Boron-containing resonance type organic compound and organic electroluminescent device containing same

Abstract

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

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of semiconductor materials, and particularly relates to a 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 the core luminescent material 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 the red light has approached the BT.2020 display index. However, the green light is limited by the relatively wide emission spectrum of phosphorescent light, which is quite different from the high-definition display index requirement, and the green phosphorescent light naturally has a high shoulder peak, which makes it relatively difficult to improve the color gamut display under the traditional device structure. Therefore, it is very critical 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: 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 resonance structure-based narrow half-peak width green light materials that can meet actual application requirements, which are aimed at 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 OLED 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 0.2 eV 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 host of an exciplex is disclosed; both of 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 boron-containing light-emitting material with a narrow half peak width 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 boron-containing organic compound and an organic electroluminescent device comprising the same. The compound of the present application can realize green light emission.

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

[0007]

[0008] In general formula (1), M1, M2, and M3 are independently one of C6-C30 aryl substituted or unsubstituted by one or more R, or 5-30 membered heteroaryl substituted or unsubstituted by one or more R;

[0009] and at least one of M1 and M3 is represented by the structure shown in general formula (1-1);

[0010] R1, R2, R3, Ar1, Ar2 are independently one of hydrogen atom, deuterium atom, halogen atom, cyano group, C1-C10 alkyl group substituted or unsubstituted with a substituent, C3-C10 cycloalkyl group substituted or unsubstituted with a substituent, C2-C10 alkenyl group substituted or unsubstituted with a substituent, C2-C10 alkynyl group substituted or unsubstituted with a substituent, C1-C10 alkoxy group substituted or unsubstituted with a substituent, C6-C10 aryloxy group substituted or unsubstituted with a substituent, arylamino group substituted or unsubstituted with a substituent, C6-C30 aryl group substituted or unsubstituted with a substituent, 5-30 membered heteroaryl group substituted or unsubstituted with a substituent, borane group substituted or unsubstituted with a substituent;

[0011] The Ar1, Ar2 are not connected or connected to one or more R substituted or unsubstituted C6-C30 aryl ring, one or more R substituted or unsubstituted 5-30 membered heteroaryl ring, one or more R substituted or unsubstituted C5-C30 aliphatic ring;

[0012] The M2 and R3 are not connected or connected to one or more R substituted or unsubstituted C6-C 30 aryl ring, one or more R substituted or unsubstituted 5-30 membered heteroaryl ring, one or more R substituted or unsubstituted C5-C 30 30 aliphatic ring;

[0013] The R is one of deuterium atom, halogen atom, cyano group, C1-C10 alkyl group substituted or unsubstituted with a substituent, C3-C10 cycloalkyl group substituted or unsubstituted with a substituent, C2-C10 alkenyl group substituted or unsubstituted with a substituent, C2-C10 alkynyl group substituted or unsubstituted with a substituent, C1-C10 alkoxy group substituted or unsubstituted with a substituent, C6-C10 aryloxy group substituted or unsubstituted with a substituent, arylamino group substituted or unsubstituted with a substituent, C6-C30 aryl group substituted or unsubstituted with a substituent, 5-30 membered heteroaryl group substituted or unsubstituted with a substituent, borane group substituted or unsubstituted with a substituent;

[0014] The R is substituted by single bond or annelated connection;

[0015] In the general formula (1-1), the asterisk indicates the site of annelated connection;

[0016] Y is the same or different at each occurrence and is O, S or N-Ra;

[0017] The Ra is one of C1-C10 alkyl group substituted or unsubstituted with a substituent, C3-C10 cycloalkyl group substituted or unsubstituted with a substituent, C6-C30 aryl group substituted or unsubstituted with a substituent, 5-30 membered heteroaryl group substituted or unsubstituted with a substituent;

[0018] Each occurrence of Z, whether the same or different, is represented as N, C-(H), or C-R0;

[0019] The R0 represents one of the following: a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group substituted or unsubstituted, a C3-C10 cycloalkyl group substituted or unsubstituted, a C2-C10 alkenyl group substituted or unsubstituted, a C2-C10 alkynyl group substituted or unsubstituted, a C1-C10 alkoxy group substituted or unsubstituted, a C6-C10 aryloxy group substituted or unsubstituted, an arylamine group substituted or unsubstituted, a C6-C30 aryl group substituted or unsubstituted, a 5-30 heteroaryl group substituted or unsubstituted, or a boraneyl group substituted or unsubstituted.

[0020] The substituent is selected from any one or more of the following: deuterium, halogen atom, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C10 cycloalkyl, deuterated C3-C10 cycloalkyl, C6-C30 aryl, deuterated C6-C30 aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl.

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

[0022] Furthermore, Ar1 and Ar2 are not connected to each other or are connected by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6) = C(R'7)-;

[0023] M2 and R3 are not connected or are connected by a single bond, double bond, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-;

[0024] The occurrence of the same or different R'1, R'2, R'3, R'4, R'5, R'6, and R'7 indicates that C1 to C1 are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0025] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 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 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl;

[0026] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0027] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas 2-1 to 2-4:

[0028]

[0029] In general formulas 2-1 to 2-4, the definitions of M1, M2, M3, Ar1, Ar2, R1, R2, R3, Y, and Z are the same as those in the above description.

[0030] X represents either a carbon atom or a silicon atom;

[0031] Z1, Z2, Z3, and Z4 are each independently represented as one of the following: C1-C10 alkyl group substituted or unsubstituted; C3-C10 cycloalkyl group substituted or unsubstituted; C2-C10 alkenyl group substituted or unsubstituted; silyl group substituted or unsubstituted; boronyl group substituted or unsubstituted; C6-C30 aryl group substituted or unsubstituted; and 5-30 heteroaryl group substituted or unsubstituted.

[0032] Z1 and Z2 are not connected or are connected to form a C6-C30 aromatic ring with or without substituents, a 5-30 membered heteroaromatic ring with or without substituents, or a C5-C30 aliphatic ring with or without substituents.

[0033] Z3 and Z4 are not connected or are connected to form C6-C30 aromatic rings substituted or unsubstituted with substituents, 5-30 heterocyclic aromatic rings substituted or unsubstituted with substituents, or C5-C30 aliphatic rings substituted or unsubstituted with substituents.

[0034] The substituent is selected from any one or more of the following: deuterium, halogen atom, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C10 cycloalkyl, deuterated C3-C10 cycloalkyl, C6-C30 aryl, deuterated C6-C30 aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl.

[0035] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0036] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas 3-1 to 3-8:

[0037]

[0038] In general formulas 3-1 to 3-8, the definitions of M1, M2, M3, Ar1, Ar2, R1, R2, R3, and Z are the same as those in the above description;

[0039] X represents either a carbon atom or a silicon atom;

[0040] Z1, Z2, Z3, and Z4 are each independently represented as one of the following: C1-C10 alkyl group substituted or unsubstituted; C3-C10 cycloalkyl group substituted or unsubstituted; C2-C10 alkenyl group substituted or unsubstituted; silyl group substituted or unsubstituted; boronyl group substituted or unsubstituted; C6-C30 aryl group substituted or unsubstituted; and 5-30 heteroaryl group substituted or unsubstituted.

[0041] Z1 and Z2 are not connected or are connected to form a C6-C30 aromatic ring with or without substituents, a 5-30 membered heteroaromatic ring with or without substituents, or a C5-C30 aliphatic ring with or without substituents.

[0042] Z3 and Z4 are not connected or are connected to form C6-C30 aromatic rings substituted or unsubstituted with substituents, 5-30 heterocyclic aromatic rings substituted or unsubstituted with substituents, or C5-C30 aliphatic rings substituted or unsubstituted with substituents.

[0043] The substituent is selected from any one or more of the following: deuterium, halogen atom, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C10 cycloalkyl, deuterated C3-C10 cycloalkyl, C6-C30 aryl, deuterated C6-C30 aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl.

[0044] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0045] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas 4-1 to 4-8:

[0046]

[0047] In general formulas 4-1 to 4-8, the definitions of Ar1, Ar2, R1, R2, R3, and Z are the same as those in the above text.

[0048] X represents either a carbon atom or a silicon atom;

[0049] Z1, Z2, Z3, and Z4 are each independently represented as one of the following: C1-C10 alkyl group substituted or unsubstituted; C3-C10 cycloalkyl group substituted or unsubstituted; C2-C10 alkenyl group substituted or unsubstituted; silyl group substituted or unsubstituted; boronyl group substituted or unsubstituted; C6-C30 aryl group substituted or unsubstituted; and 5-30 heteroaryl group substituted or unsubstituted.

[0050] Z1 and Z2 are not connected or are connected to form a C6-C30 aromatic ring with or without substituents, a 5-30 membered heteroaromatic ring with or without substituents, or a C5-C30 aliphatic ring with or without substituents.

[0051] Z3 and Z4 are not connected or are connected to form C6-C30 aromatic rings substituted or unsubstituted with substituents, 5-30 heterocyclic aromatic rings substituted or unsubstituted with substituents, or C5-C30 aliphatic rings substituted or unsubstituted with substituents.

[0052] The substituent is selected from any one or more of the following: deuterium, halogen atom, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C10 cycloalkyl, deuterated C3-C10 cycloalkyl, C6-C30 aryl, deuterated C6-C30 aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl.

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

[0054] Furthermore, Z1 and Z2 are not connected or are connected by a single bond, double bond, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6) = C(R'7)-;

[0055] Z3 and Z4 are not connected or are connected by a single bond, double bond, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-;

[0056] The occurrence of the same or different R'1, R'2, R'3, R'4, R'5, R'6, and R'7 indicates that C1 to C1 are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0057] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 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 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl;

[0058] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0059] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas 5-1 to 5-5:

[0060]

[0061] In general formulas 5-1 to 5-5, the definitions of Ar1, Ar2, R1, R2, and Y are the same as those in the above text.

[0062] X represents either a carbon atom or a silicon atom;

[0063] R4, R5, R6, R7, R8, and R9 are independently represented as one of the following: hydrogen atom, deuterium atom, halogen atom, cyano group, C1-C10 alkyl group (substituted or unsubstituted), C3-C10 cycloalkyl group (substituted or unsubstituted), C2-C10 alkenyl group (substituted or unsubstituted), C2-C10 alkynyl group (substituted or unsubstituted), C1-C10 alkoxy group (substituted or unsubstituted), C6-C10 aryloxy group (substituted or unsubstituted), arylamine group (substituted or unsubstituted), C6-C30 aryl group (substituted or unsubstituted), 5-30 heteroaryl group (substituted or unsubstituted), and borane group (substituted or unsubstituted).

[0064] a and b can be independently represented as 0, 1, 2 or 3;

[0065] c, d, e, and f are independently represented as 0, 1, 2, 3, or 4;

[0066] The substituent is selected from any one or more of the following: deuterium, halogen atom, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C10 cycloalkyl, deuterated C3-C10 cycloalkyl, C6-C30 aryl, deuterated C6-C30 aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl.

[0067] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0068] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas 6-1 to 6-5:

[0069]

[0070] In general formulas 6-1 to 6-5, the definitions of Ar1, Ar2, R1, R2, and Y are the same as those in the above description;

[0071] R4, R5, R8, and R9 are independently represented as one of the following: hydrogen atom, deuterium atom, halogen atom, cyano group, C1-C10 alkyl group substituted or unsubstituted, C3-C10 cycloalkyl group substituted or unsubstituted, C2-C10 alkenyl group substituted or unsubstituted, C2-C10 alkynyl group substituted or unsubstituted, C1-C10 alkoxy group substituted or unsubstituted, C6-C10 aryloxy group substituted or unsubstituted, arylamine group substituted or unsubstituted, C6-C30 aryl group substituted or unsubstituted, 5-30 heteroaryl group substituted or unsubstituted, and borane group substituted or unsubstituted.

[0072] The substituent is selected from any one or more of the following: deuterium, halogen atom, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C10 cycloalkyl, deuterated C3-C10 cycloalkyl, C6-C30 aryl, deuterated C6-C30 aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl.

[0073] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0074] Further, M1, M2, and M3 represent any one of the following groups substituted or unsubstituted by one or more R groups: 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;

[0075] The R and RO represent a deuterium atom, a halogen atom, a cyano group, a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), an adamantyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), a diphenyl group (substituted or unsubstituted), a terphenyl group (substituted or unsubstituted), a naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), a phenanthryl group (substituted or unsubstituted), a pyridyl group (substituted or unsubstituted), and a group (substituted or unsubstituted). Quinolinyl, furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (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), amino (substituted or unsubstituted), triazineyl (substituted or unsubstituted).

[0076] R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, and Ar2 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, 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), 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), and substituted... Or unsubstituted pyridyl, 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, 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, amino substituted or unsubstituted, triazineyl substituted or unsubstituted;

[0077] The R a Z1, Z2, Z3, and Z4 represent methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthrene (substituted or unsubstituted), pyridyl (substituted or unsubstituted), and quinolinyl (substituted or unsubstituted). Furanyl group substituted or unsubstituted; Thiophene group substituted or unsubstituted; Benzofuranyl group substituted or unsubstituted; Benzothiophene group substituted or unsubstituted; Dibenzofuranyl group substituted or unsubstituted; Dibenzothiophene group substituted or unsubstituted; Carbazoyl group substituted or unsubstituted; N-Phenylecarbazoyl group substituted or unsubstituted; 9,9-Dimethylfluorenyl group substituted or unsubstituted; 9,9-Diphenylfluorenyl group substituted or unsubstituted; Spirofluorenyl group substituted or unsubstituted; Amino group substituted or unsubstituted; Triazine group substituted or unsubstituted.

[0078] The substituents are selected from one or more of the following: deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

[0079] Furthermore, R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, 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), 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), and [other substituents / substituents]. Substituted pyridyl, 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), 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), amino (substituted or unsubstituted), triazineyl (substituted or unsubstituted).

[0080] The substituents are selected from one or more of the following: deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

[0081] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, and Ar2 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, and 9,9-dimethylfluorenyl. One of the following: spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-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, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boraneyl, methoxy, tert-butoxy, and diphenylamino;

[0082] The R and R0 represent deuterium atom, halogen atom, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl One of the following: ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-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, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, and phenyl-substituted triazineyl;

[0083] The Z1, Z2, Z3, Z4, R a The following are represented as methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl One of the following: ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-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, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, and phenyl-substituted triazineyl;

[0084] M1, M2, and M3 represent phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted... One of the following: 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, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, oxanthoneyl, and phenyl-substituted triazineyl.

[0085] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheninyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, aziphenanthryl, and diphenylamino.

[0086] Preferably, the M2 ring is represented by the following groups:

[0087]

[0088]

[0089] Any one of them;

[0090] Each occurrence of Z that is independent is represented as N, C-(H), or C-(R0);

[0091] Preferably, one of the M1 ring and the M3 ring is represented by the structure shown in general formula (1-1), and the other is represented by the following group:

[0092] Any one of them;

[0093] Each occurrence of Z that is independent is represented as N, C-(H), or C-(R0);

[0094] R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, and Ar2 are each independently represented by the following structures: hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, isopropyl group, tert-butyl group, etc.

[0095] Any one of them.

[0096] The R and R0 are independently represented by the following structures: methyl, ethyl, isopropyl, tert-butyl,

[0097]

[0098] Any one of the following. Furthermore, the specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] The present invention also provides an organic light-emitting device comprising a substrate, a first electrode, an organic functional material layer, and a second electrode, wherein the first electrode is located on the substrate, the organic functional material layer is located on the first electrode, and the second electrode is located on the functional layer, and the organic functional material layer contains the boron-containing resonant organic compound of the present invention.

[0121] Preferably, the organic functional material layer includes a light-emitting layer, which includes a host material and a dopant material, wherein the dopant material is the boron-containing resonant organic compound.

[0122] Preferably, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is a boron-containing resonant organic compound.

[0123] Furthermore, 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 the boron-containing resonant organic compound.

[0124] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0125] (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.

[0126] (2) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device.

[0127] (3) The compound of the present invention, as a green light doping material, can significantly improve device efficiency and device lifetime. Attached Figure Description

[0128] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device using the materials listed in this invention;

[0129] 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

[0130] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0131] 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.

[0132] In this invention, the substituted or unsubstituted aromatic amino group referred to in this invention means... Wherein Q1 and Q2 represent aromatic groups that are substituted or unsubstituted, and Q1 and Q2 preferably represent C6-C6 groups that are substituted or unsubstituted. 30 Aryl groups are 5-30 membered heteroaryl groups, either substituted or unsubstituted.

[0133] In this invention, C6 to C6 are substituted or unsubstituted. 30 Aryl refers to an aryl group with 6 to 30 carbon atoms, substituted or unsubstituted, preferably an aryl group with 6 to 20 carbon atoms, preferably an aryl group with 6 to 10 carbon atoms, preferably substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted para-triphenyl, substituted or unsubstituted meta-triphenyl, substituted or unsubstituted The group may include, but is not limited to, a triphenylene group substituted or unsubstituted with a substituent, a perylene group substituted or unsubstituted with a substituent, an indene group substituted or unsubstituted with a substituent, a combination thereof, or a fused ring of the aforementioned groups.

[0134] 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, phenanthrene, tetraphenyl, pyrene, biphenyl, para-triphenyl, and meta-triphenyl. Fused rings of alkyl, triphenylene, perylene, indene, or combinations thereof, but not limited to these groups.

[0135] In this invention, deuterium-substituted C6-C 30 The aryl group refers to a deuterated aryl group with 6 to 30 carbon atoms, preferably a deuterated aryl group with 6 to 20 carbon atoms, more preferably a deuterated aryl group with 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 biphenyl, deuterated para-triphenyl, deuterated meta-triphenyl, 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.

[0136] In this invention, the 5-30 membered heteroaryl group, whether substituted or unsubstituted, refers to a heteroaryl group with 5 to 30 cyclic atoms, preferably a heteroaryl group with 5 to 20 cyclic atoms, preferably a heteroaryl group with 5 to 10 cyclic atoms, preferably a furanyl group, a thiophene group, a pyrrole group, or a group with a substituted or unsubstituted cyclic atom. Substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazine group, substituted or unsubstituted Benzofuranyl (substituted or unsubstituted), benzothiopheneyl (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), and others. The following are fused rings, including but not limited to: benzothiazinyl (substituted or unsubstituted), acridineyl (substituted or unsubstituted), phenazinyl (substituted or unsubstituted), phenoxazinyl (substituted or unsubstituted), phenoxazinyl (substituted or unsubstituted), fumonyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiophenyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), combinations thereof, or combinations of the foregoing groups.

[0137] In this invention, 5-30 membered heteroaryl refers to a heteroaryl group with 5 to 30 cyclic atoms, preferably a heteroaryl group with 5 to 20 cyclic atoms, more preferably a heteroaryl group with 5 to 10 cyclic atoms, preferably furanyl, thiopheneyl, pyrroleyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiazolyl, pyridinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiopheneyl, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, acridineyl, benazinoyl, benazinothiazinyl, benazinoyloxazinyl, fumonyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, or combinations thereof or fused rings of the aforementioned groups, but not limited thereto.

[0138] In this invention, the deuterated 5-30 membered heteroaryl refers to a heteroaryl group with 5 to 30 deuterated cyclic atoms, preferably a heteroaryl group with 5 to 20 deuterated cyclic atoms, preferably a heteroaryl group with 5 to 10 deuterated cyclic atoms, preferably deuterated furanyl, deuterated thiophene, deuterated pyrrole, deuterated pyrazolyl, deuterated imidazolyl, deuterated triazolyl, deuterated oxazolyl, deuterated thiazolyl, deuterated oxadiazolyl, deuterated thiadiazolyl, deuterated pyridinyl, deuterated pyrimidinyl, deuterated pyrazinyl, and deuterated pyridinyl groups. Triazinyl, deuterated benzofuranyl, deuterated benzothiophenyl, deuterated benzimidazolyl, deuterated indolyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated quinazolinyl, deuterated quinolinyl, deuterated naphthidyl, deuterated benzoxazinyl, deuterated benzothiazinyl, deuterated acridineyl, deuterated benziazinyl, deuterated benziazinyl, deuterated benziazinyl, deuterated benziazinyl, deuterated fumonyl, deuterated dibenzofuranyl, deuterated dibenzothiaphenyl, deuterated carbazoyl, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0139] In this invention, the number of heteroatoms in the 5-30 member heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.

[0140] The C1-C1 components of this invention, whether substituted or unsubstituted, are... 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to an alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted, preferably an alkyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, etc., substituted or unsubstituted. Substituted isobutyl, 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 substituted or unsubstituted, etc., but not limited to these.

[0141] 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.

[0142] 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.

[0143] The C3-C3 groups described in this invention, whether substituted or unsubstituted, are... 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups, whether substituted or unsubstituted, are preferred; C5-C8 cycloalkyl groups, whether substituted or unsubstituted, are more preferred; and C5-C7 cycloalkyl groups, whether substituted or unsubstituted, are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl, etc., whether substituted or unsubstituted.

[0144] The C3~C of this invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups are preferred, C5-C8 cycloalkyl groups are more preferred, and C5-C7 cycloalkyl groups are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0145] The deuterium-substituted C3-C of the present invention 10Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, deuterated C4-C9 cycloalkyl groups are preferred, more preferably deuterated C5-C8 cycloalkyl groups, and particularly preferably deuterated C5-C7 cycloalkyl groups. 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.

[0146] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0147] The C1 to C of this invention 10 Alkoxy groups include, but are not limited to, alkoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or isopropoxy.

[0148] The C2~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.

[0149] The substituents described in this invention are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

[0150] 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.

[0151] 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, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 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:

[0158]

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0164]

[0165] 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.

[0166] 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.

[0167] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0168]

[0169] 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.

[0170] 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.

[0171] 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 boron-containing resonant organic compound represented by the general formula (1) of this invention.

[0172] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0173] 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;

[0174] 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.

[0175] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0176] 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 boron-containing resonance organic compound shown in the general formula (1) of this invention, when used in combination with the exciton-sensitized material, has a significant improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0177] 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.

[0178] 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.

[0179] 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.

[0180] 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:

[0181]

[0182]

[0183] 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.

[0184] 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:

[0185]

[0186] 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.

[0187] 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.

[0188] 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.

[0189] 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.

[0190] 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, BaF2, 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, Mo, Ti, or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0191] 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.

[0192] 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.

[0193] Synthesis Examples

[0194] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or obtained by conventional preparation methods in the art;

[0195] Synthesis of intermediate e1:

[0196]

[0197] Starting material A1 (20 mmol, 5.55 g) was dissolved in 30 mL of tetrahydrofuran, and NBS (20 mmol, 3.56 g) was added. The mixture was stirred at room temperature for 20 h in the dark. After the reaction was completed, the mixture was extracted with water / ethyl acetate, the solvent was removed by rotary evaporation, and then purified by silica gel column chromatography to obtain intermediate b1.

[0198] In a three-necked flask under nitrogen protection, intermediate b1 (10 mmol, 3.56 g) and 140 mL of o-dichlorobenzene were added. A 2.5 M solution of n-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, and the system was heated to 69 °C and reacted for 6 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 8 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added to the system at 0 °C, and the mixture was heated to 125 °C and reacted for 15 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c1.

[0199] Add raw material D1 (25 mmol, 4.46 g), potassium carbonate (62.5 mmol, 8.64 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 intermediate c1 (25 mmol, 7.13 g) under nitrogen protection and stir at 130 °C for 15 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate e1.

[0200] Synthesis of intermediate e2:

[0201]

[0202] The synthesis of intermediate e2 is similar to that of intermediate e1, except that raw material D1 is replaced by raw material D2.

[0203] Synthesis of intermediate e3:

[0204]

[0205] The synthesis of intermediate e3 is similar to that of intermediate e1, except that raw material D1 is replaced by raw material D3.

[0206] Synthesis of intermediate e4:

[0207]

[0208] The synthesis of intermediate b4 is similar to that of intermediate b1, except that raw material A4 is used instead of raw material A1.

[0209] The synthesis of intermediate c4 is similar to that of intermediate c1, except that intermediate b1 is replaced by intermediate b4.

[0210] The synthesis of intermediate e4 is similar to that of intermediate e1, except that intermediate c1 is replaced by intermediate c4.

[0211] Synthesis of intermediate e5:

[0212]

[0213] Add raw material A5 (8 mmol, 2.71 g) and cesium carbonate (12.5 mmol, 4.07 g) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 1 hour. Add intermediate c1 (8 mmol, 2.28 g) under nitrogen protection and stir at 50 °C for 13 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate b5.

[0214] Intermediate b5 (25 mmol, 12.41 g), BOC2O (30 mmol, 6.55 g), and triethylamine (25 mmol, 2.53 g) were added to a two-necked flask. Under nitrogen protection, 100 mL of anhydrous THF was added, and the mixture was stirred at room temperature for 30 minutes. The mixture was then filtered, washed with water, dried, and passed through a column to obtain intermediate c5.

[0215] Intermediate C5 (10 mmol, 5.96 g), tetrabutylammonium bromide (1 mmol, 0.32 g), triphenylphosphine (0.5 mmol, 0.13 g), palladium acetate (0.2 mmol, 0.05 g), potassium carbonate (20 mmol, 2.76 g), and DMAc (50 mL) were added sequentially to a sealed pressure-resistant tube. The mixture was then heated under reflux and stirred for 50 hours under nitrogen protection. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound was then separated by silica gel column chromatography to obtain intermediate D5.

[0216] Intermediate d5 (10 mmol, 5.15 g) and p-toluenesulfonic acid (20 mmol, 3.44 g) were added to a two-necked flask. Under nitrogen protection, 100 mL of anhydrous DCM was added, and the mixture was stirred at room temperature for 35 minutes. The mixture was then filtered, washed with water, dried, and passed through a column to obtain intermediate e5.

[0217] Synthesis of intermediate e6:

[0218]

[0219] Add raw material D1 (25 mmol, 4.46 g), potassium carbonate (62.5 mmol, 8.64 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 0.09 g) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 36 minutes. Add raw material A6 (25 mmol, 6.73 g) under nitrogen protection and stir at 150 °C for 12 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate e6.

[0220] Synthesis of intermediate e7:

[0221]

[0222] The synthesis of intermediate e7 is similar to that of intermediate e6, except that raw material A7 is used instead of raw material A6.

[0223] Synthesis of Compound 1:

[0224]

[0225] Add raw material F1 (20 mmol, 6.71 g) and cesium carbonate (55.2 mmol, 17.99 g) to a two-necked flask. Add 280 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 62 minutes. Add raw material G1 (20 mmol, 5.59 g) under nitrogen protection. Reflux the solution under magnetic stirring for 35 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate h1.

[0226] Intermediate h1 (10 mmol, 5.95 g) was dissolved in 120 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 5.5 hours, 30 mL of tetrahydrofuran solution of starting material I1 (10 mmol, 1.80 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 30 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 j1.

[0227] Intermediate J1 (5 mmol, 3.16 g), intermediate E1 (5 mmol, 2.31 g), CuI catalyst (1 mmol, 0.19 g), and K3PO4 (25 mmol, 5.31 g) were added sequentially to a three-necked flask. Then, under a nitrogen atmosphere, trans-1,2-cyclohexanediamine (1.8 mmol, 0.23 g) and 90 mL of dioxane were added. The mixture was stirred at 105 °C for 21 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compounds were separated by silica gel column chromatography to obtain intermediate K1.

[0228] In a three-necked flask under nitrogen protection, intermediate K1 (10 mmol, 10.11 g) and 140 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, the system was heated to 68 °C and reacted for 7 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 8 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the mixture was heated to 130 °C and reacted for 16 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 1. Compound 1 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the M peak was 22 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0229] Synthesis of compound 2:

[0230]

[0231] The synthesis of intermediate k2 is similar to that of intermediate k1, except that intermediate e1 is replaced by intermediate e2.

[0232] The synthesis of compound 2 is similar to that of compound 1, except that intermediate k1 is replaced by intermediate k2. Compound 2 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 22 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0233] Synthesis of compound 3:

[0234]

[0235] The synthesis of intermediate k3 is similar to that of intermediate k1, except that intermediate e1 is replaced by intermediate e3.

[0236] The synthesis of compound 3 is similar to that of compound 1, except that intermediate k1 is replaced by intermediate k3. Compound 3 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width at half maximum (WHM) was 23 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0237] Synthesis of compound 61:

[0238]

[0239] The synthesis of intermediate j4 is similar to that of intermediate j1, except that raw material I1 is replaced by raw material I4.

[0240] The synthesis of intermediate k4 is similar to that of intermediate k1, except that intermediate j4 is used to replace intermediate j1.

[0241] The synthesis of compound 61 is similar to that of compound 1, except that intermediate k1 is replaced by intermediate k4. Compound 61 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 23 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0242] Synthesis of compound 96:

[0243]

[0244] The synthesis of intermediate h5 is similar to that of intermediate h1, except that intermediate e5 is used to replace the raw material G1.

[0245] The synthesis of intermediate j5 is similar to that of intermediate j1, except that intermediate h1 is replaced by intermediate h5.

[0246] The synthesis of intermediate k5 is similar to that of intermediate k1, except that intermediate j5 replaces intermediate j1 and intermediate e7 replaces intermediate e1.

[0247] The synthesis of compound 96 is similar to that of compound 1, except that intermediate k1 is replaced by intermediate k5. Compound 96 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 22 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0248] Synthesis of compound 108:

[0249]

[0250] The synthesis of intermediate k6 is similar to that of intermediate k1, except that intermediate j5 replaces intermediate j1 and intermediate e6 replaces intermediate e1.

[0251] The synthesis of compound 108 is similar to that of compound 1, except that intermediate k1 is replaced by intermediate k6. Compound 108 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 22 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0252] Synthesis of compound 162:

[0253]

[0254] The synthesis of intermediate k7 is similar to that of intermediate k1, except that intermediate e1 is replaced by intermediate e4.

[0255] The synthesis of compound 162 is similar to that of compound 1, except that intermediate k1 is replaced by intermediate k7. Compound 162 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0256] Synthesis of compound 255:

[0257]

[0258] Add raw material F8 (20 mmol, 5.38 g) and cesium carbonate (55.2 mmol, 17.99 g) to a two-necked flask. Add 220 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 45 minutes. Add raw material G1 (20 mmol, 5.59 g) under nitrogen protection. Reflux the solution under magnetic stirring for 35 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate j8.

[0259] Intermediate J8 (15 mmol, 7.93 g) and cesium carbonate (30 mmol, 9.77 g) were added to a two-necked flask. Under nitrogen protection, 120 mL of anhydrous DMF was added and the mixture was stirred at room temperature for 30 minutes. Then, under nitrogen protection, intermediate E1 (15 mmol, 6.92 g) was added. The solution was refluxed for 30 hours with magnetic stirring. After cooling, filtration, washing with water, drying, and column chromatography, intermediate K8 was obtained.

[0260] In a three-necked flask under nitrogen protection, intermediate K8 (10 mmol, 9.70 g) and 140 mL of o-dichlorobenzene were added. A 2.5 M solution of n-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, and the system was heated to 75 °C and reacted for 5 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 7.5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, and the system was heated to 135 °C and reacted for 15.5 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 255. Compound 255 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) was 21 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0261] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0262] Table 1

[0263]

[0264] The following details the application effects of the organic electroluminescent materials synthesized in this invention in devices through Device Examples 1-8 and Comparative Examples 1-3. Device Examples 2-8 and Comparative Examples 1-3 of this invention have the same fabrication process as Device Example 1, and use the same substrate and electrode materials, with consistent electrode film thickness. The only difference is the replacement of the light-emitting layer material. The layer structures and test results of each device example are shown in Tables 2-1 and 3, respectively.

[0265] Device Example 1

[0266] like Figure 1As 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 1 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 1 of 69:30:1. The light-emitting layer has 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.

[0267] The application effects of the organic electroluminescent materials synthesized in this invention in devices are described in detail below through device examples 9-16 and device comparative examples 4-6. The fabrication processes of device examples 10-16 and device comparative examples 4-6 are exactly the same as those of device example 9, and the same substrate and electrode materials are used. The film thickness of the electrode materials is also kept consistent. The only difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device example are shown in Tables 2-2 and 3, respectively.

[0268] Device Example 9

[0269] 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, 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 light-emitting layer 6 of the organic electroluminescent device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first dopant, and compound 1 is used as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 1 is 66.5:30:3:0.5, and the thickness of the light-emitting layer is 30 nm. After the light-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.

[0270] The molecular structural formulas of the relevant materials are shown below:

[0271]

[0272]

[0273] 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.

[0274] Table 2-1

[0275]

[0276]

[0277] Table 2-2

[0278]

[0279]

[0280] Table 3

[0281]

[0282]

[0283] Note: Current efficiency and peak luminance were measured using an IVL (current-voltage-luminance) 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's brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0284] As can be seen from the device data results in Table 3, compared with the comparative compounds ref-1, ref-2, and ref-3, the compounds of the present invention can achieve green light emission effect very well and have higher current efficiency; compared with devices of comparative examples 1-6, the current efficiency and lifetime of the devices are significantly improved compared with devices of known materials.

[0285] 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 boron-containing resonance-type organic compound characterized by: The structure of the boron-containing resonance-type organic compound is shown in general formula (1): In general formula (1), M1, M2, M3 are independently one of C6-C30 aryl substituted or unsubstituted by one or more R, 5-30 membered heteroaryl substituted or unsubstituted by one or more R; At least one of M1 and M3 is shown in the structure of general formula (1-1); R1, R2, R3, Ar1, Ar2 are independently one of hydrogen atom, deuterium atom, halogen atom, cyano group, C1-C10 alkyl substituted or unsubstituted by substituent, C3-C10 cycloalkyl substituted or unsubstituted by substituent, C2-C10 alkenyl substituted or unsubstituted by substituent, C2-C10 alkynyl substituted or unsubstituted by substituent, C1-C10 alkoxy substituted or unsubstituted by substituent, C6-C10 aryloxy substituted or unsubstituted by substituent, arylamino substituted or unsubstituted by substituent, C6-C30 aryl substituted or unsubstituted by substituent, 5-30 membered heteroaryl substituted or unsubstituted by substituent, boron alkyl substituted or unsubstituted by substituent; Ar1 and Ar2 are not connected or connected into C6-C30 aryl ring substituted or unsubstituted by one or more R, 5-30 membered heteroaryl ring substituted or unsubstituted by one or more R, C5-C30 aliphatic ring substituted or unsubstituted by one or more R; M2 and R3 are either not connected or connected in a C6-C configuration where one or more R's are substituted or unsubstituted. 30 Aromatic rings, 5-30 membered heteroaromatic rings substituted or unsubstituted with one or more Rs, C5-C6 ... 30 Aliphatic rings; R is one of deuterium atom, halogen atom, cyano group, C1-C10 alkyl substituted or unsubstituted by substituent, C3-C10 cycloalkyl substituted or unsubstituted by substituent, C2-C10 alkenyl substituted or unsubstituted by substituent, C2-C10 alkynyl substituted or unsubstituted by substituent, C1-C10 alkoxy substituted or unsubstituted by substituent, C6-C10 aryloxy substituted or unsubstituted by substituent, arylamino substituted or unsubstituted by substituent, C6-C30 aryl substituted or unsubstituted by substituent, 5-30 membered heteroaryl substituted or unsubstituted by substituent, boron alkyl substituted or unsubstituted by substituent; The substitution mode of R is single bond or annelated connection; In general formula (1-1), the asterisk indicates the site of annelated connection; Y, which is the same or different in each occurrence, is O, S or N-Ra; Ra is one of C1-C10 alkyl substituted or unsubstituted by substituent, C3-C10 cycloalkyl substituted or unsubstituted by substituent, C6-C30 aryl substituted or unsubstituted by substituent, 5-30 membered heteroaryl substituted or unsubstituted by substituent; Z, which is the same or different in each occurrence, is N, C-(H) or C-R0; R0represents one of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group substituted or unsubstituted with a substituent, a C3-C10 cycloalkyl group substituted or unsubstituted with a substituent, a C2-C10 alkenyl group substituted or unsubstituted with a substituent, a C2-C10 alkynyl group substituted or unsubstituted with a substituent, a C1-C10 alkoxy group substituted or unsubstituted with a substituent, a C6-C10 aryloxy group substituted or unsubstituted with a substituent, an arylamine group substituted or unsubstituted with a substituent, a C6-C30 aryl group substituted or unsubstituted with a substituent, a 5-30 membered heteroaryl group substituted or unsubstituted with a substituent, a borane group substituted or unsubstituted with a substituent; the substituent is optionally one or more of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a deuterium-substituted C1-C10 alkyl group, a C3-C10 cycloalkyl group, a deuterium-substituted C3-C10 cycloalkyl group, a C6-C30 aryl group, a deuterium-substituted C6-C30 aryl group, a 5-30 membered heteroaryl group, a deuterium-substituted 5-30 membered heteroaryl group; the heteroatom in the heteroaryl group is optionally one or more of O, S, N, Si, and B.

2. The boron-containing resonance-type organic compound according to claim 1, characterized by: the boron-containing resonance-type organic compound has a structure as represented by any one of General Formula 2-1 to General Formula 2-4: in General Formula 2-1 to General Formula 2-4, M1, M2, M3, Ar1, Ar2, R1, R2, R3, Y, and Z are as defined in Claim 1; X represents one of a carbon atom and a silicon atom; Z1, Z2, Z3, and Z4 each independently represent one of a C1-C10 alkyl group substituted or unsubstituted with a substituent, a C3-C10 cycloalkyl group substituted or unsubstituted with a substituent, a C2-C10 alkenyl group substituted or unsubstituted with a substituent, a silane group substituted or unsubstituted with a substituent, a borane group substituted or unsubstituted with a substituent, a C6-C30 aryl group substituted or unsubstituted with a substituent, and a 5-30 membered heteroaryl group substituted or unsubstituted with a substituent; Z1and Z2are not connected or are connected to form a C6-C30 aromatic ring substituted or unsubstituted with a substituent, a 5-30 membered heteroaromatic ring substituted or unsubstituted with a substituent, or a C5-C30 aliphatic ring substituted or unsubstituted with a substituent; Z3and Z4are not connected or are connected to form a C6-C30 aromatic ring substituted or unsubstituted with a substituent, a 5-30 membered heteroaromatic ring substituted or unsubstituted with a substituent, or a C5-C30 aliphatic ring substituted or unsubstituted with a substituent; the substituent is optionally one or more of a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group, a deuterium-substituted C1-C10 alkyl group, a C3-C10 cycloalkyl group, a deuterium-substituted C3-C10 cycloalkyl group, a C6-C30 aryl group, a deuterium-substituted C6-C30 aryl group, a 5-30 membered heteroaryl group, a deuterium-substituted 5-30 membered heteroaryl group; the heteroatom in the heteroaryl group is optionally one or more of O, S, N, Si, and B.

3. The boron-containing resonance-type organic compound according to claim 1, characterized by: the boron-containing resonance-type organic compound has a structure as represented by any one of General Formula 3-1 to General Formula 3-8: In General Formula 3-1 to General Formula 3-8, M1, M2, M3, Ar1, Ar2, R1, R2, R3, and Z are as defined in claim 1; X represents one of a carbon atom and a silicon atom; Z1, Z2, Z3, and Z4 each independently represent one of a C1-C10 alkyl group substituted with a substituent or unsubstituted, a C3-C10 cycloalkyl group substituted with a substituent or unsubstituted, a C2-C10 alkenyl group substituted with a substituent or unsubstituted, a silyl group substituted with a substituent or unsubstituted, a boryl group substituted with a substituent or unsubstituted, a C6-C30 aryl group substituted with a substituent or unsubstituted, and a 5- to 30-membered heteroaryl group substituted with a substituent or unsubstituted; Z1and Z2are not connected or are connected to form a C6-C30 aryl ring substituted with a substituent or unsubstituted, a 5- to 30-membered heteroaryl ring substituted with a substituent or unsubstituted, or a C5-C30 aliphatic ring substituted with a substituent or unsubstituted; Z3and Z4are not connected or are connected to form a C6-C30 aryl ring substituted with a substituent or unsubstituted, a 5- to 30-membered heteroaryl ring substituted with a substituent or unsubstituted, or a C5-C30 aliphatic ring substituted with a substituent or unsubstituted; the substituent is optionally one or more of deuterium, a halogen atom, a cyano group, a C1-C10 alkyl group, a deuterium-substituted C1-C10 alkyl group, a C3-C10 cycloalkyl group, a deuterium-substituted C3-C10 cycloalkyl group, a C6-C30 aryl group, a deuterium-substituted C6-C30 aryl group, a 5- to 30-membered heteroaryl group, and a deuterium-substituted 5- to 30-membered heteroaryl group; the heteroatom in the heteroaryl group is optionally one or more of O, S, N, Si, and B.

4. The boron-containing resonance-type organic compound according to claim 1, characterized by: The boron-containing resonance-type organic compound has a structure represented by any one of General Formula 4-1 to General Formula 4-8: In General Formula 4-1 to General Formula 4-8, Ar1, Ar2, R1, R2, R3, and Z are as defined in claim 1; X represents one of a carbon atom and a silicon atom; Z1, Z2, Z3, and Z4 each independently represent one of a C1-C10 alkyl group substituted with a substituent or unsubstituted, a C3-C10 cycloalkyl group substituted with a substituent or unsubstituted, a C2-C10 alkenyl group substituted with a substituent or unsubstituted, a silyl group substituted with a substituent or unsubstituted, a boryl group substituted with a substituent or unsubstituted, a C6-C30 aryl group substituted with a substituent or unsubstituted, and a 5- to 30-membered heteroaryl group substituted with a substituent or unsubstituted; Z1and Z2are not connected or are connected to form a C6-C30 aryl ring substituted with a substituent or unsubstituted, a 5- to 30-membered heteroaryl ring substituted with a substituent or unsubstituted, or a C5-C30 aliphatic ring substituted with a substituent or unsubstituted; Z3and Z4are not connected or are connected to form a C6-C30 aryl ring substituted with a substituent or unsubstituted, a 5- to 30-membered heteroaryl ring substituted with a substituent or unsubstituted, or a C5-C30 aliphatic ring substituted with a substituent or unsubstituted; The substituent is optionally any one or more of deuterium, a halogen atom, a cyano group, a C1-C10 alkyl group, a deuterium-substituted C1-C10 alkyl group, a C3-C10 cycloalkyl group, a deuterium-substituted C3-C10 cycloalkyl group, a C6-C30 aryl group, a deuterium-substituted C6-C30 aryl group, a 5-30-membered heteroaryl group, and a deuterium-substituted 5-30-membered heteroaryl group. The heteroatom in the heteroaryl group is optionally one or more of O, S, N, Si, and B.

5. The boron-containing resonance-type organic compound according to claim 1, characterized by: The structure of the boron-containing resonance-type organic compound is as shown in any one of Formula 5-1 to Formula 5-5: In Formula 5-1 to Formula 5-5, Ar1, Ar2, R1, R2, and Y are as defined in Claim 1. X represents one of a carbon atom and a silicon atom. R4, R5, R6, R7, R8, and R9 are each independently one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group substituted or unsubstituted with a substituent, a C3-C10 cycloalkyl group substituted or unsubstituted with a substituent, a C2-C10 alkenyl group substituted or unsubstituted with a substituent, a C2-C10 alkynyl group substituted or unsubstituted with a substituent, a C1-C10 alkoxy group substituted or unsubstituted with a substituent, a C6-C10 aryloxy group substituted or unsubstituted with a substituent, an arylamine group substituted or unsubstituted with a substituent, a C6-C30 aryl group substituted or unsubstituted with a substituent, a 5-30-membered heteroaryl group substituted or unsubstituted with a substituent, and a borane group substituted or unsubstituted with a substituent. a and b are each independently 0, 1, 2, or 3. c, d, e, and f are each independently 0, 1, 2, 3, or 4. The substituent is optionally any one or more of deuterium, a halogen atom, a cyano group, a C1-C10 alkyl group, a deuterium-substituted C1-C10 alkyl group, a C3-C10 cycloalkyl group, a deuterium-substituted C3-C10 cycloalkyl group, a C6-C30 aryl group, a deuterium-substituted C6-C30 aryl group, a 5-30-membered heteroaryl group, and a deuterium-substituted 5-30-membered heteroaryl group. The heteroatom in the heteroaryl group is optionally one or more of O, S, N, Si, and B.

6. The boron-containing resonance-type organic compound according to claim 1, characterized by: The structure of the boron-containing resonance-type organic compound is as shown in any one of Formula 6-1 to Formula 6-5: In Formula 6-1 to Formula 6-5, Ar1, Ar2, R1, R2, and Y are as defined in Claim 1. R4, R5, R8, and R9 are each independently one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a C1-C10 alkyl group substituted or unsubstituted with a substituent, a C3-C10 cycloalkyl group substituted or unsubstituted with a substituent, a C2-C10 alkenyl group substituted or unsubstituted with a substituent, a C2-C10 alkynyl group substituted or unsubstituted with a substituent, a C1-C10 alkoxy group substituted or unsubstituted with a substituent, a C6-C10 aryloxy group substituted or unsubstituted with a substituent, an arylamine group substituted or unsubstituted with a substituent, a C6-C30 aryl group substituted or unsubstituted with a substituent, a 5-30-membered heteroaryl group substituted or unsubstituted with a substituent, and a borane group substituted or unsubstituted with a substituent. The substituent is optionally selected from any one or more of deuterium, a halogen atom, a cyano group, a C1 to C10 alkyl group, a deuterium-substituted C1 to C10 alkyl group, a C3 to C10 cycloalkyl group, a deuterium-substituted C3 to C10 cycloalkyl group, a C6 to C30 aryl group, a deuterium-substituted C6 to C30 aryl group, a 5- to 30-membered heteroaryl group, and a deuterium-substituted 5- to 30-membered heteroaryl group; The heteroatom in the heteroaryl group is optionally selected from one or more of O, S, N, Si, and B.

7. The boron-containing resonance-type organic compound according to any one of claims 1 to 6, wherein M1, M2, and M3 are represented by any one of a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, an indol[3,2,1-jk]carbazolyl group, a 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, and a spirofluorenyl group, which is substituted or unsubstituted with one or more R groups; R and R0 are represented by a deuterium atom, a halogen atom, a cyano group, a methyl group which is substituted or unsubstituted with a substituent, an ethyl group which is substituted or unsubstituted with a substituent, an isopropyl group which is substituted or unsubstituted with a substituent, a tert-butyl group which is substituted or unsubstituted with a substituent, a cyclohexyl group which is substituted or unsubstituted with a substituent, an adamantyl group which is substituted or unsubstituted with a substituent, a phenyl group which is substituted or unsubstituted with a substituent, a biphenyl group which is substituted or unsubstituted with a substituent, a terphenyl group which is substituted or unsubstituted with a substituent, a naphthyl group which is substituted or unsubstituted with a substituent, an anthryl group which is substituted or unsubstituted with a substituent, a phenanthryl group which is substituted or unsubstituted with a substituent, a pyridyl group which is substituted or unsubstituted with a substituent, a quinolyl group which is substituted or unsubstituted with a substituent, a furanyl group which is substituted or unsubstituted with a substituent, a thienyl group which is substituted or unsubstituted with a substituent, a benzofuranyl group which is substituted or unsubstituted with a substituent, a benzothienyl group which is substituted or unsubstituted with a substituent, a dibenzofuranyl group which is substituted or unsubstituted with a substituent, a dibenzothienyl group which is substituted or unsubstituted with a substituent, a carbazolyl group which is substituted or unsubstituted with a substituent, an N-phenylcarbazolyl group which is substituted or unsubstituted with a substituent, a 9,9-dimethylfluorenyl group which is substituted or unsubstituted with a substituent, a 9,9-diphenylfluorenyl group which is substituted or unsubstituted with a substituent, a spirofluorenyl group which is substituted or unsubstituted with a substituent, an amine group which is substituted or unsubstituted with a substituent, and a triazine group which is substituted or unsubstituted with a substituent. R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2 are independently represented by hydrogen atom, deuterium atom, halogen atom, cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted triazinyl group; The R a Z1, Z2, Z3, Z4are represented by a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted aminyl group, a substituted or unsubstituted triazinyl group; the substituent is optionally one or more selected from the group consisting of deuterium atom, chlorine atom, fluorine atom, trifluoromethyl group, adamantyl group, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-amyl group, tert-butyl group, butyl group, methoxy group, phenyl group, biphenyl group, naphthyl group, anthryl group, phenanthryl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, quinolyl group, isoquinolyl group, furanyl group, thienyl group, indolyl group, pyrrolyl group, dibenzofuranyl group, dibenzothienyl group, 9,9-dimethylfluorenyl group, spirofluorenyl group, carbazolyl group, N-phenylcarbazolyl group, carbazolinyl group, azaphenanthryl group.

8. The boron-containing resonance-type organic compound according to claim 1, characterized by: The specific structural formula of the boron-containing resonance-type organic compound is any one of the following structures:

9. An organic light emitting device comprising a substrate, a first electrode, an organic functional material layer, a second electrode, the first electrode being on the substrate, the organic functional material layer being on the first electrode, the second electrode being on the functional layer, characterized in that: The organic functional material layer comprises the boron-containing resonance-type organic compound according to any one of claims 1-8; Preferably, the organic functional material layer comprises a light-emitting layer, and the light-emitting layer comprises a host material and a dopant material, and the dopant material is the boron-containing resonance-type organic compound according to any one of claims 1-8; Preferably, the light-emitting layer comprises a first host material, a second host material, and a dopant material, at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing resonance-type organic compound according to any one of claims 1-8.

10. The organic light emitting device according to claim 9, wherein the light emitting layer comprises a host material, an exciton sensitizing material, and a dopant material, characterized in that: The exciton sensitization material is a complex containing a metal element, and the dopant material is the boron-containing resonance-type organic compound according to any one of claims 1-8.

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