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 applications. 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 aromatic diamine small molecules and aluminum complexes 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 electricity 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 may 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 doping material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials for the organic layer are classified by their functions into hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. 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 materials are classified into blue-light-emitting materials, green-light-emitting materials, red-light-emitting materials, and additionally yellow-light-emitting materials or orange-light-emitting materials according to the color of the light emitted. In addition, the light-emitting materials can also be classified into host materials and doping materials according to their functions.

[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 life of organic electroluminescent devices containing such organic electroluminescent materials, severely limiting the application of organic electroluminescent devices. Summary of the Invention

[0006] The 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 life of organic electroluminescent devices containing such organic electroluminescent materials, and further 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 can be interrupted by short non-aromatic units, and can include a spiro structure. Aryl includes, but is not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, fluorenyl, spirobifluorenyl, etc. Arylene includes, but is not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, spirobifluorenylene, etc.

[0012] In the present invention, the 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. The 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.; the 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, the hydrogen atom includes protium, deuterium and tritium.

[0015] In the present invention, when the number of carbon atoms in a group is defined within a range, the number of carbon atoms is any integer within the defined range. For example, C6-C30 aryl means that the number of carbon atoms in 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 ;

[0021] L 1 -L 13 Each is independently selected from a linking bond, a substituted or unsubstituted C6 - C30 arylene group, a substituted or unsubstituted C3 - C30 heteroarylene group;

[0022] Ar 1 -Ar 13 Each is independently selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C6 - C60 aryl group, a substituted or unsubstituted C3 - C60 heteroaryl group, a substituted or unsubstituted mono - or di - C6 - C30 arylamino group, a substituted or unsubstituted mono - or di - C6 - C30 heteroarylamino group;

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

[0024] The substituents in the substituted C6-C30 arylene group, the substituted C3-C30 heteroarylene group, the substituted C6-C60 aryl group, the substituted C3-C60 heteroaryl group, the substituted mono- or di-C6-C30 arylamino group, the substituted mono- or di-C6-C30 heteroarylamino group are each independently 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, C1-C30 alkyl group, or a combination of one or at least two of them.

[0025] Preferably, the L 1 -L 13 are each independently selected from a linking bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C3-C20 heteroarylene group;

[0026] Preferably, the L 1 -L 13 are each independently selected from a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group;

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

[0028] Preferably, the L 1 -L 13 are each independently selected from a linking bond, a phenylene group, a naphthylene group.

[0029] Preferably, at least one of Ar 1 -Ar 13 is selected from the group shown in Formula a:

[0030]

[0031] X 1 is selected from N or CR X1 and X 2 is selected from N or CR X2 and X 3 is selected from N or CR X3 and X4 Selected from N or CR X4 , X 5 Selected from N or CR X5 ;

[0032] R X1 -R X5 Each is 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, R X1 -R X5 Each independently exists, or two adjacent ones are connected to form ring A, and the ring A is a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C30 heteroaromatic ring;

[0033] The said L 1 -L 13 Each is independently selected from a linking bond, substituted or unsubstituted C6-C20 arylene, substituted or unsubstituted C3-C20 heteroarylene;

[0034] Wherein, the substituents in the substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C30 aromatic ring, substituted C3-C30 heteroaromatic ring, substituted C6-C20 arylene, and substituted C3-C20 heteroarylene 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 one or at least two of them.

[0035] Preferably, in the said X 1 -X 5 Among them,

[0036] X 1 is N, X 2 is N, X 3 is CR X3 , X 4 is CR X4 , and X 5 is CR X5 ; R X3 , R X4 , R X5 exist independently or wherein R X3 is connected to R X5 to form ring A; or,

[0037] X 1 is N, X 3 is N, X 2 is CR X2 , X 4 is CR X4 , and X 5 is CR X5 ; R X2 , R X4 , R X5 exist independently or wherein R X2 is connected to R X5 to form ring A; or,

[0038] X 1 is N, X 2 is N, X 3 is N, X 4 is CR X4 , and X 5 is CR X5 ;

[0039] wherein, the ring A is a substituted or unsubstituted C6-C20 aromatic ring and a substituted or unsubstituted C3-C20 heteroaromatic ring;

[0040] R X2 -R X5 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;

[0041] wherein, the substituents of the substituted C1-C20 alkyl, substituted C3-C20 cycloalkyl, substituted C6-C20 aryl, substituted C3-C20 heteroaryl, substituted C6-C20 aromatic ring, and substituted C3-C20 heteroaromatic ring 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, and C1-C30 alkyl, or a combination of one or at least two of them;

[0042] Preferably, the R X1 -R X5 each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted B group;

[0043] 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;

[0044] Preferably, the ring A is selected from one of benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, benzothiophene ring, benzofuran ring, indene ring;

[0045] Preferably, the R X1 -R X5 are each independently selected from hydrogen, deuterium, halogen, phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, pyridyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranphenyl.

[0046] Preferably, one of Ar 1 -Ar 13 is selected from formula a, and the others are each independently selected from hydrogen and deuterium.

[0047] Preferably, at least one of Ar 1 -Ar 13 is selected from the group shown in the following formula b:

[0048]

[0049] T 1 -T 2 are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted mono- or di-C6-C30 arylamino, substituted or unsubstituted mono- or di-C6-C30 heteroarylamino;

[0050] Among them, the substituents of the substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted mono- or di-C6-C30 arylamino, and substituted mono- or di-C6-C30 heteroarylamino 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;

[0051] 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, diarylaminophenyl, phenylbenzofuranyl;

[0052] The diarylamino group in the diarylaminophenyl is selected from: diphenylamino group, di(4-biphenylyl)amino group, N-phenyl-biphenylamine group, N-phenyl-dibenzofuranamine group;

[0053] 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;

[0054] It can be understood that the diarylaminophenyl includes diphenylaminophenyl, di(4-biphenylyl)aminophenyl, N-phenyl-biphenylaminophenyl, N-phenyl-dibenzofuranaminophenyl.

[0055] 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.

[0056] Preferably, one of Ar 1 -Ar 13 is selected from formula a, and the others are each independently selected from hydrogen and deuterium.

[0057] Preferably, the organic electroluminescent compound is selected from one of M-1 to M-290:

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] Preferably, the organic electroluminescent compound is selected from one of N-1 to N-354:

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078] The present invention also provides an organic electroluminescent material comprising the above-mentioned organic electroluminescent compound.

[0079] Preferably, the organic electroluminescent material comprises at least one of the above-mentioned compounds M1 to M290 and at least one of compounds N1 to N354.

[0080] The present invention also provides an organic electroluminescent device, which includes 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.

[0081] Preferably, the organic layer includes an electron transport layer, and the electron transport layer includes the above-mentioned organic electroluminescent compound.

[0082] Preferably, the organic layer includes a hole transport layer, and the hole transport layer includes the above-mentioned organic electroluminescent compound.

[0083] Preferably, 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 of the above-mentioned organic electroluminescent compounds;

[0084] Preferably, the host material includes 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;

[0085] Preferably, the mass ratio of the first host material to the second host material is 1:9 - 9:1;

[0086] Preferably, the mass ratio of the first host material to the second host material is 2:8 - 8:2;

[0087] More preferably, the mass ratio of the first host material to the second host material is 3:7 - 7:3;

[0088] Further preferably, the mass ratio of the first host material to the second host material is 4:6 - 6:4.

[0089] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer contains a host material, and the host material is selected from at least one of Compounds M1 to M290 and Compounds N1 to N354;

[0090] 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.

[0091] Preferably, the organic layer includes an electron buffer layer, and the electron buffer layer contains the above-mentioned organic electroluminescent material.

[0092] 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.

[0093] In the present invention, the synthesis route of the above-mentioned organic electroluminescent compound includes the following steps:

[0094] 1. Intermediate synthesis

[0095]

[0096]

[0097] 2. Synthesis of Compound M-n

[0098]

[0099] 3. Synthesis of Compound N-n 3.1 When L is a linking bond:

[0100]

[0101] 3.2 When L is an arylene or heteroarylene group:

[0102]

[0103] Wherein, X 1 -X 5 and T 1 -T 2 are defined as the same as those described above, and the definition of L is the same as that of L 1 -L 13 .

[0104] Bpin is a pinacol boranyl group.

[0105] Advantages of the present invention:

[0106] 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 planarity 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 high electron transport performance or hole transport performance; the HOMO and LUMO energy levels of the organic electroluminescent compound have a 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 low driving voltage, high luminous efficiency and long lifespan;

[0107] Furthermore, the organic electroluminescent compound provided by the present invention is based on the structure of Formula 1, and further limits that the substituents are selected from specific group Formula a. The combination 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, and the organic electroluminescent compound can cooperate with the light-emitting layer, making the organic electroluminescent device containing the organic electroluminescent compound have a low driving voltage, high luminous efficiency and long lifespan;

[0108] Furthermore, the organic electroluminescent compound provided by the present invention is based on the structure of Formula 1, and further defines 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-transporting ability, so that it can be used in the hole-transporting layer. Moreover, the organic electroluminescent compound can be combined with another compound with electron-transporting performance to form a multi-host material, enabling the organic electroluminescent device containing the organic electroluminescent compound to have a lower driving voltage, higher luminous efficiency, and longer lifespan.

[0109] Furthermore, an organic electroluminescent material provided by the present invention includes an organic electroluminescent compound based on the structure of Formula 1 and further defining 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 defining that the substituent group is selected from a specific group Formula b. The two compounds synergistically act in the light-emitting layer, effectively reducing the driving voltage of the device, improving the current operating efficiency, and extending the lifespan of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0110] 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, without creative efforts, other drawings can also be obtained based on these drawings.

[0111] Figure 1 It is a structural diagram of the organic electroluminescent device in the device embodiment of the present invention;

[0112] 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 DESCRIPTION OF THE EMBODIMENTS

[0113] The following embodiments are provided to better further understand the present invention. They are not limited to the best embodiment, and do not constitute a limitation to the content and protection scope of the present invention. Any product obtained by anyone under the inspiration of the present invention or by combining the features of the present invention with those of other prior arts and being the same or similar to the present invention falls within the protection scope of the present invention.

[0114] For those experimental steps or conditions not specified 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 specified for the manufacturer, they are all conventional reagent products that can be obtained through commercial purchase.

[0115] 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 emission 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.

[0116] 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: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds can be included in the same layer or different layers, and can be co-evaporated or co-evaporated by mixing, or can be evaporated individually.

[0117] Synthesis of intermediates:

[0118] Synthesis of intermediate M1-A

[0119]

[0120] Synthesis of intermediate M1-A-1:

[0121] Take a 100 mL three-necked round-bottom flask, place a stir bar and connect it to a reflux tube. Under nitrogen protection, successively add the raw materials, 2,5-dibromonitrobenzene (1 mmol), M1-A-a (0.9 mmol), i.e., 3-chloro-1-naphthaleneboronic acid, Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat to 60 °C and react for 5 hours. After the reaction is completed, cool to room temperature, quench with deionized aqueous solution, 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 59%).

[0122] Synthesis of intermediate M1-A-2:

[0123] Take a 100 mL three-necked round-bottom flask, add a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, sequentially add intermediate M1-A-1 (1 mmol), triphenylphosphine (3 mmol), and dichlorobenzene (10 mL). Heat the mixture to 180 °C and react for 20 hours. After the reaction is completed, cool the mixture to room temperature, quench it with deionized water solution, separate the layers, collect the organic phase, 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 58%).

[0124] Synthesis of intermediate M1-A-3:

[0125] Take a 100 mL three-necked round-bottom flask, add a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, sequentially add intermediate M1-A-2 (1 mmol), fluorobenzene (1.1 mmol), cesium carbonate (2 mmol), and N-methylpyrrolidone (10 mL). Heat the mixture to 160 °C and react for 10 hours. After the reaction is completed, cool the mixture to room temperature, quench it with deionized water solution, extract it 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-3 (yield 72%).

[0126] Synthesis of intermediate M1-A-4:

[0127] Take a 100 mL three-necked round-bottom flask, add a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, sequentially add intermediate M1-A-3 (1 mmol), cesium carbonate (2.5 mmol), Pd(PPh3)2Cl2 (0.03 mmol), and N,N-dimethylformamide (10 mL). Heat the mixture to 140 °C and react for 5 hours. After the reaction is completed, cool the mixture to room temperature, quench it with deionized water solution, extract it 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-4 (yield 82%).

[0128] Synthesis of intermediate M1-A:

[0129] 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 M1-A-4 (1 mmol), bis(boronic ester) (1.1 mmol), 1,4-dioxane (10 mL), Pd(dppf)Cl2 (0.03 mmol), potassium acetate (2.5 mmol). Heat to 110 °C and react for 5 hours. After the reaction is completed, cool to room temperature, quench with deionized water solution, 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 60%).

[0130] The preparations of intermediates M2-A-4 to M6-A-4 and M2-A to M6-A are the same as the steps of intermediates M1-A-4 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-4 to M6-A-4 and M2-A to M6-A are as follows:

[0131]

[0132] Synthesis of intermediate M7-B

[0133]

[0134] Synthesis of intermediate M7-B-1:

[0135] 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 M7-B-b (1 mmol), namely 2-bromo-5-chloronitrobenzene, 1-naphthaleneboronic acid (1.2 mmol), 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, 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 separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M7-B-1 (yield 85%).

[0136] Synthesis of intermediate M7-B-2:

[0137] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect it to a reflux condenser. Under nitrogen protection, sequentially add intermediate M7-B-1 (1 mmol), triphenylphosphine (3 mmol), and dichlorobenzene (10 mL). Heat the mixture to 180 °C and react for 20 hours. After the reaction is completed, cool the mixture to room temperature, quench it with deionized water solution, 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 M7-B-2 (yield 55%).

[0138] Synthesis of intermediate M7-B-3:

[0139] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect it to a reflux condenser. Under nitrogen protection, sequentially add intermediate M7-B-2 (1 mmol), o-bromofluorobenzene (2 mmol), cesium carbonate (2 mmol), and N-methylpyrrolidone (10 mL). Heat the mixture to 160 °C and react for 10 hours. After the reaction is completed, cool the mixture to room temperature, quench it with deionized water solution, extract it 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 M7-B-3 (yield 65%).

[0140] Synthesis of intermediate M7-B-4:

[0141] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect it to a reflux condenser. Under nitrogen protection, sequentially add intermediate M7-B-3 (1 mmol), cesium carbonate (2.5 mmol), Pd(PPh3)2Cl2 (0.03 mmol), and N,N-dimethylformamide (10 mL). Heat the mixture to 140 °C and react for 5 hours. After the reaction is completed, cool the mixture to room temperature, quench it with deionized water solution, extract it 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 M7-B-4 (yield 82%).

[0142] Synthesis of intermediate M7-B:

[0143] Take a 100 mL three-necked round-bottom flask, add a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, successively add intermediate M7-B-4 (1 mmol), bis(boronic ester) (1.1 mmol), 1,4-dioxane (10 mL), Pd(dppf)Cl2 (0.03 mmol), potassium acetate (2.5 mmol). Heat the mixture to 100 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, quench with deionized water solution, 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 M7-B (yield 65%).

[0144] The preparations of intermediates M8-B-4 to M9-B-4 and M8-A to M9-A are the same as the steps for intermediates M7-A-4 and M7-A respectively, except that substances with chlorine substitution at different sites from M7-B-b are used as reaction raw materials. The specific structures of intermediates M8-B-4 to M9-B-4 and M8-A to M9-A are as follows:

[0145]

[0146] Synthesis of intermediate M10-C

[0147]

[0148] Synthesis of intermediate M10-C-3:

[0149] Take a 100 mL three-necked round-bottom flask, add a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, successively add intermediate M10-C-2 (1 mmol), namely 7H-benzo[c]carbazole, M10-C-c (1.1 mmol), namely 1-bromo-4-chloro-2-fluorobenzene, cesium carbonate (2 mmol), N-methylpyrrolidone (10 mL). Heat the mixture to 160 °C and react for 10 hours. After the reaction is completed, cool it to room temperature, quench with deionized water solution, dry the organic phase with anhydrous magnesium sulfate, 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 M10-C-3 (yield 65%).

[0150] Synthesis of intermediate M10-C-4:

[0151] 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 intermediate M10-C-3 (1 mmol), cesium carbonate (2.5 mmol), Pd(PPh3)2Cl2 (0.03 mmol), and N-methylpyrrolidone (10 mL). Heat the mixture to 140 °C and react for 5 hours. After the reaction is completed, cool it to room temperature, quench it with deionized water solution, and extract it with ethyl acetate. Dry the organic phase with anhydrous magnesium sulfate. Remove the solvent using a rotary evaporator. Separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M10-C-4 (yield 82%).

[0152] Synthesis of intermediate M10-C:

[0153] 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 intermediate M10-C-4 (1 mmol), bis(pinacolato)diboron (1.1 mmol), N,N-dimethylformamide (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 it to room temperature, quench it with deionized water solution, extract it with ethyl acetate. Dry the organic phase with anhydrous magnesium sulfate. Remove the solvent using a rotary evaporator. Separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M10-C (yield 65%).

[0154] The preparations of the following intermediates M11-C-4 to M13-C-4 and M10-A to M13-A are the same as the steps of intermediate M10-A-4 and M10-A respectively, except that substances with chlorine substitution at different sites of M10-C-c (i.e., 1-bromo-2-fluorobenzene with chlorine substitution at different sites) are used as reaction raw materials. The specific structures of intermediates M11-C-4 to M13-C-4 and M10-A to M13-A are as follows:

[0155]

[0156] Example 1

[0157] This example provides an organic electroluminescent compound M-1. The preparation method of the organic electroluminescent compound M-1 specifically includes the following steps:

[0158]

[0159] Take a 100 mL three-necked round-bottom flask, add a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, sequentially add intermediate M1-A (1 mmol), M1-D (1.1 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 the mixture to 90 °C and react for 5 hours. After the reaction is completed, cool the reaction mixture to room temperature, filter it 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-1 (yield 55%).

[0160] Elemental analysis: C 37 H 22 For C,85.04; H,4.24; N,7.38; found: C,85.06; H,4.36; N,7.24; HRMS(ESI) m / z [M+H]+: calcd: 522.18; found: 523.17.

[0161] Example 2

[0162] This example provides an organic electroluminescent compound M-45. The preparation method of the organic electroluminescent compound M-45 specifically includes the following steps:

[0163]

[0164] Take a 100 mL three-necked round-bottom flask, add a magnetic stir bar and connect a reflux condenser. Under nitrogen protection, sequentially add intermediate M1-A (1.1 mmol), M45-D (1.0 mmol), namely 4-[1,1'-biphenyl]-4-yl-2-chloroquinazoline, Pd132 [dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium(II)] (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 the reaction mixture to room temperature, filter it 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 N-45 (yield 51%).

[0165] Elemental analysis: C 42 H 25 For C,88.24; H,4.41; N,7.35; found: C,88.20; H,4.51; N,7.29; HRMS(ESI) m / z [M+H]+: calcd: 571.20; found: 572.17.

[0166] Example 3

[0167] This embodiment provides an organic electroluminescent compound M-66. The preparation method of the organic electroluminescent compound M-66 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 tube above. Under nitrogen protection, sequentially add intermediate M2-A (1.1 mmol), M66-D (1.0 mmol), i.e., 2-chloro-4-(naphtho[2,3-b]benzofuran-2-yl)-6-phenyl-1,3,5-triazine, Pd132 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 95 °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 ortho-dichlorobenzene to obtain compound N-66 (yield 45%).

[0170] Elemental analysis: C 47 H 26 For C, H, N4O, the theoretical values are: C, 85.18; H, 3.95; N, 8.45; O, 2.41; the measured values are: C, 85.19; H, 3.95; N, 8.44; HRMS(ESI) m / z [M+H]+: the theoretical value is 662.21; the measured value is 663.25.

[0171] Example 4

[0172] This embodiment provides an organic electroluminescent compound M-127. The preparation method of the organic electroluminescent compound M-127 specifically includes the following steps:

[0173]

[0174] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux tube above. Under nitrogen protection, sequentially add intermediate M7-B (1 mmol), M127-D (1.1 mmol), i.e., 2-(4-bromophenyl)-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 ortho-dichlorobenzene to obtain compound M-127 (yield 35%).

[0175] Elemental analysis: C 43 H 26Theoretical values of N4: C, 86.26; H, 4.38; N, 9.36; Measured values: C, 86.28; H, 4.38; N, 9.34; HRMS(ESI) m / z [M+H]+: Theoretical value: 598.22; Measured value: 599.24.

[0176] Example 5

[0177] This example provides an organic electroluminescent compound M-176. The preparation method of the organic electroluminescent compound M-176 specifically includes the following steps:

[0178]

[0179] 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, add intermediate M4-A (1.1 mmol), M176-D (1.0 mmol), that is, 2-chloro-4-(naphtho[2,3-b]benzofuran-2-yl)-6-phenyl-1,3,5-triazine, Pd(PPh3)4 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat the mixture to 95 °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 N-176 (yield 45%).

[0180] Elemental analysis: C 41 H 24 Theoretical values of N4: C, 85.04; H, 4.24; N, 10.72; Measured values: C, 85.06; H, 4.24; N, 10.69; HRMS(ESI) m / z [M+H]+: Theoretical value: 572.18; Measured value: 573.19.

[0181] Example 6

[0182] This example provides an organic electroluminescent compound M-268. The preparation method of the organic electroluminescent compound M-268 specifically includes the following steps:

[0183]

[0184] 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 M10-C (1 mmol), M268-D (1.1 mmol), namely 2-(7-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine, Pd132 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL). Heat the mixture to 100 °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 ortho-dichlorobenzene to obtain compound M-268 (yield 32%).

[0185] Elemental analysis: C 47 H 28 For C 47 H 28 N4, theoretical values: C, 87.01; H, 4.35; N, 8.64; measured values: C, 87.03; H, 4.35; N, 8.62; HRMS(ESI) m / z [M+H]+: theoretical value: 648.23; measured value: 649.21.

[0186] Example 7

[0187] This example provides an organic electroluminescent compound N-1. The preparation method of the organic electroluminescent compound N-1 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 above. Under nitrogen protection, successively add diphenylamine (1.1 mmol), intermediate M1-A-4 (1 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL). Heat the mixture to 110 °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 ortho-dichlorobenzene to obtain compound N-1 (yield 65%).

[0190] Elemental analysis: C 34 H 22 For C 34 H 22 N2, theoretical values: C, 89.06; H, 4.84; N, 6.11; measured values: C, 89.00; H, 4.94; N, 6.07; HRMS(ESI) m / z [M+H]+: theoretical value: 458.18; measured value: 459.20.

[0191] Example 8

[0192] This embodiment provides an organic electroluminescent compound N-7. The preparation method of the organic electroluminescent compound N-7 specifically includes the following steps:

[0193]

[0194] 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 the raw material N-phenyldibenz[b,d]furan-1-amine (1.1 mmol), raw material A (1 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL). Heat the mixture to 110 °C and react for 5 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-7 (yield 75%).

[0195] Elemental analysis: C 40 H 24 For C, H, N2O, the theoretical values are: C, 87.57; H, 4.41; N, 5.11; the measured values are: C, 87.59; H, 4.42; N, 5.07; HRMS (ESI) m / z [M+H]+: the theoretical value is 548.19; the measured value is 549.20.

[0196] Example 9

[0197] This embodiment provides an organic electroluminescent compound N-27. The preparation method of the organic electroluminescent compound N-27 specifically includes the following steps:

[0198]

[0199] The synthesis steps of N-27 are the same as those of N-1, except that raw material N27-B is used to replace N1-B to obtain compound N-27 (yield 75%).

[0200] Elemental analysis: C 46 H 30 For C, H, N2, the theoretical values are: C, 90.46; H, 4.95; N, 4.59; the measured values are: C, 90.48; H, 4.97; N, 4.55; HRMS (ESI) m / z [M+H]+: the theoretical value is 610.24; the measured value is 611.20.

[0201] Example 10

[0202] This embodiment provides an organic electroluminescent compound N-30. The preparation method of the organic electroluminescent compound N-30 specifically includes the following steps:

[0203]

[0204] The synthesis steps of N-30 are the same as those of N-1, except that N30-B is used to replace N1-B as the raw material, and compound N-30 (yield 66%) is obtained.

[0205] Elemental analysis: C 43 H 30 Theoretical values for C, H, N2: C, 89.86; H, 5.26; N, 4.87; Measured values: C, 89.88; H, 5.27; N, 4.84; HRMS(ESI) m / z [M+H]+: Theoretical value: 574.24; Measured value: 575.23.

[0206] Example 11

[0207] This example provides an organic electroluminescent compound N-56. The preparation method of the organic electroluminescent compound N-56 specifically includes the following steps:

[0208]

[0209] The synthesis steps of N-56 are the same as those of N-1, except that intermediate M5-A-4 is used to replace M1-A-4, and raw material N56-B is used to replace N1-B, and compound N-56 (yield 66%) is obtained.

[0210] Elemental analysis: C 44 H 26 Theoretical values for C, H, N2, O: C, 88.27; H, 4.38; N, 4.68; O, 2.67; Measured values: C, 88.29; H, 4.39; N, 4.66;; HRMS(ESI) m / z [M+H]+: Theoretical value: 598.20; Measured value: 599.21.

[0211] Example 12

[0212] This example provides an organic electroluminescent compound N-63. The preparation method of the organic electroluminescent compound N-63 specifically includes the following steps:

[0213]

[0214] The synthesis steps of N-63 are the same as those of N-1, except that intermediate M8-B-4 is used to replace M1-A-4, and raw material N63-B is used to replace N1-B, and compound N-63 (yield 62%) is obtained.

[0215] Elemental analysis: C 44 H 26Theoretical values of N2O: C, 88.27; H, 4.38; N, 4.68; O, 2.67; Measured values: C, 88.28; H, 4.39; N, 4.66;; HRMS(ESI) m / z [M+H]+: Theoretical value: 598.20; Measured value: 599.21.

[0216] Example 13

[0217] This example provides the organic electroluminescent compound N-80. The preparation method of the organic electroluminescent compound N-80 specifically includes the following steps:

[0218]

[0219] The synthesis steps of N-80 are the same as those of N-1, except that intermediate M12-C-4 is used to replace M1-A-4, and raw material N80-B replaces N1-B, to obtain compound N-80 (yield 62%).

[0220] Elemental analysis: C53H34N2 Theoretical values: C, 91.09; H, 4.90; N, 4.01; Measured values: C, 91.11; H, 4.92; N, 3.97; HRMS(ESI) m / z [M+H]+: Theoretical value: 698.27; Measured value: 699.29.

[0221] Example 14

[0222] This example provides the organic electroluminescent compound N-88. The preparation method of the organic electroluminescent compound N-88 specifically includes the following steps:

[0223]

[0224] The synthesis steps of N-88 are the same as those of N-80, except that raw material N88-B replaces N80-B, to obtain compound N-88 (yield 60%).

[0225] Elemental analysis: C 44 H 28 N4 Theoretical values: C, 86.25; H, 4.61; N, 9.14; Measured values: C, 86.26; H, 4.64; N, 9.10;

[0226] HRMS(ESI) m / z [M+H]+: Theoretical value: 612.23; Measured value: 613.25.

[0227] Example 15

[0228] This example provides the organic electroluminescent compound N-105. The preparation method of the organic electroluminescent compound N-105 specifically includes the following steps:

[0229]

[0230] The synthesis steps of N-105 are the same as those of N-1, except that intermediate M10-C-4 is used to replace M1-A-4, and raw material N105-B is used to replace N1-B, to obtain compound N-105 (yield 71%).

[0231] Elemental analysis: C 46 H 29 Theoretical values for C, H, N3: C, 88.58; H, 4.69; N, 6.74; Measured values: C, 88.61; H, 4.68; N, 6.72; HRMS(ESI) m / z [M+H]+: Theoretical value: 623.24; Measured value: 624.22.

[0232] Example 16

[0233] This example provides an organic electroluminescent compound N-112. The preparation method of the organic electroluminescent compound N-112 specifically includes the following steps:

[0234]

[0235] The synthesis steps of N-112 are the same as those of N-1, except that intermediate M10-C-4 is used to replace M1-A-4, and raw material N112-B is used to replace N1-B, to obtain compound N-112 (yield 64%).

[0236] Elemental analysis: C 52 H 35 Theoretical values for C, H, N3: C, 88.99; H, 5.03; N, 5.99; Measured values: C, 89.02; H, 5.04; N, 5.94; HRMS(ESI) m / z [M+H]+: Theoretical value: 701.28; Measured value: 702.30.

[0237] Example 17

[0238] This example provides an organic electroluminescent compound N-116. The preparation method of the organic electroluminescent compound N-116 specifically includes the following steps:

[0239]

[0240] The synthesis steps of N-116 are the same as those of N-1, except that intermediate M10-C-4 is used to replace M1-A-4, and raw material N116-B is used to replace N1-B, to obtain compound N-116 (yield 58%).

[0241] Elemental analysis: C 46 H 28Theoretical values of N2O: C, 88.44; H, 4.52; N, 4.48; O, 2.56; Measured values: C, 88.46; H, 4.51; N, 4.47; HRMS(ESI) m / z [M+H]+: Theoretical value: 624.22; Measured value: 625.24.

[0242] Example 18

[0243] This example provides an organic electroluminescent compound N-174. The preparation method of the organic electroluminescent compound N-174 specifically includes the following steps:

[0244]

[0245] The synthesis steps of N-174 are the same as those of N-1, except that intermediate M2-A-4 is used to replace M1-A-4, and raw material N174-B is used to replace N1-B, to obtain compound N-174 (yield 45%).

[0246] Elemental analysis: C 44 H 26 Theoretical values of N2O: C, 88.27; H, 4.38; N, 4.68; O, 2.67; Measured values: C, 88.29; H, 4.39; N, 4.65;; HRMS(ESI) m / z [M+H]+: Theoretical value: 598.20; Measured value: 599.22.

[0247] Example 19

[0248] This example provides an organic electroluminescent compound N-195. The preparation method of the organic electroluminescent compound N-195 specifically includes the following steps:

[0249]

[0250] The synthesis steps of N-195 are the same as those of N-1, except that intermediate M6-A-4 is used to replace M1-A-4, and raw material N195-B is used to replace N1-B, to obtain compound N-195 (yield 68%).

[0251] Elemental analysis: C 44 H 26 Theoretical values of N2O: C, 88.27; H, 4.38; N, 4.68; O, 2.67; Measured values: C, 88.29; H, 4.39; N, 4.65;; HRMS(ESI) m / z [M+H]+: Theoretical value: 598.20; Measured value: 599.25.

[0252] Example 20

[0253] This embodiment provides an organic electroluminescent compound N-212. The preparation method of the organic electroluminescent compound N-212 specifically includes the following steps:

[0254]

[0255] The synthesis steps of N-212 are the same as those of N-1, except that intermediate M9-B-4 is used to replace M1-A-4, and raw material N212-B is used to replace N1-B, obtaining compound N-212 (yield 52%).

[0256] Elemental analysis: C 48 H 30 Theoretical values for N2: C, 90.82; H, 4.76; N, 4.41; Measured values: C, 90.84; H, 4.77; N, 4.38;; HRMS(ESI) m / z [M+H]+: Theoretical value: 634.24; Measured value: 635.22.

[0257] Example 21

[0258] This embodiment provides an organic electroluminescent compound N-272. The preparation method of the organic electroluminescent compound N-272 specifically includes the following steps:

[0259]

[0260] The synthesis steps of N-272 are the same as those of N-1, except that intermediate M11-C-4 is used to replace M1-A-4, and raw material N272-B is used to replace N1-B, obtaining compound N-272 (yield 67%).

[0261] Elemental analysis: C 44 H 28 Theoretical values for N2: C, 90.38; H, 4.83; N, 4.79; Measured values: C, 90.39; H, 4.84; N, 4.77; HRMS(ESI) m / z [M+H]+: Theoretical value: 584.23; Measured value: 585.24.

[0262] Example 22

[0263] This embodiment provides an organic electroluminescent compound N-343. The preparation method of the organic electroluminescent compound N-343 specifically includes the following steps:

[0264]

[0265] The synthesis steps of N-343 are the same as those of N-1, except that intermediate M11-C-4 is used to replace M1-A-4, and raw material N272-B is used to replace N1-B, obtaining compound N-272 (yield 67%).

[0266] Elemental analysis: C46H30N2 Theoretical values: C, 90.46; H, 4.95; N, 4.59; Measured values: C, 90.48; H, 4.96; N, 4.56; HRMS(ESI) m / z [M+H]+: Theoretical value: 610.24; Measured value: 611.26.

[0267] Example 23

[0268] This example provides an organic electroluminescent compound N-346. The preparation method of the organic electroluminescent compound N-346 specifically includes the following steps:

[0269]

[0270] The synthesis steps of N-346 are the same as those of N-1, except that intermediate M5-A-4 is used to replace M1-A-4, and raw material N346-B replaces N1-B, to obtain compound N-346 (yield 71%).

[0271] Elemental analysis: C42H26N2 Theoretical values: C, 90.29; H, 4.69; N, 5.01; Measured values: C, 90.31; H, 4.71; N, 4.97; HRMS(ESI) m / z [M+H]+: Theoretical value: 558.21; Measured value: 559.23.

[0272] Example 24

[0273] This example provides an organic electroluminescent compound N-349. The preparation method of the organic electroluminescent compound N-349 specifically includes the following steps:

[0274]

[0275] The synthesis steps of N-349 are the same as those of N-1, except that intermediate M5-A-4 is used to replace M1-A-4, and raw material N349-B replaces N1-B, to obtain compound N-349 (yield 69%).

[0276] Elemental analysis: C 46 H 29 N3 Theoretical values: C, 88.58; H, 4.69; N, 6.74; Measured values: C, 88.59; H, 4.71; N, 6.71; HRMS(ESI) m / z [M+H]+: Theoretical value: 623.24; Measured value: 624.26.

[0277] The preparation methods of Examples 25 - 31 are similar to those of Example 1. Specifically, the raw materials used and the products obtained in Examples 25 - 31 are shown in Table 1 below.

[0278] Table 1

[0279]

[0280]

[0281] The characterization data of the products prepared in Examples 25 - 31 are shown in Table 2 as follows:

[0282] Table 2

[0283]

[0284] Device Examples and Comparative Examples

[0285] Some of the materials for manufacturing the organic light - emitting devices in the device examples and comparative examples are as follows:

[0286]

[0287]

[0288] The organic light - emitting devices in the device examples and comparative examples have similar structures (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 which are sequentially stacked on a substrate 1. Their 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).

[0289] The preparation of the organic light - emitting devices in the device examples and comparative examples includes the following steps:

[0290] 1) Substrate cleaning:

[0291] The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol - based solvent ≤ 10 wt%, triethanolamine ≤ 1 wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (the volume ratio of acetone to ethanol is 1:1), baked in a clean environment until all moisture is removed, and then cleaned with ultraviolet light and ozone.

[0292] 2) Organic layer preparation:

[0293] Transfer the ITO transparent substrate to an evaporation device and evacuate to 1×10 -6 to 2×10 -4Pa, a 10 nm hole injection layer (HIL) / 80 nm hole transport layer (HTL) / 30 nm emission layer (EML) / 30 nm electron transport layer (ETL) / 1 nm electron injection layer (EIL) / 90 nm thick cathode (Al) were sequentially deposited on the anode.

[0294] Among them:

[0295] The material of the hole injection layer (HIL) is a mixture of HATCN and HT, where the mass ratio of HATCN to HT is 3:97; the deposition is carried out by co-evaporation;

[0296] The material of the hole transport layer (HTL) is shown in Table 3;

[0297] The specific material of the emission layer (EML) is a mixture of CBP and (piq)2Ir(acac), and the mass ratio of CBP to (piq)2Ir(acac) is 95:5. The deposition is carried out by co-evaporation;

[0298] The specific material of the electron transport layer (ETL) is shown in Table 3, and the deposition is carried out by co-evaporation;

[0299] The material of the electron injection layer (EIL) is LiQ;

[0300] The thickness and material of each layer are shown in Table 3.

[0301] The specific materials and thicknesses of the device examples and comparative examples are shown in Table 3 below:

[0302] Table 3

[0303]

[0304]

[0305]

[0306] The examples in Table 3 refer to device examples, and the comparative examples refer to device comparative examples.

[0307] Test Example

[0308] The organic light-emitting devices obtained from device examples 1-23 and comparative examples 1-3 in the device examples were tested.

[0309] Instrument: The current, voltage, brightness, emission spectrum and other characteristics of the device were synchronously tested using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0310] Test conditions: The optoelectronic characteristic test condition: the current density is 10 mA / cm2.

[0311] Lifetime test: The current density is 50 mA / cm 2 , and record the time (in hours) when the device brightness drops to 95% of the original brightness.

[0312] The test results of device performance are shown in Table 4:

[0313] Table 4

[0314]

[0315]

[0316] The examples in Table 4 refer to device examples, and the comparative examples refer to device comparative examples.

[0317] It can be seen from Table 4 that:

[0318] The organic materials provided by the embodiments of the present invention can match the corresponding light-emitting layer, and have certain electron-transporting 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;

[0319] The organic materials provided by the embodiments of the present invention can match the corresponding light-emitting layer, and have certain hole-transporting ability;

[0320] As a light-emitting material, this material combines compound M with electron-transporting performance and N with hole-transporting 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, and making remarkable progress in the application of the host material.

[0321] 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.

[0322] Obviously, the above embodiments are only examples given 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 ; L 1 -L 13 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 13 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 of them.

2. The organic electroluminescent compound according to claim 1, characterized in that, Said L 1 -L 13 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 13 are each independently selected from a linking bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, and a substituted or unsubstituted naphthylene; Among them, the substituents in the substituted phenylene, substituted biphenylene, substituted terphenylene, 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 13 are each independently selected from a linking bond, a phenylene group, and a naphthylene group.

3. The organic electroluminescent compound according to claim 1 or 2, characterized in that, Ar 1 -Ar 13 At least one is selected from the group represented by formula a: X 1 selected from N or CR X1 , X 2 selected from N or CR X2 , X 3 selected from N or CR X3 , X 4 selected from N or CR X4 , X 5 selected from N or CR X5 ; R X1 -R X5 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, R X1 -R X5 Each exists independently, or two adjacent ones are connected to form ring A, and the ring A is a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C30 heteroaromatic ring; The said L 1 -L 13 Each independently selected from a linking group, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C3-C20 heteroarylene group; Among them, the substituents in the substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C30 aromatic ring, substituted C3-C30 heteroaromatic ring, substituted C6-C20 arylene, substituted C3-C20 heteroarylene 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 of them.

4. The organic electroluminescent compound according to any one of claims 1-3, wherein In the said X 1 -X 5 among them X 1 is N, X 2 is N, X 3 is CR X3 , X 4 is CR X4 , and X 5 is CR X5 ; R X3 , R X4 , R X5 exist independently or where R X3 is connected to R X5 to form ring A; or, X 1 is N, X 3 is N, X 2 is CR X2 , X 4 is CR X4 , and X 5 is CR X5 ; R X2 , R X4 , R X5 exist independently or wherein R X2 is connected to R X5 to form ring A; or, X 1 are N, X 2 are N, X 3 are N, X 4 is CR X4 , and X 5 is CR X5 ; Among them, the ring A is a substituted or unsubstituted C6-C20 aromatic ring and a substituted or unsubstituted C3-C20 heteroaromatic ring; R X2 -R X5 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, substituted C6-C20 aromatic ring, substituted C3-C20 heteroaromatic ring 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 of them; Preferably, the R X1 -R X5 are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted B groups; 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 ring A is selected from one of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a benzothiophene ring, a benzofuran ring, an indene ring; Preferably, the R X1 -R X5 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 13 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 13 At least one is selected from the group represented by the following formula b: T 1 -T 2 Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted mono- or di-C6-C30 arylamino, substituted or unsubstituted mono- or di-C6-C30 heteroarylamino; 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, 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, C1-C30 alkyl group, or a combination of one or 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, diarylaminophenyl, phenylbenzofuranyl; The diarylamino group in the diarylaminophenyl is selected from: diphenylamino group, di(4-biphenylyl)amino group, N-phenyl-biphenylamine group, N-phenyl-dibenzofuranamine group; 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, C1-C30 alkyl group, or a combination of one or 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-290:

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-354:

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, characterized in that, 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, characterized in that, 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, 9.

14. The organic electroluminescent device according to claim 11, characterized in that, 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 second host material; wherein, the first host material is selected from the organic electroluminescent compounds described in any one of claims 1-5 and claim 8; the second host material is selected from the organic electroluminescent compounds described in 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 host material to the second host material is 2:8 - 8:2; More preferably, the mass ratio of the first host material to the second host material is 3:7 - 7:3; Further preferably, the mass ratio of the first host material to the second host material is 4:6 - 6:

4.

15. Application of the organic electroluminescent device according to claim 11 in a fiber optic 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.

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