Organic compound containing boron-10 isotope and application thereof

Abstract

The invention relates to an organic compound containing boron-10 isotope as shown in a general formula (I-1), (I-2) or (I-3) or a stereoisomer thereof, and application thereof. 10B with the atomic abundance larger than 90% is introduced into the boron-containing compound, substituent groups are arranged on the two adjacent aromatic rings connected with boron, large steric hindrance is achieved, the two adjacent aromatic rings connected with boron are not coplanar, a twisted conjugated structure is formed, and therefore the novel 10B-containing organic compound is obtained. When the organic compound is applied to the electroluminescent device, the blue light emitting efficiency can be improved, the service life of the blue light emitting device can be prolonged, and the organic compound has a good light emitting effect and can be used as a light emitting layer material in an organic electroluminescent element, so that the obtained electroluminescent device has excellent electroluminescent property and stability. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the technical field of organic electronic devices and relates to organic electroluminescent materials, in particular to an organic compound containing boron-10 isotope and application thereof in organic electronic devices. Background Art

[0002] Organic light-emitting diodes (OLEDs) have great potential for application in optoelectronic devices such as flat panel displays and lighting due to their wide variety, low manufacturing cost, and good optical and electrical properties.

[0003] The phenomenon of organic electroluminescence (EL) refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic electroluminescent element that utilizes the organic electroluminescence phenomenon usually has a structure with a positive electrode and a negative electrode and an organic layer between them. In order to improve the efficiency and life of the organic electroluminescent element, the organic layer has a multilayer structure, and each layer contains different organic substances. Specifically, it can include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In this organic electroluminescent element, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the positive electrode, and electrons are injected into the organic layer from the negative electrode. When the injected holes meet the electrons, excitons are formed, and light is emitted when the excitons transition back to the ground state. This organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] In order to obtain efficient organic electroluminescent devices, phosphorescent materials or thermally activated delayed fluorescence materials (TADF) are currently mainly used as luminescent materials. Among them, the use of elements such as boron, phosphorus, oxygen, and nitrogen to connect aromatic rings into condensed aromatic hydrocarbons (EP3109253B1, CN106905367A) can make such heterocyclic aromatic hydrocarbons have a shorter phosphorescence wavelength (Nature Photonics 2019, 13,678, DOI: 10.1038 / s41566-019-0476-5), and blue-light-emitting organic luminescent materials can be obtained. However, the device life of such boron-containing compounds is still insufficient. Summary of the invention

[0005] Based on this, the present invention provides a class of organic compounds containing boron-10 isotope, which can effectively improve the luminescence life of organic electroluminescent devices.

[0006] The present invention includes the following technical solutions.

[0007] In the first aspect, the present invention provides an organic compound containing a boron-10 isotope or a stereoisomer thereof as shown in the general formula (I-1), (I-2) or (I-3):

[0008]

[0009] Among them, each Y 1 , Y 2 , Y 3 are independently selected from any one of N and B, and at least one of them is B, and the B element 10 The atomic abundance of B is greater than 90%;

[0010] Each X 1 , X 2 , X 3 , X 4 , X 5 , X 6 Each independently selected from: O, NR 1 , S, or does not exist, wherein the non-existence refers to A 2 , A 3 , A 4 , A 5 , A 6 and / or A 7 With A 1 There is no chemical bond between them;

[0011] Each A 1 are independently selected from: substituted or unsubstituted C 6 ~C 40 Aryl, substituted or unsubstituted 5-40 membered heteroaryl;

[0012] Each A 2 , A 3 , A 4 , A 5 , A 6 , A 7 Each independently selected from: substituted C 6 ~C 40 Aryl, substituted 5-40 membered heteroaryl;

[0013] Each R 1 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 20 Alkyl, R substituted or unsubstituted C 1 ~C 20 Alkoxy, R substituted or unsubstituted C 1 ~C 20 Alkylthio, R substituted or unsubstituted C 3 ~C 20Cycloalkyl, R substituted or unsubstituted C 3 ~C 20 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 20 Cycloalkylthio, R substituted or unsubstituted C 3 ~C 20 Silane, R substituted or unsubstituted C 1 ~C 20 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 20 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 40 aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C 6 ~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy;

[0014] Each R is independently selected from: hydroxyl, halogen, C 1 ~C 20 Alkyl, C 1 ~C 20 Alkoxy, C 1 ~C 20 Alkylthio, C 3 ~C 20 Cycloalkyl, C 3 ~C 20 Cycloalkoxy, C 3 ~C 20 Cycloalkylthio, C 1 ~C 20 Alkylcarbonyl, C 1 ~C 20 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 40 Aryl, 5-40 membered heteroaryl, C 6 ~C 40 Aryloxy, 5-40 membered heteroaryloxy.

[0015] In a second aspect, the present invention provides a mixture comprising at least one organic compound containing boron-10 isotope as described in the present invention, and another organic functional material; the other organic functional material is selected from: at least one of hole injection material, hole transport material, electron transport material, electron injection material, electron blocking material, hole blocking material, luminescent material, host material and organic dye.

[0016] In a third aspect, the present invention provides a composition comprising at least one mixture as described in the present invention or at least one organic compound containing boron-10 isotope as described in the present invention, and at least one organic solvent.

[0017] In a fourth aspect, the present invention provides the use of the organic compound containing boron-10 isotope or its stereoisomer, or the mixture, or the composition as a functional material in the preparation of a functional layer of an organic electronic device or an organic electronic device.

[0018] In a fifth aspect, the present invention provides an organic electronic device comprising the organic compound containing boron-10 isotope or its stereoisomer, or the mixture, or the combination as described in the present invention.

[0019] The present invention has the following beneficial effects:

[0020] The present invention introduces a boron-containing compound with an atomic abundance greater than 90%. 10 B, and the two adjacent aromatic rings connected to boron have substituents, which have a large steric hindrance, so that the two adjacent aromatic rings connected to boron are not coplanar, forming a distorted conjugated structure, thus obtaining a new type of containing 10 When the organic compound of the present invention is used in an electroluminescent device, the blue light luminescence efficiency and life span can be improved, and ... BRIEF DESCRIPTION OF THE DRAWINGS

[0021] Figure 1 101 is a substrate, 102 is an anode, 103 is a hole injection layer (HIL), 104 is a hole transport layer (HTL), 105 is a light emitting layer, 106 is an electron injection layer (EIL) or an electron transport layer (ETL), and 107 is a cathode. DETAILED DESCRIPTION

[0022] In order to facilitate the understanding of the present invention, the present invention will be described more fully below. The present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the disclosure of the present invention more thorough and comprehensive.

[0023] The experimental methods in the following examples without specifying specific conditions are usually carried out under conventional conditions or conditions recommended by the manufacturers. The various commonly used chemical reagents used in the examples are all commercially available products.

[0024] Unless otherwise defined, all technical and scientific terms used in the present invention have the same meaning as those commonly understood by those skilled in the art to which the present invention belongs. The terms used in the specification of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the present invention. The term "and / or" used in the present invention includes any and all combinations of one or more of the related listed items.

[0025] In addition, as used in the present invention, the term "or" is an inclusive "or" symbol and is equivalent to the term "and / or", unless the context clearly dictates otherwise. The term "based on" is not exclusive and allows for being based on other factors not described, unless the context clearly dictates otherwise. In addition, throughout the specification, the meanings of "a", "an", and "the" include plural referents. The meaning of "in..." includes "in..." and "on...".

[0026] In the compounds described in the present invention, when any variable (such as R 1 , etc.) occurs more than once in any component, its definition at each occurrence is independent of its definition at every other occurrence. Likewise, combinations of substituents and variables are permissible so long as such combinations result in stable compounds. It is to be understood that one of ordinary skill in the art can select substituents and substitution patterns for the compounds of the invention to provide chemically stable compounds that can be readily synthesized from readily available raw materials by techniques in the art and the methods set forth below. If a substituent is itself substituted with more than one group, it is to be understood that these groups may be on the same carbon atom or on different carbon atoms so long as the structure is stable.

[0027] To facilitate understanding of the present technology, certain terms and phrases are defined below.

[0028] In the present invention, boron-10 isotope refers to boron-10 ( 10 B), a boron isotope with an abundance of approximately 19.8% in nature.

[0029] In the present invention, "substituted" means that a hydrogen atom in the structure is replaced by a substituent.

[0030] In the present invention, the term "alkyl" is intended to include branched and straight chain saturated aliphatic hydrocarbon groups having a specific number of carbon atoms. 1 -C 6 "C" in "alkyl" 1 -C 6 The definition of " includes groups having 1, 2, 3, 4, 5 or 6 carbon atoms in a straight or branched chain arrangement. For example, "C 1 -C 6"Alkyl" specifically includes methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, pentyl, hexyl. The term "cycloalkyl" refers to a monocyclic saturated aliphatic hydrocarbon group having a specific number of carbon atoms. For example, "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, etc.

[0031] In the present invention, the term "alkoxy" refers to a group having an -O-alkyl structure, such as -OCH 3 、-OCH 2 CH 3 、-OCH 2 CH 2 CH 3 、-O-CH 2 CH(CH 3 ) 2 、-OCH 2 CH 2 CH 2 CH 3 、-O-CH(CH 3 ) 2 wait.

[0032] In the present invention, the term "heterocycloalkyl" is a saturated or partially unsaturated monocyclic or polycyclic cyclic substituent, wherein one or more ring atoms are selected from N, O or S(O)m (wherein m is an integer from 0 to 2) heteroatoms, and the remaining ring atoms are carbon, for example: morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, dihydroimidazolyl, dihydroisoxazolyl, dihydroisothiazolyl, dihydrooxadiazolyl, dihydrooxazolyl, dihydropyrazinyl, dihydropyrazolyl, dihydropyridinyl, dihydropyrimidinyl, dihydropyrrolyl, dihydrotetrazolyl, dihydrothiadiazolyl, dihydrothiazolyl, dihydrothiophenyl, dihydrotriazolyl, dihydroazetidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, etc., and N-oxides thereof. The connection of the heterocyclic substituent can be achieved through a carbon atom or through a heteroatom.

[0033] In the present invention, "aromatic group" or "aromatic ring system" refers to a hydrocarbon group containing at least one aromatic ring, including monocyclic groups and polycyclic ring systems. "Heteroaromatic group" or "heteroaromatic ring system" refers to a hydrocarbon group (containing heteroatoms) containing at least one aromatic heterocycle, including monocyclic groups and polycyclic ring systems. These polycyclic rings can have two or more rings, in which two carbon atoms are shared by two adjacent rings, i.e., condensed rings. At least one of these polycyclic ring species is aromatic or heteroaromatic. For the purpose of the present invention, aromatic or heteroaromatic ring systems include not only systems of aromatic or heteroaromatic groups, but also, wherein multiple aromatic or heteroaromatic groups may be interrupted by short non-aromatic units (such as C, N, O, Si, S or P atoms). Therefore, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, etc. are also considered to be aromatic ring systems for the purpose of this invention.

[0034] Specifically, examples of the aromatic group are benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, pyrene, benzopyrene, triphenylene, acenaphthene, fluorene, and derivatives thereof.

[0035] Specifically, examples of heteroaromatic groups include furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furanopyrrole, furanofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-naphthylidene, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone, and derivatives thereof.

[0036] In the present invention, the term "heteroaryl" or "heteroaromatic ring" refers to an aromatic ring containing one or more heteroatoms selected from O, N, S, Si, or P. The heteroaryl within the scope of the present invention includes, but is not limited to, quinolyl, pyrazolyl, pyrrolyl, thienyl, furanyl, pyridyl, pyrimidyl, pyrazinyl, triazolyl, imidazolyl, oxazolyl, isoxazolyl, pyridazinyl, and can also be understood as keto compounds such as: etc.; "heteroaryl" is also understood to include the N-oxide derivative of any nitrogen-containing heteroaryl. Attachment of the heterocyclic substituent may be achieved via a carbon atom or via a heteroatom.

[0037] In the present invention, the term "halo" or "halo" means chlorine, fluorine, bromine and iodine.

[0038] Unless otherwise defined, alkyl, cycloalkyl, aryl, heteroaryl and heterocycloalkyl substituents may be unsubstituted or substituted. 1 -C 6 The alkyl group may be substituted with one, two or three substituents selected from OH, halogen, alkoxy, dialkylamino or heterocyclic groups such as morpholinyl, piperidinyl and the like.

[0039] In some embodiments of the present invention, an organic compound containing boron-10 isotope or a stereoisomer thereof is involved, as shown in general formula (I-1), (I-2) or (I-3):

[0040]

[0041] Among them, each Y 1 , Y 2 , Y 3 are independently selected from any one of N and B, and at least one of them is B, and the B element 10 The atomic abundance of B is greater than 90%;

[0042] Each X 1 , X2 , X 3 , X 4 , X 5 , X 6 Each independently selected from: O, NR 1 , S, or does not exist, wherein the non-existence refers to A 2 , A 3 , A 4 , A 5 , A 6 and / or A 7 With A 1 There is no chemical bond between them;

[0043] Each A 1 are independently selected from: substituted or unsubstituted C 6 ~C 40 Aryl, substituted or unsubstituted 5-40 membered heteroaryl;

[0044] Each A 2 , A 3 , A 4 , A 5 , A 6 , A 7 Each independently selected from: substituted C 6 ~C 40 Aryl, substituted 5-40 membered heteroaryl;

[0045] Each R 1 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 20 Alkyl, R substituted or unsubstituted C 1 ~C 20 Alkoxy, R substituted or unsubstituted C 1 ~C 20 Alkylthio, R substituted or unsubstituted C 3 ~C 20 Cycloalkyl, R substituted or unsubstituted C 3 ~C 20 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 20 Cycloalkylthio, R substituted or unsubstituted C 3 ~C 20 Silane, R substituted or unsubstituted C 1 ~C 20 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 20 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C40 aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C 6 ~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy;

[0046] Each R is independently selected from: hydroxyl, halogen, C 1 ~C 20 Alkyl, C 1 ~C 20 Alkoxy, C 1 ~C 20 Alkylthio, C 3 ~C 20 Cycloalkyl, C 3 ~C 20 Cycloalkoxy, C 3 ~C 20 Cycloalkylthio, C 1 ~C 20 Alkylcarbonyl, C 1 ~C 20 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 40 Aryl, 5-40 membered heteroaryl, C 6 ~C 40 Aryloxy, 5-40 membered heteroaryloxy.

[0047] In some embodiments, Y 1 , Y 2 , Y 3 At least one of 10 B, preferably both 10 B.

[0048] In some embodiments, each A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 are independently selected from the following ring structures:

[0049]

[0050]

[0051] Wherein, each W is independently selected from: N, CR 2 , C=O;

[0052] Each X 7 Each independently selected from: CR 32 , C=O, O, S, S=O, S=(O) 2 NR 3 ;

[0053] Each R 2 , R 3 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 20 Alkyl, R substituted or unsubstituted C 1 ~C 20 Alkoxy, R substituted or unsubstituted C 1 ~C 20 Alkylthio, R substituted or unsubstituted C 3 ~C 20 Cycloalkyl, R substituted or unsubstituted C 3 ~C 20 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 20 Cycloalkylthio, R substituted or unsubstituted C 3 ~C 20 Silane, R substituted or unsubstituted C 1 ~C 20 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 20 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 40 aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C 6 ~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy, or two adjacent R 2 and / or R 3 Can be connected to form a ring;

[0054] A 2 , A 3 , A 4 , A 5 , A 6 , A 7 Each ring in has at least one R that is not H or D. 2 or R 3 , that is, A 2 and A 3 , A 4 and A 5 , A 6 and A 7 There is a large steric hindrance within the three adjacent ring groups, making A 2 and A3 Not coplanar, A 4 and A 5 Not coplanar, A 6 and A 7 Not coplanar.

[0055] In some embodiments, the organic compound containing boron-10 isotope is selected from the following structural formula:

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063] Wherein, each W is independently selected from: N, CR 2 , C=O;

[0064] Each R 2 Selected from: H, D, R substituted or unsubstituted C 1 ~C 20 Alkyl, R substituted or unsubstituted C 1 ~C 20 Alkoxy, R substituted or unsubstituted C 1 ~C 20 Alkylthio, R substituted or unsubstituted C 3 ~C 20 Cycloalkyl, R substituted or unsubstituted C 3 ~C 20 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 20 Cycloalkylthio, R substituted or unsubstituted C 3 ~C 20 Silane, R substituted or unsubstituted C 1 ~C 20 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 20 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 40aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C 6 ~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy, or two adjacent R 2 Can be connected to form a ring;

[0065] Each R 4 are independently selected from: R substituted or unsubstituted C 1 ~C 20 Alkyl, R substituted or unsubstituted C 1 ~C 20 Alkoxy, R substituted or unsubstituted C 1 ~C 20 Alkylthio, R substituted or unsubstituted C 3 ~C 20 Cycloalkyl, R substituted or unsubstituted C 3 ~C 20 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 20 Cycloalkylthio, R substituted or unsubstituted C 3 ~C 20 Silane, R substituted or unsubstituted C 1 ~C 20 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 20 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 40 aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C 6 ~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy;

[0066] Each R 5 , R 6 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 20 Alkyl, R substituted or unsubstituted C 1 ~C 20 Alkoxy, R substituted or unsubstituted C 1 ~C 20 Alkylthio, R substituted or unsubstituted C 3 ~C 20 Cycloalkyl, R substituted or unsubstituted C 3 ~C 20 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 20Cycloalkylthio, R substituted or unsubstituted C 3 ~C 20 Silane, R substituted or unsubstituted C 1 ~C 20 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 20 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 40 aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C 6 ~C 40 aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy; and R 5 , R 6 Not H and / or D at the same time;

[0067] Each R 7 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 20 Alkyl, R substituted or unsubstituted C 1 ~C 20 Alkoxy, R substituted or unsubstituted C 1 ~C 20 Alkylthio, R substituted or unsubstituted C 3 ~C 20 Cycloalkyl, R substituted or unsubstituted C 3 ~C 20 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 20 Cycloalkylthio, R substituted or unsubstituted C 3 ~C 20 Silane, R substituted or unsubstituted C 1 ~C 20 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 20 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 40 aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C 6 ~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy.

[0068] In some embodiments, the aromatic or heteroaromatic groups are independently selected from benzene, biphenyl, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridine, pyrimidine, triazine, fluorene, dithiophene, silafluorene, carbazole, thiophene, furan, thiazole, triphenylamine, triphenylphosphine, tetraphenylsilane, spirofluorene, spirosiliconfluorene, pyrazine, oxadiazole and their derivatives.

[0069] In some embodiments, each W is independently selected from: N, CR 2 , C=O;

[0070] Each X 7 Each independently selected from: CR 3 2 , C=O, O, S, S=O, S=(O) 2 NR 3 ';

[0071] Each R 2 , R 3 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 6 Alkyl, R substituted or unsubstituted C 1 ~C 6 Alkoxy, R substituted or unsubstituted C 1 ~C 6 Alkylthio, R substituted or unsubstituted C 3 ~C 8 Cycloalkyl, R substituted or unsubstituted C 3 ~C 8 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 8 Cycloalkylthio, R substituted or unsubstituted C 1 ~C 6 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 6 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 20 aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C 6 ~C 20 Aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy, or two adjacent R 2 They may be linked to form a 5-20 membered cycloalkyl or heterocyclic ring group;

[0072] Each R 3 'are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 6Alkyl, R substituted or unsubstituted C 3 ~C 8 Cycloalkyl, R substituted or unsubstituted C 1 ~C 6 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 6 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryl, R substituted or unsubstituted 5-20 membered heteroaryl;

[0073] Each R is independently selected from: hydroxyl, halogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 3 ~C 8 Cycloalkyl, C 3 ~C 8 Cycloalkoxy, C 3 ~C 8 Cycloalkylthio, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 20 Aryl, 5-20 membered heteroaryl, C 6 ~C 20 Aryloxy, 5-20 membered heteroaryloxy;

[0074] A 2 , A 3 , A 4 , A 5 , A 6 , A 7 Each ring in has at least one R that is not H or D. 2 .

[0075] In some embodiments, each W is independently selected from: CH, CD, CR 2 ;

[0076] Each X 7 Each independently selected from: C=O, O, S, S=O, S=(O) 2 NR 3 ';

[0077] Each R2 are independently selected from: R substituted or unsubstituted C 1 ~C 4 Alkyl, R substituted or unsubstituted C 1 ~C 3 Alkoxy, R substituted or unsubstituted C 1 ~C 3 Alkylthio, R substituted or unsubstituted C 3 ~C 6 Cycloalkyl, R substituted or unsubstituted C 3 ~C 6 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 6 Cycloalkylthio, R substituted or unsubstituted C 1 ~C 3 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 3 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 10 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 10 aryl, R substituted or unsubstituted 5-10 membered heteroaryl, R substituted or unsubstituted C 6 ~C 10 Aryloxy, R substituted or unsubstituted 5-10 membered heteroaryloxy, or two adjacent R 2 They may be linked to form a 5-8 membered cycloalkyl or heterocyclic ring group;

[0078] Each R 3 'are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 3 Alkyl, R substituted or unsubstituted C 3 ~C 6 Cycloalkyl, R substituted or unsubstituted C 1 ~C 3 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 3 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 10 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 10 Aryl, R substituted or unsubstituted 5-10 membered heteroaryl;

[0079] Each R is independently selected from: hydroxyl, halogen, C 1 ~C 3 Alkyl, C 1 ~C 3 Alkoxy, C 1 ~C3 Alkylthio, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkoxy, C 3 ~C 6 Cycloalkylthio, C 1 ~C 3 Alkylcarbonyl, C 1 ~C 3 Alkoxycarbonyl, C 6 ~C 10 Aryloxycarbonyl, C 6 ~C 10 Aryl, 5-10 membered heteroaryl, C 6 ~C 10 Aryloxy, 5-10 membered heteroaryloxy;

[0080] A 2 , A 3 , A 4 , A 5 , A 6 , A 7 On each ring in the 2 .

[0081] In some embodiments, each R 4 are independently selected from: R substituted or unsubstituted C 1 ~C 6 Alkyl, R substituted or unsubstituted C 1 ~C 6 Alkoxy, R substituted or unsubstituted C 1 ~C 6 Alkylthio, R substituted or unsubstituted C 3 ~C 8 Cycloalkyl, R substituted or unsubstituted C 3 ~C 8 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 8 Cycloalkylthio, R substituted or unsubstituted C 1 ~C 6 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 6 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 20 aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C 6 ~C 20Aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy.

[0082] In some embodiments, each R 4 are independently selected from: R substituted or unsubstituted C 1 ~C 4 Alkyl, R substituted or unsubstituted C 1 ~C 3 Alkoxy, R substituted or unsubstituted C 1 ~C 3 Alkylthio, R substituted or unsubstituted C 3 ~C 6 Cycloalkyl, R substituted or unsubstituted C 3 ~C 6 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 6 Cycloalkylthio, R substituted or unsubstituted C 1 ~C 3 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 3 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 10 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 10 aryl, R substituted or unsubstituted 5-10 membered heteroaryl, R substituted or unsubstituted C 6 ~C 10 Aryloxy, R substituted or unsubstituted 5-10 membered heteroaryloxy.

[0083] In some embodiments, each R 5 , R 6 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 6 Alkyl, R substituted or unsubstituted C 1 ~C 6 Alkoxy, R substituted or unsubstituted C 1 ~C 6 Alkylthio, R substituted or unsubstituted C 3 ~C 8 Cycloalkyl, R substituted or unsubstituted C 3 ~C 8 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 8 Cycloalkylthio, R substituted or unsubstituted C 1 ~C 6 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 6 Alkoxycarbonyl, R substituted or unsubstituted C6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 20 aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C 6 ~C 20 aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy; and R 5 , R 6 Not H and / or D at the same time.

[0084] In some embodiments, each R 5 , R 6 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 4 Alkyl, R substituted or unsubstituted C 1 ~C 3 Alkoxy, R substituted or unsubstituted C 1 ~C 3 Alkylthio, R substituted or unsubstituted C 3 ~C 6 Cycloalkyl, R substituted or unsubstituted C 3 ~C 6 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 6 Cycloalkylthio, R substituted or unsubstituted C 1 ~C 3 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 3 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 10 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 10 aryl, R substituted or unsubstituted 5-10 membered heteroaryl, R substituted or unsubstituted C 6 ~C 10 aryloxy, R substituted or unsubstituted 5-10 membered heteroaryloxy; and R 5 , R 6 Not H and / or D at the same time.

[0085] In some embodiments, each R 7 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 6 Alkyl, R substituted or unsubstituted C 1 ~C 6 Alkoxy, R substituted or unsubstituted C 1 ~C 6 Alkylthio, R substituted or unsubstituted C3 ~C 8 Cycloalkyl, R substituted or unsubstituted C 3 ~C 8 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 8 Cycloalkylthio, R substituted or unsubstituted C 1 ~C 6 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 6 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 20 aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C 6 ~C 20 Aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy.

[0086] In some embodiments, each R 7 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 4 Alkyl, R substituted or unsubstituted C 1 ~C 3 Alkoxy, R substituted or unsubstituted C 1 ~C 3 Alkylthio, R substituted or unsubstituted C 3 ~C 6 Cycloalkyl, R substituted or unsubstituted C 3 ~C 6 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 6 Cycloalkylthio, R substituted or unsubstituted C 1 ~C 3 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 3 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 10 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 10 aryl, R substituted or unsubstituted 5-10 membered heteroaryl, R substituted or unsubstituted C 6 ~C 10 Aryloxy, R substituted or unsubstituted 5-10 membered heteroaryloxy.

[0087] In some embodiments, each R is independently selected from: hydroxyl, halogen, C 1 ~C 6 Alkyl, C1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 3 ~C 8 Cycloalkyl, C 3 ~C 8 Cycloalkoxy, C 3 ~C 8 Cycloalkylthio, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 20 Aryl, 5-20 membered heteroaryl, C 6 ~C 20 Aryloxy, 5-20 membered heteroaryloxy.

[0088] In some embodiments, each R is independently selected from: hydroxyl, halogen, C 1 ~C 3 Alkyl, C 1 ~C 3 Alkoxy, C 1 ~C 3 Alkylthio, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkoxy, C 3 ~C 6 Cycloalkylthio, C 1 ~C 3 Alkylcarbonyl, C 1 ~C 3 Alkoxycarbonyl, C 6 ~C 10 Aryloxycarbonyl, C 6 ~C 10 Aryl, 5-10 membered heteroaryl, C 6 ~C 10 Aryloxy, 5-10 membered heteroaryloxy.

[0089] In some embodiments, each X 1 , X 2 , X 3 , X 4 , X 5 , X 6 Each independently selected from: O, NR 1 , S, or does not exist; each R 1 are independently selected from: H, D, R substituted or unsubstituted C 1~C 6 Alkyl, R substituted or unsubstituted C 1 ~C 6 Alkoxy, R substituted or unsubstituted C 1 ~C 6 Alkylthio, R substituted or unsubstituted C 3 ~C 8 Cycloalkyl, R substituted or unsubstituted C 3 ~C 8 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 8 Cycloalkylthio, R substituted or unsubstituted C 1 ~C 6 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 6 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 20 aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C 6 ~C 20 Aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy; each R is independently selected from: hydroxyl, halogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 3 ~C 8 Cycloalkyl, C 3 ~C 8 Cycloalkoxy, C 3 ~C 8 Cycloalkylthio, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 20 Aryl, 5-20 membered heteroaryl, C 6 ~C 20 Aryloxy, 5-20 membered heteroaryloxy.

[0090] In some embodiments, each R 1 Each independently selected from: H, D, C 1 ~C 6 Alkyl, phenyl, naphthyl.

[0091] In some embodiments, the organic compound containing boron-10 isotope is selected from the following formula (II-1), formula (II-2), formula (II-3), formula (II-4), formula (II-5), formula (II-6), formula (II-7) or formula (II-8):

[0092]

[0093]

[0094] Among them, X 1 , X 2 , X 3 , X 4 Each independently selected from: O, NR 1 , S;

[0095] Each R 3 'are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 6 Alkyl, R substituted or unsubstituted C 3 ~C 8 Cycloalkyl, R substituted or unsubstituted C 1 ~C 6 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 6 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryl, R substituted or unsubstituted 5-20 membered heteroaryl;

[0096] Each R is independently selected from: hydroxyl, halogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 3 ~C 8 Cycloalkyl, C 3 ~C 8 Cycloalkoxy, C 3 ~C 8 Cycloalkylthio, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 20 Aryl, 5-20 membered heteroaryl, C6 ~C 20 Aryloxy, 5-20 membered heteroaryloxy;

[0097] R 8 Selected from: R 2 or

[0098] In some embodiments, X 1 , X 2 , X 3 , X 4 Each independently selected from: O, NR 1 , S;

[0099] Each R 1 are independently selected from: H, D, R substituted or unsubstituted C 1 ~C 6 Alkyl, R substituted or unsubstituted C 1 ~C 6 Alkoxy, R substituted or unsubstituted C 1 ~C 6 Alkylthio, R substituted or unsubstituted C 3 ~C 8 Cycloalkyl, R substituted or unsubstituted C 3 ~C 8 Cycloalkoxy, R substituted or unsubstituted C 3 ~C 8 Cycloalkylthio, R substituted or unsubstituted C 1 ~C 6 Alkylcarbonyl, R substituted or unsubstituted C 1 ~C 6 Alkoxycarbonyl, R substituted or unsubstituted C 6 ~C 20 Aryloxycarbonyl, R substituted or unsubstituted C 6 ~C 20 aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C 6 ~C 20 Aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy;

[0100] Each R is independently selected from: hydroxyl, halogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 3 ~C 8 Cycloalkyl, C 3 ~C 8 Cycloalkoxy, C 3~C 8 Cycloalkylthio, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 20 Aryl, 5-20 membered heteroaryl, C 6 ~C 20 Aryloxy, 5-20 membered heteroaryloxy.

[0101] In some embodiments, each R 1 Each independently selected from: H, D, C 1 ~C 6 Alkyl, phenyl, naphthyl.

[0102] In some embodiments, each W is independently selected from: CH, CD, CR 2 ;

[0103] Each R 2 Each independently selected from: C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 3 ~C 8 Cycloalkyl, C 3 ~C 8 Cycloalkoxy, C 3 ~C 8 Cycloalkylthio, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 20 Aryl, 5-20 membered heteroaryl, C 6 ~C 20 Aryloxy, 5-20 membered heteroaryloxy.

[0104] In some embodiments, each R 2 Each of the following is independently selected from the group consisting of: methyl, ethyl, propyl, butyl, phenyl, and naphthyl.

[0105] In some embodiments, each R 3 'are independently selected from: H, D, C 1~C 6 Alkyl, C 6 ~C 10 Aryl.

[0106] In some embodiments, each R 3 ' are independently selected from: H, D, methyl, ethyl, propyl, butyl, phenyl, naphthyl.

[0107] In some embodiments, each R 4 Each independently selected from: C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 3 ~C 8 Cycloalkyl, C 3 ~C 8 Cycloalkoxy, C 3 ~C 8 Cycloalkylthio, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 20 Aryl, 5-20 membered heteroaryl, C 6 ~C 20 Aryloxy, 5-20 membered heteroaryloxy.

[0108] In some embodiments, each R 4 Each is independently selected from the group consisting of: methyl, ethyl, propyl, butyl, phenyl, and naphthyl.

[0109] In some embodiments, each R 5 , R 6 Each independently selected from: H, D, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 3 ~C 8 Cycloalkyl, C 3 ~C 8 Cycloalkoxy, C 3 ~C 8 Cycloalkylthio, C1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 20 Aryl, 5-20 membered heteroaryl, C 6 ~C 20 aryloxy, 5-20 membered heteroaryloxy; and R 5 , R 6 Not H and / or D at the same time.

[0110] In some embodiments, each R 5 , R 6 are independently selected from: H, D, methyl, ethyl, propyl, butyl, phenyl, naphthyl; and R 5 , R 6 Not H and / or D at the same time.

[0111] In some embodiments, each R 7 Each independently selected from: H, D, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 3 ~C 8 Cycloalkyl, C 3 ~C 8 Cycloalkoxy, C 3 ~C 8 Cycloalkylthio, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 6 ~C 20 Aryloxycarbonyl, C 6 ~C 20 Aryl, 5-20 membered heteroaryl, C 6 ~C 20 Aryloxy, 5-20 membered heteroaryloxy.

[0112] In some embodiments, each R 7 Each of the following is independently selected from the group consisting of: H, D, methyl, ethyl, propyl, butyl, phenyl, and naphthyl.

[0113] In some embodiments, each R 3' are independently selected from: H, D, methyl, ethyl, propyl, butyl, phenyl, naphthyl.

[0114] In some embodiments, the organic compound containing boron-10 isotope is selected from the following compounds:

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] The organic compound containing boron-10 isotope provided by the present invention can be used as a functional material in the functional layer of an electronic device. The organic functional layer includes, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), an electron injection layer (EIL), an electron blocking layer (EBL), a hole blocking layer (HBL), and a light-emitting layer.

[0126] In one embodiment of the present invention, a mixture is provided, comprising at least one organic compound containing boron-10 isotope according to the present invention, and another organic functional material; the other organic functional material is selected from: at least one of hole injection material (HIM), hole transport material (HTM), electron transport material (ETM), electron injection material (EIM), electron blocking material (EBM), hole blocking material (HBM), luminescent material (Emitter), host material (Host) and organic dye. For example, in WO2010135519A1, US20090134784A1 and WO

[0127] Various organic functional materials are described in detail in 2011110277A1, and the contents of these three patent documents are hereby incorporated into this article as a reference.

[0128] In one embodiment of the present invention, a composition is further provided, comprising at least one mixture as described in the present invention or at least one organic compound containing boron-10 isotope as described in the present invention, and at least one organic solvent.

[0129] The organic solvent is selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefin compounds, or borate or phosphate compounds, or a mixture of two or more solvents.

[0130] In some preferred embodiments, the at least one organic solvent is selected from aromatic or heteroaromatic based solvents.

[0131] Examples of aromatic or heteroaromatic solvents suitable for the present invention include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0132] Examples of aromatic ketone-based solvents suitable for the present invention include, but are not limited to: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0133] Examples of aromatic ether-based solvents suitable for the present invention include, but are not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether.

[0134] In some preferred embodiments, according to the composition of the present invention, the at least one solvent can be selected from: aliphatic ketones, for example, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0135] In other preferred embodiments, according to the composition of the present invention, the at least one solvent can be selected from ester-based solvents: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0136] The solvent may be used alone or as a mixture of two or more organic solvents.

[0137] In certain preferred embodiments, a composition of the present invention may further comprise another organic solvent. Examples of another organic solvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and / or mixtures thereof.

[0138] In some preferred embodiments, solvents particularly suitable for the present invention are solvents having a Hansen solubility parameter in the following ranges:

[0139] δ d (Dispersion force) 17.0~23.2MPa 1 / 2 range, especially in the range of 18.5~21.0MPa 1 / 2 scope;

[0140] δ p (Polar force) 0.2~12.5MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 scope;

[0141] δ h (Hydrogen bond force) 0.9~14.2MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range.

[0142] In the composition of the present invention, the boiling point parameter of the organic solvent should be considered when selecting. In the present invention, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; more preferably ≥250°C; and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head. The organic solvent can be evaporated from the solvent system to form a film containing a functional material.

[0143] In some preferred embodiments, the composition of the present invention is a solution.

[0144] In other preferred embodiments, the composition of the present invention is a suspension.

[0145] In some preferred embodiments, the composition of the present invention may include 0.01 to 10 wt % of the organic compound or mixture containing boron-10 isotope described in the present invention, preferably 0.1 to 15 wt %, more preferably 0.2 to 5 wt %, and most preferably 0.25 to 3 wt %.

[0146] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices, and particularly preferably a preparation method by printing or coating.

[0147] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, slot extrusion coating, etc. Preferred are gravure printing, nozzle printing and inkjet printing. The solution or suspension may further include one or more components such as surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc. For detailed information on printing technology and its related requirements for related solutions, such as solvents and concentrations, viscosity, etc., please refer to the "Handbook of Print Media: Technologies and Production Methods" edited by Helmut Kipphan, ISBN 3-540-67326-1.

[0148] In some embodiments of the present invention, there is also provided the use of the organic compound containing boron-10 isotope or its stereoisomer, the mixture, or the composition as a functional material in the preparation of a functional layer of an organic electronic device or an organic electronic device.

[0149] The organic electronic device can be selected from, but not limited to, organic light emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting cells (OLEECs), organic field effect transistors (OFETs), organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors and organic plasmon emitting diodes (Organic Plasmon Emitting Diodes), etc., and OLEDs are particularly preferred.

[0150] The functional layers of the organic electronic device include a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and a light-emitting layer. The present invention preferably uses the organic compound containing boron-10 isotope for the hole injection or transport layer or the light-emitting layer of the OLED device.

[0151] In some embodiments of the present invention, an organic electronic device is also provided, comprising the organic compound containing boron-10 isotope or its stereoisomer, or the mixture, or the composition as described in the present invention.

[0152] Generally, the organic electronic device comprises at least one cathode, one anode and a functional layer between the cathode and the anode, wherein the functional layer comprises at least one organic compound containing boron-10 isotope as described in the present invention. The organic electronic device can be selected from, but not limited to, organic light emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting cells (OLEECs), organic field effect transistors (OFETs), organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors and organic plasmon emitting diodes (Organic Plasmon Emitting Diodes), etc., and organic electroluminescent devices such as OLEDs, OLEECs and organic light emitting field effect transistors are particularly preferred.

[0153] The light emitting device described above, especially OLED, comprises a substrate, an anode, at least one light emitting layer, and a cathode.

[0154] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. It is best that the substrate has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred embodiment, the substrate is flexible and can be selected from polymer films or plastics, and its glass transition temperature Tg is above 150°C, preferably above 200°C, more preferably above 250°C, and preferably above 300°C. Examples of suitable flexible substrates include poly (ethylene terephthalate) (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0155] The anode may include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL) or the hole transport layer (HTL) or the light emitting layer.

[0156] In some embodiments, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light emitter in the light-emitting layer or the p-type semiconductor material as the HIL or HTL or the electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be easily selected for use by a person of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare the device of the present invention.

[0157] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In some embodiments, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL) or the electron transport layer (ETL) or the hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs may be used as cathode materials for the device of the present invention. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloys, BaF 2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0158] OLEDs may also include other functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, and the contents of these three patent documents are hereby incorporated herein by reference.

[0159] Furthermore, the organic electronic device is an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor and an organic plasmon emitting diode (Organic Plasmon Emitting Diode).

[0160] As the instruction manual Figure 1 As shown, in the organic electronic device, an anode (102), a hole injection layer (HIL) (103), a hole transport layer (HTL) (104), a light-emitting layer (105), an electron blocking layer (EBL), an electron injection layer (EIL) or an electron transport layer (ETL) (106), and a cathode (107) are sequentially stacked on a substrate (101). In the element, the organic thin film layer is a stacked structure consisting of a hole injection layer (HIL) (103), a hole transport layer (HTL) (104), a light-emitting layer (105), an electron blocking layer (EBL), an electron injection layer (EIL) or an electron transport layer (ETL) (106). Among the layers forming these organic thin film layers, at least one layer contains the organic compound containing the boron-10 isotope of the present invention, thereby achieving electroluminescence of the organic electronic device and also achieving a longer life.

[0161] The content of the material is preferably 1 to 100 mol % based on the layer forming the organic thin film layer containing the organic compound containing the boron-10 isotope of the present invention.

[0162] The present invention also relates to the application of the electroluminescent device of the present invention in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, etc.

[0163] The present invention is further described in detail below with reference to specific embodiments.

[0164] Unless otherwise specified, the equivalents in the following examples refer to molar equivalents.

[0165] Example 1 Synthesis of Compound B-1

[0166]

[0167] In a nitrogen atmosphere, a 2.6 M n-butyl lithium hexane solution (11.8 ml) was added to a flask containing compound A1 (2.9 g) and o-xylene (160 ml) at 0°C. After the addition was completed, the temperature was raised to 100°C and stirred for 4 hours, and then the hexane was distilled off. The mixture was cooled to -50°C and added. 10BBr (3.4 ml), then heated at room temperature and stirred for 1 hour. Thereafter, cooled again to 0°C and added N,N-diisopropylethylamine (10.0 ml), stirred at room temperature until the exotherm stopped, and heated and stirred at 120°C for 4 hours. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution and ethyl acetate were added for liquid separation. After the solvent was distilled off under reduced pressure and precipitated, it was purified by column chromatography, and then the solvent was removed under reduced pressure to obtain solid compound B-1 (0.77 g, 26%), MS: [M+H] + =298; 1 H NMR (300 MHz, CDCl 3 ): δ8.36(1H,t),8.23-8.18(2H,m),7.81-7.39(4H,m),7.14(2H,d),2.18(6H,s).

[0168] Example 2 Synthesis of Compound B-2

[0169]

[0170] Under nitrogen protection, add 2.5 mL (20 mmol) of freshly steamed compound A2 ether complex to a 250 mL three-necked flask and cool it in an ice bath. Slowly add compound A3 (65 mmol) and stir vigorously. After the addition is complete, stir at room temperature for 12 hours. Add 50 mL of water to quench the reaction, extract with chloroform, dry the organic phase, column chromatograph with petroleum ether as the developing solvent, and recrystallize with ethanol to obtain solid compound B-2 (3.82 g, 52%), MS: [M+H]+=368; 1 HNMR (300MHz, CDCl 3 ): δ6.82(6H,s),2.34(9H,s),2.01(18H,s).

[0171] Example 3 Synthesis of Compound B-3

[0172]

[0173] Under nitrogen protection, add freshly steamed compound A2 ether complex (1 equ) to a 250 ml three-necked flask and cool in an ice bath. Slowly add compound A3 (2 equ) and stir vigorously. After the addition is complete, stir at room temperature for 12 hours. Under nitrogen protection, slowly add compound A5 (1 equ) dropwise. After the addition is complete, stir for 12 hours. Add 50 ml of water to quench the reaction, extract with chloroform, dry the organic phase, and perform column chromatography with petroleum ether as the developing solvent. Recrystallize from ethanol to obtain solid compound B-3, MS: [M+H]+=574; 1 H NMR (300 MHz, CDCl 3): δ7.71(4H,d),6.97(8H,s),2.40-2.33(24H,d),2.11(12H,s).

[0174] Example 4 Synthesis of Compound B-4

[0175]

[0176] In a nitrogen atmosphere, a 2.6 M n-butyllithium hexane solution (3 equ) was added to a flask containing compound A6 (1 equ) and o-xylene (100 equ) at 0°C. After the addition was completed, the temperature was raised to 100°C and stirred for 4 hours, and then the hexane was distilled off. The mixture was cooled to -50°C and added 10 BBr (1 equ), then heated at room temperature and stirred for 1 hour. Thereafter, cooled again to 0°C and added N,N-diisopropylethylamine (10 equ), stirred at room temperature until the exotherm stopped, and heated and stirred at 120°C for 4 hours. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution and ethyl acetate were added for liquid separation. After the solvent was distilled off under reduced pressure and precipitated, it was purified by column chromatography, and then the solvent was removed under reduced pressure to obtain solid compound B-4, MS: [M+H] + =408; 1 H NMR (300 MHz, CDCl 3 ): δ7.85-7.40(5H,m),6.92-6.82(4H,m),3.56(4H,d),2.39(6H,s),1.51-1.31(8H,m),0.67(6H,t).

[0177] Example 5 Synthesis of Compound B-5

[0178]

[0179] Under nitrogen protection, add freshly steamed compound A2 ether complex (1 equ) to a 250 ml three-necked flask and cool in an ice bath. Slowly add compound A7 (2 equ) and stir vigorously. After the addition is complete, stir at room temperature for 12 hours. Under nitrogen protection, slowly add compound A9 (1 equ) dropwise. After the addition is complete, stir for 12 hours. Add 50 ml of water to quench the reaction, extract with chloroform, dry the organic phase, and column chromatograph with petroleum ether as the developing solvent. Recrystallize from ethanol to obtain solid compound B-5, MS: [M+H]+=476; 1 HNMR (300MHz, CDCl 3 ): δ8.56(2H,d),8.45(2H,s),7.81(4H,m),7.48-7.36(7H,m),6.92(2H,t),3.86(6H,s),2.35(6H,s).

[0180] Example 6 Synthesis of Compound B-6

[0181]

[0182] In a nitrogen atmosphere, a 2.6 M n-butyl lithium hexane solution (3 equ) was added to a flask containing compound A10 (1 equ) and o-xylene (100 equ) at 0°C. After the addition was completed, the temperature was raised to 100°C and stirred for 4 hours, and then the hexane was distilled off. The mixture was cooled to -50°C and added 10 BBr (1 equ), then heated at room temperature and stirred for 1 hour. Thereafter, cooled again to 0°C and added N,N-diisopropylethylamine (10 equ), stirred at room temperature until the exotherm stopped, and heated and stirred at 120°C for 4 hours. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution and ethyl acetate were added for liquid separation. After the solvent was distilled off under reduced pressure and precipitated, it was purified by column chromatography, and then the solvent was removed under reduced pressure to obtain solid compound B-6, MS: [M+H] + =398; 1 HNMR (300MHz, CDCl 3 ): δ8.66-8.49(6H,m),8.03(1H,t),7.71-7.60(4H,m),7.21(2H,b),2.48(6H,s).

[0183] Example 7 Synthesis of Compound B-7

[0184]

[0185] In a nitrogen atmosphere, a 2.6 M n-butyllithium hexane solution (3 equ) was added to a flask containing compound A11 (1 equ) and o-xylene (100 equ) at 0°C. After the addition was completed, the temperature was raised to 100°C and stirred for 4 hours, and then the hexane was distilled off. The mixture was cooled to -50°C and added 10 BBr (1 equ), then heated at room temperature and stirred for 1 hour. Thereafter, cooled again to 0°C and added N,N-diisopropylethylamine (10 equ), stirred at room temperature until the exotherm stopped, and heated and stirred at 120°C for 4 hours. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution and ethyl acetate were added for liquid separation. After the solvent was distilled off under reduced pressure and precipitated, it was purified by column chromatography, and then the solvent was removed under reduced pressure to obtain solid compound B-7, MS: [M+H] + =536; 1 H NMR (300 MHz, CDCl 3): δ8.43-8.27(8H,m),7.99(1H,t),7.52-7.41(2H,m),3.54(6H,s),2.35(6H,s),2.21(4H,t),1.53(4H,m),1.30(4H,m),0.89(6H,t).

[0186] Example 8 Synthesis of Compound B-8

[0187]

[0188] In a nitrogen atmosphere, a 2.6 M n-butyllithium hexane solution (3 equ) was added to a flask containing compound A12 (1 equ) and o-xylene (100 equ) at 0°C. After the addition was completed, the temperature was raised to 100°C and stirred for 4 hours, and then the hexane was distilled off. The mixture was cooled to -50°C and added 10 BBr (1 equ), then heated at room temperature and stirred for 1 hour. Thereafter, cooled again to 0°C and added N,N-diisopropylethylamine (10 equ), stirred at room temperature until the exotherm stopped, and heated and stirred at 120°C for 4 hours. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution and ethyl acetate were added for liquid separation. After the solvent was distilled off under reduced pressure and precipitated, it was purified by column chromatography, and then the solvent was removed under reduced pressure to obtain solid compound B-8, MS: [M+H] + =374; 1 H NMR (300 MHz, CDCl 3 ): δ8.31-8.29(2H,m),7.35-7.11(6H,m),7.02(2H,m),6.88(1H,s)3.42(6H,s),2.31(6H,s).

[0189] Example 9 Synthesis of Compound B-9

[0190]

[0191] In a nitrogen atmosphere, a 2.6 M n-butyl lithium hexane solution (3 equ) was added to a flask containing compound A13 (1 equ) and o-xylene (100 equ) at 0°C. After the addition was completed, the temperature was raised to 100°C and stirred for 4 hours, and then the hexane was distilled off. The mixture was cooled to -50°C and added 10BBr (1 equ), then heated at room temperature and stirred for 1 hour. Thereafter, cooled again to 0°C and added N,N-diisopropylethylamine (10 equ), stirred at room temperature until the exotherm stopped, and heated and stirred at 120°C for 4 hours. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution and ethyl acetate were added for liquid separation. After the solvent was distilled off under reduced pressure and precipitated, it was purified by column chromatography, and then the solvent was removed under reduced pressure to obtain solid compound B-9, MS: [M+H] + =498; 1 H NMR (300 MHz, CDCl 3 ): δ8.11-8.02(2H,m),7.48-6.97(18H,m),7.02(2H,m),6.48(1H,s),2.40(6H,s).

[0192] Example 10 Synthesis of Compound B-10

[0193]

[0194] In a nitrogen atmosphere, a 2.6 M n-butyllithium hexane solution (6 equ) was added to a flask containing compound A14 (1 equ) and o-xylene (100 equ) at 0°C. After the addition was completed, the temperature was raised to 100°C and stirred for 4 hours, and then the hexane was distilled off. The mixture was cooled to -50°C and added 10 BBr (2 equ), then heated at room temperature and stirred for 1 hour. Thereafter, cooled again to 0°C and added N,N-diisopropylethylamine (10 equ), stirred at room temperature until the exotherm stopped, and heated and stirred at 120°C for 4 hours. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution and ethyl acetate were added for liquid separation. After the solvent was distilled off under reduced pressure and precipitated, it was purified by column chromatography, and then the solvent was removed under reduced pressure to obtain solid compound B-10, MS: [M+H] + =715; 1 H NMR (300 MHz, CDCl 3 ): δ7.41-7.05(10H,m),6.98-6.92(4H,m),4.13(3H,t),3.36(12H,s),2.39(6H,s),1.73(2H,m),1.20(2H,m),0.85(3H,t).

[0195] Example 11 Synthesis of Compound B-11

[0196]

[0197] In a nitrogen atmosphere, a 2.6 M n-butyllithium hexane solution (6 equ) was added to a flask containing compound A15 (1 equ) and o-xylene (100 equ) at 0°C. After the addition was completed, the temperature was raised to 100°C and stirred for 4 hours, and then the hexane was distilled off. The mixture was cooled to -50°C and added 10 BBr (2 equ), then heated at room temperature and stirred for 1 hour. Thereafter, cooled again to 0°C and added N,N-diisopropylethylamine (10 equ), stirred at room temperature until the exotherm stopped, and heated and stirred at 120°C for 4 hours. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution and ethyl acetate were added for liquid separation. After the solvent was distilled off under reduced pressure and precipitated, it was purified by column chromatography, and then the solvent was removed under reduced pressure to obtain solid compound B-11, MS: [M+H] + =518; 1 H NMR (300 MHz, CDCl 3 ): δ7.67-7.55(4H,m),7.23-6.81(8H,m),4.13(3H,t),3.36(12H,s),2.41(12H,s).

[0198] Example 12 Synthesis of Compound B-12

[0199]

[0200] In a nitrogen atmosphere, a 2.6 M n-butyllithium hexane solution (6 equ) was added to a flask containing compound A16 (1 equ) and o-xylene (100 equ) at 0°C. After the addition was completed, the temperature was raised to 100°C and stirred for 4 hours, and then the hexane was distilled off. The mixture was cooled to -50°C and added 10 BBr (2 equ), then heated at room temperature and stirred for 1 hour. Thereafter, cooled again to 0°C and added N,N-diisopropylethylamine (10 equ), stirred at room temperature until the exotherm stopped, and heated and stirred at 120°C for 4 hours. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution and ethyl acetate were added for liquid separation. After the solvent was distilled off under reduced pressure and precipitated, it was purified by column chromatography, and then the solvent was removed under reduced pressure to obtain solid compound B-12, MS: [M+H] + =570; 1 H NMR (300 MHz, CDCl 3 ): δ7.76-7.10(8H,m),7.02-6.88(4H,m),3.48(12H,s),2.42(12H,s).

[0201] Example 13 Synthesis of Compound B-13

[0202]

[0203] Under nitrogen protection, add freshly steamed compound A2 ether complex (1 equ) to a 250 ml three-necked flask and cool in an ice bath. Slowly add compound A3 (2 equ) and stir vigorously. After the addition is complete, stir at room temperature for 12 hours. Under nitrogen protection, slowly add compound A17 (3 equ) dropwise. After the addition is complete, stir for 12 hours. Add 50 ml of water to quench the reaction, extract with chloroform, dry the organic phase, and column chromatograph with petroleum ether as the developing solvent. Recrystallize from ethanol to obtain solid compound B-13, MS: [M+H]+=971; 1 HNMR (300MHz, CDCl 3 ): δ8.45-8.33(6H,m),7.61(3H,d),7.11(12H,s),2.40(36H,s),2.18(18H,s).

[0204] Example 14 Preparation and Characterization of OLED Devices

[0205] The materials used in each layer of the OLED device are as follows:

[0206]

[0207] The device structure is: ITO / HI(10nm) / HT-1(120nm) / HT-2(10nm) / BH:

[0208] BD (25nm) / ET: LiQ (30nm) / LiQ (1nm) / Al (100nm), the specific preparation steps are as follows:

[0209] a. Cleaning of the conductive glass substrate: When used for the first time, it can be cleaned with a variety of solvents, such as chloroform, ketone, isopropanol (electronic grade acetone is used for cleaning in this embodiment), and then subjected to ultraviolet ozone plasma treatment.

[0210] b. Preparation of each layer structure: The ITO substrate was moved into a vacuum vapor deposition device and heated in a high vacuum (1×10 -6 At 100 mbar, HT-1 and F4TCNQ were co-deposited at a ratio of 98:2 to form a 10 nm injection layer by resistive heating evaporation, followed by sequential evaporation to obtain 120 nm HT-1 and 10 nm HT-2 layers. BH and BD were then co-deposited at a ratio of 97:3 to form a 25 nm light-emitting layer. ET and LiQ were then placed in different evaporation units and co-deposited at a ratio of 50 wt %, respectively, to form a 30 nm electron transport layer on the light-emitting layer, followed by deposition of 1 nm LiQ as an electron injection layer on the electron transport layer, and finally a 100 nm thick Al cathode was deposited on the electron injection layer.

[0211] c. Packaging: The device is packaged with ultraviolet curing resin in a nitrogen glove box to obtain an OLED device.

[0212] All OLED devices except BD use different compounds as dopants, and other materials and preparation methods are the same. The current-voltage (JV) characteristics of each OLED device, i.e., the JV curve, are tested according to the general method, and the efficiency, life and voltage are recorded. After testing, the luminous efficiency and life of the obtained OLED device using the compound B-1 to the compound B-12 of the present invention as the dopant of the light-emitting layer material are improved compared with the materials in the comparative example, as shown in Table 1.

[0213] Compared with the compounds in the comparative examples, the organic compounds of the present invention contain boron-10 isotopes and have twisted molecular conjugated structures, that is, two adjacent aromatic rings connected to boron have substituents, which have large steric hindrance, so that the two adjacent aromatic rings connected to boron are not coplanar, forming a twisted conjugated structure. As can be seen from the data in Table 1, when the compounds of the present invention are used in electroluminescent devices, the blue light luminescence efficiency and life can be improved by introducing the boron-10 isotope combined with the twisted conjugated structure, thereby having a better luminescent effect and can be better applied to electroluminescent devices.

[0214] Table 1

[0215]

[0216] The above-mentioned embodiments only express several implementation methods of the present invention, and the descriptions thereof are relatively specific and detailed, but they cannot be understood as limiting the scope of the invention patent. It should be pointed out that, for ordinary technicians in this field, several variations and improvements can be made without departing from the concept of the present invention, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention shall be subject to the attached claims.

Claims

1. An organic compound containing boron-10 isotope as represented by general formula (I-1), (I-2) or (I-3) or a stereoisomer thereof: in, Each Y 1 , Y 2 , Y 3 are independently selected from any one of N and B, and at least one of them is B, and the B element 10 The atomic abundance of B is greater than 90%; Each X 1 , X 2 , X 3 , X 4 , X 5 , X 6 Each independently selected from: O, NR 1 , S, or does not exist, wherein the non-existence refers to A 2 , A 3 , A 4 , A 5 , A 6 and / or A 7 With A 1 There is no chemical bond between them; Each A 1 are independently selected from: substituted or unsubstituted C6 to C 40 Aryl, substituted or unsubstituted 5-40 membered heteroaryl; Each A 2 , A 3 , A 4 , A 5 , A 6 , A 7 Each independently selected from: substituted C6~C 40 Aryl, substituted 5-40 membered heteroaryl; Each R 1 Each independently selected from: H, D, R substituted or unsubstituted C1~C 20 Alkyl, R substituted or unsubstituted C1~C 20 Alkoxy, R substituted or unsubstituted C1~C 20 Alkylthio, R substituted or unsubstituted C3~C 20 Cycloalkyl, R substituted or unsubstituted C3~C 20 Cycloalkoxy, R substituted or unsubstituted C3~C 20 Cycloalkylthio, R substituted or unsubstituted C3~C 20 Silane group, R substituted or unsubstituted C1~C 20 Alkylcarbonyl, R substituted or unsubstituted C1~C 20 Alkoxycarbonyl, R substituted or unsubstituted C6~C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 40 Aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C6~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy; Each R is independently selected from: hydroxyl, halogen, C1-C 20 Alkyl, C1~C 20 Alkoxy, C1~C 20 Alkylthio, C3~C 20 Cycloalkyl, C3~C 20 Cycloalkoxy, C3~C 20 Cycloalkylthio, C1~C 20 Alkylcarbonyl, C1~C 20 Alkoxycarbonyl, C6~C 20 Aryloxycarbonyl, C6~C 40 Aryl, 5-40 membered heteroaryl, C6~C 40 Aryloxy, 5-40 membered heteroaryloxy.

2. The organic compound containing boron-10 isotope or its stereoisomer according to claim 1, characterized in that: Each A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 are independently selected from the following ring structures: Wherein, each W is independently selected from: N, CR 2 , C=O; Each X 7 Each independently selected from: CR 3 2. C=O, O, S, S=O, S=(O)2, NR 3 ; Each R 2 , R 3 Each independently selected from: H, D, R substituted or unsubstituted C1~C 20 Alkyl, R substituted or unsubstituted C1~C 20 Alkoxy, R substituted or unsubstituted C1~C 20 Alkylthio, R substituted or unsubstituted C3~C 20 Cycloalkyl, R substituted or unsubstituted C3~C 20 Cycloalkoxy, R substituted or unsubstituted C3~C 20 Cycloalkylthio, R substituted or unsubstituted C3~C 20 Silane group, R substituted or unsubstituted C1~C 20 Alkylcarbonyl, R substituted or unsubstituted C1~C 20 Alkoxycarbonyl, R substituted or unsubstituted C6~C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 40 Aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C6~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy, or two adjacent R 2 and / or R 3 Can be connected to form a ring; A 2 , A 3 , A 4 , A 5 , A 6 , A 7 Each ring in has at least one R that is not H or D. 2 or R 3 .

3. The organic compound containing boron-10 isotope or its stereoisomer according to claim 1, characterized in that: The organic compound containing boron-10 isotope is selected from the following structural formula: Wherein, each W is independently selected from: N, CR 2 , C=O; Each R 2 Selected from: H, D, R substituted or unsubstituted C1~C 20 Alkyl, R substituted or unsubstituted C1~C 20 Alkoxy, R substituted or unsubstituted C1~C 20 Alkylthio, R substituted or unsubstituted C3~C 20 Cycloalkyl, R substituted or unsubstituted C3~C 20 Cycloalkoxy, R substituted or unsubstituted C3~C 20 Cycloalkylthio, R substituted or unsubstituted C3~C 20 Silane group, R substituted or unsubstituted C1~C 20 Alkylcarbonyl, R substituted or unsubstituted C1~C 20 Alkoxycarbonyl, R substituted or unsubstituted C6~C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 40 Aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C6~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy, or two adjacent R 2 Can be connected to form a ring; Each R 4 are independently selected from: R substituted or unsubstituted C1 to C 20 Alkyl, R substituted or unsubstituted C1~C 20 Alkoxy, R substituted or unsubstituted C1~C 20 Alkylthio, R substituted or unsubstituted C3~C 20 Cycloalkyl, R substituted or unsubstituted C3~C 20 Cycloalkoxy, R substituted or unsubstituted C3~C 20 Cycloalkylthio, R substituted or unsubstituted C3~C 20 Silane group, R substituted or unsubstituted C1~C 20 Alkylcarbonyl, R substituted or unsubstituted C1~C 20 Alkoxycarbonyl, R substituted or unsubstituted C6~C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 40 Aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C6~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy; Each R 5 , R 6 Each independently selected from: H, D, R substituted or unsubstituted C1~C 20 Alkyl, R substituted or unsubstituted C1~C 20 Alkoxy, R substituted or unsubstituted C1~C 20 Alkylthio, R substituted or unsubstituted C3~C 20 Cycloalkyl, R substituted or unsubstituted C3~C 20 Cycloalkoxy, R substituted or unsubstituted C3~C 20 Cycloalkylthio, R substituted or unsubstituted C3~C 20 Silane group, R substituted or unsubstituted C1~C 20 Alkylcarbonyl, R substituted or unsubstituted C1~C 20 Alkoxycarbonyl, R substituted or unsubstituted C6~C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 40 Aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C6~C 40 aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy; and R 5 , R 6 Not H and / or D at the same time; Each R 7 Each independently selected from: H, D, R substituted or unsubstituted C1~C 20 Alkyl, R substituted or unsubstituted C1~C 20 Alkoxy, R substituted or unsubstituted C1~C 20 Alkylthio, R substituted or unsubstituted C3~C 20 Cycloalkyl, R substituted or unsubstituted C3~C 20 Cycloalkoxy, R substituted or unsubstituted C3~C 20 Cycloalkylthio, R substituted or unsubstituted C3~C 20 Silane group, R substituted or unsubstituted C1~C 20 Alkylcarbonyl, R substituted or unsubstituted C1~C 20 Alkoxycarbonyl, R substituted or unsubstituted C6~C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 40 Aryl, R substituted or unsubstituted 5-40 membered heteroaryl, R substituted or unsubstituted C6~C 40 Aryloxy, R substituted or unsubstituted 5-40 membered heteroaryloxy.

4. The organic compound containing boron-10 isotope or its stereoisomer according to any one of claims 1 to 3, characterized in that: The aromatic or heteroaromatic groups are independently selected from the group consisting of benzene, biphenyl, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridine, pyrimidine, triazine, fluorene, dithiophene, silafluorene, carbazole, thiophene, furan, thiazole, triphenylamine, triphenylphosphine, tetraphenylsilane, spirofluorene, spirosiliconfluorene, pyrazine, oxadiazole and their derivatives.

5. The organic compound containing boron-10 isotope or its stereoisomer according to claim 2 or 3, characterized in that: Each W is independently selected from: N, CR 2 , C=O; Each X 7 Each independently selected from: CR 3 2. C=O, O, S, S=O, S=(O)2, NR 3 '; Each R 2 , R 3 R substituted or unsubstituted C1-C6 alkyl, R substituted or unsubstituted C1-C6 alkoxy, R substituted or unsubstituted C1-C6 alkylthio, R substituted or unsubstituted C3-C8 cycloalkyl, R substituted or unsubstituted C3-C8 cycloalkyloxy, R substituted or unsubstituted C3-C8 cycloalkylthio, R substituted or unsubstituted C1-C6 alkylcarbonyl, R substituted or unsubstituted C1-C6 alkoxycarbonyl, R substituted or unsubstituted C6-C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 20 Aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C6~C 20 Aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy, or two adjacent R 2 They may be linked to form a 5-20 membered cycloalkyl or heterocyclic ring group; Each R 3 'are independently selected from: H, D, R substituted or unsubstituted C1~C6 alkyl, R substituted or unsubstituted C3~C8 cycloalkyl, R substituted or unsubstituted C1~C6 alkylcarbonyl, R substituted or unsubstituted C1~C6 alkoxycarbonyl, R substituted or unsubstituted C6~C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 20 Aryl, R substituted or unsubstituted 5-20 membered heteroaryl; Each R is independently selected from the group consisting of hydroxyl, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, C3-C8 cycloalkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C6-C 20 Aryloxycarbonyl, C6~C 20 Aryl, 5-20 membered heteroaryl, C6~C 20 Aryloxy, 5-20 membered heteroaryloxy; A 2 , A 3 , A 4 , A 5 , A 6 , A 7 Each ring in has at least one R that is not H or D. 2 .

6. The organic compound containing boron-10 isotope or its stereoisomer according to claim 5, characterized in that: Each W is independently selected from: CH, CD, CR 2 ; Each X 7 Each independently selected from: C=O, O, S, S=O, S=(O)2, NR 3 '; Each R 2 R substituted or unsubstituted C1-C4 alkyl, R substituted or unsubstituted C1-C3 alkoxy, R substituted or unsubstituted C1-C3 alkylthio, R substituted or unsubstituted C3-C6 cycloalkyl, R substituted or unsubstituted C3-C6 cycloalkoxy, R substituted or unsubstituted C3-C6 cycloalkylthio, R substituted or unsubstituted C1-C3 alkylcarbonyl, R substituted or unsubstituted C1-C3 alkoxycarbonyl, R substituted or unsubstituted C6-C 10 Aryloxycarbonyl, R substituted or unsubstituted C6~C 10 Aryl, R substituted or unsubstituted 5-10 membered heteroaryl, R substituted or unsubstituted C6~C 10 Aryloxy, R substituted or unsubstituted 5-10 membered heteroaryloxy, or two adjacent R 2 They may be linked to form a 5-8 membered cycloalkyl or heterocyclic ring group; Each R 3 'are independently selected from: H, D, R substituted or unsubstituted C1~C3 alkyl, R substituted or unsubstituted C3~C6 cycloalkyl, R substituted or unsubstituted C1~C3 alkylcarbonyl, R substituted or unsubstituted C1~C3 alkoxycarbonyl, R substituted or unsubstituted C6~C 10 Aryloxycarbonyl, R substituted or unsubstituted C6~C 10 Aryl, R substituted or unsubstituted 5-10 membered heteroaryl; Each R is independently selected from the group consisting of hydroxyl, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C3-C6 cycloalkylthio, C1-C3 alkylcarbonyl, C1-C3 alkoxycarbonyl, C6-C 10 Aryloxycarbonyl, C6~C 10 Aryl, 5-10 membered heteroaryl, C6~C 10 Aryloxy, 5-10 membered heteroaryloxy; A 2 , A 3 , A 4 , A 5 , A 6 , A 7 On each ring in the 2 .

7. The organic compound containing boron-10 isotope or its stereoisomer according to claim 3, characterized in that: Each R 4 are independently selected from: R substituted or unsubstituted C1-C6 alkyl, R substituted or unsubstituted C1-C6 alkoxy, R substituted or unsubstituted C1-C6 alkylthio, R substituted or unsubstituted C3-C8 cycloalkyl, R substituted or unsubstituted C3-C8 cycloalkyloxy, R substituted or unsubstituted C3-C8 cycloalkylthio, R substituted or unsubstituted C1-C6 alkylcarbonyl, R substituted or unsubstituted C1-C6 alkoxycarbonyl, R substituted or unsubstituted C6-C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 20 Aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C6~C 20 Aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy; and / or, Each R 5 , R 6 R substituted or unsubstituted C1-C6 alkyl, R substituted or unsubstituted C1-C6 alkoxy, R substituted or unsubstituted C1-C6 alkylthio, R substituted or unsubstituted C3-C8 cycloalkyl, R substituted or unsubstituted C3-C8 cycloalkyloxy, R substituted or unsubstituted C3-C8 cycloalkylthio, R substituted or unsubstituted C1-C6 alkylcarbonyl, R substituted or unsubstituted C1-C6 alkoxycarbonyl, R substituted or unsubstituted C6-C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 20 Aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C6~C 20 aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy; and R 5 , R 6 is not H and / or D at the same time; and / or, Each R 7 R substituted or unsubstituted C1-C6 alkyl, R substituted or unsubstituted C1-C6 alkoxy, R substituted or unsubstituted C1-C6 alkylthio, R substituted or unsubstituted C3-C8 cycloalkyl, R substituted or unsubstituted C3-C8 cycloalkyloxy, R substituted or unsubstituted C3-C8 cycloalkylthio, R substituted or unsubstituted C1-C6 alkylcarbonyl, R substituted or unsubstituted C1-C6 alkoxycarbonyl, R substituted or unsubstituted C6-C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 20 Aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C6~C 20 Aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy; and / or, Each R is independently selected from the group consisting of hydroxyl, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, C3-C8 cycloalkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C6-C 20 Aryloxycarbonyl, C6~C 20 Aryl, 5-20 membered heteroaryl, C6~C 20 Aryloxy, 5-20 membered heteroaryloxy.

8. The organic compound containing boron-10 isotope or its stereoisomer according to claim 7, characterized in that: Each R 4 R substituted or unsubstituted C1-C4 alkyl, R substituted or unsubstituted C1-C3 alkoxy, R substituted or unsubstituted C1-C3 alkylthio, R substituted or unsubstituted C3-C6 cycloalkyl, R substituted or unsubstituted C3-C6 cycloalkoxy, R substituted or unsubstituted C3-C6 cycloalkylthio, R substituted or unsubstituted C1-C3 alkylcarbonyl, R substituted or unsubstituted C1-C3 alkoxycarbonyl, R substituted or unsubstituted C6-C 10 Aryloxycarbonyl, R substituted or unsubstituted C6~C 10 Aryl, R substituted or unsubstituted 5-10 membered heteroaryl, R substituted or unsubstituted C6~C 10 Aryloxy, R substituted or unsubstituted 5-10 membered heteroaryloxy; and / or, Each R 5 , R 6 R substituted or unsubstituted C1-C4 alkyl, R substituted or unsubstituted C1-C3 alkoxy, R substituted or unsubstituted C1-C3 alkylthio, R substituted or unsubstituted C3-C6 cycloalkyl, R substituted or unsubstituted C3-C6 cycloalkyloxy, R substituted or unsubstituted C3-C6 cycloalkylthio, R substituted or unsubstituted C1-C3 alkylcarbonyl, R substituted or unsubstituted C1-C3 alkoxycarbonyl, R substituted or unsubstituted C6-C 10 Aryloxycarbonyl, R substituted or unsubstituted C6~C 10 Aryl, R substituted or unsubstituted 5-10 membered heteroaryl, R substituted or unsubstituted C6~C 10 aryloxy, R substituted or unsubstituted 5-10 membered heteroaryloxy; and R 5 , R 6 is not H and / or D at the same time; and / or, Each R 7 R substituted or unsubstituted C1-C4 alkyl, R substituted or unsubstituted C1-C3 alkoxy, R substituted or unsubstituted C1-C3 alkylthio, R substituted or unsubstituted C3-C6 cycloalkyl, R substituted or unsubstituted C3-C6 cycloalkyloxy, R substituted or unsubstituted C3-C6 cycloalkylthio, R substituted or unsubstituted C1-C3 alkylcarbonyl, R substituted or unsubstituted C1-C3 alkoxycarbonyl, R substituted or unsubstituted C6-C 10 Aryloxycarbonyl, R substituted or unsubstituted C6~C 10 Aryl, R substituted or unsubstituted 5-10 membered heteroaryl, R substituted or unsubstituted C6~C 10 Aryloxy, R substituted or unsubstituted 5-10 membered heteroaryloxy; and / or, Each R is independently selected from the group consisting of hydroxyl, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C3-C6 cycloalkylthio, C1-C3 alkylcarbonyl, C1-C3 alkoxycarbonyl, C6-C 10 Aryloxycarbonyl, C6~C 10 Aryl, 5-10 membered heteroaryl, C6~C 10 Aryloxy, 5-10 membered heteroaryloxy.

9. The organic compound containing boron-10 isotope or its stereoisomer according to any one of claims 1 to 3, characterized in that: Each X 1 , X 2 , X 3 , X 4 , X 5 , X 6 Each independently selected from: O, NR 1 , S, or does not exist; Each R 1 R substituted or unsubstituted C1-C6 alkyl, R substituted or unsubstituted C1-C6 alkoxy, R substituted or unsubstituted C1-C6 alkylthio, R substituted or unsubstituted C3-C8 cycloalkyl, R substituted or unsubstituted C3-C8 cycloalkyloxy, R substituted or unsubstituted C3-C8 cycloalkylthio, R substituted or unsubstituted C1-C6 alkylcarbonyl, R substituted or unsubstituted C1-C6 alkoxycarbonyl, R substituted or unsubstituted C6-C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 20 Aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C6~C 20 Aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy; Each R is independently selected from the group consisting of hydroxyl, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, C3-C8 cycloalkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C6-C 20 Aryloxycarbonyl, C6~C 20 Aryl, 5-20 membered heteroaryl, C6~C 20 Aryloxy, 5-20 membered heteroaryloxy; Preferably, each R 1 Each of them is independently selected from: H, D, C1-C6 alkyl, phenyl, and naphthyl.

10. The organic compound containing boron-10 isotope or its stereoisomer according to any one of claims 1 to 3, characterized in that: The organic compound containing boron-10 isotope is selected from the following formula (II-1), formula (II-2), formula (II-3), formula (II-4), formula (II-5), formula (II-6), formula (II-7) or formula (II-8): Among them, X 1 , X 2 , X 3 , X 4 Each independently selected from: O, NR 1 , S; Each R 3 'are independently selected from: H, D, R substituted or unsubstituted C1~C6 alkyl, R substituted or unsubstituted C3~C8 cycloalkyl, R substituted or unsubstituted C1~C6 alkylcarbonyl, R substituted or unsubstituted C1~C6 alkoxycarbonyl, R substituted or unsubstituted C6~C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 20 Aryl, R substituted or unsubstituted 5-20 membered heteroaryl; Each R is independently selected from the group consisting of hydroxyl, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, C3-C8 cycloalkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C6-C 20 Aryloxycarbonyl, C6~C 20 Aryl, 5-20 membered heteroaryl, C6~C 20 Aryloxy, 5-20 membered heteroaryloxy; R 8 Selected from: R 2 or 11. The organic compound containing boron-10 isotope or its stereoisomer according to claim 10, characterized in that: X 1 , X 2 , X 3 , X 4 Each independently selected from: O, NR 1 , S; Each R 1 R substituted or unsubstituted C1-C6 alkyl, R substituted or unsubstituted C1-C6 alkoxy, R substituted or unsubstituted C1-C6 alkylthio, R substituted or unsubstituted C3-C8 cycloalkyl, R substituted or unsubstituted C3-C8 cycloalkyloxy, R substituted or unsubstituted C3-C8 cycloalkylthio, R substituted or unsubstituted C1-C6 alkylcarbonyl, R substituted or unsubstituted C1-C6 alkoxycarbonyl, R substituted or unsubstituted C6-C 20 Aryloxycarbonyl, R substituted or unsubstituted C6~C 20 Aryl, R substituted or unsubstituted 5-20 membered heteroaryl, R substituted or unsubstituted C6~C 20 Aryloxy, R substituted or unsubstituted 5-20 membered heteroaryloxy; Each R is independently selected from the group consisting of hydroxyl, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, C3-C8 cycloalkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C6-C 20 Aryloxycarbonyl, C6~C 20 Aryl, 5-20 membered heteroaryl, C6~C 20 Aryloxy, 5-20 membered heteroaryloxy; Preferably, each R 1 Each of them is independently selected from: H, D, C1-C6 alkyl, phenyl, and naphthyl.

12. The organic compound containing boron-10 isotope or its stereoisomer according to claim 10, characterized in that: Each W is independently selected from: CH, CD, CR 2 ; Each R 2 Each of the following is independently selected from: C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C3-C8 cycloalkyl, C3-C8 cycloalkyloxy, C3-C8 cycloalkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C6-C 20 Aryloxycarbonyl, C6~C 20 Aryl, 5-20 membered heteroaryl, C6~C 20 Aryloxy, 5-20 membered heteroaryloxy; Preferably, each R 2 Each of the following is independently selected from the group consisting of: methyl, ethyl, propyl, butyl, phenyl, and naphthyl.

13. The organic compound containing boron-10 isotope or its stereoisomer according to claim 10, characterized in that: Each R 3 'are independently selected from: H, D, C1~C6 alkyl, C6~C 10 Aryl; and / or Each R 4 Each of the following is independently selected from: C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C3-C8 cycloalkyl, C3-C8 cycloalkyloxy, C3-C8 cycloalkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C6-C 20 Aryloxycarbonyl, C6~C 20 Aryl, 5-20 membered heteroaryl, C6~C 20 Aryloxy, 5-20 membered heteroaryloxy; and / or, Each R 5 , R 6 Each of the following is independently selected from: H, D, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C3-C8 cycloalkyl, C3-C8 cycloalkyloxy, C3-C8 cycloalkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C6-C 20 Aryloxycarbonyl, C6~C 20 Aryl, 5-20 membered heteroaryl, C6~C 20 aryloxy, 5-20 membered heteroaryloxy; and R 5 , R 6 is not H and / or D at the same time; and / or, Each R 7 Each of the following is independently selected from: H, D, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C3-C8 cycloalkyl, C3-C8 cycloalkyloxy, C3-C8 cycloalkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C6-C 20 Aryloxycarbonyl, C6~C 20 Aryl, 5-20 membered heteroaryl, C6~C 20 Aryloxy, 5-20 membered heteroaryloxy.

14. The organic compound containing boron-10 isotope or its stereoisomer according to claim 13, characterized in that: Each R 3 'are independently selected from: H, D, methyl, ethyl, propyl, butyl, phenyl, naphthyl; and / or, Each R 4 are independently selected from: methyl, ethyl, propyl, butyl, phenyl, naphthyl; and / or, Each R 5 , R 6 are independently selected from: H, D, methyl, ethyl, propyl, butyl, phenyl, naphthyl; and R 5 , R 6 is not H and / or D at the same time; and / or, Each R 7 Each of the following is independently selected from the group consisting of: H, D, methyl, ethyl, propyl, butyl, phenyl, and naphthyl.

15. The organic compound containing boron-10 isotope or its stereoisomer according to claim 1, characterized in that: Selected from the following compounds:

16. The organic compound containing boron-10 isotope or its stereoisomer according to claim 1, characterized in that: Selected from the following compounds:

17. A mixture, characterized in that It comprises at least one organic compound containing boron-10 isotope as described in any one of claims 1 to 16, and another organic functional material; the other organic functional material is selected from: at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent material, a host material and an organic dye.

18. A composition, characterized in that The method comprises at least one mixture according to claim 17 or at least one organic compound containing boron-10 isotope according to any one of claims 1 to 16, and at least one organic solvent.

19. Use of the organic compound containing boron-10 isotope or its stereoisomer according to any one of claims 1 to 16, or the mixture according to claim 17, or the composition according to claim 18 as a functional material in the preparation of a functional layer of an organic electronic device or an organic electronic device; Preferably, the functional layers of the organic electronic device include a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and a light-emitting layer; Preferably, the organic electronic device is selected from: an organic light emitting diode, an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor and an organic plasmon emission diode.

20. An organic electronic device, characterized in that: An organic compound containing a boron-10 isotope or a stereoisomer thereof according to any one of claims 1 to 16, or a mixture according to claim 17, or a composition according to claim 18; Preferably, the functional layer of the organic electronic device comprises the organic compound containing boron-10 isotope or its stereoisomer according to any one of claims 1 to 16; Preferably, the functional layer of the organic electronic device is a light-emitting layer; Preferably, the organic electronic device is an organic light emitting diode, an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor and an organic plasmon emission diode.

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