Organic electroluminescent compound and application thereof

Abstract

The invention relates to the technical field of display, in particular to an organic electroluminescent compound and application thereof. The organic electroluminescent compound provided by the invention has a structure shown as follows: # imgabs0 #, so that an organic electroluminescent device containing the organic electroluminescent compound has relatively low driving voltage, relatively high luminous efficiency and relatively long service life.

Description

Technical Field

[0001] The present invention relates to the field of display technologies, and particularly to an organic electroluminescent compound and its application. Background Art

[0002] An electroluminescent device (EL device) is a self-luminous device, which has the advantages of providing a wider viewing angle, a higher contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak by using an aromatic diamine small molecule and an aluminum complex as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

[0003] An organic EL device (OLED) is a device that converts electrical energy into light by applying an electric current to an organic electroluminescent material, and generally has a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the organic EL device can be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (which includes a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used for the organic layer are classified into a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. according to their functions. In the organic EL device, due to the applied voltage, holes are injected from the anode into the light-emitting layer, electrons are injected from the cathode into the light-emitting layer, and high-energy excitons are formed by the recombination of holes and electrons. Through this energy, the organic light-emitting compound reaches an excited state, and light is emitted by the energy generated when the excited state of the organic light-emitting compound returns to the ground state.

[0004] The most important factor determining the luminous efficiency in an organic EL device is the light-emitting material. The light-emitting material must have a high quantum efficiency, as well as high electron and hole mobilities, and the formed light-emitting material layer must be uniform and stable. The light-emitting material is classified into a blue light-emitting material, a green light-emitting material, a red light-emitting material, and additionally a yellow light-emitting material or an orange light-emitting material according to the color of the emitted light. In addition, the light-emitting material can also be classified into a host material and a dopant material according to its function.

[0005] Developing an organic EL device that can provide high efficiency and long life is an urgent issue. Specifically, considering the EL characteristic requirements of OLEDs for medium or larger-sized panels, it is necessary to develop materials that can exhibit better characteristics than conventional materials. However, the HOMO and LUMO energy levels of existing organic electroluminescent materials have a poor match with adjacent energy levels, resulting in problems such as low stability of organic electroluminescent materials and imbalance in carrier mobility, causing high driving voltage, low luminous efficiency, and short lifespan of organic electroluminescent devices containing such organic electroluminescent materials, severely limiting the application of organic electroluminescent devices. Summary of the Invention

[0006] An object of the present invention is to overcome the problems that the HOMO and LUMO energy levels of existing organic electroluminescent materials have a poor match with adjacent energy levels, thus resulting in low stability of organic electroluminescent materials and imbalance in carrier mobility, causing high driving voltage, low luminous efficiency, and short lifespan of organic electroluminescent devices containing such organic electroluminescent materials, and further to provide an organic electroluminescent compound and its application.

[0007] Definition of substituent terms in the present invention:

[0008] As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine, or iodine.

[0009] As used in the present invention, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 30 carbon atoms, and its examples include but are not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0010] As used in the present invention, the term "C3-C30 cycloalkyl" refers to a monocyclic hydrocarbon or polycyclic hydrocarbon derived from a ring main-chain having 1 to 30 carbon atoms, and the cycloalkane may include cyclopropyl, cyclobutyl, adamantyl, etc.

[0011] In the present invention, aryl and arylene include monocyclic, polycyclic, or fused-ring aryl, the rings may be interrupted by short non-aromatic units, and may include a spiro structure. Aryl includes but is not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, fluorenyl, spirobifluorenyl, etc., and arylene includes but is not limited to phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, spirobifluorenylene, etc.

[0012] In the present invention, heteroaryl and heteroarylene include monocyclic, polycyclic or fused-ring heteroaryl, and the rings can be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen and sulfur. Heteroaryl includes but is not limited to furyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and their derivatives, etc.; heteroarylene includes but is not limited to furylene, phenylthioylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazanylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, benzofurylene, benzothienylene, isobenzofurylene, dibenzofurylene, dibenzothienylene, benzimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoxazolylene, isoindolylene, indolylene, indazolylene, benzothiadiazolylene, quinolinylene, isoquinolinylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenoxazinylene, phenothiazinylene, phenanthridinylene, benzodioxolylene, dihydroacridinylene, and their derivatives, etc.

[0013] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position is not limited to a specific position as long as the hydrogen at that position can be replaced by a substituent. When there are two or more substituents, the two or more substituents can be the same or different.

[0014] As used in the present invention, unless otherwise specified, hydrogen atoms include protium, deuterium and tritium.

[0015] In the present invention, when the range of the number of carbon atoms is defined in the definition of a group, the number of carbon atoms is any integer within the defined range. For example, C6-C30 aryl means that the number of carbon atoms of the aryl can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30, etc.

[0016] In the present invention, represents a connecting bond.

[0017] The solution adopted in the present invention is as follows:

[0018] The present invention provides an organic electroluminescent compound having the structure shown below:

[0019]

[0020] R 1 is -L 1 Ar 1 、R 2 is -L 2 Ar 2 、R 3 is -L 3 Ar 3 、R 4 is -L 4 Ar 4 、R 5 is -L 5 Ar 5 、R 6 is -L 6 Ar 6 、R 7 is -L 7 Ar 7 、R 8 is -L 8 Ar 8 、R 9 is -L 10 Ar 9 、R 10 is -L 10 Ar 10 、R 11 is -L 11 Ar 11 、R 12 is -L 12 Ar 12 、R 13 is -L 13 Ar 13 、R 14 is -L 14 Ar 14 ,R 15 is -L 15 Ar 15 ;

[0021] L 1 -L 15 Each is independently selected from a linking bond, a substituted or unsubstituted C6 - C30 arylene group, and a substituted or unsubstituted C3 - C30 heteroarylene group;

[0022] Ar 1 -Ar 15Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted mono- or di-C6-C30 arylamino, substituted or unsubstituted mono- or di-C6-C30 heteroarylamino;

[0023] The heteroatoms in the substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted mono- or di-C6-C30 heteroarylamino are independently selected from N, O or S;

[0024] The substituents in the substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C60 aryl, substituted C3-C60 heteroaryl, substituted mono- or di-C6-C30 arylamino, substituted mono- or di-C6-C30 heteroarylamino are each independently selected from deuterium, halogen, cyano, unsubstituted C3-C30 heteroaryl, C3-C30 heteroaryl substituted with C1-C6 alkyl or C6-C30 aryl, unsubstituted C6-C30 aryl, C6-C30 aryl substituted with cyano or C3-C30 heteroaryl or mono- or di-C6-C30 arylamino, mono- or di-C6-C30 arylamino, C1-C30 alkyl, or a combination of one or at least two thereof.

[0025] Preferably, the L 1 -L 15 Each independently selected from a linking bond, substituted or unsubstituted C6-C20 arylene, substituted or unsubstituted C3-C20 heteroarylene;

[0026] Preferably, the L 1 -L 15 Each independently selected from a linking bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted naphthylene;

[0027] Among them, the substituents in the substituted phenylene, substituted biphenylene, substituted terphenylene, substituted dibenzofuranylene, substituted naphthylene are each independently selected from a combination of one or at least two of C1-C6 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, C3-C25 heteroaryl;

[0028] Preferably, the L 1 -L 15 Each independently selected from a linking bond, phenylene, naphthylene, dibenzofuranylene.

[0029] Preferably, at least one of Ar 1 -Ar 15 is selected from the group shown in Formula a:

[0030]

[0031] R X1 、R X2 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0032] Wherein, the substituents of the substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C6-C30 aryl, and substituted C3-C30 heteroaryl are selected from deuterium, halogen, cyano, unsubstituted C3-C30 heteroaryl, C3-C30 heteroaryl substituted by C1-C6 alkyl or C6-C30 aryl, unsubstituted C6-C30 aryl, C6-C30 aryl substituted by cyano or C3-C30 heteroaryl or mono- or di-C6-C30 arylamino, mono- or di-C6-C30 arylamino, and C1-C30 alkyl, or a combination of at least two of them.

[0033] Preferably,

[0034] R X1 、R X2 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl;

[0035] Wherein, the substituents of the substituted C1-C20 alkyl, substituted C3-C20 cycloalkyl, substituted C6-C20 aryl, and substituted C3-C20 heteroaryl are selected from deuterium, halogen, cyano, unsubstituted C3-C30 heteroaryl, C3-C30 heteroaryl substituted by C1-C6 alkyl or C6-C30 aryl, unsubstituted C6-C30 aryl, C6-C30 aryl substituted by cyano or C3-C30 heteroaryl or mono- or di-C6-C30 arylamino, mono- or di-C6-C30 arylamino, and C1-C30 alkyl, or a combination of at least two of them;

[0036] Preferably, the said R X1 、R X2 Each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted B group;

[0037] The group B is selected from one of the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, phenylnaphthyl, naphthylphenyl, pyridyl, bipyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, carbazolylphenyl, phenylcarbazolyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranphenyl, dibenzothiophenphenyl, dimethylfluorenylphenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl;

[0038] Preferably, the R X1 , R X2 are each independently selected from hydrogen, deuterium, halogen, phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, pyridyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranphenyl.

[0039] Preferably, one of Ar 1 -Ar 15 is selected from formula a, and the others are each independently selected from hydrogen and deuterium.

[0040] Preferably, at least one of Ar 1 -Ar 15 is selected from the group shown in the following formula b:

[0041]

[0042] T 1 -T 2 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted mono- or di-C6-C30 arylamino group, and a substituted or unsubstituted mono- or di-C6-C30 heteroarylamino group;

[0043] Among them, the substituents of the substituted C6-C30 aryl group, the substituted C3-C30 heteroaryl group, the substituted mono- or di-C6-C30 arylamino group, and the substituted mono- or di-C6-C30 heteroarylamino group are selected from deuterium, halogen, cyano, an unsubstituted C3-C30 heteroaryl group, a C3-C30 heteroaryl group substituted with a C1-C6 alkyl group or a C6-C30 aryl group, an unsubstituted C6-C30 aryl group, a C6-C30 aryl group substituted with a cyano group or a C3-C30 heteroaryl group or a mono- or di-C6-C30 arylamino group, a mono- or di-C6-C30 arylamino group, and a C1-C30 alkyl group, or a combination of at least two of them;

[0044] Preferably, T 1 -T 2Each independently selected from substituted or unsubstituted C groups, and the C group is selected from one of the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, binaphthyl, triphenylene, phenylnaphthyl, naphthylphenyl, pyridyl, pyridylphenyl, phenylpyridyl, bipyridyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzofuranylphenyl, dibenzothiophenylphenyl, carbazolyl, benzocarbazolyl, phenylcarbazolyl, dimethylfluorenyl, benzodimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dimethylfluorenylphenyl;

[0045] Among them, the substituents of the substituted C group are selected from one or a combination of at least two of deuterium, halogen, cyano, unsubstituted C3-C30 heteroaryl, C3-C30 heteroaryl substituted by C1-C6 alkyl or C6-C30 aryl, unsubstituted C6-C30 aryl, C6-C30 aryl substituted by cyano or C3-C30 heteroaryl or mono- or di-C6-C30 arylamino, mono- or di-C6-C30 arylamino, C1-C30 alkyl;

[0046] Preferably, T 1 -T 2 Each independently selected from phenyl, biphenyl, terphenyl, phenanthryl, phenylnaphthyl, naphthylphenyl, pyridyl, pyridylphenyl, phenylpyridyl, bipyridyl, dibenzofuranyl, benzonaphthofuranyl, carbazolyl, benzocarbazolyl, dimethylfluorenyl, benzodimethylfluorenyl, diphenylfluorenyl.

[0047] Preferably, Ar 1 -Ar 13 One of them is selected from formula a, and the others are each independently selected from hydrogen and deuterium.

[0048] Preferably, the organic electroluminescent compound is selected from one of M-1 to M-94 or N-1 to N-200:

[0049]

[0050]

[0051]

[0052]

[0053] Preferably, the organic electroluminescent compound is selected from one of N-1 to N-200:

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061] The present invention also provides an organic electroluminescent material, which comprises the above-mentioned organic electroluminescent compound.

[0062] Preferably, the organic electroluminescent material comprises at least one of the compounds M1 to M94 and at least one of the compounds N1 to N200 described above.

[0063] The present invention also provides an organic electroluminescent device, which comprises a cathode, an anode, and an organic layer located between the cathode and the anode, and the organic layer comprises the above-mentioned organic electroluminescent compound or the above-mentioned organic electroluminescent material.

[0064] Preferably, the organic layer comprises an electron transport layer, and the electron transport layer comprises the above-mentioned organic electroluminescent compound.

[0065] Preferably, the organic layer comprises a hole transport layer, and the hole transport layer comprises the above-mentioned organic electroluminescent compound.

[0066] Preferably, the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host material, and the host material comprises at least one of the above-mentioned organic electroluminescent compounds;

[0067] Preferably, the host material comprises a first host material and a second host material; wherein, the first host material is selected from the above-mentioned corresponding organic electroluminescent compounds; the second host material is selected from the above-mentioned corresponding organic electroluminescent compounds;

[0068] Preferably, the mass ratio of the first host material to the second host material is 1:9 - 9:1;

[0069] Preferably, the mass ratio of the first host material to the second host material is 2:8 - 8:2;

[0070] More preferably, the mass ratio of the first host material to the second host material is 3:7 - 7:3;

[0071] Further preferably, the mass ratio of the first host material to the second host material is 4:6 - 6:4.

[0072] Preferably, the organic layer includes a light-emitting layer, the light-emitting layer contains a host material, and the host material is selected from at least one of compounds M1 to M94 and compounds N1 to N200;

[0073] Preferably, the host material includes a first host material and a second host material; wherein, the first host material is selected from at least one of compounds M1 to M290; the second host material is selected from at least one of compounds N1 to N354.

[0074] Preferably, the organic layer includes an electron buffer layer, and the electron buffer layer contains the above-mentioned organic electroluminescent material.

[0075] The present invention also provides the application of the above-mentioned organic electroluminescent device in optical fiber devices, lighting devices, electrophotographic photoreceptor devices, photoelectric converters, organic solar cells, switching element devices, organic light-emitting field effect transistors, image sensors or dye lasers.

[0076] In the present invention, the synthesis route of the above-mentioned organic electroluminescent compound includes the following steps:

[0077] 1. Intermediate synthesis

[0078]

[0079] 2. Synthesis of compound M-n

[0080]

[0081] 3. Synthesis of compound N-n

[0082] 3.1 When L is a linking bond:

[0083]

[0084] 3.2 When L is an arylene or heteroarylene:

[0085]

[0086] Wherein, the definitions of R X1 , R X2 , T 1 -T 2 are the same as those defined above, and the definition of L is the same as that of L 1 -L 15 . Bpin is a pinacol boranyl group.

[0087] The beneficial effects of the present invention:

[0088] The organic electroluminescent compound provided by the present invention is based on the structure of Formula 1. The parent nucleus increases the structural stability, making the planar property of the parent nucleus structure better, which is beneficial to improving the lifespan of the organic electroluminescent device; the structure of Formula 1 combined with different substituents can make the compound as a whole exhibit relatively high electron transport performance or hole transport performance; the HOMO and LUMO energy levels of the organic electroluminescent compound have a relatively high degree of matching with adjacent energy levels, making the carrier mobility of the organic electroluminescent compound relatively balanced, and further making the organic electroluminescent device containing the organic electroluminescent compound have a lower driving voltage, higher luminous efficiency and longer lifespan;

[0089] Furthermore, the organic electroluminescent compound provided by the present invention is based on the structure of Formula 1, and further limits that the substituent group is selected from a specific group Formula a. The mutual cooperation of Formula 1 and Formula a can endow the organic electroluminescent compound with good electron transport ability, so that it can be used in the electron transport layer. Moreover, the organic electroluminescent compound can cooperate with the light-emitting layer, making the organic electroluminescent device containing the organic electroluminescent compound have a lower driving voltage, higher luminous efficiency and longer lifespan;

[0090] Furthermore, the organic electroluminescent compound provided by the present invention is based on the structure of Formula 1, and further limits that the substituent group is selected from a specific group Formula b. The mutual cooperation of Formula 1 and Formula b can endow the organic electroluminescent compound with good hole transport ability, so that it can be used in the hole transport layer. Moreover, the organic electroluminescent compound can cooperate with another compound with electron transport performance to form a multi-host material, making the organic electroluminescent device containing the organic electroluminescent compound have a lower driving voltage, higher luminous efficiency and longer lifespan;

[0091] Furthermore, the present invention provides an organic electroluminescent material, which includes an organic electroluminescent compound based on the structure of Formula 1 and further limited that the substituent group is selected from a specific group Formula a, and an organic electroluminescent compound based on the structure of Formula 1 and further limited that the substituent group is selected from a specific group Formula b. The two compounds synergistically act on each other in the light-emitting layer, effectively reducing the driving voltage of the device, improving the current working efficiency and prolonging the lifespan of the device. Description of the Drawings

[0092] In order to more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the following will briefly introduce the drawings required for use in the description of the specific embodiments or the prior art. Obviously, the drawings in the following description are some embodiments of the present invention. For those of ordinary skill in the art, other drawings can be obtained based on these drawings without creative efforts.

[0093] Figure 1This is the structural diagram of the organic electroluminescent device in the device embodiment of the present invention;

[0094] 1 - Substrate; 2 - Anode; 3 - Hole injection layer; 4 - Hole transport layer; 5 - Light-emitting layer; 6 - Electron transport layer; 7 - Electron injection layer; 8 - Cathode. Detailed implementation manners

[0095] The following embodiments are provided to better further understand the present invention, which are not limited to the described optimal implementation manners, and do not limit the content and protection scope of the present invention. Any product identical or similar to the present invention obtained by anyone under the inspiration of the present invention or by combining the features of the present invention with those of other existing technologies falls within the protection scope of the present invention.

[0096] For those not specifying specific experimental steps or conditions in the embodiments, the operations or conditions of the conventional experimental steps described in the literature in this field can be followed. For the reagents or instruments not specifying the manufacturers, they are all conventional reagent products that can be obtained through commercial purchase.

[0097] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0098] The term "multiple organic electroluminescent materials" in the present disclosure means one or more combinations of organic electroluminescent materials containing at least two compounds, and the materials can be included in any layer constituting the organic electroluminescent device. It can mean both the materials before being included in the organic electroluminescent device (e.g., before vapor deposition) and the materials after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the multiple organic electroluminescent materials can be a combination of at least two compounds, and the materials can be included in at least one of the following: hole injection layer, hole transport layer, hole auxiliary layer, light-emitting auxiliary layer, electron blocking layer, light-emitting layer, electron buffer layer, hole blocking layer, electron transport layer, and electron injection layer. The at least two compounds can be included in the same layer or different layers, and can be mixed-evaporated or co-evaporated, or can be evaporated individually.

[0099] Synthesis of intermediates:

[0100] Synthesis of intermediate M1-A

[0101]

[0102] Synthesis of Intermediate M1-A-1:

[0103] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, successively add Intermediate M1-A-a (1 mmol), M1-A-b (0.9 mmol), 1-bromo-9H-carbazole, potassium carbonate (2.5 mmol), and N,N-dimethylformamide (10 mL). Heat the mixture to 130 °C and react for 5 hours. After the reaction is completed, cool the mixture to room temperature, quench it with deionized water, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain Intermediate M1-A-1 (yield 80%).

[0104] Synthesis of Intermediate M1-A-2:

[0105] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, successively add Intermediate M1-A-1 (1 mmol), Pd(PPh3)2Cl2 (0.02 mmol), sodium acetate (2.5 mmol), and DMF (10 mL). Heat the mixture to 130 °C and react for 5 hours. After the reaction is completed, cool the mixture to room temperature, quench it with deionized water, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain Intermediate M1-A-2 (yield 56%).

[0106] Synthesis of Intermediate M1-A:

[0107] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, successively add Intermediate M1-A-2 (1 mmol), bis(pinacolato)diboron (1.1 mmol), 1,4-dioxane (10 mL), Pd(dppf)Cl2 (0.03 mmol), and potassium acetate (2.5 mmol). Heat the mixture to 100 °C and react for 5 hours. After the reaction is completed, cool the mixture to room temperature, quench it with deionized water, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain Intermediate M1-A (yield 83%).

[0108] The preparations of the following Intermediates M2-A-2 to M8-A-2 and M2-A to M8-A are the same as the steps of Intermediate M1-A-2 and M1-A respectively, except that substances with chlorine substitution at different sites from M1-A-a are used as reaction raw materials. The specific structures of Intermediates M2-A-2 to M8-A-2 and M2-A to M8-A are as follows:

[0109]

[0110] Synthesis of Intermediate M9-A'

[0111]

[0112] Synthesis of Intermediate M9-A'-a: Take a 100 mL three-necked round-bottom flask and place a magnetic stir bar in it. Under nitrogen protection, sequentially add Intermediate M9-A'-a-1 (1 mmol), tetrahydrofuran (10 mmol), and cool the temperature to -78 °C. At this temperature, slowly add dropwise LDA (1.2 mmol). After the addition is complete, slowly warm up to room temperature and react for 1 hour. Then cool the temperature to -78 °C again. At this temperature, slowly add dropwise trimethyl borate (1.2 mmol), slowly warm up to room temperature, and react for 2 hours. After the reaction is completed, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and purify the crude product by recrystallization with ethanol to obtain Intermediate M9-A'-a (yield 52%).

[0113] Synthesis of Intermediate M9-A'-1: Take a 100 mL three-necked round-bottom flask and place a magnetic stir bar and a reflux condenser in it. Under nitrogen protection, sequentially add Intermediate M9-A'-a (1 mmol), M9-A'-b (1.2 mmol), i.e., 1-bromo-2-chloro-9H-carbazole, cesium carbonate (2.5 mmol), and DMF (10 mL). Heat up to 130 °C and react for 5 hours. After the reaction is completed, cool down to room temperature, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain Intermediate M9-A'-1 (yield 59%).

[0114] Synthesis of Intermediate M9-A'-2: Take a 100 mL three-necked round-bottom flask and place a magnetic stir bar and a reflux condenser in it. Under nitrogen protection, sequentially add Intermediate M9-A'-1 (1 mmol), potassium carbonate (2.5 mmol), and DMF (10 mL). Heat up to 90 °C and react for 5 hours. After the reaction is completed, cool down to room temperature, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain Intermediate M9-A'-2 (yield 48%).

[0115] Synthesis of Intermediate M9-A': Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect a reflux tube. Under nitrogen protection, sequentially add Intermediate M9-A'-2 (1 mmol), bis(pinacolato)diboron (1.1 mmol), 1,4-dioxane (10 mL), Pd(dppf)Cl2 (0.03 mmol), potassium acetate (2.5 mmol). Heat to 100 °C and react for 5 hours. After the reaction is completed, cool to room temperature, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain Intermediate M9-A' (yield 76%).

[0116] The preparations of the following intermediates M10-A'-2 to M10-A'-2 and M10-A' to M15-A' are the same as the steps of Intermediate M9-A'-2 and M9-A' respectively, except that substances with chlorine substitution at different sites from M9-A'-b are used as reaction raw materials. The specific structures of Intermediates M10-A'-2 to M10-A'-2 and M10-A' to M15-A' are as follows:

[0117]

[0118]

[0119] Example 1

[0120] This example provides an organic electroluminescent compound M-1. The preparation method of the organic electroluminescent compound M-1 specifically includes the following steps:

[0121]

[0122] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar and connect a reflux tube. Under nitrogen protection, sequentially add Intermediate M1-A (1 mmol), M1-B (0.9 mmol), namely 2-chloro-4,6-diphenyl-1,3,5-triazine, Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is completed, cool to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain Compound M-1 (yield 49%).

[0123] Elemental analysis: C 41 H 24Theoretical values of N4: C, 85.99; H, 4.22; N, 9.78; Measured values: C, 85.87; H, 4.43; N, 9.70; HRMS(ESI) m / z [M+H]+: Theoretical value: 572.20; Measured value: 573.45.

[0124] Example 2

[0125] This example provides an organic electroluminescent compound M-9. The preparation method of the organic electroluminescent compound M-9 specifically includes the following steps:

[0126]

[0127] Synthesis of compound M-9: Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. Under nitrogen protection, successively add intermediate M9-A' (1 mmol), M1-B (0.9 mmol), that is, 2-chloro-4,6-diphenyl-1,3,5-triazine, Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 90 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, filter by suction, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain compound M-9 (yield 51%).

[0128] Elemental analysis: C 41 H 24 Theoretical values of N4: C, 85.99; H, 4.22; N, 9.78; Measured values: C, 85.87; H, 4.43; N, 9.71; HRMS(ESI) m / z [M+H]+: Theoretical value: 572.20; Measured value: 573.45.

[0129] Example 3

[0130] This example provides an organic electroluminescent compound M-19. The preparation method of the organic electroluminescent compound M-19 is similar to that of the organic electroluminescent compound M-1 in Example 1, except that M4-A is used instead of M1-A and M19-B is used instead of M1-B to obtain compound M-19 (yield 47%).

[0131]

[0132] Elemental analysis: C 45 H 26Theoretical values of N4: C, 86.79; H, 4.21; N, 9.00; Measured values: C, 86.87; H, 4.54; N, 8.59; HRMS(ESI) m / z [M+H]+: Theoretical value: 622.22; Measured value: 623.65.

[0133] Example 4

[0134] This example provides an organic electroluminescent compound M-42. The preparation method of the organic electroluminescent compound M-42 is similar to that of the organic electroluminescent compound M-1 in Example 1, except that M7-A is used to replace M1-A and M42-B is used to replace M1-B, to obtain compound M-42 (yield 57%).

[0135]

[0136] Elemental analysis: C 47 H 26 Theoretical values of N4O: C, 85.18; H, 3.95; N, 8.45; O, 2.41; Measured values: C, 85.21; H, 3.97; N, 8.40; HRMS(ESI) m / z [M+H]+: Theoretical value: 662.21; Measured value: 663.35.

[0137] Example 5

[0138] This example provides an organic electroluminescent compound M-47. The preparation method of the organic electroluminescent compound M-47 is similar to that of the organic electroluminescent compound M-1 in Example 1, except that M47-B is used to replace M1-B, to obtain compound M-47 (yield 68%).

[0139]

[0140] Elemental analysis: C 51 H 30 Theoretical values of N4: C, 87.66; H, 4.33; N, 8.02; Measured values: C, 87.69; H, 4.33; N, 7.98; HRMS(ESI) m / z [M+H]+: Theoretical value: 698.25; Measured value: 699.37.

[0141] Example 6

[0142] This example provides an organic electroluminescent compound M-60. The preparation method of the organic electroluminescent compound M-60 is similar to that of the organic electroluminescent compound M-1 in Example 1, except that M4-A is used to replace M1-A and M60-B is used to replace M1-B, to obtain compound M-60 (yield 57%).

[0143]

[0144] Elemental analysis: C 51 H 28 For N4O, theoretical values: C, 85.94; H, 3.96; N, 7.86; O, 2.24; measured values: C, 85.97; H, 3.87; N, 7.92; HRMS(ESI) m / z [M+H]+: theoretical value: 712.23; measured value: 713.35.

[0145] Example 7

[0146] This example provides an organic electroluminescent compound M-69. The preparation method of the organic electroluminescent compound M-69 is similar to that of the organic electroluminescent compound M-1 in Example 1, except that M9-A' is used to replace M1-A and M69-B is used to replace M1-B, to obtain compound M-69 (yield 69%).

[0147]

[0148] Elemental analysis: C 46 H 27 For N5, theoretical values: C, 85.03; H, 4.19; N, 10.78; measured values: C, 85.07; H, 4.22; N, 10.72; HRMS(ESI) m / z [M+H]+: theoretical value: 649.23; measured value: 650.26.

[0149] Example 8

[0150] This example provides an organic electroluminescent compound M-81. The preparation method of the organic electroluminescent compound M-81 is similar to that of the organic electroluminescent compound M-1 in Example 1, except that M4-A is used to replace M1-A and M81-B is used to replace M1-B, to obtain compound M-81 (yield 62%).

[0151]

[0152] Elemental analysis: C 47 H 28 For N4, theoretical values: C, 87.01; H, 4.35; N, 8.64; measured values: C, 87.23; H, 4.52; N, 8.22; HRMS(ESI) m / z [M+H]+: theoretical value: 648.23; measured value: 649.62.

[0153] Example 9

[0154] This embodiment provides an organic electroluminescent compound M-84. The preparation method of the organic electroluminescent compound M-84 is similar to that of the organic electroluminescent compound M-1 in Example 1, except that M4-A is used to replace M1-A and M84-B is used to replace M1-B, to obtain compound M-84 (yield 58%).

[0155]

[0156] Elemental analysis: C 51 H 30 For C44H28N4, theoretical values: C, 87.66; H, 4.33; N, 8.02; measured values: C, 87.82; H, 4.56; N, 7.62; HRMS(ESI) m / z [M+H]+: theoretical value: 698.25; measured value: 699.36.

[0157] Example 10

[0158] This embodiment provides an organic electroluminescent compound M-93. The preparation method of the organic electroluminescent compound M-93 is similar to that of the organic electroluminescent compound M-1 in Example 1, except that M4-A is used to replace M1-A and M93-B is used to replace M1-B, to obtain compound M-93 (yield 54%).

[0159]

[0160] Elemental analysis: C 53 H 30 For C46H28N4O, theoretical values: C, 86.16; H, 4.09; N, 7.58; O, 2.17; measured values: C, 86.16; H, 4.09; N, 7.58; HRMS(ESI) m / z [M+H]+: theoretical value: 738.24; measured value: 739.19.

[0161] Example 11

[0162] This embodiment provides an organic electroluminescent compound N-4. The preparation method of the organic electroluminescent compound N-4 specifically includes the following steps:

[0163]

[0164] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. Under nitrogen protection, sequentially add raw material M12-A'-2 (1 mmol), raw material N4-B (1.1 mmol), namely N-phenyldibenz[b,d]furan-1-amine, tris(dibenzylideneacetone)palladium(0) (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 120 °C and react for 10 hours. After the reaction is completed, cool it to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain compound N-4 (yield 64%).

[0165] Elemental analysis: C 44 H 26 Theoretical values for C, H, N2O: C, 88.27; H, 4.38; N, 4.68; O, 2.67; Measured values: C, 88.20; H, 4.53; N, 4.56; HRMS(ESI) m / z [M+H]+: Theoretical value: 598.20; Measured value: 599.18.

[0166] Example 12

[0167] This example provides an organic electroluminescent compound N-25. The preparation method of the organic electroluminescent compound N-25 specifically includes the following steps:

[0168]

[0169] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. Under nitrogen protection, sequentially add raw material M9-A'-2 (1 mmol), raw material N25-B (1.1 mmol), N-phenyl-4-biphenylamine, tris(dibenzylideneacetone)palladium(0) (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 120 °C and react for 10 hours. After the reaction is completed, cool it to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain compound N-25 (yield 66%).

[0170] Elemental analysis: C 44 H 28 Theoretical values for C, H, N2: C, 90.38; H, 4.83; N, 4.79; Measured values: C, 90.30; H, 4.93; N, 4.76; HRMS(ESI) m / z [M+H]+: Theoretical value: 584.23; Measured value: 585.20.

[0171] Example 13

[0172] This embodiment provides an organic electroluminescent compound N-47. The preparation method of the organic electroluminescent compound N-47 specifically includes the following steps:

[0173]

[0174] Take a 100-milliliter three-necked round-bottom flask, place a magnetic stir bar in it, and connect it to a reflux condenser. Under nitrogen protection, sequentially add raw material M15-A'-2 (1 mmol), raw material N47-B (1.1 mmol), that is, N-phenyldibenzo[b,d]thiophen-4-amine, tris(dibenzylideneacetone)palladium(0) (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 120 °C and react for 12 hours. After the reaction is completed, cool the mixture to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain compound N-47 (yield 69%).

[0175] Elemental analysis: C 44 H 26 Theoretical values for C, H, N2S: C, 85.97; H, 4.26; N, 4.56; S, 5.21; Measured values: C, 86.02; H, 4.33; N, 4.46; S, 5.14; HRMS(ESI) m / z [M+H]+: Theoretical value: 614.18; Measured value: 615.20.

[0176] Example 14

[0177] This embodiment provides an organic electroluminescent compound N-80. The preparation method of the organic electroluminescent compound N-80 specifically includes the following steps:

[0178]

[0179] Take a 100-milliliter three-necked round-bottom flask, place a magnetic stir bar in it, and connect it to a reflux condenser. Under nitrogen protection, sequentially add raw material M10-A'-2 (1 mmol), raw material N80-B (1.1 mmol), 4-(2-naphthyl)-N-phenylaniline, tris(dibenzylideneacetone)palladium(0) (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 120 °C and react for 14 hours. After the reaction is completed, cool the mixture to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain compound N-80 (yield 63%).

[0180] Elemental analysis: C 48 H 30Theoretical values of N2: C, 90.82; H, 4.76; N, 4.41; Measured values: C, 90.85; H, 4.79; N, 4.36; HRMS(ESI) m / z [M+H]+: Theoretical value: 634.24; Measured value: 635.20.

[0181] Example 15

[0182] This example provides an organic electroluminescent compound N-118. The preparation method of the organic electroluminescent compound N-118 specifically includes the following steps:

[0183]

[0184] Take a 100 mL three-necked round-bottom flask, place a stir bar in it, and connect it to a reflux condenser. Under nitrogen protection, sequentially add raw material N4-A-2 (1 mmol), raw material N118-B (1.1 mmol), namely N-phenylnaphtho[2,1-b]benzofuran-1-amine, tris(dibenzylideneacetone)palladium(0) (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 120 °C and react for 12 hours. After the reaction is completed, cool it to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain compound N-118 (yield 65%).

[0185] Elemental analysis: C 48 H 28 Theoretical values of N2O: C, 88.87; H, 4.35; N, 4.32; O, 2.47; Measured values: C, 88.82; H, 4.39; N, 4.32; HRMS(ESI) m / z [M+H]+: Theoretical value: 648.22; Measured value: 649.19.

[0186] Example 16

[0187] This example provides an organic electroluminescent compound N-189. The preparation method of the organic electroluminescent compound N-189 specifically includes the following steps:

[0188]

[0189] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser on top. Under nitrogen protection, sequentially add raw material M5-A-2 (1 mmol), raw material N189-B (1.1 mmol), namely N-phenylnaphtho[1,2-b]benzofuran-9-amine, tris(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 120 °C and react for 10 hours. After the reaction is completed, cool it to room temperature, perform suction filtration, wash the filter cake twice with deionized water and twice with ethanol. The obtained crude product is recrystallized and purified twice with o-dichlorobenzene to obtain compound N-189 (yield 60%).

[0190] Elemental analysis: C 48 H 28 Theoretical values for C, H, N2O: C, 88.87; H, 4.35; N, 4.32; O, 2.47; Measured values: C, 88.84; H, 4.43; N, 4.26; HRMS(ESI) m / z [M+H]+: Theoretical value: 648.22; Measured value: 649.20.

[0191] Device examples and comparative examples

[0192] Some of the materials for manufacturing the organic light-emitting devices in the device examples and comparative examples are as follows:

[0193]

[0194] The organic light-emitting devices in the device examples and comparative examples have a similar structure (as Figure 1 shown), including an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8 sequentially stacked on a substrate 1. The device structure is: substrate + anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / light-emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0195] The preparation of the organic light-emitting devices in the device examples and comparative examples includes the following steps:

[0196] 1) Substrate cleaning:

[0197] Ultrasonically treat a glass substrate coated with transparent ITO in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol-based solvent ≤ 10 wt%, triethanolamine ≤ 1 wt%), then rinse it in deionized water, ultrasonically degrease it in a mixed solvent of acetone and ethanol (volume ratio of acetone to ethanol is 1:1), bake it in a clean environment until all moisture is removed, and then clean it with ultraviolet light and ozone.

[0198] 2) Preparation of the organic layer:

[0199] Transfer the ITO transparent substrate to the evaporation equipment and evacuate it to 1×10 -6 to 2×10 -4 Pa, and then evaporate 10 nm of hole injection layer (HIL) / 80 nm of hole transport layer (HTL) / 30 nm of emitting layer (EML) / 30 nm of electron transport layer (ETL) / 1 nm of electron injection layer (EIL) / 90 nm thick cathode (Al) on the anode in sequence.

[0200] Among them:

[0201] The material of the hole injection layer (HIL) is a mixture of HATCN and HT, and the mass ratio of HATCN to HT is 3:97; the evaporation is carried out by co-evaporation;

[0202] The material of the hole transport layer (HTL) is shown in Table 3;

[0203] The specific material of the emitting layer (EML) is a mixture of CBP and (piq)2Ir(acac), and the mass ratio of CBP to (piq)2Ir(acac) is 95:5, and the evaporation is carried out by co-evaporation;

[0204] The specific material of the electron transport layer (ETL) is shown in Table 3, and the evaporation is carried out by co-evaporation;

[0205] The material of the electron injection layer (EIL) is LiQ;

[0206] The thickness and material of each layer are shown in Table 3.

[0207] The specific materials and thicknesses of the device examples and comparative examples are shown in Table 3 below:

[0208] Table 3

[0209]

[0210]

[0211]

[0212] The examples in Table 3 refer to device examples, and the comparative examples refer to device comparative examples.

[0213] Test examples

[0214] Test the organic light-emitting devices obtained from device examples 1-16 and comparative examples 1-3 in the device examples.

[0215] Instrument: The characteristics of the device such as current, voltage, brightness, and emission spectrum were synchronously measured using a PR 650 spectral scanning luminance meter and a Keithley K2400 digital source meter system.

[0216] Test conditions: For the optoelectronic characteristics test, the current density was 10 mA / cm 2 .

[0217] Lifetime test: The current density was 50 mA / cm 2 , and the time (in hours) was recorded when the brightness of the device dropped to 95% of the original brightness.

[0218] The test results of the device performance are shown in Table 4:

[0219] Table 4

[0220]

[0221]

[0222] The examples in Table 4 refer to device examples, and the comparative examples refer to device comparative examples.

[0223] As can be seen from Table 4:

[0224] The organic materials provided by the embodiments of the present invention can match the corresponding light-emitting layer, and have a certain electron transport ability. At the same time, during the preparation of the device, the evaporation temperature is also correspondingly reduced, which is beneficial to the preparation of the device;

[0225] The organic materials provided by the embodiments of the present invention can match the corresponding light-emitting layer and have a certain hole transport ability;

[0226] As a light-emitting material, this material combines a compound M with electron transport performance and an N with hole transport performance, and interacts synergistically in the light-emitting layer, effectively reducing the driving voltage of the device, improving the current working efficiency, and extending the device lifetime, achieving remarkable progress in the application of the host material.

[0227] In summary, the present invention provides a new organic electroluminescent material with HOMO, LUMO, and ET1 values that are close to each other, which can reduce the driving voltage of the device, improve the light-emitting efficiency of the device, and extend the service life of the device.

[0228] Obviously, the above embodiments are only examples for clear illustration and are not limitations on the implementation manners. For those of ordinary skill in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to enumerate all the implementation manners here. And the obvious changes or modifications derived therefrom are still within the protection scope of the present invention.

Claims

1. An organic electroluminescent compound, characterized in that, It has the structure shown below: R 1 is - L 1 Ar 1 、R 2 is - L 2 Ar 2 、R 3 is - L 3 Ar 3 、R 4 is - L 4 Ar 4 、R 5 is - L 5 Ar 5 、R 6 is - L 6 Ar 6 、R 7 is - L 7 Ar 7 、R 8 is - L 8 Ar 8 、R 9 is - L 10 Ar 9 、R 10 is - L 10 Ar 10 、R 11 is - L 11 Ar 11 、R 12 is - L 12 Ar 12 、R 13 is - L 13 Ar 13 、R 14 is - L 14 Ar 14 ,R 15 is - L 15 Ar 15 ; L 1 -L 15 Each independently selected from a linking group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group; Ar 1 -Ar 15 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted mono- or di-C6-C30 arylamino, substituted or unsubstituted mono- or di-C6-C30 heteroarylamino; The heteroatoms in the substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted mono- or di-C6-C30 heteroarylamino are selected from N, O or S; The substituents in the substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C60 aryl, substituted C3-C60 heteroaryl, substituted mono- or di-C6-C30 arylamino, substituted mono- or di-C6-C30 heteroarylamino are each independently selected from deuterium, halogen, cyano, unsubstituted C3-C30 heteroaryl, C3-C30 heteroaryl substituted with C1-C6 alkyl or C6-C30 aryl, unsubstituted C6-C30 aryl, C6-C30 aryl substituted with cyano or C3-C30 heteroaryl or mono- or di-C6-C30 arylamino, mono- or di-C6-C30 arylamino, C1-C30 alkyl, or a combination of one or at least two thereof.

2. The organic electroluminescent compound according to claim 1, characterized in that, The said L 1 -L 15 Each independently selected from a linking group, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C3-C20 heteroarylene group; Preferably, the L 1 -L 15 are each independently selected from a linking bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted naphthylene; Among them, the substituents in the substituted phenylene, substituted biphenylene, substituted terphenylene, substituted dibenzofuranyl, substituted naphthylene are each independently selected from a combination of one or at least two of C1-C6 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, C3-C25 heteroaryl; Preferably, the L 1 -L 15 are each independently selected from a linking bond, a phenylene group, a naphthylene group, and a dibenzofuranyl group.

3. The organic electroluminescent compound according to claim 1 or 2, characterized in that, Ar 1 -Ar 15 At least one is selected from the group represented by formula a: R X1 、R X2 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; Among them, the substituents in the substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C6-C30 aryl, substituted C3-C30 heteroaryl are selected from deuterium, halogen, cyano, unsubstituted C3-C30 heteroaryl, C3-C30 heteroaryl substituted with C1-C6 alkyl or C6-C30 aryl, unsubstituted C6-C30 aryl, C6-C30 aryl substituted with cyano or C3-C30 heteroaryl or mono- or di-C6-C30 arylamino, mono- or di-C6-C30 arylamino, C1-C30 alkyl, or a combination of one or at least two thereof.

4. The organic electroluminescent compound according to claims 1-3, characterized in that R X1 、R X2 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl; Among them, the substituents in the substituted C1-C20 alkyl, substituted C3-C20 cycloalkyl, substituted C6-C20 aryl, substituted C3-C20 heteroaryl are selected from deuterium, halogen, cyano, unsubstituted C3-C30 heteroaryl, C3-C30 heteroaryl substituted with C1-C6 alkyl or C6-C30 aryl, unsubstituted C6-C30 aryl, C6-C30 aryl substituted with cyano or C3-C30 heteroaryl or mono- or di-C6-C30 arylamino, mono- or di-C6-C30 arylamino, C1-C30 alkyl, or a combination of one or at least two thereof; Preferably, the R X1 , R X2 each independently selected from hydrogen, deuterium, halogen, a substituted or unsubstituted B group; The B group is selected from one of the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, phenylnaphthyl, naphthylphenyl, pyridyl, bipyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, carbazolylphenyl, phenylcarbazolyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranphenyl, dibenzothiophenphenyl, dimethylfluorenylphenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl; Preferably, the R X1 and R X2 are each independently selected from hydrogen, deuterium, halogen, phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, pyridyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranphenyl.

5. The organic electroluminescent compound according to any one of claims 1-4, characterized in that, Ar 1 -Ar 15 One of them is selected from formula a, and the others are each independently selected from hydrogen and deuterium.

6. The organic electroluminescent compound according to any one of claims 1-5, characterized in that, Ar 1 -Ar 15 At least one is selected from the groups represented by the following formula b: T 1 -T 2 Each is independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted mono- or di-C6-C30 arylamino, and substituted or unsubstituted mono- or di-C6-C30 heteroarylamino; Among them, the substituents of the substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, substituted mono- or di-C6-C30 arylamino group, and substituted mono- or di-C6-C30 heteroarylamino group are selected from deuterium, halogen, cyano, unsubstituted C3-C30 heteroaryl group, C3-C30 heteroaryl group substituted by C1-C6 alkyl or C6-C30 aryl group, unsubstituted C6-C30 aryl group, C6-C30 aryl group substituted by cyano or C3-C30 heteroaryl group or mono- or di-C6-C30 arylamino group, mono- or di-C6-C30 arylamino group, and C1-C30 alkyl group, or a combination of at least two of them; Preferably, T 1 -T 2 each independently selected from substituted or unsubstituted C groups, and the C groups are selected from one of the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, binaphthyl, triphenylene, phenylnaphthyl, naphthylphenyl, pyridyl, pyridylphenyl, phenylpyridyl, bipyridyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzofuranylphenyl, dibenzothiophenylphenyl, carbazolyl, benzocarbazolyl, phenylcarbazolyl, dimethylfluorenyl, benzodimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dimethylfluorenylphenyl; Among them, the substituents of the substituted C group are selected from deuterium, halogen, cyano, unsubstituted C3-C30 heteroaryl group, C3-C30 heteroaryl group substituted by C1-C6 alkyl or C6-C30 aryl group, unsubstituted C6-C30 aryl group, C6-C30 aryl group substituted by cyano or C3-C30 heteroaryl group or mono- or di-C6-C30 arylamino group, mono- or di-C6-C30 arylamino group, and C1-C30 alkyl group, or a combination of at least two of them; Preferably, T 1 -T 2 each independently selected from phenyl, biphenyl, terphenyl, phenanthryl, phenylnaphthyl, naphthylphenyl, pyridyl, pyridylphenyl, phenylpyridyl, bipyridyl, dibenzofuranyl, benzonaphthofuranyl, carbazolyl, benzocarbazolyl, dimethylfluorenyl, benzodimethylfluorenyl, diphenylfluorenyl.

7. The organic electroluminescent compound according to any one of claims 1-6, characterized in that, Ar 1 -Ar 13 One of them is selected from Formula a, and the others are each independently selected from hydrogen and deuterium.

8. The organic electroluminescent compound according to any one of claims 1-7, characterized in that, The organic electroluminescent compound is selected from one of M-1 to M-94:

9. The organic electroluminescent compound according to any one of claims 1-7, characterized in that, The organic electroluminescent compound is selected from one of N-1 to N-200:

10. An organic electroluminescent material, characterized in that, Comprising the organic electroluminescent compound according to any one of claims 1-9.

11. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a cathode, an anode, and an organic layer located between the cathode and the anode, and the organic layer comprises the organic electroluminescent compound according to any one of claims 1-9 or the organic electroluminescent material according to claim 10.

12. The organic electroluminescent device according to claim 11, wherein The organic layer includes an electron transport layer, and the electron transport layer comprises the organic electroluminescent compound according to any one of claims 1-5 and claim 8.

13. The organic electroluminescent device according to claim 11, wherein The organic layer includes a hole transport layer, and the hole transport layer comprises the organic electroluminescent compound according to any one of claims 1, 2, 6, 7, and 9.

14. The organic electroluminescent device according to claim 11, wherein The organic layer includes a light-emitting layer, and the light-emitting layer includes a host material, and the host material includes at least one organic electroluminescent compound according to any one of claims 1-9; Preferably, the host material includes a first host material and a first host material; wherein, the first host material is selected from the organic electroluminescent compound according to any one of claims 1-5 and claim 8; the second host material is selected from the organic electroluminescent compound according to any one of claims 1, 2, 6, 7, and 9; Preferably, the mass ratio of the first host material to the second host material is 1:9-9:1; Preferably, the mass ratio of the first main material to the second main material is 2:8 - 8:2; More preferably, the mass ratio of the first main material to the second main material is 3:7 - 7:3; Even more preferably, the mass ratio of the first main material to the second main material is 4:6 - 6:

4.

15. Use of the organic electroluminescent device according to claim 11 in an optical fiber device, a lighting device, an electrophotographic photoreceptor device, a photoelectric converter, an organic solar cell, a switching element device, an organic light-emitting field effect transistor, an image sensor or a dye laser.

Images