Double-boron-containing resonance type organic compound and organic electroluminescent device containing double-boron-containing resonance type organic compound

Abstract

The invention relates to a double-boron-containing resonance type organic compound and an organic electroluminescent device containing the same, and belongs to the technical field of semiconductors. The structure of the double-boron-containing resonance type organic compound is shown as a general formula (1). When the double-boron-containing resonance type organic compound is used as a doping material in a luminescent layer material of an organic electroluminescent device, the double-boron-containing resonance type organic compound can be used as a luminescent layer green light doping material of the organic electroluminescent device, so that the efficiency of the device is improved, and the service life of the device is prolonged.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of semiconductor technology, and in particular to a double-boron-containing resonance type organic compound and an organic electroluminescent device comprising the same. BACKGROUND

[0002] Compared with liquid crystal display (LCD), organic light-emitting diode (OLED) has the technical advantages of lighter and thinner, high color contrast, low power consumption, fast response, high definition, and flexibility, and is considered to dominate the future display terminal products. With the advent of the 5G era, the new information display industry urgently needs to develop iteratively, and the early lower color gamut standards (BT.709 and DCIP3) cannot meet the high-quality technical development needs of display products. To achieve the performance requirements of ultra-high definition and higher picture quality of display products, the new generation of display standards (BT.2020) drive the development of organic electroluminescent materials towards high color purity, which requires core light-emitting materials to have a narrower emission spectrum. Among the three color display technologies of commercially available OLEDs, blue light uses the traditional fluorescent three triplet-three triplet conversion (TTF) technology, which has a low efficiency but a high color purity and has basically met the BT.2020 display index; green light and red light use phosphorescent light-emitting technology, which has a high efficiency, and red light has approached the BT.2020 display index. However, green light is limited by the relatively wide emission spectrum of phosphorescent light, and there is a large difference between the high shoulder peak of green phosphorescent light and the high-definition display index requirement. Therefore, it is relatively difficult to improve the color gamut display under the traditional device structure, and thus it is very crucial to develop a new generation of high color purity green organic electroluminescent material.

[0003] Since 2020, narrow half-peak width green light materials (half-peak width < 30 nm) based on boron-nitrogen resonance structures have been reported one after another, and from 2022 to 2023, a number of green boron-nitrogen narrow emission materials and device effects have been reported, such as: DOI: 10.1002 / anie.202301930, DOI: 10.1038 / s41566-022-01106-8, DOI: 10.1002 / anie.202313254, DOI: 10.1038 / s41566-022-01083-y, DOI: 10.1002 / anie.202202380, etc., which exhibit high color purity and efficiency, and have great potential as a new generation of green organic electroluminescent display materials. However, there are still many technical difficulties in the development of green light ultra-high color purity materials containing boron-nitrogen structures, and the existing materials also have defects such as efficiency and service life that cannot meet the needs of mass production. Therefore, it is a key technical point to develop boron-nitrogen-based resonance structure narrow half-peak width green light materials that can meet actual application requirements for the next generation of display devices with high color purity, high color gamut coverage, high efficiency, and high immersion.

[0004] In addition, the sensitization technology combines the triplet exciton sensitization material (including but not limited to TADF material and phosphorescent material) with the fluorescent dopant material, uses the triplet exciton sensitization material as an exciton sensitization medium, fully utilizes the triplet exciton, and transfers the energy to the fluorescent dopant material through energy transfer, so that the device internal quantum efficiency (DOI: 10.1038 / ncomms5016, DOI: 10.1038 / s41566-022-00958-4) can also reach 100%, which can make up for the shortcomings of insufficient utilization of excitons of the fluorescent dopant material, effectively play the characteristics of high fluorescent quantum yield, high device stability, high color purity and low cost of the fluorescent dopant material, and has broad prospects in OLEDs application. In CN 107507921A and CN 110492006A, a combination technology of a light-emitting layer containing a TADF material with a lowest singlet and a lowest triplet energy level difference less than or equal to 0.2eV as a host and a boron-containing material as a dopant is disclosed; and in CN 110492005A and CN 110492009A, a combination scheme of a light-emitting layer containing a boron-containing material as a dopant and a ground-state complex as a host is disclosed, which can achieve an efficiency comparable to phosphorescence and a relatively narrow half-peak width. Therefore, the development of a sensitization technology based on a narrow half-peak width boron-containing light-emitting material has unique advantages and strong potential in the face of BT.2020 display indicators. SUMMARY

[0005] In view of the above problems existing in the prior art, the present application provides a double-boron-containing resonant organic compound and an organic electroluminescent device comprising the same. The compound of the present application can emit green light when used as a light-emitting layer dopant material of an organic electroluminescent device.

[0006] The technical scheme of the present application is as follows: a double-boron-containing resonant organic compound, the structure of the double-boron-containing resonant organic compound is shown in general formula (1):

[0007]

[0008] In general formula (1), Z, which is the same or different each time, represents C-(H) or C-(R0); R0, which is the same or different each time, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C6alkyl group, a substituted or unsubstituted C3-C6cycloalkyl group, a substituted or unsubstituted C2-C6alkenyl group, a substituted or unsubstituted C2-C6alkynyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C2-C10heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted silane group. 10 alkyl group, a substituted or unsubstituted C3-C6cycloalkyl group, a substituted or unsubstituted C2-C6alkenyl group, a substituted or unsubstituted C2-C6alkynyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C2-C10heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted silane group. 10 alkyl group, a substituted or unsubstituted C3-C6cycloalkyl group, a substituted or unsubstituted C2-C6alkenyl group, a substituted or unsubstituted C2-C6alkynyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C2-C10heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted silane group. 10 alkyl group, a substituted or unsubstituted C3-C6cycloalkyl group, a substituted or unsubstituted C2-C6alkenyl group, a substituted or unsubstituted C2-C6alkynyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C2-C10heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted silane group. 10 alkyl group, a substituted or unsubstituted C3-C6cycloalkyl group, a substituted or unsubstituted C2-C6alkenyl group, a substituted or unsubstituted C2-C6alkynyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C2-C10heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted silane group. 30 alkyl group, a substituted or unsubstituted C3-C6cycloalkyl group, a substituted or unsubstituted C2-C6alkenyl group, a substituted or unsubstituted C2-C6alkynyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C2-C10heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted silane group. 30 alkyl group, a substituted or unsubstituted C3-C6cycloalkyl group, a substituted or unsubstituted C2-C6alkenyl group, a substituted or unsubstituted C2-C6alkynyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C2-C10heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted silane group.

[0009] M1 and M2 rings are represented by C6-C6 rings that are substituted or unsubstituted with one or more R groups. 30 The aromatic ring, C2-C2 with or without one or more R-substituted or unsubstituted R-substituted rings. 30 Heteroaromatic rings, C6-C6 substituted or unsubstituted with one or more R groups. 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring;

[0010] The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0011] The replacement of R is either a single bond or a parallel ring connection;

[0012] Ar1, Ar2, and Ar3 are independently represented as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0013] Any two adjacent R0s are not connected or are connected by a single bond, double bond, -O-, -S-, or -N(R). c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect;

[0014] The Ar1 and M1 rings are not connected or are connected by single bonds, double bonds, -O-, -S-, or -N(R). c )-、-C(Rd (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect;

[0015] The Ar1 and M2 rings are not connected or are connected by single bonds, double bonds, -O-, -S-, or -N(R). c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect;

[0016] The R c R d R e R f R g R p R q Represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane;

[0017] The R d and R e They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene;

[0018] The R f and R g They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene;

[0019] X represents either a carbon atom or a silicon atom;

[0020] The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C10 C3-C10cycloalkyl, deuterium-substituted C3-C10cycloalkyl, 10 C6-C10aryl, deuterium-substituted C6-C10aryl, 30 C6-C10aryl, deuterium-substituted C6-C10aryl, 30 C6-C10aryl, deuterium-substituted C6-C10aryl, 10 C6-C10aryl, deuterium-substituted C6-C10aryl, 30 C6-C10aryl, deuterium-substituted C6-C10aryl, 30 C6-C10aryl, deuterium-substituted C6-C10aryl, 30 C6-C10aryl, deuterium-substituted C6-C10aryl,

[0021] The heteroatom in the heteroaryl group is optionally one or more of O, S, N, Si, B.

[0022] Further, the double-boron resonance-containing organic compound structure is shown in general formula (2):

[0023]

[0024] In general formula (2), the meanings of X, Z, Ar1, Ar2, and Ar3 are the same as defined in general formula (1).

[0025] Z1is C-(H) or C-(R a ); R a each occurrence, the same or different, is a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10alkyl group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C2-C10alkenyl group, a substituted or unsubstituted C2-C10alkynyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C2-C10heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted silane group; 10 C3-C10cycloalkyl, deuterium-substituted C3-C10cycloalkyl, 10 C2-C10alkenyl, deuterium-substituted C2-C10alkenyl, 10 C2-C10alkenyl, deuterium-substituted C2-C10alkenyl, 10 C2-C10alkynyl, deuterium-substituted C2-C10alkynyl, 30 C6-C10aryl, deuterium-substituted C6-C10aryl, 30 C2-C10heteroaryl, deuterium-substituted C2-C10heteroaryl,

[0026] Z2is C-(H) or C-(R b ); R b each occurrence, the same or different, is a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10alkyl group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C2-C10alkenyl group, a substituted or unsubstituted C2-C10alkynyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C2-C10heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted silane group; 10 C3-C10cycloalkyl, deuterium-substituted C3-C10cycloalkyl, 10 C2-C10alkenyl, deuterium-substituted C2-C10alkenyl, 10 C2-C10alkenyl, deuterium-substituted C2-C10alkenyl, 10 C2-C10alkynyl, deuterium-substituted C2-C10alkynyl, 30 C6-C10aryl, deuterium-substituted C6-C10aryl, 30 C2-C10heteroaryl, deuterium-substituted C2-C10heteroaryl,

[0027] Ar1and R a are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R c )-, -C(R d )(R e )-, -Si(R f )(R g )- or -C(R p )=C(R q )-;

[0028] Ar1and R b are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R c )-, -C(R d )(R e )-, -Si(R f )(R g )- or -C(R p )=C(R q )-;

[0029] R c , R d , R e , R f , R g , R p , R q each independently represent one of 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 arylamine, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 borane;

[0030] R d and R e are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(ph)-, dimethyl substituted methylene, diphenyl substituted methylene;

[0031] R f and R g are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(ph)-, dimethyl substituted methylene, diphenyl substituted methylene;

[0032] The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0033] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0034] Furthermore, the structure of the double-boron resonance-type organic compound is shown in general formula (A-1) or general formula (A-2):

[0035]

[0036] In general formulas (A-1) and (A-2), the meanings of X, Z, Ar2, and Ar3 are the same as those defined in general formula (1);

[0037] X1 is represented as O, S, N(R) i One of them;

[0038] R i Indicated as 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 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane;

[0039] M represents substituted or unsubstituted C6-C. 30 Aromatic ring, substituted or unsubstituted C2-C 30 One of the aromatic rings;

[0040] The R i It is not connected to adjacent Z bonds or is connected via single bonds, double bonds, -O-, -S-, or -N(R). c )-、-C(Rd (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect;

[0041] The R i It is not connected to M or is connected via a single bond, double bond, -O-, -S-, -N(R) c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect;

[0042] The R c R d R e R f R g R p R q Each C1 to C2 is represented independently as substituted or unsubstituted. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane;

[0043] The R d and R e They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene;

[0044] The R f and R g They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene;

[0045] The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;

[0046] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0047] Furthermore, the structure of the double-boron resonance-type organic compound is shown in any one of general formulas (A-3) to (A-6):

[0048]

[0049] In general formulas (A-3) to (A-6), the meanings of X, Z, Ar2, and Ar3 are the same as those defined in general formula (1);

[0050] Y represents either a carbon atom or a silicon atom;

[0051] Ar4 and Ar5 are represented independently as substituted or unsubstituted C1 to C2, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0052] The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;

[0053] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B;

[0054] Preferably, the double-boron resonance type organic compound has a structure represented by any one of General Formula (A-7) to General Formula (A-9):

[0055]

[0056] In General Formula (A-7) to General Formula (A-9), the meanings of X and Z are the same as defined in General Formula (1).

[0057] Y represents one of a carbon atom or a silicon atom;

[0058] Preferably, the double-boron resonance type organic compound has a structure represented by any one of General Formula (A-10) to General Formula (A-12):

[0059]

[0060]

[0061] In General Formula (A-10) to General Formula (A-12), the meanings of X and Z are the same as defined in General Formula (1).

[0062] Y represents one of a carbon atom or a silicon atom.

[0063] Preferably, the double-boron resonance type organic compound has a structure represented by any one of General Formula (A-13) to General Formula (A-15):

[0064]

[0065] In General Formula (A-13) to General Formula (A-15), R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , and R 12 each independently represent one of 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 arylamine group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted silane group;

[0066] X represents one of a carbon atom or a silicon atom;

[0067] Y represents one of a carbon atom or a silicon atom;

[0068] The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;

[0069] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0070] Furthermore, the structure of the double-boron resonance-type organic compound is shown in any one of general formulas (B-1) to (B-2):

[0071]

[0072] In general formulas (B-1) and (B-2), Z, Ar2, Ar3, and X have the same meaning as defined in general formula (1) of claim 1;

[0073] M4 indicates substituted or unsubstituted C6-C. 30 Aromatic ring, substituted or unsubstituted C2-C 30 One of the aromatic rings;

[0074] Ar7 and Ar8 are each represented independently as hydrogen atoms, substituted or unsubstituted C1 to C1 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0075] The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;

[0076] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B;

[0077] Preferably, the structure of the double-boron resonance-type organic compound is as shown in any one of general formulas (B-3) to (B-6):

[0078]

[0079]

[0080] In general formulas (B-3) to (B-6), the definitions of Z, Ar2, Ar3, Ar7, Ar8, and X are the same as those in general formulas (B-1) and (B-2);

[0081] Preferably, the structure of the double-boron resonance-type organic compound is shown in any one of general formulas (B-7) to (B-10):

[0082]

[0083] In general formulas (B-7) to (B-10), the definitions of Z, Ar7, Ar8, and X are the same as those in general formulas (B-1) and (B-2);

[0084] Preferably, the structure of the double-boron resonance-type organic compound is shown in any one of general formulas (B-11) to (B-14):

[0085]

[0086] In formulas (B-11) to (B-14), the definitions of Z, Ar7, Ar8, and X are the same as those in formulas (B-1) and (B-2); preferably, the structure of the double-boron resonance-type organic compound is shown in any one of formulas (B-15) to (B-18):

[0087]

[0088]

[0089] In General Formula (B-15) to General Formula (B-18), Ar7, Ar8, and X are the same as defined in General Formula (B-1) and General Formula (B-2).

[0090] R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 alkyl group, substituted or unsubstituted C3-C 10 cycloalkyl group, substituted or unsubstituted C2-C 10 alkenyl group, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C2-C 30 heteroaryl group, substituted or unsubstituted borane group, substituted or unsubstituted silane group;

[0091] The substituents for substituting the above substitutable groups are optionally selected from deuterium atom, halogen atom, cyano group, C1-C 10 alkyl group, deuterium-substituted C1-C 10 alkyl group, C3-C 10 cycloalkyl group, deuterium-substituted C3-C 10 cycloalkyl group, C6-C 30 aryl group, deuterium-substituted C6-C 30 aryl group, C1-C 10 alkyl-substituted C6-C 30 aryl group, C2-C 30 heteroaryl group, deuterium-substituted C2-C 30 heteroaryl group;

[0092] The heteroatom in the heteroaryl group is optionally one or more selected from O, S, N, Si, and B.

[0093] Further, the double-boron resonance type organic compound has a structure as shown in General Formula (C-1):

[0094]

[0095] In General Formula (C-1), X and Z are the same as defined in General Formula (1).

[0096] Z3, Z4, and Z5 are each independently C-(H) or C-(R0); and R0 is deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 alkyl group, substituted or unsubstituted C3-C 10 cycloalkyl group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C 30Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane;

[0097] The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups;

[0098] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0099] Furthermore, the structure of the double-boron resonance-type organic compound is shown in general formula (D-1):

[0100]

[0101] In general formula (D-1), M1 and M2 represent C6 to C6 molecules substituted or unsubstituted by one or more R molecules. 30 The aromatic ring, C2-C2 with or without one or more R-substituted or unsubstituted R-substituted rings. 30 Heteroaromatic rings, C6-C6 substituted or unsubstituted with one or more R groups. 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring;

[0102] The M3 ring represents C3-C6 with or without substitution. 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0103] The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0104] The replacement of R is either a single bond or a parallel ring connection;

[0105] Ar2 and Ar3 are represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0106] X represents either a carbon atom or a silicon atom;

[0107] R1, R2, R3, R4, and R5 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, and substituted or unsubstituted C1-C1 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0108] m can be represented as 0, 1, 2, 3 or 4;

[0109] n and s represent 0, 1, 2 or 3;

[0110] o1 represents 0 or 1;

[0111] X1 represents a single bond, double bond, -O-, -S-, -N(R) c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-;

[0112] The Rc It is not connected to the M1 ring or is connected via a single bond, double bond, -O-, -S-, or -N(R) c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-;

[0113] The R c It is not connected to the M3 ring or is connected via a single bond, double bond, -O-, -S-, or -N(R) c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-;

[0114] The R c R d R e R f R g R p R q Represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane;

[0115] The R d and R e They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene;

[0116] The R f and R g They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene;

[0117] The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10alkyl group, deuterium-substituted C1-C 10 alkyl group, C3-C 10 cycloalkyl group, deuterium-substituted C3-C 10 cycloalkyl group, C6-C 30 aryl group, deuterium-substituted C6-C 30 aryl group, C1-C 10 alkyl-substituted C6-C 30 aryl group, C2-C 30 heteroaryl group, deuterium-substituted C2-C 30 heteroaryl group, deuterium-substituted C2-C

[0118] the heteroatom in said heteroaryl group is optionally one or more selected from O, S, N, Si, B;

[0119] Preferably, said double-boron resonance-containing organic compound has a structure as shown in general formula (D-2):

[0120]

[0121] In general formula (D-2), Ar2, Ar3, X, X1, R1, R2, R3, R4, R5, o1, m, n, s are defined as in general formula (D-1);

[0122] R6is one of 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 arylamine group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group;

[0123] k is 0, 1 or 2;

[0124] the substituents of the above-mentioned substituents are optionally selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, deuterium-substituted C1-C 10 alkyl group, C3-C 10 cycloalkyl group, deuterium-substituted C3-C 10 cycloalkyl group, C6-C 30 aryl group, deuterium-substituted C6-C 30 aryl group, C1-C 10 alkyl-substituted C6-C 30 aryl group, C2-C 30 heteroaryl group, deuterium-substituted C2-C30 Any one or more of the heteroaryl groups;

[0125] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B;

[0126] Preferably, the structure of the double-boron resonance-type organic compound is as shown in any one of general formulas (D-3) to (D-5):

[0127]

[0128]

[0129] In general formulas (D-3) to (D-5), the definitions of Ar2, Ar3, X, R1, R2, R3, R4, R5, m, n, and s are the same as those in general formula (D-1);

[0130] Ar4 and Ar5 are represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0131] R6, R7, R8, R9, R 10 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or 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 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0132] k represents 0, 1, or 2;

[0133] h represents 0, 1, 2, 3, 4 or 5;

[0134] j represents 0, 1, 2, 3 or 4;

[0135] i and g represent 0, 1, 2 or 3;

[0136] o2, o3 represent 0 or 1;

[0137] X2, X3 independently represent a single bond, a double bond, -O-, -S-, -N(R c )-, -C(R d )(R e )-, -Si(R f )(R g )- or -C(R p )=C(R q )-;

[0138] said R c , R d , R e , R f , R g , R p , R q independently represent one of 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 C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted borane group;

[0139] said R d and R e are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, diphenyl-substituted methylene;

[0140] said R f and R g are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, diphenyl-substituted methylene;

[0141] the substituents of the above substitutable groups are optionally 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 deuterium-substituted C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C1-C 10 alkyl-substituted C6-C 30 aryl group, a C2-C 30heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0142] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B;

[0143] Preferably, the structure of the double-boron resonance-type organic compound is as shown in any one of general formulas (D-6) to (D-10):

[0144]

[0145] In general formulas (D-6) to (D-10), the definitions of Ar2, Ar3, X, R1, R2, R3, R4, R5, m, n, and s are the same as those in general formula (D-1);

[0146] Ar4 and Ar5 are represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0147] R6, R7, R8, R9, R 11 R 12 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or 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 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0148] k represents 0, 1, or 2;

[0149] j, t, y represent 0, 1, 2, 3 or 4;

[0150] i and g represent 0, 1, 2 or 3;

[0151] The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0152] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0153] Preferably, the structure of the double-boron resonance-type organic compound is shown in any one of general formulas (D-11) to (D-16):

[0154]

[0155]

[0156] In general formulas (D-11) to (D-16), the definitions of Ar2, Ar3, X, R1, R2, R3, R4, m, n, and s are the same as those in general formula (D-1);

[0157] Ar4 and Ar5 are represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0158] R7, R8, R9, R 10 R 11 R 12 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or 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 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0159] The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

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

[0161] Further, the M1 and M2 rings represent any one of the following groups that are R-substituted or unsubstituted: phenyl, naphthyl, anthraceneyl, phenanthryl, pyridinyl, quinolinyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazoyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl;

[0162] The M, M3, and M4 rings represent any one of the following: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraxyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted indole[3,2,1-jk]carbazoyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and substituted or unsubstituted spirofluorenyl.

[0163] The R, R0, R a R bRepresented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthraquinyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiopheneyl group, substituted... Or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, 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 diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl;

[0164] The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 Represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophene group. Substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl;

[0165] The R i R c R d R e Rf R g R p R q Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are independently represented as 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 anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, etc. Substituted or unsubstituted thiophene group, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted 9,9-dimethylfluorenyl group, substituted or unsubstituted 9,9-diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted triazine group, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, substituted or unsubstituted diphenylamino group, substituted or unsubstituted indole group, substituted or unsubstituted benzoindole group;

[0166] The substituents used for the substituent groups are selected from deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indoleyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, azirphenanthreneyl, diphenylamino, 1,1,4, 4-Tetramethyl-1,2,3,4-tetrahydronaphthyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl; one or more of these.

[0167] Preferably, the M1 and M4 rings are independently represented by the following ring structures:

[0168]

[0169] any one of them;

[0170] The M2, M3, and M rings are represented by the following groups:

[0171] any one of them;

[0172] Each occurrence of Z, whether the same or different, is represented as C-(H) or C-(R0);

[0173] The R, R0, R a R b , R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 Each can be represented independently as shown in the following structure:

[0174] Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl

[0175] any one of them;

[0176] The R i R c R d R e R f R g R p R q Ar1, Ar2, Ar3, Ar4, Ar5, Ar7, and Ar8 are represented by the following structures: methyl, ethyl, isopropyl, tert-butyl.

[0177]

[0178] Any one of them.

[0179] Furthermore, the specific structural formula of the double-boron resonance-type organic compound is any one of the following structures:

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] The present invention also provides an organic light-emitting device, comprising a substrate, a first electrode, a second electrode, and a functional layer in sequence, wherein the functional layer is located between the first electrode and the second electrode, and the functional layer contains the double-boron resonant organic compound of the present invention.

[0202] Preferably, the functional layer includes a light-emitting layer, which comprises a host material and a dopant material, wherein the dopant material is the double-boron resonant organic compound of the present invention.

[0203] Preferably, the functional layer includes a light-emitting layer, which includes 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 a double-boron resonant organic compound as described in this invention.

[0204] Furthermore, the functional layer includes a light-emitting layer, which comprises a host material, an exciton-sensitizing material, and a dopant material. The exciton-sensitizing material is a complex containing a metal element, and the dopant material is the double-boron resonant organic compound described in this invention.

[0205] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0206] (1) The compound of the present invention can be used in organic electroluminescent devices as a doping material for the light-emitting layer. It can emit green fluorescence under the action of an electric field and can be applied in the fields of OLED lighting or OLED display.

[0207] (2) The compound of the present invention, as a doping material, introduces a phosphorus photosensitizer, which can effectively improve device efficiency and lifespan;

[0208] (3) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device and enhance the luminous efficiency of the device;

[0209] (4) The compound of the present invention is used as a doping material, and TADF sensitizer is introduced as a second host, which can effectively improve device efficiency;

[0210] The compounds of this invention have a narrow half-width at half-maximum (WHM) characteristic and can be used as green light doping materials for the emitting layer of organic electroluminescent devices, thereby improving the efficiency and lifetime of the devices. Attached Figure Description

[0211] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device using the materials listed in this invention;

[0212] Wherein, 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. Detailed Implementation

[0213] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0214] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.

[0215] In this invention, the substituted or unsubstituted aromatic amino group refers to... Wherein Q1 and Q2 represent substituted or unsubstituted aromatic groups, and Q1 and Q2 preferably represent substituted or unsubstituted C6-C6 groups. 30 Aryl or substituted or unsubstituted C2-C 30 Mixed aromatic compounds.

[0216] In this invention, C6 to C6 are substituted or unsubstituted. 30 Aryl refers to an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, preferably an aryl group with 6 to 20 substituted or unsubstituted carbon atoms, preferably an aryl group with 6 to 10 substituted or unsubstituted carbon atoms, preferably an aryl group with 8 to 10 substituted or unsubstituted carbon atoms, preferably substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrene, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted The group may contain, but is not limited to, a fused ring consisting of a substituted or unsubstituted triphenyl group, a substituted or unsubstituted peryl group, a substituted or unsubstituted indole group, a combination thereof, or a combination of the aforementioned groups.

[0217] In this invention, C6~C 30 Aryl refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and even more preferably an aryl group having 6 to 10 carbon atoms. Other preferred aryl groups include phenyl, naphthyl, anthraceneyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, phenanthryl, tetraphenyl, pyrene, diphenyl, and terphenyl. Fused rings of alkyl, triphenylene, perylene, indene, or combinations thereof, but not limited to these groups.

[0218] In this invention, deuterium-substituted C6-C 30 Aryl refers to a deuterated aryl group having 6 to 30 carbon atoms, preferably a deuterated aryl group having 6 to 20 carbon atoms, more preferably a deuterated aryl group having 6 to 10 carbon atoms, and preferably deuterated phenyl, deuterated naphthyl, deuterated anthracene, deuterated fluorenyl, deuterated dimethylfluorenyl, deuterated diphenylfluorenyl, deuterated spirofluorenyl, deuterated phenanthrene, deuterated tetraphenyl, deuterated pyrene, deuterated diphenyl, deuterated terphenyl, and deuterated... The group may include, but is not limited to, fused rings of alkyl, deuterated triphenylene, deuterated peryl, deuterated indene, combinations thereof, or combinations of the aforementioned groups.

[0219] In this invention, C2 to C are substituted or unsubstituted.30 Heteroaryl refers to a heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms, preferably a heteroaryl group with 2 to 20 substituted or unsubstituted carbon atoms, preferably a heteroaryl group with 4 to 20 substituted or unsubstituted carbon atoms, preferably a heteroaryl group with 4 to 10 substituted or unsubstituted carbon atoms, preferably a heteroaryl group with 5 to 10 substituted or unsubstituted carbon atoms, preferably a furanyl group, a thiophene group, a pyrrole group, a pyrazolyl group, a pyrazolyl group, a substituted imidazolyl group, a triazolyl group, a substituted oxazolyl group, a substituted thiazolyl group, a substituted oxadiazolyl group, a substituted thiadiazolyl group, a substituted pyridyl group, a substituted pyrimidinyl group, a substituted pyrimidinyl group, a substituted pyrazinyl group, or a substituted triazinyl group. The following are substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphthidyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted benziazinyl, substituted or unsubstituted benziazinyl, substituted or unsubstituted benziazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted benzoindolyl, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0220] In this 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, more preferably a heteroaryl group having 4 to 20 carbon atoms, and more preferably a heteroaryl group having 4 to 10 carbon atoms. It is particularly suitable for furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, and benzofuran. The following groups are included in the following categories: benzothiophene, benzimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, acridineyl, phenazinyl, phenthiazinyl, phenoxazinyl, fumonyl, dibenzofuranyl, dibenzothiophene, carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, benzoindolyl, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0221] In this invention, deuterium-substituted C2-C 30The heteroaryl group refers to a heteroaryl group with 5 to 30 deuterated carbon atoms, preferably a heteroaryl group with 5 to 20 deuterated carbon atoms, more preferably a heteroaryl group with 5 to 10 deuterated carbon atoms, and preferably deuterated furanyl, deuterated thiophene, deuterated pyrrole, deuterated pyrazolyl, deuterated imidazolyl, deuterated triazolyl, deuterated oxazolyl, deuterated thiazolyl, deuterated oxadiazolyl, deuterated thiadiazolyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated triazine, deuterated benzofuranyl, or deuterated benzothiophene. The following groups are included: deuterated benzimidazolyl, deuterated indolyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated quinazolinyl, deuterated quinolinyl, deuterated naphridyl, deuterated benzoxazinyl, deuterated benzothiazinyl, deuterated acridineyl, deuterated benzazinyl, deuterated benzthiazinyl, deuterated benzoxazinyl, deuterated fumonyl, deuterated dibenzofuranyl, deuterated dibenzothiophenyl, deuterated carbazoyl, deuterated substituted N-phenylcarbazoyl, deuterated benzoindolyl, combinations thereof, or fused rings of the aforementioned groups, but not limited thereto.

[0222] In this invention, C2 to C are substituted or unsubstituted. 30 The number of heteroatoms in the heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.

[0223] The substituted or unsubstituted C1-C of this invention 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to alkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, preferably alkyl groups with 1 to 5 substituted or unsubstituted carbon atoms, preferably alkyl groups with 1 to 4 substituted or unsubstituted 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 to these.

[0224] The C1 to C of this invention 10Alkyl (including straight-chain alkyl and branched-chain alkyl) 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, and 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 to these.

[0225] The deuterium-substituted C1-C of the present invention 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to a deuterated alkyl group having 1 to 10 carbon atoms, preferably a deuterated alkyl group having 1 to 5 carbon atoms, preferably a deuterated alkyl group having 1 to 4 carbon atoms, preferably deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated tert-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated neopentyl, deuterated n-pentyl, deuterated isopentyl, deuterated octyl, deuterated heptyl, deuterated n-decyl, deuterated 1-methylpentyl, deuterated 2-methylpentyl, deuterated 3-methylpentyl, deuterated 1-butylpentyl, etc., but not limited to these.

[0226] The substituted or unsubstituted C3-C of this invention 10 The cycloalkyl group preferably uses substituted or unsubstituted C4-C9 cycloalkyl groups, more preferably substituted or unsubstituted C5-C8 cycloalkyl groups, and particularly preferably substituted or unsubstituted C5-C7 cycloalkyl groups. Non-limiting examples may include, but are not limited to, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted 4-methylcyclohexyl, substituted or unsubstituted 4,4-dimethylcyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted cycloheptyl.

[0227] The C3~C of this invention 10 The cycloalkyl group is preferably C4-C9 cycloalkyl, more preferably C5-C8 cycloalkyl, and particularly preferably C5-C7 cycloalkyl. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0228] The deuterium-substituted C3-C of the present invention 10The cycloalkyl group is preferably a deuterated C4-C9 cycloalkyl group, more preferably a deuterated C5-C8 cycloalkyl group, and particularly preferably a deuterated C5-C7 cycloalkyl group. Non-limiting examples may include, but are not limited to, deuterated cyclopropyl, deuterated cyclobutyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated 4-methylcyclohexyl, deuterated 4,4-dimethylcyclohexyl, deuterated adamantyl, and deuterated cycloheptyl.

[0229] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0230] The C1 to C of this invention 10 Alkoxy groups include, but are not limited to, alkoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or isopropoxy.

[0231] The C2 to C of this invention 10 Alkenyl refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 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 is not limited to these.

[0232] In this invention, the substituents used for the substituent groups are selected from deuterium, cyano, adamantyl, methyl, ethyl, n-propyl, isopropyl, tert-amyl, tert-butyl, n-butyl, isobutyl, sec-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, furanyl, thiophene, indole, pyrrole, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazole, N-phenylcarbazole, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and methyl-substituted benzene. One or more of the following: methyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, and deuterated tert-butyl-substituted diphenyl.

[0233] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent PI film substrates; and opaque substrates, such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent glass substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0234] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may 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). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, or Cr, or it may be an alloy of several metals, or a combination of metals, metal oxides, or metal alloys. The thickness of the first electrode layer depends on the material used, and is typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0235] The organic functional material layer disposed between the first electrode and the second electrode includes, from bottom to top, a hole transport region, a light-emitting layer, and an electron transport region.

[0236] In this invention, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0237] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer, any material can be selected from known materials used in organic electroluminescent devices.

[0238] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

[0239] Based on the above empirical summary, for hole-based host organic materials with different HOMO energy levels, it is necessary to select different P-doped materials to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0240] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from compounds disclosed in the prior art, such as those disclosed in JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, and CN105439999A, but is not limited thereto.

[0241] Preferably, the p-type doped material is a charge-conducting compound disclosed in the prior art. The p-type dopant can be selected from compounds disclosed in any of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE10200703122. 0A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but not limited to these.

[0242] In one embodiment of the invention, the hole injection layer comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0243] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0244] 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.

[0245] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0246]

[0247]

[0248] Preferably, the main organic material used as the hole transport layer material and the hole injection layer of the present invention is selected from the same compound.

[0249] 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.

[0250] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0251]

[0252] 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.

[0253] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.

[0254] The light-emitting layer may include a host material and a dopant material. The host material may be a green light host material commonly used in the art, and the dopant material may be a double-boron resonant organic compound represented by the general formula (1) of this invention.

[0255] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0256] The dual-body material comprises a first body material and a second body material, wherein preferably at least one of the first body material and the second body material is a TADF material;

[0257] TADF materials refer to materials with thermally activated delayed fluorescence properties. They are characterized by a small energy difference between the first excited singlet and triplet states, allowing for the simultaneous utilization of both singlet and triplet excitons generated within the device, thus enabling the exciton utilization rate of electrogenerated excitons within the device to approach 100%. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0258] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0259] Exciton-sensitized materials refer to materials that enable the luminescent material in the luminescent layer to fully utilize electroexcitons, thereby allowing the luminescent layer to ultimately produce the emission spectrum of the sensitized material. Exciton sensitizers may perform functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The combination of the bisboron-containing organic compound shown in formula (1) of this invention and the exciton-sensitized material has a significant improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0260] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0261] The thickness of the light-emitting layer can be adjusted to optimize luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and even more preferably 15-40 nm, but the thickness is not limited to this range.

[0262] In this invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light-emitting layer, but is not limited thereto.

[0263] A hole-blocking layer is a layer that prevents holes injected from the anode from penetrating the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its performance. The hole-blocking layer of this invention can be disposed on top of the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, for example:

[0264]

[0265] The thickness of the hole blocking layer of the present invention can be 2-200nm, preferably 5-150nm, more preferably 5-50nm, but the thickness is not limited to this range.

[0266] An electron transport layer may be disposed above the light-emitting layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers these received electrons to the light-emitting layer. Preferably, a material with high electron mobility is used. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials disclosed in the prior art for organic electroluminescent devices can be used, for example:

[0267]

[0268] In a preferred embodiment of the invention, the electron transport layer further includes other compounds conventionally used in electron transport layers, such as Alq3, LiQ, preferably LiQ.

[0269] 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.

[0270] An electron injection layer can be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, which facilitates electron injection into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of this invention, 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.

[0271] 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.

[0272] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0273] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.

[0274] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0275] Preparation of compounds

[0276] 1. Synthesis of intermediate P

[0277] Synthesis of intermediate P1:

[0278]

[0279] The following reactants were added sequentially to a three-necked flask: T1 (5.5 mmol, 1.49 g), R1 (5 mmol, 1.41 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (50 mL). The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 12 hours. After the reaction mixture cooled to room temperature, it was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate P1.

[0280] Synthesis of intermediate P2:

[0281]

[0282] Add raw material T2 (25 mmol, 10.1 g), potassium carbonate (62.5 mmol, 8.6 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 160 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 45 minutes. Add raw material R2 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 12 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate X1.

[0283]

[0284] Add raw material T3 (18.4 mmol, 3.9 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add intermediate X1 (20.2 mmol, 11.0 g) under nitrogen protection. Reflux the solution under magnetic stirring for 25 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate P2.

[0285] Synthesis of intermediate P3:

[0286]

[0287] Add raw material T3 (25 mmol, 7.3 g), potassium carbonate (62.5 mmol, 8.6 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material R3 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 12 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate X2.

[0288]

[0289] Add raw material T3 (18.4 mmol, 3.9 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add intermediate X2 (20.2 mmol, 8.7 g) under nitrogen protection. Reflux the solution for 24 hours with magnetic stirring. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate P3.

[0290] 2. Synthesis of intermediate Q

[0291] Synthesis of intermediate Q1:

[0292]

[0293] Add raw material M1 (18.4 mmol, 6.2 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material M2 (20.2 mmol, 5.6 g) under nitrogen protection. Reflux the solution under magnetic stirring for 24 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate Y1.

[0294]

[0295] Intermediate Y1 (5.1 mmol, 3.0 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.7 mL of n-butyllithium (2.5 M, 11.7 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 15 mL of tetrahydrofuran solution of starting material M3 (5.5 mmol, 1.6 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1.0 M), distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were 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 then slowly quenched with an aqueous solution of sodium bicarbonate (NaHCO3). Next, the aqueous layer was separated, extracted with dichloromethane, dried with sodium sulfate, filtered, distilled under reduced pressure, and passed through a column to obtain intermediate Q1.

[0296] Synthesis of intermediate Q2:

[0297]

[0298] Intermediate Y1 (5.1 mmol, 3.0 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.7 mL of n-butyllithium (2.5 M, 11.7 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 15 mL of tetrahydrofuran solution of starting material M4 (5.5 mmol, 2.2 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1.0 M), distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were 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 then slowly quenched with an aqueous solution of sodium bicarbonate (NaHCO3). Next, the aqueous layer was separated, extracted with dichloromethane, dried with sodium sulfate, filtered, distilled under reduced pressure, and passed through a column to obtain intermediate Q2.

[0299] Synthesis of intermediate Q3:

[0300]

[0301] Intermediate Y1 (5.1 mmol, 3.0 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.7 mL of n-butyllithium (2.5 M, 11.7 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 15 mL of tetrahydrofuran solution of starting material M5 (5.5 mmol, 1.8 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1.0 M), distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were 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 then slowly quenched with an aqueous solution of sodium bicarbonate (NaHCO3). Next, the aqueous layer was separated, extracted with dichloromethane, dried with sodium sulfate, filtered, distilled under reduced pressure, and passed through a column to obtain intermediate Q3.

[0302] 3. Synthesis of the Examples

[0303] Example 1: Synthesis of Compound 31:

[0304]

[0305] Intermediate Q3 (5.5 mmol, 4.31 g), starting material A1 (5 mmol, 0.75 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (150 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 20 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate J1.

[0306]

[0307] Intermediate P1 (5.5 mmol, 2.59 g), intermediate J1 (5 mmol, 4.26 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (150 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate K1.

[0308]

[0309] In a three-necked flask under nitrogen protection, intermediate K1 (2 mmol, 2.48 g) and 120 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the system was heated to 60 °C and reacted for 6 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the system at 0 °C, and the mixture was heated to 120 °C and reacted for another 12 hours. After the reaction was complete, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was concentrated under reduced pressure, purified by silica gel column chromatography, and dried under vacuum to give compound 31. In toluene solution (1 × 10⁻⁶), -5 The half-width at half maximum (WHM) is 24 nm.

[0310] Example 2: Synthesis of compound 39:

[0311]

[0312] Intermediate Q1 (5.5 mmol, 4.03 g), starting material A2 (5 mmol, 0.75 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (150 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 21 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate J2.

[0313]

[0314] The following ingredients were added sequentially to a three-necked flask: starting material B1 (5.5 mmol, 2.58 g), intermediate J2 (5 mmol, 4.01 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (150 mL). The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate K2.

[0315]

[0316] In a three-necked flask under nitrogen protection, intermediate K2 (2 mmol, 2.38 g) and 120 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the system was heated to 60 °C and reacted for 5 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the system at 0 °C, and the mixture was heated to 120 °C and reacted for another 12 hours. After the reaction was complete, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was concentrated under reduced pressure, purified by silica gel column chromatography, and dried under vacuum to give compound 39. (The compound was then dissolved in toluene solution (1 × 10⁻⁶)). -5 The half-width at half maximum (WHM) is 22 nm.

[0317] Example 3: Synthesis of compound 41:

[0318]

[0319] Intermediate Q2 (5.5 mmol, 4.65 g), starting material A1 (5 mmol, 0.75 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (180 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 22 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate J3.

[0320]

[0321] The following ingredients were added sequentially to a three-necked flask: starting material B1 (5.5 mmol, 2.58 g), intermediate J3 (5 mmol, 4.57 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (200 mL). The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate K3.

[0322]

[0323] In a three-necked flask under nitrogen protection, intermediate K3 (2 mmol, 2.60 g) and 120 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the mixture was heated to 60 °C and reacted for 6 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the mixture at 0 °C, and the mixture was heated to 120 °C and reacted for another 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, quenched with methanol, and the organic layer was concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography and dried under vacuum to give compound 41. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 23 nm.

[0324] Example 4: Synthesis of Compound 112:

[0325]

[0326] The following ingredients were added sequentially to a three-necked flask: starting material B2 (5.5 mmol, 4.09 g), intermediate J2 (5 mmol, 4.01 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (200 mL). The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 28 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate K4.

[0327]

[0328] In a three-necked flask under nitrogen protection, intermediate K4 (2 mmol, 2.93 g) and 180 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the mixture was heated to 60 °C and reacted for 6 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the mixture at 0 °C, and the mixture was heated to 120 °C and reacted for another 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, quenched with methanol, and the organic layer was concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography and dried under vacuum to give compound 112. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 24 nm.

[0329] Example 5: Synthesis of Compound 129:

[0330]

[0331] Intermediate Q1 (11 mmol, 8.07 g), starting material A1 (5 mmol, 0.75 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (30 mmol, 2.88 g), and toluene (160 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 27 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate J5.

[0332]

[0333] In a three-necked flask under nitrogen protection, intermediate J5 (2 mmol, 2.91 g) and 180 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the mixture was heated to 60 °C and reacted for 10 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 10 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the mixture at 0 °C, and the mixture was heated to 120 °C and reacted for another 16 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, quenched with methanol, and the organic layer was concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography and dried under vacuum to give compound 129. (1 × 10⁻⁶) -5 The full width at half maximum (FWHM) is 21 nm.

[0334] Example 6: Synthesis of Compound 130:

[0335]

[0336] Intermediate Q1 (11 mmol, 8.07 g), starting material A2 (5 mmol, 0.75 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (30 mmol, 2.88 g), and toluene (160 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 28 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate J6.

[0337]

[0338] In a three-necked flask under nitrogen protection, intermediate J6 (2 mmol, 2.91 g) and 180 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the system was heated to 60 °C and reacted for 10 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 10 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the system at 0 °C, and the mixture was heated to 120 °C and reacted for another 16 hours. After the reaction was complete, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was concentrated under reduced pressure, purified by silica gel column chromatography, and dried under vacuum to give compound 130. In toluene solution (1 × 10⁻⁶ g / mL) -5 The half-width at half maximum (WHM) is 20 nm.

[0339] Example 7: Synthesis of Compound 132:

[0340]

[0341] Intermediate Q1 (11 mmol, 8.07 g), starting material A3 (5 mmol, 1.02 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (30 mmol, 2.88 g), and toluene (150 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate J6.

[0342]

[0343] In a three-necked flask under nitrogen protection, intermediate J6 (2 mmol, 3.02 g) and 180 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the mixture was heated to 60 °C and reacted for 8 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 10 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the mixture at 0 °C, and the mixture was heated to 120 °C and reacted for another 14 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, quenched with methanol, and the organic layer was concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography and dried under vacuum to give compound 132. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 24 nm.

[0344] Example 8: Synthesis of Compound 179:

[0345]

[0346] Intermediate P2 (5.5 mmol, 4.03 g), intermediate J2 (5 mmol, 4.01 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (200 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate K8.

[0347]

[0348] In a three-necked flask under nitrogen protection, intermediate K8 (2 mmol, 2.91 g) and 180 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the mixture was heated to 60 °C and reacted for 6 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the mixture at 0 °C, and the mixture was heated to 120 °C and reacted for another 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, quenched with methanol, and the organic layer was concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography and dried under vacuum to give compound 179. (The remaining text appears to be incomplete and requires further context.) -5 The half-width at half maximum (WHM) is 23 nm.

[0349] Example 9: Synthesis of Compound 227:

[0350]

[0351] Intermediate P3 (5.5 mmol, 3.42 g), intermediate J2 (5 mmol, 4.01 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (180 mL) were added sequentially to a three-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate K9.

[0352]

[0353] In a three-necked flask under nitrogen protection, intermediate K9 (2 mmol, 2.68 g) and 180 mL of tert-butylbenzene were added. A 1.6 M tert-butyllithium solution in pentane (5 mmol, 3.1 mL) was slowly added at -40 °C, and the mixture was heated to 60 °C and reacted for 6 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly brought to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the mixture at 0 °C, and the mixture was heated to 120 °C and reacted for another 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, quenched with methanol, and the organic layer was concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography and dried under vacuum to give compound 227. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 24 nm.

[0354] Note: Half-width at half-maximum (FWHM) was measured using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0355] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0356] Table 1

[0357] Compounds Structural characterization 31 LC-MS: found: 1188.78 ([M+H] + ), exact mass: 1187.65. <!-- 63 -->]]> 39 LC-MS: found: 1136.82 ([M+H] + ), exact mass: 1135.61.]] 41 LC-MS: found: 1248.76 ([M+H] + ), exact mass: 1247.74.]] 112 LC-MS: found: 1410.88 ([M+H] + ), exact mass: 1409.79.]] 129 LC-MS: found: 1400.93 ([M+H] + ), exact mass: 1399.71.]] 130 LC-MS: found: 1400.89 ([M+H] + ), exact mass: 1399.71.]] 132 LC-MS: found: 1454.73 ([M+H] + ), exact mass: 1453.76.]] 179 LC-MS: found: 1400.74 ([M+H] + ), exact mass: 1399.80.]] 227 LC-MS: found: 1288.71 ([M+H] + ), exact mass: 1287.68.]]

[0358] The following describes in detail the application effects of the organic electroluminescent material synthesized in the present invention in devices through device examples 1-9 and device comparative example 1. Device examples 2-9 and device comparative example 1 are fabricated using the same process as device example 1, employing the same substrate and electrode materials, and maintaining the same electrode film thickness. The only difference is the replacement of the doping material in the light-emitting layer. The layer structures and test results of each device example are shown in Tables 2-1 and 3, respectively.

[0359] Device Example 1

[0360] like Figure 1 As shown, the transparent substrate layer 1 is transparent glass. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, HT-1 and HI-1 with a thickness of 10nm are deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the organic electroluminescent device is fabricated, using GH-1 and GH-2 as the host materials and compound 31 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 31 of 69:30:1, and a film thickness of 30nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.

[0361] The application effects of the organic electroluminescent material synthesized in this invention in devices are described in detail below through device examples 10-18 and device comparative example 2. The fabrication processes of device examples 11-18 and device comparative example 2 are completely identical to those of device example 10, and the same substrate and electrode materials are used, with the same electrode film thickness. The only difference is the replacement of the doping material in the light-emitting layer. The layer structures and test results of each device example are shown in Tables 2-2 and 3, respectively.

[0362] Device Example 10

[0363] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the 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 dopant, and compound 31 is used as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 31 is 66.5:30:3:0.5, and the thickness of the emitting layer is 30 nm. After the emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1, with a thickness of 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated by vacuum evaporation device, with a Mg:Ag mass ratio of 1:9. This layer is used as the cathode layer 10.

[0364] The molecular structural formulas of the relevant materials are shown below:

[0365]

[0366]

[0367] After the organic electroluminescent device is completed as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency and lifetime of the device are measured. Examples and comparisons of devices prepared using the same method are shown in Tables 2-1 and 2-2; the test results of the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0368] Table 2-1

[0369]

[0370]

[0371] Table 2-2

[0372]

[0373] Table 3

[0374]

[0375] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0376] As can be seen from the device data results in Table 3, the emission peak of the compound of the present invention is between 510 and 540 nm, which can achieve the effect of green light emission very well. Compared with the devices of Comparative Examples 1-2, the organic light-emitting device of the present invention has a significantly improved lifetime compared with organic electroluminescent devices of known materials, whether in a single-doped system or a double-doped system. When using an exciton-sensitized material as the first dopant, the device efficiency and lifetime are significantly improved compared with single doping.

[0377] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A double-boron resonance-type organic compound, characterized in that: The structure of the double-boron resonance-type organic compound is shown in general formula (1): In general formula (1), each occurrence of Z, whether the same or different, is represented by C-(H) or C-(R0); each occurrence of R0, whether the same or different, is represented by a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1 to C2 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; M1 and M2 rings are represented by C6-C6 rings that are substituted or unsubstituted with one or more R groups. 30 The aromatic ring, C2-C2 with or without one or more R-substituted or unsubstituted R-substituted rings. 30 Heteroaromatic rings, C6-C6 substituted or unsubstituted with one or more R groups. 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring; The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; The replacement of R is either a single bond or a parallel ring connection; Ar1, Ar2, and Ar3 are independently represented as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Any two adjacent R0s are not connected or are connected by a single bond, double bond, -O-, -S-, or -N(R). c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect; The Ar1 and M1 rings are not connected or are connected by single bonds, double bonds, -O-, -S-, or -N(R). c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect; The Ar1 and M2 rings are not connected or are connected by single bonds, double bonds, -O-, -S-, or -N(R). c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect; The R c R d R e R f R g R p R q Represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane; The R d and R e They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; The R f and R g They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; X represents either a carbon atom or a silicon atom; The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

2. The double-boron resonance-type organic compound according to claim 1, characterized in that, The structure of the double-boron resonance-type organic compound is shown in general formula (2): In general formula (2), the meanings of X, Z, Ar1, Ar2, and Ar3 are the same as those defined in general formula (1); Z1 is represented as C-(H) or C-(R) a ); R a Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or substituted or unsubstituted C1-C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; Z2 is represented as C-(H) or C-(R) b ); R b Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or substituted or unsubstituted C1-C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; The Ar1 and R a They are not connected or are connected by single bonds, double bonds, -O-, -S-, -N(R) c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect; The Ar1 and R b They are not connected or are connected by single bonds, double bonds, -O-, -S-, -N(R) c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect; The R c R d R e R f R g R p R q Each C1 to C2 is represented independently as substituted or unsubstituted. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boroalkyl groups; The R d and R e They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; The R f and R g They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

3. The double-boron resonance-type organic compound according to claim 1, characterized in that, The structures of the double-boron resonance-type organic compounds are shown in general formula (A-1) or general formula (A-2): In general formulas (A-1) and (A-2), the meanings of X, Z, Ar2, and Ar3 are the same as those defined in general formula (1); X1 is represented as O, S, N(R) i One of them; R i Indicated as 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 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane; M represents substituted or unsubstituted C6-C. 30 Aromatic ring, substituted or unsubstituted C2-C 30 One of the aromatic rings; The R i It is not connected to adjacent Z bonds or is connected via single bonds, double bonds, -O-, -S-, or -N(R). c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect; The R i It is not connected to M or is connected via a single bond, double bond, -O-, -S-, -N(R) c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-connect; The R c R d R e R f R g R p R q Each C1 to C2 is represented independently as substituted or unsubstituted. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane; The R d and R e They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; The R f and R g They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

4. The double-boron resonance-type organic compound according to claim 1, characterized in that, The structure of the double-boron resonance-type organic compound is shown in any one of general formulas (A-3) to (A-6): In general formulas (A-3) to (A-6), the meanings of X, Z, Ar2, and Ar3 are the same as those defined in general formula (1); Y represents either a carbon atom or a silicon atom; Ar4 and Ar5 are represented independently as substituted or unsubstituted C1 to C2, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B; Preferably, the structure of the double-boron resonance-type organic compound is shown in any one of general formulas (A-7) to (A-9): In general formulas (A-7) to (A-9), the meanings of X and Z are the same as those defined in general formula (1); Y represents either a carbon atom or a silicon atom; Preferably, the structure of the double-boron resonance-type organic compound is shown in any one of general formulas (A-10) to (A-12): In general formulas (A-10) to (A-12), the meanings of X and Z are the same as those defined in general formula (1); Y represents either a carbon atom or a silicon atom; Preferably, the structure of the double-boron resonance-type organic compound is shown in any one of general formulas (A-13) to (A-15): In general formulas (A-13) to (A-15), R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or 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 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; X represents either a carbon atom or a silicon atom; Y represents either a carbon atom or a silicon atom; The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

5. The double-boron resonance-type organic compound according to claim 1, characterized in that, The structure of the double-boron resonance-type organic compound is shown in any one of general formulas (B-1) to (B-2): In general formulas (B-1) and (B-2), Z, Ar2, Ar3, and X have the same meaning as defined in general formula (1) of claim 1; M4 indicates substituted or unsubstituted C6-C. 30 Aromatic ring, substituted or unsubstituted C2-C 30 One of the aromatic rings; Ar7 and Ar8 are each represented independently as hydrogen atoms, substituted or unsubstituted C1 to C1 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B; Preferably, the structure of the double-boron resonance-type organic compound is as shown in any one of general formulas (B-3) to (B-6): In general formulas (B-3) to (B-6), the definitions of Z, Ar2, Ar3, Ar7, Ar8, and X are the same as those in general formulas (B-1) and (B-2); Preferably, the structure of the double-boron resonance-type organic compound is as shown in any one of general formulas (B-7) to (B-10): In general formulas (B-7) to (B-10), the definitions of Z, Ar7, Ar8, and X are the same as those in general formulas (B-1) and (B-2); Preferably, the structure of the double-boron resonance-type organic compound is shown in any one of general formulas (B-11) to (B-14): In formulas (B-11) to (B-14), the definitions of Z, Ar7, Ar8, and X are the same as those in formulas (B-1) and (B-2); preferably, the structure of the double-boron resonance-type organic compound is shown in any one of formulas (B-15) to (B-18): In general formulas (B-15) to (B-18), the definitions of Ar7, Ar8, and X are the same as those in general formulas (B-1) and (B-2); R1, R2, R3, R4, R5, R6, R7, R8, and R9 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, and substituted or unsubstituted C1-C1 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

6. The double-boron resonance-type organic compound according to claim 1, characterized in that, The structure of the double-boron resonance-type organic compound is shown in general formula (C-1): In general formula (C-1), the definitions of X and Z are the same as those in general formula (1); Z3, Z4, and Z5 are independently represented as C-(H) or C-(R0); R0 represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1 to C2 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane; The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterated C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

7. The double-boron resonance-type organic compound according to claim 1, characterized in that, The structure of the double-boron resonance-type organic compound is shown in general formula (D-1): In general formula (D-1), M1 and M2 represent C6 to C6 molecules substituted or unsubstituted by one or more R molecules. 30 The aromatic ring, C2-C2 with or without one or more R-substituted or unsubstituted R-substituted rings. 30 Heteroaromatic rings, C6-C6 substituted or unsubstituted with one or more R groups. 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring; The M3 ring represents C3-C6 with or without substitution. 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; The replacement of R is either a single bond or a parallel ring connection; Ar2 and Ar3 are represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; X represents either a carbon atom or a silicon atom; R1, R2, R3, R4, and R5 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, and substituted or unsubstituted C1-C1 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; m can be represented as 0, 1, 2, 3 or 4; n and s represent 0, 1, 2 or 3; o1 represents 0 or 1; X1 represents a single bond, double bond, -O-, -S-, -N(R) c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-; The R c It is not connected to the M1 ring or is connected via a single bond, double bond, -O-, -S-, or -N(R) c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-; The R c It is not connected to the M3 ring or is connected via a single bond, double bond, -O-, -S-, or -N(R) c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-; The R c R d R e R f R g R p R q Represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane; The R d and R e They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; The R f and R g They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B; Preferably, the structure of the double-boron resonance-type organic compound is as shown in general formula (D-2): In general formula (D-2), the definitions of Ar2, Ar3, X, X1, R1, R2, R3, R4, R5, o1, m, n, and s are the same as those in general formula (D-1); R6 represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; k represents 0, 1, or 2; The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B; Preferably, the structure of the double-boron resonance-type organic compound is as shown in any one of general formulas (D-3) to (D-5): General formula (D-5) In general formulas (D-3) to (D-5), the definitions of Ar2, Ar3, X, R1, R2, R3, R4, R5, m, n, and s are the same as those in general formula (D-1); Ar4 and Ar5 are represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R6, R7, R8, R9, R 10 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or 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 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; k represents 0, 1, or 2; h represents 0, 1, 2, 3, 4 or 5; j represents 0, 1, 2, 3 or 4; i and g represent 0, 1, 2 or 3; o2 and o3 represent 0 or 1; X2 and X3 are independently represented as single bond, double bond, -O-, -S-, and -N(R) bonds, respectively. c )-、-C(R d (R) e )-、-Si(R f (R) g - or -C(R) p )=C(R q )-; The R c R d R e R f R g R p R q Represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane; The R d and R e They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; The R f and R g They are not connected to each other or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B; Preferably, the structure of the double-boron resonance-type organic compound is as shown in any one of general formulas (D-6) to (D-10): In general formulas (D-6) to (D-10), the definitions of Ar2, Ar3, X, R1, R2, R3, R4, R5, m, n, and s are the same as those in general formula (D-1); Ar4 and Ar5 are represented independently as hydrogen atoms, substituted or unsubstituted C1 to C2 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R6, R7, R8, R9, R 11 R 12 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or 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 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; k represents 0, 1, or 2; j, t, y represent 0, 1, 2, 3 or 4; i and g represent 0, 1, 2 or 3; The substituents of the above-mentioned substituted groups may be selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

8. The double-boron resonance-type organic compound according to any one of claims 1-7, characterized in that, The M1 and M2 rings are represented by any one of the following groups, either R-substituted or unsubstituted: phenyl, naphthyl, anthraceneyl, phenanthryl, pyridyl, quinolinyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazoyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl. The M, M3, and M4 rings represent any one of the following: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraxyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted indole[3,2,1-jk]carbazoyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and substituted or unsubstituted spirofluorenyl. The R, R0, R a R b Represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthraquinyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiopheneyl group, substituted... Or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, 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 diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl; The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 Represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophene group. Substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl; The R i R c R d R e R f R g R p R q Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are independently represented as 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 anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, etc. Substituted or unsubstituted thiophene group, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted 9,9-dimethylfluorenyl group, substituted or unsubstituted 9,9-diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted triazine group, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, substituted or unsubstituted diphenylamino group, substituted or unsubstituted indole group, substituted or unsubstituted benzoindole group; The substituents used for the substituent groups are selected from deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indoleyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, azirphenanthreneyl, diphenylamino, 1,1,4, 4-Tetramethyl-1,2,3,4-tetrahydronaphthyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl 9. The double-boron resonance-type organic compound according to claim 1, characterized in that: The specific structural formula of the double-boron resonance-type organic compound is any one of the following structures:

10. An organic light-emitting device, comprising a substrate, a first electrode, a second electrode, and a functional layer, wherein the functional layer is located between the first electrode and the second electrode, characterized in that: The functional layer contains the double-boron resonant organic compound as described in any one of claims 1-8; Preferably, the functional layer includes a light-emitting layer, the light-emitting layer includes a host material and a dopant material, and the dopant material is a double-boron resonant organic compound as described in any one of claims 1-8; Preferably, the functional layer includes a light-emitting layer, which includes 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 a double-boron resonant organic compound as described in any one of claims 1-8.

11. The organic light-emitting device according to claim 10, wherein the functional layer comprises a light-emitting layer, the light-emitting layer comprises a host material, an exciton-sensitizing material and a dopant material, the exciton-sensitizing material is a complex containing a metal element, and the dopant material is a double-boron resonant organic compound according to any one of claims 1-8.

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