply linked to each other or fused to each other. Examples of such aryl include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthryl, pyrenyl, triphenylenyl, fluoranthenyl, dimethyl 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, etc.

[0048] As used in the present invention, the term "arylene" refers to a divalent aryl derived by removing one hydrogen atom from "aryl". For example, removing one hydrogen atom from phenyl gives phenylene, and removing one hydrogen atom from naphthyl gives naphthylene.

[0049] As used in the present invention, the term "heteroaryl having 3 to 60 carbon atoms" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon, preferably 1 - 3 carbons in the ring are replaced by a heteroatom such as N, O, S, P, B or Si. Further, such heteroaryl may have a form in which two or more of the rings are simply linked to each other or fused to each other or fused to an aryl. Examples of such heteroaryl include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridyl, purinyl, phenanthrolinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furyl, thienyl, benzofuryl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, carbazolyl, dibenzofuryl, dibenzothienyl, etc., and the present invention is not limited thereto.

[0050] As used in the present invention, the term "heteroarylene" refers to a divalent heteroaryl derived by removing one hydrogen atom from "heteroaryl". For example, removing one hydrogen atom from pyridyl gives pyridylene.

[0051] As used in the present invention, in the expression "Z group having AA - BB carbon atoms" or "Z group of C(AA - BB)", "having AA - BB carbon atoms" means the number of carbon atoms of the Z group when unsubstituted, excluding the carbon atoms of the substituents when substituted. For example, aryl having 6 to 30 carbon atoms means that when unsubstituted, the number of carbon atoms in the aryl is any integer from 6 to 30, 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... 30.

[0052] As used in the present invention, the term "single bond" means that the groups are directly connected. For example, in formula (1), where L 1 is a single bond, which means

[0053] As used in the present invention, "when a is selected from 0, does not exist", that is

[0054] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position where substitution occurs can be the position where the hydrogen atom is replaced. That is, this position is not limited to a specific position, as long as the hydrogen at this position can be replaced by a substituent. For example, the carbazolyl group, unless otherwise specified in this specification, includes any of the following groups, but is not limited thereto,

[0055] represents the substitution position. "Unsubstituted" means that a hydrogen atom is retained, and in this case, the hydrogen atom includes protium, deuterium, and tritium.

[0056] As used in the present invention, the term "phenylene naphthyl" means

[0057] As used in the present invention, the term "phenyl naphthyl" includes

[0058] refers to the substitution position.

[0059] When two or more substituents are present, the two or more substituents may be the same or different.

[0060] As used in the present invention, the hydrogen atom includes protium, deuterium, and tritium. The compounds described in the present invention may contain deuterium atoms of natural origin, or deuterium atoms may be introduced by deuterating a part or all of the starting compounds. If deuterium atoms are introduced from the starting materials, the deuteration rate may be 100%, or less than 100%, or less than 95%, or less than 90%, or less than 80%, and the deuteration rate may also be 1% or more, or 5% or more, or 10% or more. If the deuteration rate is not 100%, it represents a mixture of deuterated compounds and non-deuterated compounds, or a mixture of fully deuterated compounds and incompletely deuterated compounds, or a mixture of fully deuterated compounds, non-deuterated compounds, and incompletely deuterated compounds.

[0061] As used in the present invention, terms such as the first, the second, A, B, etc. are used. The above terms are only used to distinguish the components and do not limit the nature or order of the components corresponding to the terms.

[0062] Organic electroluminescent element

[0063] The structure used in the organic electroluminescent element of the present invention is a publicly known structure, including an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound of the present invention.

[0064] The organic layer may further include one or more of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.

[0065] The light-emitting element of the present invention can be fluorescent emission, phosphorescent emission, or a combination thereof. The light-emitting element can be a single light-emitting element or a series type of multiple light-emitting units.

[0066] As a simple light-emitting element, the following can be cited, but are not limited thereto.

[0067] (1) Hole transport layer / Fluorescent light-emitting layer / Electron transport layer;

[0068] (2) Hole transport layer / Phosphorescent light-emitting layer / Electron transport layer;

[0069] (3) Hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer;

[0070] (4) Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer / Electron transport layer;

[0071] (5) Hole transport layer / Fluorescent light-emitting layer / Spacer layer / Phosphorescent light-emitting layer / Electron transport layer;

[0072] (6) Hole transport layer / Light-emitting auxiliary layer / Fluorescent light-emitting layer / Electron transport layer;

[0073] (7) Hole transport layer / Light-emitting auxiliary layer / Fluorescent light-emitting layer / Hole blocking layer / Electron transport layer;

[0074] (8) Hole transport layer / Light-emitting auxiliary layer / Phosphorescent light-emitting layer / Electron transport layer;

[0075] (9) Hole transport layer / Light-emitting auxiliary layer / Phosphorescent light-emitting layer / Hole blocking layer / Electron transport layer;

[0076] (10) Hole injection layer / Hole transport layer / Phosphorescent light-emitting layer / Electron transport layer / Electron injection layer;

[0077] (11) Hole injection layer / Hole transport layer / Fluorescent light-emitting layer / Electron transport layer / Electron injection layer;

[0078] (12) Hole injection layer / Hole transport layer / Light-emitting auxiliary layer / Phosphorescent light-emitting layer / Electron transport layer / Electron injection layer;

[0079] (13)Hole injection layer / hole transport layer / luminescence assisting layer / fluorescent luminescence layer / electron transport layer / electron injection layer;

[0080] Each of the above phosphorescent / fluorescent luminescence layers can emit light of different colors.

[0081] As a tandem organic electroluminescent element, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can generally also be referred to as a charge generation layer, an electron extraction layer, a connection layer, etc. For example, when stacking a fluorescent luminescence layer and a phosphorescent luminescence layer, in order to prevent excitons generated in the phosphorescent luminescence layer from diffusing to the fluorescent luminescence layer, or to adjust the carrier balance, an intermediate layer is placed between the fluorescent luminescence layer and the phosphorescent luminescence layer.

[0082] When the organic light-emitting element includes a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.

[0083] The organic electroluminescent element of the present specification can be manufactured by materials and methods known in the art, except that one or more of the organic material layers are formed by using the compound of formula (1).

[0084] As an anode material, a material having a relatively large work function can be used, and a transparent conductive oxide, a metal, a conductive polymer, etc. can be used.

[0085] As a cathode material, a material having a low work function is usually used to facilitate electron injection into the organic material layer, and a metal, a metal oxide, a conductive polymer, etc. can be used.

[0086] The hole injection layer is a layer that injects holes from the electrode and has the ability to transport holes. In order to reduce the energy level difference between the electrodes, the hole injection layer is mainly prepared based on aromatic amine compounds, and other materials having hole transport ability can also be used.

[0087] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material can appropriately be a material having a high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer.

[0088] The luminescence assisting layer is a layer that blocks electrons from reaching the anode, can adjust the energy level difference between the hole transport region and the light-emitting layer, facilitates holes to enter the light-emitting layer, and at the same time reduces the probability of electrons entering the hole transport region from the light-emitting layer. Commonly used ones are aromatic amine derivatives.

[0089] A luminescent material is a material that can receive holes and electrons from a hole transport layer and an electron transport layer respectively, and combine the holes and electrons to emit light in the visible light region. The luminescent layer material includes a host material and a dopant material. Red, green, or blue luminescent materials can be used, and if necessary, two or more luminescent materials can be mixed. As the luminescent material, a fluorescent material can be used, or a phosphorescent material can also be used. As the luminescent material, a single-component material can be adopted, or a multi-component material can also be adopted.

[0090] An electron transport layer is a layer that receives electrons from an electron injection layer and transports the electrons to the luminescent layer, and the electron transport material is a material with a high electron mobility that can receive electrons from the cathode and transfer the electrons to the luminescent layer. Metal complexes such as triazine derivatives, oxadiazole derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used, and polymer materials and small molecule materials can also be used.

[0091] An electron injection layer is a layer that injects electrons from an electrode.

[0092] According to the materials used, the organic light-emitting device of this specification can be a top-emitting device, a bottom-emitting device, or a dual-emission type device.

[0093] Synthesis general formula: The following general formula is only one synthesis method of the compounds of the present invention, and the compounds of the present invention can also be synthesized by other methods.

[0094]

[0095] Wherein X represents a halogen. For different substitution positions, the same synthesis method can be adopted. L 1 -L 3 、Ar 1 -Ar 3 has the same meaning as that represented in Claim 1.

[0096] Compound preparation examples

[0097] The present invention will be specifically described through Compound Examples 1-14.

[0098] Compound Example 1: Preparation of Compound 1-1

[0099]

[0100] (1) Dissolve 1-1-0 (42.0 g, 149.4 mmol) in ethyl acetate (500 mL), then add Raney nickel (20 g) and react at room temperature for 48 hours. After confirming the completion of the reaction by TLC, remove the catalyst using a diatomaceous earth column. At room temperature, add a pd / C (10 g, 5%) catalyst and carry out a hydrogen reaction under a hydrogen pressure of about 100 psi. The reaction is completed after 72 hours. Remove the solvent under reduced pressure, and purify the product by silica gel column chromatography to obtain pure 1-1-1 (35.7 g, yield 83%).

[0101] LC-MS (APCI) (M+H) + : 285.82

[0102] (2) Dissolve 1-1-1 (5.70 g, 20.0 mmol) in tetrahydrofuran (200 mL). Slowly add n-butyllithium (13.2 ml, 1.6 M) dropwise at -40 °C and stir for half an hour. Then add triisopropyl borate (3.95 g, 21.0 mmol) dropwise at -40 °C and stir at -40 °C for 1 hour. Then stir at room temperature for 4 hours, and add dilute hydrochloric acid (5%) and stir for 2 hours. After the reaction is completed, extract with distilled water and ethyl acetate. The organic layer is dried over MgSO 4 and filtered and concentrated. Use ethyl acetate and n-hexane as the developing agents and purify by column chromatography to obtain pure 1-1-2 (4.15 g, yield 83%).

[0103] LC-MS (APCI) (M+H) + : 251.48

[0104] (3) Completely dissolve the intermediate compound 1-1-3 (6.41 g, 37.9 mmol) and 1-1-4 (8.83 g, 37.9 mmol) in 110 mL of xylene, then add NaOt-Bu (4.17 g, 43.4 mmol). After adding bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 3.1 mmol), heat and stir for 3 hours. After the reaction is completed, cool to room temperature and extract with distilled water and ethyl acetate. The organic layer is dried over MgSO 4 and filtered and concentrated. Use ethyl acetate and n-hexane as the developing agents and purify by column chromatography to obtain the intermediate compound 1-1-5 (9.75 g, yield 80%).

[0105] LC-MS (APCI) (M+H) + : 322.08

[0106] (4) Dissolve 1-1-6 (3.14 g, 20.1 mmol) in tetrahydrofuran (200 mL). Slowly add n-butyllithium (13.2 mL, 1.6 M) dropwise at -40 °C and stir for half an hour. Then add triisopropyl borate (3.95 g, 21.0 mmol) dropwise at -40 °C. Stir at -40 °C for 1 hour, then stir at room temperature for 4 hours. Add dilute hydrochloric acid (5%) and stir for 2 hours. After the reaction is completed, extract with distilled water and ethyl acetate. The organic layer is dried over MgSO 4 and filtered and concentrated. Use ethyl acetate and n-hexane as the eluent and purify by column chromatography to obtain pure 1-1-7 (2.32 g, yield 95%).

[0107] LC-MS (APCI) (M+H) + : 122.81

[0108] (5) Under a nitrogen atmosphere, add 1-1-8 (13.36 g, 42.2 mmol) and compound 1-1-7 (5.40 g, 44.3 mmol) to a four-necked flask. Add toluene (70 mL), ethanol (30 mL), water (30 mL), potassium carbonate (11.61 g, 84.2 mmol). After adding tetrakis(triphenylphosphine)palladium(0) (0.97 g, 8.4 mmol), heat and stir for 3 hours. After the reaction is completed, cool to room temperature, wash with water, and the organic layer is dried over MgSO 4 and filtered and concentrated. Purification can be carried out by column chromatography or distillation to obtain the intermediate compound 1-1-9 (6.76 g, yield: 60%).

[0109] LC-MS (APCI) (M+H) + : 267.95

[0110] (6) Completely dissolve the intermediate compound 1-1-9 (8.78 g, 32.8 mmol) and 1-1-5 (10.29 g, 32.0 mmol) in 105 mL of xylene. Then add NaOt-Bu (4.17 g, 43.4 mmol). After adding bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 3.1 mmol), heat and stir for 3 hours. After the reaction is completed, cool to room temperature and extract with distilled water and ethyl acetate. The organic layer is dried over MgSO 4 and filtered and concentrated. Use ethyl acetate and n-hexane as the eluent and purify by column chromatography to obtain the intermediate compound 1-1-10 (11.71 g, yield 72%).

[0111] LC-MS (APCI) (M+H) + : 508.46

[0112] (7) Under a nitrogen atmosphere, 1-1-10 (17.88 g, 35.2 mmol) and Compound 1-1-2 (9.70 g, 38.8 mmol) were added to a three-necked flask, followed by the addition of toluene (70 mL), ethanol (30 mL), water (30 mL), potassium carbonate (11.61 g, 84.2 mmol). After adding tetrakis(triphenylphosphine)palladium(0) (0.97 g, 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 MgSO 4 and filtered and concentrated. The intermediate compound 1-1 (18.70 g, yield: 78%) was obtained by purification through column chromatography.

[0113] LC-MS (APCI) (M+H) + : 678.24

[0114] Compound Example 2: Preparation of Compound 1-3

[0115]

[0116] Prepared according to the same synthesis method as in Compound Example 1 above, replacing Compound 1-1-4 with Compound 1-3-4, the compound of Structural Formula 1-3 can be synthesized according to the above synthetic route (22.80 g, yield 89%, the synthesis yield of the reaction of 1-3-10 and 1-1-2).

[0117] LC-MS (APCI) (M+H) + : 728.33

[0118] Compound Example 3: Preparation of Compound 1-7

[0119]

[0120] Prepared according to the same synthesis method as in Compound Example 1 above, replacing Compound 1-1-4 with Compound 1-7-4, the compound of Structural Formula 1-7 can be synthesized according to the above synthetic route (21.19 g, yield 87%, the synthesis yield of the reaction of 1-7-10 and 1-1-2).

[0121] LC-MS (APCI) (M+H) + : 692.27

[0122] Compound Example 4: Preparation of Compound 1-11

[0123]

[0124] Prepared according to the same synthesis method as in Compound Example 1 above, replacing Compound 1-1-4 with Compound 1-11-4, and the compound of Structural Formula 1-11 can be synthesized according to the above synthetic route (22.93 g, yield 92%, the yield is the synthetic yield of the reaction of 1-11-10 and 1-1-2).

[0125] LC-MS(APCI)(M+H) + : 708.39

[0126] Compound Example 5: Preparation of Compound 1-14

[0127]

[0128] Prepared according to the same synthesis method as in Compound Example 1 above, replacing Compound 1-1-7 with Compound 1-14-7 and Compound 1-1-5 with Compound 1-14-5, and the compound of Structural Formula 1-14 can be synthesized according to the above synthetic route (25.47 g, yield 90%, the yield is the synthetic yield of the reaction of 1-14-10 and 1-1-2).

[0129] LC-MS(APCI)(M+H) + : 804.61

[0130] Compound Example 6: Preparation of Compound 1-17

[0131]

[0132] Prepared according to the same synthesis method as in Compound Example 1 above, replacing Compound 1-1-7 with Compound 1-17-7, and the compound of Structural Formula 1-17 can be synthesized according to the above synthetic route (24.29 g, yield 88%, the yield is the synthetic yield of the reaction of 1-17-10 and 1-1-2).

[0133] LC-MS(APCI)(M+H) + : 784.76

[0134] Compound Example 7: Preparation of Compound 1-24

[0135]

[0136] Prepared according to the same synthesis method as in Compound Example 1 above, replacing Compound 1-1-7 with Compound 1-24-7, and the compound of Structural Formula 1-24 can be synthesized according to the above synthetic route (24.87 g, yield 89%, the yield is the synthetic yield of the reaction of 1-24-10 and 1-1-2).

[0137] LC-MS(APCI)(M+H)+ : 794.76

[0138] Compound Example 8: Preparation of Compound 2-3

[0139]

[0140] Prepared according to the same synthesis method as Compound Example 2 above. Replace Compound 1-1-0 with Compound 2-3-0. According to the above synthesis route, the compound with the structural formula 2-3 can be synthesized (22.48 g, yield 91%, the synthesis yield of the reaction of 1-3-10 and 2-3-2).

[0141] LC-MS(APCI)(M+H) + : 702.28

[0142] Compound Example 9: Preparation of Compound 2-11

[0143]

[0144] Prepared according to the same synthesis method as Compound Example 4 above. Replace Compound 1-1-0 with Compound 2-3-0. According to the above synthesis route, the compound with the structural formula 2-11 can be synthesized (22.08 g, yield 92%, the synthesis yield of the reaction of 1-11-10 and 2-3-2).

[0145] LC-MS(APCI)(M+H) + : 682.36

[0146] Compound Example 10: Preparation of Compound 2-18

[0147]

[0148] Prepared according to the same synthesis method as Compound Example 1 above. Replace Compound 1-1-0 with Compound 2-3-0 and Compound 1-1-7 with Compound 2-18-7. According to the above synthesis route, the compound with the structural formula 2-18 can be synthesized (24.33 g, yield 90%, the synthesis yield of the reaction of 2-18-10 and 2-3-2).

[0149] LC-MS(APCI)(M+H) + : 768.56

[0150] Compound Example 11: Preparation of Compound 2-21

[0151]

[0152] Prepared according to the same synthesis method as in Compound Example 1 above. Replace Compound 1-1-0 with Compound 2-3-0 and Compound 1-1-7 with Compound 2-21-7. The compound with Structural Formula 2-21 can be synthesized according to the above synthetic route (22.72 g, yield 87%, the yield is the synthetic yield of the reaction of 2-21-10 and 2-3-2).

[0153] LC-MS(APCI)(M+H) + : 742.43

[0154] Compound Example 12: Preparation of Compound 2-26

[0155]

[0156] Prepared according to the same synthesis method as in Compound Example 1 above. Replace Compound 1-1-0 with Compound 2-3-0 and Compound 1-1-4 with Compound 2-26-4. The compound with Structural Formula 2-26 can be synthesized according to the above synthetic route (25.59 g, yield 89%, the yield is the synthetic yield of the reaction of 2-26-10 and 2-3-2).

[0157] LC-MS(APCI)(M+H) + : 816.76

[0158] Compound Example 13: Preparation of Compound 2-32

[0159]

[0160] Prepared according to the same synthesis method as in Compound Example 1 above. Replace Compound 1-1-0 with Compound 2-3-0, Compound 1-1-4 with Compound 2-32-4, and Compound 1-1-7 with Compound 2-32-7. The compound with Structural Formula 2-32 can be synthesized according to the above synthetic route (25.35 g, yield 88%, the yield is the synthetic yield of the reaction of 2-26-10 and 2-3-2).

[0161] LC-MS(APCI)(M+H) + : 818.32

[0162] Compound Example 14: Preparation of Compound 2-36

[0163]

[0164] Prepared according to the same synthesis method as in Example 1 of the above compound, replacing Compound 1-1-0 with Compound 2-3-0, Compound 1-1-4 with Compound 2-36-4, and Compound 1-1-9 with Compound 2-36-9, the compound with the structural formula 2-36 can be synthesized according to the above synthetic route (25.82 g, yield 90%, the synthesis yield of the reaction of 2-36-10 and 2-3-2).

[0165] LC-MS(APCI)(M+H) + : 814.99

[0166] Device Preparation Example

[0167] Through Application Example 1, the application effect of the compound of the present invention as a light-emitting auxiliary layer in a device is illustrated.

[0168] Application Example 1

[0169] This example provides an organic electroluminescent element, as Figure 1 shown, including an anode 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 cathode 7 stacked from bottom to top. The hole injection layer 2, the hole transport layer 3, and the light-emitting auxiliary layer 4 are the hole transport regions.

[0170] The specific device structure is as follows:

[0171] ITO / HATCN(5 nm) / HT(60 nm) / EB(5 nm) / GH+GD(3 wt%)(20 nm) / ET(15 nm) / Al(100 nm).

[0172] Device preparation process:

[0173] Evaporate HATCN on the ITO substrate to form a first hole injection layer (HIL) with a thickness of , evaporate HT on the above first hole injection layer to form a hole transport layer (HTL) with a thickness of , evaporate EB on the above hole transport layer to form a light-emitting auxiliary layer (EBL) with a thickness of , evaporate GH+GD(3 wt%) on the light-emitting auxiliary layer to form a light-emitting layer (EML) with a thickness of , successively evaporate an electron transport layer (ETL) with a thickness of , evaporate Al (with a thickness of ) to form a cathode, thereby manufacturing an organic electroluminescent device. Recorded as Comparative Example 1.

[0174]

[0175] Device Comparative Example 2

[0176] The light-emitting auxiliary layer is prepared by replacing the EB material with EB-1 to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device is fabricated using the same method as in the implementation scheme of Comparative Example 1 above.

[0177] Device Comparative Example 3

[0178] The light-emitting auxiliary layer is prepared by replacing the EB material with EB-2 to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device is fabricated using the same method as in the implementation scheme of Comparative Example 1 above.

[0179] Device Example 1

[0180] The light-emitting auxiliary layer is prepared by replacing the EB material with the compound obtained in Compound Example 1 of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device is fabricated using the same method as in the implementation scheme of Comparative Example 1 above.

[0181] Device Example 2

[0182] The light-emitting auxiliary layer is prepared by replacing the EB material with the compound obtained in Compound Example 2 of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device is fabricated using the same method as in the implementation scheme of Comparative Example 1 above.

[0183] Device Example 3

[0184] The light-emitting auxiliary layer is prepared by replacing the EB material with the compound obtained in Compound Example 3 of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device is fabricated using the same method as in the implementation scheme of Comparative Example 1 above.

[0185] Device Example 4

[0186] The light-emitting auxiliary layer is prepared by replacing the EB material with the compound obtained in Compound Example 4 of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device is fabricated using the same method as in the implementation scheme of Comparative Example 1 above.

[0187] Device Example 5

[0188] The light-emitting auxiliary layer is prepared by replacing the EB material with the compound obtained in Compound Example 5 of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device is fabricated using the same method as in the implementation scheme of Comparative Example 1 above.

[0189] Device Example 6

[0190] The light-emitting auxiliary layer is prepared by replacing the EB material with the compound obtained in Compound Example 6 of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device is fabricated using the same method as in the implementation scheme of Comparative Example 1 above.

[0191] Device Example 7

[0192] The light-emitting auxiliary layer was prepared by replacing the EB material with the compound obtained in Example 7 of the compound of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device was fabricated using the same method as in Comparative Example 1 above.

[0193] Device Example 8

[0194] The light-emitting auxiliary layer was prepared by replacing the EB material with the compound obtained in Example 8 of the compound of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device was fabricated using the same method as in Comparative Example 1 above.

[0195] Device Example 9

[0196] The light-emitting auxiliary layer was prepared by replacing the EB material with the compound obtained in Example 9 of the compound of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device was fabricated using the same method as in Comparative Example 1 above.

[0197] Device Example 10

[0198] The light-emitting auxiliary layer was prepared by replacing the EB material with the compound obtained in Example 10 of the compound of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device was fabricated using the same method as in Comparative Example 1 above.

[0199] Device Example 11

[0200] The light-emitting auxiliary layer was prepared by replacing the EB material with the compound obtained in Example 11 of the compound of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device was fabricated using the same method as in Comparative Example 1 above.

[0201] Device Example 12

[0202] The light-emitting auxiliary layer was prepared by replacing the EB material with the compound obtained in Example 12 of the compound of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device was fabricated using the same method as in Comparative Example 1 above.

[0203] Device Example 13

[0204] The light-emitting auxiliary layer was prepared by replacing the EB material with the compound obtained in Example 13 of the compound of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device was fabricated using the same method as in Comparative Example 1 above.

[0205] Device Example 14

[0206] The light-emitting auxiliary layer was prepared by replacing the EB material with the compound obtained in Example 14 of the compound of the present invention to prepare the light-emitting auxiliary layer 4, and an organic electroluminescent device was fabricated using the same method as in Comparative Example 1 above.

[0207] Test Results

[0208] Lifetime test method: Apply a voltage to the obtained organic electroluminescent device so that the current density reaches 30 mA / cm 2 , measure the time until the luminance becomes 95% of the initial luminance (LT95 (unit: hours)), take the lifetime of Comparative Example 1 as 100%, and obtain the relative lifetime values of each comparative example and example.

[0209] The driving voltage is tested at a current density of 15 mA / cm 2 , take the driving voltage of Comparative Example 1 as 100%, and obtain the relative driving voltage values of each comparative example and example.

[0210] The current efficiency is tested at a current density of 15 mA / cm 2 , take the current efficiency of Comparative Example 1 as 100%, and obtain the relative current efficiency values of each comparative example and example. The test results are shown in Table 1.

[0211] Table 1

[0212]

[0213]

[0214] From the results shown in Table 1 above, it can be seen that when the organic compound of the present invention is applied in the light-emitting auxiliary layer, compared with the comparative examples, the driving voltage is reduced, and the luminous efficiency and lifetime are significantly improved.

[0215] The above shows and describes the basic principles, main features and advantages of the present invention. Those skilled in the art should understand that the present invention is not limited by the above embodiments, and the above embodiments and the descriptions in the specification only illustrate the principles of the present invention. Without departing from the spirit and scope of the present invention, the present invention will have various changes and improvements, and these changes and improvements all fall within the scope of the present invention claimed. The scope of the present invention claimed is defined by the appended claims and their equivalents.

[0216] Although the present invention has been particularly described with exemplary embodiments, it should be understood that various forms and details can be changed by those of ordinary skill in the art without departing from the spirit and scope of the present invention defined by the claims.

Claims

1. An organic compound, characterized in that the compound has the structure shown in formula (1): wherein, a is selected from integers from 0 to 2, and when a is selected as 0, does not exist L 1 -L 3 Each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group Ar 1- Ar 3 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, When the "substituted or unsubstituted" is substituted, the substituents are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl, and the heteroatoms of the heteroaryl are selected from one or more of oxygen, sulfur, and nitrogen.

2. The organic compound according to claim 1, characterized in that: the compound has the structures shown in formula (2) and formula (3):

3. The organic compound according to claim 1, characterized in that: The said L 1 -L 3 Each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted fluoranthenylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted perylenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted yl, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted 9,9-dimethylfluorenylene, a substituted or unsubstituted 9,9-diphenylfluorenylene, a substituted or unsubstituted spirobifluorenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazolyl.

4. The organic compound according to claim 1, characterized in that: The Ar 1 -Ar 3 are each independently selected from hydrogen, 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 phenylnaphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group.

5. The organic compound according to claim 1, characterized in that: When the "substituted or unsubstituted" is substituted, the substituents are each independently selected from one or more combinations of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, fluoranthenyl, triphenylene, group, dibenzofuranyl, dibenzothiophenyl.

6. The organic compound according to claim 1, characterized in that the compound is selected from any one of the following compounds numbered 1-1 to 1-36 and 2-1 to 2-36:

7. Use of the compound according to claims 1-6 as an organic electroluminescent material.

8. The organic electroluminescent device according to claim 7, characterized in that: the organic electroluminescent device comprises a substrate, an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode, the light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the cathode; the hole transport region contains the compound according to claims 1-6.

9. The organic electroluminescent device according to claim 7, characterized in that: the hole transport region comprises at least one layer of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer; the light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer; the light-emitting auxiliary layer contains the organic compound according to any one of claims 1-6.

10. An electronic device, comprising: one or more of a display, a monitor, and a lighting device, including the organic electroluminescent device according to claim 8 or 9; and a control unit for driving the above display device.

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