Boron-containing organic compound and organic electroluminescent device prepared from same

Abstract

The invention relates to a boron-containing organic compound and an organic electroluminescent device prepared from the boron-containing organic compound, belongs to the technical field of semiconductors, and provides the boron-containing organic compound with a structure shown as a general formula (A): # imgabs0. The compound disclosed by the invention is used as a doping material in a luminescent layer material of the organic electroluminescent device; the material can be used as a luminescent layer green light doping material of an organic electroluminescent device to emit green light.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and particularly to a boron-containing organic compound and an organic electroluminescent device prepared therefrom. Background Art

[0002] Limited by early technologies, traditional fluorescent doping materials can only utilize 25% of singlet excitons formed by electrical excitation for luminescence. The internal quantum efficiency of the device is relatively low (up to 25%), and the external quantum efficiency is generally lower than 5%, showing a significant gap compared with the efficiency of phosphorescent devices. Due to the strong spin-orbit coupling of heavy atom centers, phosphorescent materials can enhance intersystem crossing, effectively utilize both singlet excitons and triplet excitons formed by electrical excitation for luminescence, and achieve an internal quantum efficiency of 100% for the device. However, most phosphorescent materials are expensive, with poor material stability, poor color purity, and serious device efficiency roll-off, which limit their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements are put forward for the color rendering standard. In addition to high efficiency and stability, luminescent materials also require a narrower full width at half maximum to improve the color purity of device luminescence. Fluorescent doping materials can achieve high fluorescence quantum yield and narrow full width at half maximum through molecular engineering. Breakthroughs have been achieved in blue fluorescent doping materials, and the full width at half maximum of boron-based materials can be reduced to less than 30 nm. In the green light region, to which the human eye is more sensitive, research mainly focuses on phosphorescent doping materials, but it is difficult to narrow their emission peak shape through simple methods. Therefore, it is of great significance to study highly efficient green fluorescent doping materials with narrow full width at half maximum to meet higher color rendering standards.

[0004] In addition, the sensitization technology combines triplet exciton sensitizing materials with fluorescent doping materials. Using triplet exciton sensitizing materials as the exciton sensitization medium, triplet excitons are fully utilized, and the energy is transferred to the fluorescent doping materials through energy transfer, which can also achieve an internal quantum efficiency of 100% for the device. This technology can make up for the deficiency of the exciton utilization rate of fluorescent doping materials and effectively exert the characteristics of high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects in the application of OLEDs.

[0005] Boron compounds with resonance structures are more likely to achieve narrow full-width at half-maximum (FWHM) luminescence. When such materials are applied in sensitization technologies, devices with high efficiency and narrow FWHM emission can be fabricated. For example, in CN 107507921 A and CN 110492006 A, a luminescent layer combination technology is disclosed, which uses a thermally activated delayed fluorescence (TADF) material with a lowest singlet-triplet energy level difference less than or equal to 0.2 eV as the host and a boron-containing material as the dopant; in CN 110492005 A and CN 110492009 A, a luminescent layer combination scheme is disclosed, which uses an exciplex as the host and a boron-containing material as the dopant; both can achieve efficiency comparable to phosphorescence and a relatively narrow FWHM. Developing sensitization technologies based on narrow FWHM boron-based luminescent materials has unique advantages and strong potential in meeting the BT.2020 display standards. Summary of the Invention

[0006] In view of the above problems existing in the prior art, the present invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention can be used as a dopant material for the luminescent layer of an organic electroluminescent device, emitting green light.

[0007] The technical solution of the present invention is as follows: A boron-containing organic compound, the structure of the boron-containing organic compound is shown in the general formula (A):

[0008]

[0009] In the general formula (A), R5-R 15 Each occurrence, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 30 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0010] R5-R 13 Any two adjacent ones of them can be connected to form a ring;

[0011] R 14 and R 15 can be connected to form a ring;

[0012] Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 each independently represent, each occurrence being the same or different, a hydrogen atom, a C1-C alkyl group which may or may not be substituted by R, a C3-C cycloalkyl group which may or may not be substituted by R, a C2-C alkenyl group which may or may not be substituted by R, a C2-C alkynyl group which may or may not be substituted by R, a silyl group which may or may not be substituted by R, a boranyl group which may or may not be substituted by R, a C1-C alkoxy group which may or may not be substituted by R, a C6-C aryloxy group which may or may not be substituted by R, an arylamino group which may or may not be substituted by R, a C6-C aryl group which may or may not be substituted by R, or a heteroaryl group which may or may not be substituted by R; 10 a C3-C cycloalkyl group which may or may not be substituted by R, 10 a C2-C alkenyl group which may or may not be substituted by R, 10 a C2-C alkynyl group which may or may not be substituted by R, a silyl group which may or may not be substituted by R, a boranyl group which may or may not be substituted by R, a C1-C alkoxy group which may or may not be substituted by R, 10 a C6-C aryloxy group which may or may not be substituted by R, an arylamino group which may or may not be substituted by R, a C6-C aryl group which may or may not be substituted by R, or a heteroaryl group which may or may not be substituted by R; 10 a C6-C aryloxy group which may or may not be substituted by R, 30 an arylamino group which may or may not be substituted by R, a C6-C aryl group which may or may not be substituted by R, or a heteroaryl group which may or may not be substituted by R; 30 a C6-C aryl group which may or may not be substituted by R, 30 or a heteroaryl group which may or may not be substituted by R;

[0013] Each occurrence of R, each occurrence being the same or different, represents a deuterium atom, a halogen atom, a cyano group, a C1-C alkyl group which may or may not be substituted, a C3-C cycloalkyl group which may or may not be substituted, a C2-C alkenyl group which may or may not be substituted, a C2-C alkynyl group which may or may not be substituted, a silyl group which may or may not be substituted, a boranyl group which may or may not be substituted, a C1-C alkoxy group which may or may not be substituted, a C6-C aryloxy group which may or may not be substituted, an arylamino group which may or may not be substituted, a C6-C aryl group which may or may not be substituted, or a heteroaryl group which may or may not be substituted; 10 a C3-C cycloalkyl group which may or may not be substituted, 10 a C2-C alkenyl group which may or may not be substituted, 10 a C2-C alkynyl group which may or may not be substituted, a silyl group which may or may not be substituted, a boranyl group which may or may not be substituted, a C1-C alkoxy group which may or may not be substituted, 10 a C6-C aryloxy group which may or may not be substituted, an arylamino group which may or may not be substituted, a C6-C aryl group which may or may not be substituted, or a heteroaryl group which may or may not be substituted; 10 a C6-C aryloxy group which may or may not be substituted, 30 an arylamino group which may or may not be substituted, a C6-C aryl group which may or may not be substituted, or a heteroaryl group which may or may not be substituted; 30 a C6-C aryl group which may or may not be substituted, 30 or a heteroaryl group which may or may not be substituted;

[0014] Ar3 and Ar4 may be joined to form a ring;

[0015] Ar4 and Ar5 may be joined to form a ring;

[0016] M1, M2, and M3 each independently represent a substituted or unsubstituted C6-C aromatic ring, a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, or a substituted or unsubstituted C6-C aliphatic ring; 30 a substituted or unsubstituted C6-C aromatic ring, 10 a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, or a substituted or unsubstituted C6-C aliphatic ring;

[0017] X represents C or Si;

[0018] The substituents for the substituents of the groups are each independently selected from deuterium, a halogen atom, a cyano group, a C1-C alkyl group, a deuterium-substituted C1-C alkyl group, a C6-C aryl group, or a deuterium-substituted C6-C aryl group; 10 a deuterium-substituted C1-C alkyl group, 10 a C6-C aryl group, 30 a deuterium-substituted C6-C aryl group; 30Aryl, C2-C 30 Heteroaryl, deuterium-substituted C2-C 30 Any one of heteroaryls.

[0019] Furthermore, in general formula (A), R5-R 15 Each occurrence, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, a substituted or unsubstituted C3-C 10 Cycloalkyl, a substituted or unsubstituted C2-C 10 Alkenyl, a substituted or unsubstituted C2-C 10 Alkynyl, a substituted or unsubstituted silyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 Alkoxy, a substituted or unsubstituted C6-C 30 Aryloxy, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 Aryl, a substituted or unsubstituted C2-C 30 One of heteroaryls;

[0020] R5-R 13 Any two adjacent ones of which may be connected to form a ring;

[0021] R 14 And R 15 May be connected to form a ring;

[0022] Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, each occurrence, which may be the same or different, represents a hydrogen atom, a substituted or unsubstituted C1-C 10 Alkyl, a substituted or unsubstituted C3-C 10 Cycloalkyl, a substituted or unsubstituted C2-C 10 Alkenyl, a substituted or unsubstituted C2-C 10 Alkynyl, a substituted or unsubstituted silyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 Alkoxy, a substituted or unsubstituted C6-C 30 Aryloxy, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 Aryl, a substituted or unsubstituted C2-C 30 One of heteroaryls;

[0023] Ar3 and Ar4 may be connected to form a ring;

[0024] Ar4 and Ar5 may be connected to form a ring;

[0025] M1, M2, M3 each independently represents a substituted or unsubstituted C6-C 30of an aromatic ring, a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, a substituted or unsubstituted C6-C 10 one of aliphatic rings;

[0026] X represents C, Si;

[0027] The substituents for the substituting groups are each independently selected from deuterium, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C2-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group.

[0028] Preferably, any two adjacent ones of R5-R 13 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )- or -C(R f )=C(R g )-;

[0029] R 14 and R 15 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )- or -C(R f )=C(R g )-;

[0030] Ar3 and Ar4 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )- or -C(R f )=C(R g )-;

[0031] Ar4 and Ar5 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(Rd R e )- or -C(R f )=C(R g )-linked;

[0032] The said R a , R b , R c , R d , R e , R f , R g are each independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 - C 10 alkyl group, a substituted or unsubstituted C3 - C 10 cycloalkyl group, a substituted or unsubstituted C2 - C 10 alkenyl group, a substituted or unsubstituted C6 - C 30 aryl group, a substituted or unsubstituted C2 - C 30 heteroaryl group;

[0033] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1 - C 10 alkyl group, a deuterium-substituted C1 - C 10 alkyl group, a C3 - C 10 cycloalkyl group, a C6 - C 30 aryl group, a deuterium-substituted C6 - C 30 aryl group, a C5 - C 30 heteroaryl group, a deuterium-substituted C2 - C 30 heteroaryl group, or any one or more of them.

[0034] Furthermore, the structure of the boron-containing organic compound is represented by general formula (A-1) or general formula (A-2):

[0035]

[0036] In general formula (A-1) and general formula (A-2), R1 - R 15 each occurrence, whether the same or different, is represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 - C 10 alkyl group, a substituted or unsubstituted C3 - C 10 cycloalkyl group, a substituted or unsubstituted C1 - C 10 alkoxy group, a substituted or unsubstituted C6 - C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6 - C 30 aryl group, a substituted or unsubstituted C2 - C 30 heteroaryl group;

[0037] R1 - R 13Any two adjacent ones among them can be connected to form a ring;

[0038] R 14 and R 15 can be connected to form a ring;

[0039] Each occurrence of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, which may be the same or different, represents a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0040] M1 represents a substituted or unsubstituted C6-C 30 aryl ring, a substituted or unsubstituted 5- to 30-membered heteroaryl ring, a substituted or unsubstituted C6-C 10 aliphatic ring;

[0041] X represents C or Si;

[0042] The substituents for the substituent groups are each independently selected from deuterium, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C2-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group.

[0043] Preferably, any two adjacent ones among R1-R 13 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )- or -C(R f )=C(R g )-;

[0044] R 14 and R 15 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(Rd R e )- or -C(R f )=C(R g )-linked;

[0045] Said R a , R b , R c , R d , R e , R f , R g are each independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 - C 10 alkyl group, a substituted or unsubstituted C3 - C 10 cycloalkyl group, a substituted or unsubstituted C2 - C 10 alkenyl group, a substituted or unsubstituted C6 - C 30 aryl group, a substituted or unsubstituted C2 - C 30 heteroaryl group;

[0046] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1 - C 10 alkyl group, a deuterium-substituted C1 - C 10 alkyl group, a C3 - C 10 cycloalkyl group, a C6 - C 30 aryl group, a deuterium-substituted C6 - C 30 aryl group, a C5 - C 30 heteroaryl group, a deuterium-substituted C2 - C 30 heteroaryl group, any one or more thereof.

[0047] Furthermore, the structure of the boron-containing organic compound is represented by any one of general formula (1-1) to general formula (1-4):

[0048]

[0049]

[0050] In general formula (1-1) to general formula (1-4), R1 - R 17 each occurrence, whether the same or different, is represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 - C 10 alkyl group, a substituted or unsubstituted C3 - C 10 cycloalkyl group, a substituted or unsubstituted C1 - C 10 alkoxy group, a substituted or unsubstituted C6 - C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6 - C 30 aryl group, a substituted or unsubstituted C2 - C 30 heteroaryl group;

[0051] R1-R 17 Any two adjacent ones among them can be connected to form a ring;

[0052] Each occurrence of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, which may be the same or different, represents a hydrogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0053] X represents C or Si;

[0054] The substituents for the substituting groups are each independently selected from deuterium, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C2-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group;

[0055] Preferably, any two adjacent ones among R1-R 17 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )- or -C(R f )=C(R g )-;

[0056] Said R a 、R b 、R c 、R d 、R e 、R f 、R g each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C6-C 30An aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0057] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, any one or more of them.

[0058] Furthermore, the structure of the boron-containing organic compound is represented by any one of general formula (1-5) to general formula (1-6):

[0059]

[0060] In general formula (1-5) to general formula (1-6), R5-R 15 each occurrence, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 30 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0061] R5-R 15 any two adjacent ones of them can be connected to form a ring;

[0062] Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, each occurrence, which may be the same or different, represents a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30One of heteroaryls;

[0063] Ar3 and Ar4 can be connected to form a ring;

[0064] Ar4 and Ar5 can be connected to form a ring;

[0065] X represents C or Si;

[0066] The substituents for the substituting groups are each independently selected from deuterium, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C2-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one of them.

[0067] Preferably, any two adjacent ones of R5-R 15 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )-, or -C(R f )=C(R g )-;

[0068] There is no connection between the said Ar3 and Ar4 or they are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )-, or -C(R f )=C(R g )-;

[0069] There is no connection between the said Ar4 and Ar5 or they are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )-, or -C(R f )=C(R g )-;

[0070] The said R a 、R b 、R c 、R d 、R e 、Rf , R g are each independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0071] The substituents of the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C5-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group, or any one or more thereof.

[0072] Furthermore, the structure of the boron-containing organic compound is represented by any one of general formula (1-7) to general formula (1-9):

[0073]

[0074]

[0075] In general formula (1-7) to general formula (1-9), the meanings of R6, R9, R 12 , R 14 , Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and X are the same as the definitions in general formula (A) above.

[0076] Furthermore, the structure of the boron-containing organic compound is represented by any one of general formula (2-1) to general formula (2-2):

[0077]

[0078] In general formula (2-1) to general formula (2-2), the meanings of R6, R9, R 14 , Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and X are the same as the definitions in general formula (A) above;

[0079] Each occurrence of R1-R4 is the same or different and is represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boranyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl;

[0080] Any two of R1-R4 that are adjacent to each other can be connected to form a ring;

[0081] The substituents for the substitutable groups are each independently selected from deuterium, a halogen atom, a cyano group, C1-C 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C6-C 30 Aryl, deuterium-substituted C6-C 30 Aryl, C2-C 30 Heteroaryl, deuterium-substituted C2-C 30 Any one of heteroaryl.

[0082] Preferably, any two of R1-R4 that are adjacent to each other are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )- or -C(R f )=C(R g )-;

[0083] Said R a , R b , R c , R d , R e , R f , R g Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl;

[0084] The substituents for the above-mentioned substitutable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, C1-C 10An alkyl group, a deuterium-substituted C1-C 10 An alkyl group, a C3-C 10 Cycloalkyl group, a C6-C 30 An aryl group, a deuterium-substituted C6-C 30 An aryl group, a C5-C 30 A heteroaryl group, a deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups.

[0085] Furthermore, the structure of the boron-containing organic compound is represented by any one of general formulas (3-1) to (3-3):

[0086]

[0087] In general formulas (3-1) to (3-3), R1-R 25 Each occurrence, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl group, a substituted or unsubstituted C3-C 10 Cycloalkyl group, a substituted or unsubstituted C2-C 10 Alkenyl group, a substituted or unsubstituted C2-C 10 Alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted C1-C 10 Alkoxy group, a substituted or unsubstituted C6-C 30 Aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 Aryl group, a substituted or unsubstituted C2-C 30 Heteroaryl group;

[0088] R1-R 25 Any two adjacent ones of which may be connected to form a ring;

[0089] Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, each occurrence, which may be the same or different, represents a substituted or unsubstituted C1-C 10 Alkyl group, a substituted or unsubstituted C3-C 10 Cycloalkyl group, a substituted or unsubstituted C1-C 10 Alkoxy group, a substituted or unsubstituted C6-C 10 Aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 Aryl group, a substituted or unsubstituted C2-C 30 Heteroaryl group;

[0090] X represents C, Si;

[0091] X1 represents O, S, N(R'1), C(R'2)(R'3);

[0092] R'1, R'2, and R'3 are each independently represented as a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0093] R'2 and R'3 may be connected by a single bond, O, or S;

[0094] The substituents for the substitutable groups are each independently selected from deuterium, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C2-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group.

[0095] Preferably, any two adjacent ones of R1-R 25 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )-, or -C(R f )=C(R g )-;

[0096] R a 、R b 、R c 、R d 、R e 、R f 、R g are each independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0097] The substituents for the above-mentioned substitutable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10cycloalkyl, C6-C 30 aryl, deuterium-substituted C6-C 30 aryl, C5-C 30 heteroaryl, deuterium-substituted C2-C 30 any one or more of heteroaryl.

[0098] Furthermore, the R1-R 25 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzindolyl group;

[0099] Each occurrence of R, which can be the same or different, represents one of a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzindolyl group;

[0100] Each of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 independently represents one of a hydrogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzindolyl group;

[0101] M1, M2, and M3 are each independently represented by any one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzopyrrolyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted indolo[3,2,1-jk]carbazolyl group, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl group, and a substituted or unsubstituted spirofluorene group;

[0102] R'1, R'2, and R'3 are each independently represented by any one of a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted indolyl group, and a substituted or unsubstituted benzindolyl group;

[0103] The substituents replacing the above-mentioned replaceable groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group, a diphenylamino group, a 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenyl group substituted with a deuterated methyl group, a phenyl group substituted with a deuterated ethyl group, a phenyl group substituted with a deuterated isopropyl group, a phenyl group substituted with a deuterated tert-butyl group, a biphenyl group substituted with a deuterated methyl group, a biphenyl group substituted with a deuterated ethyl group, a biphenyl group substituted with a deuterated isopropyl group, a biphenyl group substituted with a deuterated tert-butyl group.

[0104] Furthermore, the R a 、R b 、R c 、R d 、R e 、R f 、R g are each independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzindolyl group;

[0105] The substituents replacing the above-mentioned replaceable groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group, a diphenylamino group, a 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenyl group substituted with a deuterated methyl group, a phenyl group substituted with a deuterated ethyl group, a phenyl group substituted with a deuterated isopropyl group, a phenyl group substituted with a deuterated tert-butyl group, a biphenyl group substituted with a deuterated methyl group, a biphenyl group substituted with a deuterated ethyl group, a biphenyl group substituted with a deuterated isopropyl group, a biphenyl group substituted with a deuterated tert-butyl group.

[0106] Further, the R, R1-R 17 , R a , R b , R c , R d , R e , R f , R g each independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a cyclopentyl group substituted with a methyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a diphenyl ether group, a diphenyl ether group substituted with a methyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyridyl group substituted with a phenyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a phenyl group substituted with a methyl group, a phenyl group substituted with an ethyl group, a phenyl group substituted with an isopropyl group, a phenyl group substituted with a tert-butyl group, a biphenyl group substituted with a methyl group, a biphenyl group substituted with an ethyl group, a biphenyl group substituted with an isopropyl group, a biphenyl group substituted with a tert-butyl group, a phenyl group substituted with a deuterated methyl group, a phenyl group substituted with a deuterated ethyl group, a phenyl group substituted with a deuterated isopropyl group, a phenyl group substituted with a deuterated tert-butyl group, a biphenyl group substituted with a deuterated methyl group, a biphenyl group substituted with a deuterated ethyl group, a biphenyl group substituted with a deuterated isopropyl group, a biphenyl group substituted with a deuterated tert-butyl group, a dibenzofuranyl group substituted with a tert-butyl group, a phenyl group substituted with a tert-butyl group, an oxanthrone group, a triazinyl group substituted with a phenyl group, a boranyl group substituted with a phenyl group, a methoxy group, a tert-butoxy group;

[0107] Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 each independently represent phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthenone group, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, tert-butoxy;

[0108] M1, M2, and M3 represent phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuryl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, xanthenone group;

[0109] The substituents substituting the above-mentioned substituable groups are each independently selected from one or more of deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-pentyl, tert-butyl, butyl, methoxy, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furyl, thienyl, indolyl, pyrrolyl, dibenzofuryl, dibenzothienyl, 9,9-dimethylfluorenyl, spirofluorene, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azaphenanthryl;

[0110] Preferably, M1, M2, and M3 represent the following ring structures:

[0111]

[0112] any one of;

[0113] wherein Z is represented as C-R a ;

[0114] R a each occurrence independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a trideuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthone group, a phenyl-substituted triazine group, a phenyl-substituted boranyl group, a methoxy group, a tert-butoxy group;

[0115] Preferably, R, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R a each occurrence, the same or different, represents: a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group,

[0116] any one of; Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are represented by the following structures:

[0117]

[0118] Any one of the following.

[0119] Furthermore, the specific structural formula of the boron-containing organic compound is any one of the following structures:

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] The present invention also provides an organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer comprises a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound of the present invention;

[0137] Preferably, the light-emitting layer comprises a host material and a dopant material, and the dopant material contains the boron-containing organic compound of the present invention.

[0138] Furthermore, the light-emitting layer comprises a first host material, a second host material and a dopant material, at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing organic compound of the present invention.

[0139] Furthermore, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a doping material. The exciton-sensitizing material is a metal-element-containing complex, and the doping material is the boron-containing organic compound of the present invention.

[0140] The beneficial technical effects of the present invention are as follows:

[0141] (1) The compound of the present invention is applied to an OLED device and can be used as a doping material for a light-emitting layer material. Under the action of an electric field, it can emit green fluorescence and can be applied to the fields of OLED lighting or OLED display;

[0142] (2) As a doping material, the compound of the present invention can significantly improve the device lifetime. Description of the Drawings

[0143] Figure 1 It is a schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0144] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer;

[0145] Figure 2 It is an emission spectrum diagram of Compound 52 tested in a toluene solution (1×10 -5 mol / L);

[0146] Figure 3 It is the 1 1H NMR spectrum of Compound 52;

[0147] Figure 4 It is an emission spectrum diagram of Compound 28 tested in a toluene solution (1×10 -5 mol / L);

[0148] Figure 5 It is the 1 1H NMR spectrum of Compound 28. Specific Embodiments

[0149] Next, the technical solutions in the embodiments of the present invention will be clearly and completely described in conjunction with the drawings in the embodiments of the present invention. Without conflict, the embodiments in the present invention and the features in the embodiments can be combined with each other. The present invention will be further described below in conjunction with the drawings and specific embodiments, but it is not a limitation of the present invention.

[0150] In the present invention, when describing electrodes, organic electroluminescent devices, and other structural bodies, the orientation terms such as "upper", "lower", "top", and "bottom" are used to represent the orientation in a specific state only, and do not mean that the relevant structures can only exist in the described orientation; on the contrary, if the structural body can change its position, for example, be inverted, the orientation of the structural body will be changed accordingly. Specifically, in the present invention, the "bottom" and "lower" sides of the electrode refer to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" and "upper" sides.

[0151] In the present invention, the substituted or unsubstituted arylamino group described in the present invention refers to wherein Q1 and Q2 represent substituted or unsubstituted aromatic groups, and Q1 and Q2 preferably represent substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 heteroaryl.

[0152] In the present invention, the substituted or unsubstituted silyl group described in the present invention refers to wherein Q3, Q4, and Q5 represent C1-C 10 alkyl, C3-C 10 cycloalkyl.

[0153] In the present invention, the substituted or unsubstituted boranyl group described in the present invention refers to wherein Q6 and Q7 represent C1-C 10 alkyl, C3-C 10 cycloalkyl.

[0154] In the present invention, the substituted or unsubstituted C6-C 30 aryl refers to a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, preferably a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, preferably a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, preferably a substituted or unsubstituted aryl group having 8 to 10 carbon atoms, preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted A group, a substituted or unsubstituted di(terphenyl), a substituted or unsubstituted perylene group, a substituted or unsubstituted indene group, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl group, a fused ring of a combination thereof or a combination of the aforementioned groups, but not limited thereto.

[0155] In the present invention, the substituted or unsubstituted C6-C 30 An aromatic ring refers to an aryl group having 6 to 30 carbon atoms, preferably a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, preferably a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, preferably a substituted or unsubstituted aryl group having 8 to 10 carbon atoms, preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted A group, a substituted or unsubstituted di(terphenyl), a substituted or unsubstituted perylene group, a substituted or unsubstituted indene group, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl group, a fused ring of a combination thereof or a combination of the aforementioned groups, but not limited thereto.

[0156] In the present invention, C6~C 30 An aryl group refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 18 carbon atoms, preferably an aryl group having 6 to 10 carbon atoms, preferably a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirofluorenyl group, a phenanthryl group, a condensed tetraphenyl group, a pyrenyl group, a biphenylene group, a terphenyl group, A group, a di(terphenyl), a perylene group, an indene group, a 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a fused ring of a combination thereof or a combination of the aforementioned groups, but not limited thereto.

[0157] In the present invention, the substituted or unsubstituted C2~C 30Heteroaryl refers to substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, preferably substituted or unsubstituted heteroaryl having 4 to 20 carbon atoms, preferably substituted or unsubstituted heteroaryl having 5 to 20 carbon atoms, preferably substituted or unsubstituted heteroaryl having 4 to 10 carbon atoms, preferably substituted or unsubstituted heteroaryl having 5 to 10 carbon atoms, preferably substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoindolyl, combinations thereof or fused rings of combinations of the foregoing groups, but not limited thereto.

[0158] In the present invention, the substituted or unsubstituted 5- to 30-membered heteroaryl ring is preferably substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, combinations thereof or fused rings of combinations of the foregoing groups, but not limited thereto.

[0159] In the present invention, C2-C 30 The heteroaryl group refers to a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 20 carbon atoms, preferably a heteroaryl group having 4 to 20 carbon atoms, preferably a heteroaryl group having 4 to 10 carbon atoms, preferably a heteroaryl group having 6 to 12 carbon atoms, preferably furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuryl, benzothienyl, benzimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzoxazinyl, benzothiazinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, fluorenyl, dibenzofuryl, dibenzothienyl, carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, benzoindolyl, a fused ring of a combination thereof or a combination of the aforementioned groups, but not limited thereto.

[0160] In the present invention, the heteroatom in the heteroaryl group is optionally selected from one or more of O, S, N, Si, and B.

[0161] In the present invention, the substituted or unsubstituted C2-C 30 The number of heteroatoms in the heteroaryl group is 1-5, preferably 1-4. Preferably 1-3, preferably 1-2.

[0162] The substituted or unsubstituted C1-C in the present invention 10 The alkyl group (including straight-chain alkyl and branched-chain alkyl) refers to a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, preferably substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted neopentyl, substituted or unsubstituted n-pentyl, substituted or unsubstituted isopentyl, substituted or unsubstituted octyl, substituted or unsubstituted heptyl, substituted or unsubstituted n-decyl, substituted or unsubstituted 1-methylpentyl, substituted or unsubstituted 2-methylpentyl, substituted or unsubstituted 3-methylpentyl, substituted or unsubstituted 1-butylpentyl, etc., but not limited thereto.

[0163] The C1-C described in the present invention 10An alkyl group (including linear and branched alkyl groups) refers to an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but not limited thereto.

[0164] The substituted or unsubstituted C3-C 10 The cycloalkyl group preferably uses a substituted or unsubstituted C4-C9 cycloalkyl group, more preferably a substituted or unsubstituted C5-C8 cycloalkyl group, and particularly preferably a substituted or unsubstituted C5-C7 cycloalkyl group. Non-limiting examples thereof may include a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted 4-methylcyclohexyl group, a substituted or unsubstituted 4,4-dimethylcyclohexyl group, a substituted or unsubstituted adamantyl group, and a substituted or unsubstituted cycloheptyl group, etc., but not limited thereto.

[0165] The C3-C of the present invention 10 The cycloalkyl group preferably uses a C4-C9 cycloalkyl group, more preferably a C5-C8 cycloalkyl group, and particularly preferably a C5-C7 cycloalkyl group. Non-limiting examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 4,4-dimethylcyclohexyl group, an adamantyl group, and a cycloheptyl group, etc., but not limited thereto.

[0166] The halogen atom in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0167] The C1-C of the present invention 10 The alkoxy group refers to methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, isopropoxy, etc., but not limited thereto.

[0168] The C2-C of the present invention 10 The alkenyl group refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylethylene, 1,2-diphenylethylene, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl, etc., but not limited thereto.

[0169] In the present invention, deuterium-substituted C6-C 30An aryl group refers to an aryl group having 6 to 30 carbon atoms substituted with deuterium, preferably an aryl group having 6 to 20 carbon atoms substituted with deuterium, more preferably an aryl group having 6 to 18 carbon atoms substituted with deuterium, still more preferably an aryl group having 6 to 10 carbon atoms substituted with deuterium, preferably a phenyl group substituted with deuterium, a naphthyl group substituted with deuterium, an anthracenyl group substituted with deuterium, a fluorenyl group substituted with deuterium, a dimethylfluorenyl group substituted with deuterium, a diphenylfluorenyl group substituted with deuterium, a spirofluorene group substituted with deuterium, a phenanthryl group substituted with deuterium, a condensed tetraphenyl group substituted with deuterium, a pyrenyl group substituted with deuterium, a biphenyl group substituted with deuterium, a terphenyl group substituted with deuterium, a group substituted with deuterium, a bi(terphenyl) group substituted with deuterium, a perylene group substituted with deuterium, an indenyl group substituted with deuterium, a 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted with deuterium, a fused ring of a combination thereof or a combination of the foregoing groups, but not limited thereto.

[0170] In the present invention, the deuterium-substituted C2-C 30 A heteroaryl group refers to a heteroaryl group having 5 to 30 carbon atoms substituted with deuterium, preferably a heteroaryl group having 5 to 20 carbon atoms substituted with deuterium, more preferably a heteroaryl group having 5 to 10 carbon atoms substituted with deuterium, still more preferably a heteroaryl group having 6 to 12 carbon atoms substituted with deuterium, preferably a furyl group substituted with deuterium, a thienyl group substituted with deuterium, a pyrrolyl group substituted with deuterium, a pyrazolyl group substituted with deuterium, an imidazolyl group substituted with deuterium, a triazolyl group substituted with deuterium, an oxazolyl group substituted with deuterium, a thiazolyl group substituted with deuterium, an oxadiazolyl group substituted with deuterium, a thiadiazolyl group substituted with deuterium, a pyridyl group substituted with deuterium, a pyrimidinyl group substituted with deuterium, a pyrazinyl group substituted with deuterium, a triazinyl group substituted with deuterium, a benzofuryl group substituted with deuterium, a benzothienyl group substituted with deuterium, a benzimidazolyl group substituted with deuterium, an indolyl group substituted with deuterium, a quinolinyl group substituted with deuterium, an isoquinolinyl group substituted with deuterium, a quinazolinyl group substituted with deuterium, a quinoxalinyl group substituted with deuterium, a naphthyridinyl group substituted with deuterium, a benzoxazinyl group substituted with deuterium, a benzothiazinyl group substituted with deuterium, an acridinyl group substituted with deuterium, a phenazinyl group substituted with deuterium, a phenothiazinyl group substituted with deuterium, a phenoxazinyl group substituted with deuterium, a fluorenyl group substituted with deuterium, a dibenzofuryl group substituted with deuterium, a dibenzothienyl group substituted with deuterium, a carbazolyl group substituted with deuterium, a substituted N-phenylcarbazolyl group substituted with deuterium, a benzoindolyl group substituted with deuterium, a combination thereof or a fused ring of a combination of the foregoing groups, but not limited thereto.

[0171] The deuterium-substituted C1-C of the present invention 10The alkyl group (including straight-chain alkyl groups and branched-chain alkyl groups) refers to a deuterium-substituted alkyl group having 1 to 10 carbon atoms, preferably a deuterium-substituted alkyl group having 1 to 5 carbon atoms, preferably a deuterium-substituted alkyl group having 1 to 4 carbon atoms, preferably deuterium-substituted methyl, deuterium-substituted ethyl, deuterium-substituted propyl, deuterium-substituted isopropyl, deuterium-substituted butyl, deuterium-substituted tert-butyl, deuterium-substituted isobutyl, deuterium-substituted sec-butyl, deuterium-substituted neopentyl, deuterium-substituted n-pentyl, deuterium-substituted isopentyl, deuterium-substituted octyl, deuterium-substituted heptyl, deuterium-substituted n-decyl, deuterium-substituted 1-methylpentyl, deuterium-substituted 2-methylpentyl, deuterium-substituted 3-methylpentyl, deuterium-substituted 1-butylpentyl, etc., but not limited thereto.

[0172] The substituent is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group, a 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenyl group substituted with deuterated methyl, a phenyl group substituted with deuterated ethyl, a phenyl group substituted with deuterated isopropyl, a phenyl group substituted with deuterated tert-butyl, a biphenyl group substituted with deuterated methyl, a biphenyl group substituted with deuterated ethyl, a biphenyl group substituted with deuterated isopropyl, a biphenyl group substituted with deuterated tert-butyl.

[0173] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent PI film substrates; opaque substrates such as silicon substrates. Different substrates have different mechanical strengths, thermal stabilities, transparencies, surface smoothnesses, and water resistances. Depending on the nature of the substrate, its usage directions are different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0174] A first electrode is formed on a substrate, and the first electrode and the second electrode can face each other. The first electrode can be an anode. The first electrode can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it can be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO), etc. When the first electrode is a semi-transmissive electrode or a reflective electrode, it can include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, or Cr, and can also be an alloy of several metals, or a combination of a metal, a metal oxide, and a metal alloy. The thickness of the first electrode layer depends on the material used and is generally 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0175] The organic functional material layer disposed between the first electrode and the second electrode sequentially includes a hole transport region, a light-emitting layer, and an electron transport region from bottom to top.

[0176] In the present invention, examples of the hole transport region constituting the organic electroluminescent device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0177] As the materials for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials for organic electroluminescent devices for use.

[0178] The hole injection layer contains a host organic material that can conduct holes and also contains a P-type doping material with a deep HOMO energy level (the corresponding LUMO energy level will also be deep). Based on empirical summaries, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the host organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doping material in order to expect the occurrence of a charge transfer state between the host material and the doping material, achieve Ohmic contact between the buffer layer and the anode, and achieve efficient injection from the electrode to hole injection conduction.

[0179] In view of the above empirical summaries, therefore, for hole-type host organic materials with different HOMO energy levels, different P-doping materials need to be selected to match them in order to achieve Ohmic contact at the interface and improve the hole injection effect.

[0180] Preferably, as the host organic material of the hole injection layer of the present invention, any compound disclosed in the following prior arts can be optionally selected: JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN105439999A or CN103108859A.

[0181] Preferably, the p-type doping material is a compound having charge conductivity selected from those disclosed in the prior art, and the p-type dopant can be selected from any compound disclosed in any of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE102007031220A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but not limited thereto.

[0182] In one embodiment of the present invention, the hole injection layer comprises a p-type doping material having charge conductivity selected from the following: quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanomethanylylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0183] In the hole injection layer of the present invention, the ratio of the hole transport material to the p-type doping material used is 99:1 - 95:5, preferably 99:1 - 97:3, based on mass.

[0184] The thickness of the hole injection layer of the present invention can be 5 - 100 nm, preferably 5 - 50 nm, and more preferably 5 - 20 nm, but the thickness is not limited to this range.

[0185] Preferably, as the hole transport layer material of the present invention, any compound disclosed in the following prior arts can be optionally selected:

[0186] JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN103108859A.

[0187] Preferably, the hole transport layer material of the present invention and the host organic material in the hole injection layer are selected from the same compound.

[0188] The thickness of the hole transport layer of the present invention can be 5 - 200 nm, preferably 10 - 150 nm, and more preferably 20 - 100 nm, but the thickness is not limited to this range.

[0189] In one embodiment of the present invention, as the electron blocking layer material of the present invention, any compound disclosed in the following prior arts can be optionally selected:

[0190] CN102046613A, CN105408448A, KR1020160049955A, CN103108859A, KR1020130106255A, EP2922932A1, CN102224150A, US20170018710A1.

[0191] The thickness of the electron blocking layer of the present invention can be 1 - 50 nm, preferably 5 - 40 nm, but the thickness is not limited to this range.

[0192] After forming the hole injection layer, the hole transport layer and the electron blocking layer, a corresponding light emitting layer is formed on the electron blocking layer.

[0193] The light emitting layer can include a host material and a doping material. The host material can use common green light host materials in the art, and the doping material uses the boron-containing organic compound represented by the general formula (1) of the present invention.

[0194] The light emitting layer can include a single host material or a dual host material;

[0195] The dual host material includes a first host material and a second host material. At least one of the first host material and the second host material is preferably a TADF material;

[0196] The TADF material refers to a material with thermally activated delayed fluorescence properties, characterized by having a small energy level difference between the first excited singlet state and the first excited triplet state. Therefore, singlet excitons and triplet excitons generated can be utilized simultaneously in the device, enabling the utilization rate of excitons generated electro-optically inside the device to be as close as possible to 100%. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0197] The light-emitting layer may include a host material, an exciton-sensitizing material, and a doping material;

[0198] The exciton-sensitizing material refers to a material that can enable the luminescent material in the light-emitting layer to make full use of electrogenerated excitons, so that the light-emitting layer finally generates the emission spectrum of the sensitized material. The exciton sensitizer may undertake functions such as exciton capture, exciton conversion, and exciton transfer in the electroluminescent device. The boron-containing organic compound shown in the general formula (1) of the present invention is used in combination with the exciton-sensitizing material, which has an obvious improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0199] In the light-emitting layer of the present invention, the ratio of the host material to the doping material used is 99:1 - 70:30, preferably 99:1 - 85:15, and more preferably 97:3 - 87:13, based on mass.

[0200] The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, further preferably 10 - 50 nm, and more preferably 15 - 40 nm, but the thickness is not limited to this range.

[0201] In the present invention, the electron transport region may sequentially include a hole blocking layer, an electron transport layer, and an electron injection layer disposed above the light-emitting layer from bottom to top, but is not limited thereto.

[0202] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby prolonging the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be disposed above the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds having a hole blocking effect known in the prior art can be used, such as the compounds disclosed in the following prior arts: Appl.Phys.Lett.75,4(1999), Appl.Phys.Lett.83,3858(2003), JP2015111679A, KR1020180043220A, CN109564982A, KR1020180065246A.

[0203] The thickness of the hole blocking layer of the present invention can be 2 - 200 nm, preferably 5 - 150 nm, and more preferably 5 - 50 nm, but the thickness is not limited to this range.

[0204] The electron transport layer can be disposed above the light-emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that can easily receive electrons from the cathode and transfer the received electrons to the light-emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer materials disclosed in the prior art for organic electroluminescent devices can be used, such as the compounds disclosed in the following prior art: CN1784388A, CN1625552A, CN107431141A, CN107431141A, KR1020160149041A, KR1020160149041A, CN103827256A, KR101847347B1, KR1020190050658A, CN102574813A, CN107721979A, KR1020100073954A.

[0205] In a preferred embodiment of the present invention, the electron transport layer further includes other compounds conventionally used in the electron transport layer, such as, for example, Alq3, LiQ, preferably LiQ.

[0206] The thickness of the electron transport layer of the present invention can be 10 - 80 nm, preferably 20 - 60 nm, and more preferably 25 - 45 nm, but the thickness is not limited to this range.

[0207] The electron injection layer can be disposed above the electron transport layer. The electron injection layer material is usually a material preferably having a low work function, so that electrons can be easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer materials disclosed in the prior art for organic electroluminescent devices can be used, such as: LiF, Cs2CO3, CsF, Csq, NaF, MgF2, CaF2, Al2O3, Yb, etc.

[0208] The thickness of the electron injection layer of the present invention can be 0.1 - 5 nm, preferably 0.5 - 3 nm, and more preferably 0.8 - 1.5 nm, but the thickness is not limited to this range.

[0209] The second electrode may be disposed over the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0210] The organic electroluminescent device of the present invention may further include a packaging structure. The packaging structure may be a protective structure for preventing external substances such as moisture and oxygen from entering the organic layers of the organic electroluminescent device. The packaging structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.

[0211] A method for manufacturing the organic electroluminescent device of the present invention includes successively laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a covering layer on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, the LB method, inkjet printing, laser printing, or LITI may be used, but are not limited thereto. In the present invention, it is preferred to use the vacuum evaporation method to form the respective layers. Those skilled in the art can conventionally select the respective process conditions in the vacuum evaporation method according to actual needs.

[0212] The raw materials involved in the synthesis examples of the present invention can all be purchased from the market or prepared by conventional preparation methods in the art;

[0213] Intermediate synthesis:

[0214] Synthesis of intermediate R series:

[0215]

[0216] Synthesis of Intermediate S3: Add raw material S1 (10 mmol, 3.4 g) and raw material S2 (10 mmol, 3.2 g) into a three-necked flask, dissolve them with a mixed solvent (70 mL of 1,4-dioxane / water (volume ratio: 4:1), 35 mL of ethanol), then add Pd(dppf)Cl2 (0.10 mmol, 0.07 g) and 15 mL of 3 mol / L aqueous K2CO3 solution. Heat under reflux for 4 hours under nitrogen protection. Take a sample for TLC to confirm the completion of the reaction. After cooling to room temperature, filter the reaction mixture through a diatomaceous earth pad, wash it with chloroform, and evaporate the obtained filtrate under vacuum. Purify the obtained residue by column chromatography on silica gel using hexane / toluene as the eluent to obtain Intermediate S3.

[0217]

[0218] Synthesis of Intermediate R1: Dissolve Intermediate S3 (1.4 g, 3.6 mmol) and raw material S4 (0.7 g, 4.3 mmol) in THF (80 ml), and successively add PdCl2(PPh3)2 (0.1 g, 0.15 mmol), CuI (0.07 g, 0.36 mmol) and triethylamine (40 ml). After displacing nitrogen three times, slowly heat the mixture to 80 °C and keep it for 10 hours. After cooling to room temperature, filter the reaction mixture to remove inorganic salts, and rotary evaporate to remove triethylamine. Pour the product into acidic water, wash the precipitate five times with deionized water, and dry it at 80 °C under vacuum overnight. Purify the crude product by silica gel column chromatography using petroleum ether as the eluent to obtain the crude product, and then obtain Intermediate R1 by recrystallization.

[0219]

[0220] Synthesis of Intermediate R2 refers to the synthesis of Intermediate R1, the difference is that raw material S5 is used to replace Intermediate S3, and raw material S6 is used to replace raw material S4.

[0221] Synthesis of Intermediate G Series:

[0222]

[0223] Synthesis of Intermediate G1: Add raw material R2 (4.5 g, 25 mmol), potassium carbonate (8.6 g, 62.5 mmol), tricyclohexylphosphine (0.4 g, 1.25 mmol), palladium acetate (0.1 g, 0.4 mmol) into a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material P1 (6.7 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and elute through a column with PE:EA = 20:1 to obtain Intermediate G1.

[0224]

[0225] Synthesis of Intermediate G2: Add raw material R3 (7.3 g, 25 mmol), potassium carbonate (8.6 g, 62.5 mmol), tricyclohexylphosphine (0.4 g, 1.25 mmol), and palladium acetate (0.1 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P1 (6.7 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G2.

[0226]

[0227] Synthesis of Intermediate G3: Add raw material R2 (4.5 g, 25 mmol), potassium carbonate (8.6 g, 62.5 mmol), tricyclohexylphosphine (0.4 g, 1.25 mmol), and palladium acetate (0.1 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P2 (6.7 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G3.

[0228]

[0229] Synthesis of Intermediate G4: Add raw material R3 (7.3 g, 25 mmol), potassium carbonate (8.6 g, 62.5 mmol), tricyclohexylphosphine (0.4 g, 1.25 mmol), and palladium acetate (0.1 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P2 (6.7 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G4.

[0230]

[0231] Synthesis of Intermediate G5: Add intermediate R1 (12.0 g, 25 mmol), potassium carbonate (8.6 g, 62.5 mmol), tricyclohexylphosphine (0.4 g, 1.25 mmol), and palladium acetate (0.1 g, 0.4 mmol) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material P1 (6.7 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 h under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate G5.

[0232]

[0233] The synthesis of intermediate G6 refers to intermediate G5, except that intermediate R2 is used to replace intermediate R1.

[0234] Example 1: Synthesis of Compound 15:

[0235]

[0236] Synthesis of intermediate B1: Add raw material E1 (1.7 g, 5 mmol) and cesium carbonate (4.1 g, 12.5 mmol) into a two-necked flask, add 50 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material A1 (1.4 g, 5 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA=20:1 to obtain intermediate B1.

[0237] Synthesis of intermediate C1: Intermediate B1 (3.0 g, 5.1 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution, and 3.8 mL of n-butyl lithium (1.6 M) n-hexane solution was slowly added under nitrogen at 0°C; after stirring at 0°C for 2 hours, 10 mL of tetrahydrofuran solution of raw material F1 (2.1 g, 5.5 mmol) was slowly added. Then the reaction mixture was slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water and ethyl acetate were added to the reaction mixture, the water layer was separated, and extracted with ethyl acetate three times. The combined organic layer was dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with NaHCO3 aqueous solution. Then the water layer was separated and extracted with dichloromethane. Drying with sodium sulfate, filtering, and evaporation by rotary concentration and column column were obtained to obtain intermediate C1.

[0238] Synthesis of intermediate D1: Under nitrogen protection, intermediate C1 (2.1 g, 2.5 mmol) was dissolved in 50 mL of toluene solution, and intermediate G1 (0.8 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.6 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 10 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring and filtered to obtain intermediate D1.

[0239] Synthesis of Compound 15: Intermediate D1 (13.4 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 10 mL of a 1.6 M solution of tert-butyllithium in n-pentane was slowly added. After stirring at 60 °C for 2 hours, boron tribromide (6.3 g, 25 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 1 hour. N,N-Diisopropylethylamine (DIPEA) (3.3 g, 25.2 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 6 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated, and extraction was carried out with water and dichloromethane. The combined organic layers were condensed in vacuo, and column chromatography was performed to obtain Compound 15.

[0240] Synthesis of Examples 1-10 and Their Corresponding Compounds 15, 16, 17, 18, 27, 28, 29, 30, 111, and 52:

[0241] The following target compounds were synthesized with reference to the preparation process of Compound 15 in Example 1; the reaction conditions were the same, and the starting material E1 used was the same, except that the starting materials A, starting material F, and intermediate G listed in Table 2-1 below were used;

[0242] Table 2-1

[0243]

[0244]

[0245]

[0246] The structural characterizations, mass spectrometry analyses, and test results of the physical and chemical properties of the compounds obtained in each example are as follows:

[0247] The theoretical values of the structural formula (C 79 H 59 BN2) of Compound 15: C, 90.61; H, 5.68; N, 2.68; The measured values: C, 90.64; H, 5.73; N, 2.61. LC-MS: The measured value: 1047.75 ([M+H] + ), exact mass: 1046.48. The FWHM in toluene solution (1×10 - 5 M) is 25 nm.

[0248] The theoretical values of the structural formula (C 71 H 53BN2) Theoretical values: C, 90.24; H, 5.65; N, 2.96; Test values: C, 90.17; H, 5.61; N, 3.00. LC-MS: Measured value: 945.39 ([M+H] + ) and exact mass: 944.43. FWHM in toluene solution (1×10 -5 M) is 24 nm.

[0249] Structural formula of compound 17 (C 79 H 59 BN2) Theoretical values: C, 90.61; H, 5.68; N, 2.68; Test values: C, 90.56; H, 5.69; N, 2.63. LC-MS: Measured value: 1047.41 ([M+H] + ) and exact mass: 1046.48. FWHM in toluene solution (1×10 - 5 M) is 23 nm.

[0250] Structural formula of compound 18 (C 71 H 53 BN2) Theoretical values: C, 90.24; H, 5.65; N, 2.96; Test values: C, 90.34; H, 5.73; N, 3.06. LC-MS: Measured value: 945.68 ([M+H] + ) and exact mass: 944.43. FWHM in toluene solution (1×10 -5 M) is 22 nm.

[0251] Structural formula of compound 27 (C 87 H 75 BN2) Theoretical values: C, 90.13; H, 6.52; N, 2.42; Test values: C, 90.17; H, 6.56; N, 2.39. LC-MS: Measured value: 1159.84 ([M+H] + ) and exact mass: 1158.60. FWHM in toluene solution (1×10 - 5 M) is 25 nm.

[0252] Structural formula of compound 28 (C 79 H 69 BN2) Theoretical values: C, 89.75; H, 6.58; N, 2.65; Test values: C, 89.77; H, 6.59; N, 2.69. LC-MS: Measured value: 1057.65 ([M+H] + ) and exact mass: 1056.56. FWHM in toluene solution (1×10 - 5The FWHM of (M) is 25 nm.

[0253] The structural formula of Compound 29 (C 87 H 75 BN2): Theoretical values: C, 90.13; H, 6.52; N, 2.42; Measured values: C, 90.23; H, 6.55; N, 2.46. LC-MS: Measured value: 1159.46 ([M+H] + ), Exact mass: 1158.60. In toluene solution (1×10 - 5 The FWHM of (M) is 24 nm.

[0254] The structural formula of Compound 30 (C 79 H 69 BN2): Theoretical values: C, 89.75; H, 6.58; N, 2.65; Measured values: C, 89.69; H, 6.64; N, 2.57. LC-MS: Measured value: 1057.71 ([M+H] + ), Exact mass: 1056.56. In toluene solution (1×10 - 5 The FWHM of (M) is 23 nm.

[0255] The structural formula of Compound 111 (C 95 H 91 BN2): Theoretical values: C, 89.73; H, 7.21; N, 2.20; Measured values: C, 89.81; H, 7.17; N, 2.16. LC-MS: Measured value: 1271.83 ([M+H] + ), Exact mass: 1270.73. In toluene solution (1×10 -5 The FWHM of (M) is 25 nm.

[0256] The structural formula of Compound 52 (C 87 H 85 BN2): Theoretical values: C, 89.35; H, 7.33; N, 2.40; Measured values: C, 89.62; H, 7.20; N, 2.36. LC-MS: Measured value: 1169.74 ([M+H] + ), Exact mass: 1168.68. In toluene solution (1×10 - 5 The FWHM of (M) is 26 nm.

[0257] Note: FWHM (Full Width at Half Maximum) was measured by a Horiba Fluorolog-3 series fluorescence spectrometer.

[0258] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 1-9 and Device Comparative Examples 1-5. The manufacturing processes of Device Examples 2-9 and Device Comparative Examples 1-5 of the present invention are exactly the same as that of Device Example 1, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Tables 3 and 4 respectively.

[0259] Device Example 1

[0260] As Figure 1 shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, and Compound 15 is used as the doping material. The mass ratio of GH-1, GH-2, and Compound 15 is 69:30:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously vacuum-evaporated with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9. This layer is used as the cathode layer 10.

[0261] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 10-32 and Device Comparative Examples 6-10. The manufacturing processes of Device Examples 11-32 and Device Comparative Examples 6-10 of the present invention are exactly the same as that of Device Example 10, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Tables 3 and 4 respectively.

[0262] Device Example 10

[0263] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first doping material, and compound 15 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and compound 15 is 66.5:30:3:0.5, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously evaporated by vacuum evaporation, with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously evaporated by vacuum evaporation, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated by a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated by a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0264] The molecular structural formulas of the related materials are as follows:

[0265]

[0266] The comparative compounds ref-1, ref-2, ref-3, ref-4, and ref-5 are prepared by referring to the methods described in the prior art.

[0267] After the OLED light-emitting device is completed as described above, the anode and the cathode are connected by a known driving circuit, and the current efficiency and the lifetime of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 3; the test results of the current efficiency and the lifetime of the obtained devices are shown in Table 4.

[0268] Table 3

[0269]

[0270]

[0271]

[0272]

[0273]

[0274] Table 4

[0275]

[0276]

[0277] Note: The current efficiency and emission peak are measured using an IVL (current-voltage-brightness) test system (Suzhou FushiDa Scientific Instruments Co., Ltd.); the lifetime test system is the EAS-62C OLED device lifetime tester of System Technology Co., Ltd. in Japan; LT95 refers to the time when the device brightness decays to 95%; all data are tested at 10 mA / cm 2 below.

[0278] From the device data results in Table 4, it can be seen that compared with Comparative Examples 1-5 of the device, the device lifetime of the compound of the present invention in the single-doping system device is higher than that of Comparative Examples 1-5; in the single-doping system device, the device efficiency also shows good results; compared with Comparative Examples 6-10 of the device, in the double-doping system device using an exciton sensitizing material as the first doping, both the current efficiency and the device lifetime of the device are greatly improved compared with the OLED devices of known materials, and in the double-doping device, the device efficiency is also significantly improved compared with that in the single-doping case.

[0279] In summary, the above are only the preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principle of the present invention shall be included within the protection scope of the present invention.

Claims

1. A boron-containing organic compound, characterized in that The structure of the boron-containing organic compound is shown in general formula (A): In the general formula (A), R5-R 15 Each occurrence of the same or different radicals may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; R5-R 13 Any two adjacent ones can be connected to form a ring; R 14 and R 15 Can be connected into a ring; Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, which are the same or different each time, represent hydrogen atoms, C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C2~C 10 Alkenyl, C2~C 10 Alkynyl, silyl substituted or unsubstituted by R, boryl substituted or unsubstituted by R, C1~C 10 Alkoxy, R-substituted or unsubstituted C6~C 30 Aryloxy, arylamine substituted or unsubstituted by R, C6~C 30 Aryl, C2~C 30 One of the heteroaryl groups; The R may be the same or different each time and may be a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Ar3 and Ar4 can be connected to form a ring; Ar4 and Ar5 can be connected to form a ring; M1, M2, and M3 are each independently substituted or unsubstituted C6 to C 30 aromatic ring, substituted or unsubstituted 5- to 30-membered heteroaromatic ring, substituted or unsubstituted C6~C 10 One of the aliphatic rings; X represents C, Si; The substituents for the substituent groups are selected from deuterium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 Any of the heteroaryl groups.

2. The boron-containing organic compound according to claim 1, characterized in that In the general formula (A), R5-R 15 Each occurrence of the same or different radicals may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; R5-R 13 Any two adjacent ones can be connected to form a ring; R 14 and R 15 Can be connected into a ring; Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 each time they appear, the same or different, represents a hydrogen atom, a substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Ar3 and Ar4 can be connected to form a ring; Ar4 and Ar5 can be connected to form a ring; M1, M2, and M3 are each independently substituted or unsubstituted C6 to C 30 aromatic ring, substituted or unsubstituted 5- to 30-membered heteroaromatic ring, substituted or unsubstituted C6~C 10 One of the aliphatic rings; X represents C, Si; The substituents for the substituent groups are selected from deuterium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 Any of the heteroaryl groups.

3. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is shown in the general formula (A-1) or the general formula (A-2): In the general formula (A-1) and the general formula (A-2), R1-R 15 Each occurrence of the same or different radicals may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; R1-R 13 Any two adjacent ones can be connected to form a ring; R 14 and R 15 Can be connected into a ring; Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 each time they appear, the same or different, represents a hydrogen atom, a substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; M1 represents a substituted or unsubstituted C6~C 30 aromatic ring, substituted or unsubstituted 5- to 30-membered heteroaromatic ring, substituted or unsubstituted C6~C 10 One of the aliphatic rings; X represents C, Si; The substituents for the substituent groups are selected from deuterium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 Any of the heteroaryl groups.

4. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (1-1) to (1-4): In the general formula (1-1) to the general formula (1-4), R1-R 17 Each occurrence of the same or different radicals may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; R1-R 17 Any two adjacent ones can be connected to form a ring; Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 each time they appear, the same or different, represents a hydrogen atom, a substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; X represents C, Si; The substituents for the substituent groups are selected from deuterium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 Any of the heteroaryl groups.

5. The boron-containing organic compound according to claim 2, characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (1-5) to (1-6): In the general formula (1-5) to the general formula (1-6), R5-R 15 Each occurrence of the same or different radicals may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; R5-R 15 Any two adjacent ones can be connected to form a ring; Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, which are the same or different when they appear, represent substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Ar3 and Ar4 can be connected to form a ring; Ar4 and Ar5 can be connected to form a ring; X represents C, Si; The substituents for the substituent groups are selected from deuterium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 Any of the heteroaryl groups.

6. The boron-containing organic compound according to claim 2, characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (1-7) to (1-9): In the general formula (1-7) to the general formula (1-9), R6, R9, R 12 , R 14 , Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and X have the same meanings as defined in the general formula (A) of claim 2.

7. The boron-containing organic compound according to claim 2, characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (2-1) to (2-2): In the general formula (2-1) to the general formula (2-2), R6, R9, R 14 , Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and X have the same meanings as defined in the general formula (A) of claim 2; R1-R4, which are the same or different each time, represent hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Any two adjacent R1-R4 can be connected to form a ring; The substituents for the substituent groups are selected from deuterium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 Any of the heteroaryl groups.

8. The boron-containing organic compound according to claim 1, characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (3-1) to (3-3): In the general formula (3-1) to the general formula (3-3), R1-R 25 Each occurrence of the same or different radicals may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; R1-R 25 Any two adjacent ones can be connected to form a ring; Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, which are the same or different when they appear, represent substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; X represents C, Si; X1 represents O, S, N(R'1), C(R'2)(R'3); The R'1, R'2, and R'3 are independently substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; The R'2 and R'3 can be connected by a single bond, O or S; The substituents for the substituent groups are selected from deuterium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium substituted C6~C 30 Aryl, C2~C 30 Heteroaryl, deuterium substituted C2~C 30 Any of the heteroaryl groups.

9. The boron-containing organic compound according to any one of claims 1 to 8, characterized in that The R1-R 25 Each of the following independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazine, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzindolyl; The R which is the same or different each time appears is a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, One of substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazine, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzindolyl; Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently a hydrogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted diphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted Thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazine, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzindolyl; The M1, M2, and M3 are substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzopyrrolyl, substituted or unsubstituted benzene. any one of thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted indolo[3,2,1-jk]carbazolyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl, and substituted or unsubstituted spirofluorenyl; The R'1, R'2 and R'3 are independently substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted thiophene, substituted or unsubstituted thiophene, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene ... One of substituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazine, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted 1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzindolyl; The substituents for substituting the above substitutable groups may be selected from a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, One or more of spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazoline, phenanthrenyl, diphenylamine, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, 1,2,3,4-tetrahydronaphthyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, and deuterated tert-butyl-substituted biphenyl.

10. The boron-containing organic compound according to any one of claims 1 to 7, characterized in that: R, R1-R 17 Each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, methyl substituted biphenyl, ethyl substituted biphenyl, isopropyl substituted biphenyl, tert-butyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted biphenyl, deuterated ethyl substituted biphenyl, deuterated isopropyl substituted biphenyl, deuterated tert-butyl substituted biphenyl, tert-butyl substituted dibenzofuranyl, phenyl substituted tert-butyl, xanthone, phenyl substituted triazine, phenyl substituted boryl, methoxy, tert-butoxy; The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, methyl substituted biphenyl substituted phenyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, phenyl substituted amino, tert-butylbenzene substituted amino, tert-butyl substituted dibenzofuranyl, phenyl substituted tert-butyl, xanthone, phenyl substituted triazine, phenyl substituted boryl, methoxy, tert-butoxy; The M1, M2, and M3 are represented by phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, and xanthone; The substituent replacing the above substitutable group is selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group; Preferably, M1, M2, and M3 represent the following ring structures: Any of; The Z is represented by CR a ; R a Each occurrence independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group , ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazine, phenyl-substituted boryl, methoxy, tert-butoxy; Preferably R, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R a Each occurrence of the same or different is represented by: hydrogen atom, deuterium atom, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, trifluoromethyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, Any of; Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 are represented by the following structures: Any of .

11. The boron-containing organic compound according to claim 1, characterized in that The specific structural formula of the boron-containing organic compound is any one of the following structures:

12. An organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer comprises a light-emitting layer, characterized in that: The light-emitting layer contains the boron-containing organic compound according to any one of claims 1 to 11; Preferably, the light-emitting layer comprises a host material and a doping material, and the doping material comprises the boron-containing organic compound according to any one of claims 1-11.

13. The organic electroluminescent device according to claim 12, wherein the light-emitting layer comprises a first host material, a second host material and a doping material, wherein: At least one of the first main material and the second main material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1-11.

14. The organic light-emitting device according to claim 12, wherein the light-emitting layer comprises a host material, an exciton sensitizing material and a doping material, wherein: The exciton sensitizing material is a complex containing a metal element, and the doping material is a boron-containing organic compound according to any one of claims 1 to 11.

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