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

Abstract

The invention discloses a boron-containing organic compound and an organic electroluminescent device prepared from the same, and belongs to the technical field of semiconductors. The structure of the organic compound is shown as a general formula (1), # imgabs0. When the compound is used as a doping material in a light-emitting layer material of an OLED light-emitting device, the compound can be used as a light-emitting layer green light doping material of the organic light-emitting device, so that the light-emitting efficiency of the device is improved, and the service life of the device is prolonged.

Description

Technical Field

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

[0002] Compared with liquid crystal display (LCD), organic light-emitting diode (OLED) has technical advantages such as lighter and thinner, high color contrast, low power consumption, fast response, high clarity, and flexibility, and is believed to dominate future display terminal products. With the advent of the 5G era, the new information display industry is in urgent need of iterative development. The early lower color gamut standards (BT.709 and DCIP3) can no longer meet the high-quality technical development needs of display products. In order to achieve the performance requirements of ultra-high definition and higher picture quality of display products, the new generation of display standards (BT.2020) drives OLED luminescent materials to develop towards high color purity, which requires the core luminescent materials to have a narrower emission spectrum. Among the three commercialized OLED red, green and blue color rendering technologies, blue light uses traditional fluorescent triplet-triplet conversion (TTF) technology, which has low efficiency but high color purity and basically meets the BT.2020 display indicators; green and red light use phosphorescence technology, which has high efficiency. Red light is close to the BT.2020 display indicators, while green light is limited by the wider emission spectrum of phosphorescence, which is quite different from the requirements of high-definition display indicators. Therefore, it is very critical to develop high-color-purity green light OLED materials.

[0003] Since 2020, green light materials with narrow half-width (half-width <30nm) based on boron-nitrogen resonance structures have been reported one after another: DOI:10.1002 / adom.201902142, DOI:10.1002 / anie.202008264, DOI:10.1021 / jacs.0c10081, DOI:10.1038 / s41566-022-01083-y, DOI:10.1038 / s41467-022-32607-3, DOI:10.1002 / anie.202202380, etc., showing the high color purity and efficiency of this type of material, which has become the development trend of high color purity green light OLEDs. However, there are still many technical difficulties in the development of green light ultra-high color purity materials containing boron and nitrogen structures. The existing materials also have the defects that their efficiency and lifespan cannot meet the needs of mass production. The development of narrow half-width green light materials based on boron and nitrogen resonance structures that can meet practical applications is a key technical point for the next generation of high color purity, high color gamut coverage, high efficiency and high immersion display devices.

[0004] In addition, the sensitization technology combines triplet exciton-sensitizing materials (including but not limited to TADF materials and phosphorescent materials) with fluorescent doping materials, utilizes triplet exciton-sensitizing materials as exciton-sensitizing media, fully utilizes triplet excitons, and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% device internal quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLEDs applications. For example, CN 107507921 A and CN110492006A disclose a luminescent layer combination technology with TADF materials with a difference of the lowest singlet and triplet energy levels of less than or equal to 0.2 eV as the main body and boron-containing materials as doping; CN 110492005 A and CN 110492009A disclose a luminescent layer combination scheme with an exciplex as the main body and boron-containing materials as doping; both can achieve efficiency comparable to phosphorescence and a relatively narrow half-peak width. Therefore, the development of sensitization technology based on narrow half-peak width boron-based luminescent materials has unique advantages and strong potential in terms of BT.2020 display indicators. Summary of the invention

[0005] In view of the above problems existing in the prior art, the present invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention can simultaneously achieve the technical characteristics of green light emission and narrow half-peak width, and can be used as a green light doping material for the light-emitting layer of an organic electroluminescent device.

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

[0007]

[0008] In the general formula (1), M 2 Represented by one or more R substituted or unsubstituted C 6 ~C 30 aromatic ring, one or more R substituted or unsubstituted 5-30 membered heteroaromatic ring, one or more R substituted or unsubstituted C 6 ~C 30 One of the aliphatic rings;

[0009] Ar 1 Represented by R substituted or unsubstituted C 6 ~C 30 Aryl, or a 5-30 membered heteroaryl group which may be substituted by R;

[0010] M 1 Expressed as Where X represents O, S, -N(Q0 )-、-C(Q 3 )(Q 4 )-、-Si(Q 5 )(Q 6 )-one of;

[0011] c 1 、c 2 、c 3 、c 4 Indicates M 1 The connection site on

[0012] Each occurrence of R is the same or different and represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane;

[0013] R 1 , R 2 , R 3 , R 4 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane;

[0014] Ra, Rb, Rc, Q 1 , Q 2 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane;

[0015] Q 0 Represented by R substituted or unsubstituted C 1 ~C 10 Alkyl, R-substituted or unsubstituted C 3 ~C 10 Cycloalkyl, R-substituted or unsubstituted C 6 ~C 30 Aryl, 5-30 membered heteroaryl substituted or unsubstituted by R;

[0016] Q 3 , Q 4 , Q 5 , Q 6 Each independently represents a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane;

[0017] When there are multiple Rs, any two adjacent Rs are not connected or connected by a single bond, double bond, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect;

[0018] R 1 and Q 0 They are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect;

[0019] Q 0 and c 1 The sites are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect;

[0020] Rc and Q 1 They are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect;

[0021] Q 1 With Q 2 They are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )connect;

[0022] Q 3 With Q 4They are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect;

[0023] Q 5 With Q 6 They are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect;

[0024] The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine;

[0025] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

[0026] Furthermore, the M 1 Expressed as

[0027]

[0028] c 1 、c 2 、c 3 、c 4 represents the junction site;

[0029] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane;

[0030] The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine;

[0031] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

[0032] Furthermore, the structure of the boron-containing organic compound is shown in any one of the general formulas (1-1) to (1-6):

[0033]

[0034] M 1 、M 2 、Ra、Rb、Rc、Q 1 , Q 2 ,Ar 1 has the meaning defined in the general formula (1);

[0035] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane;

[0036] The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine;

[0037] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

[0038] Furthermore, the structure of the boron-containing organic compound is shown in any one of the general formulas (1-7) to (1-12):

[0039]

[0040] Ra, Rb, Rc, Q 1 , Q 2 ,Ar 1 has the meaning defined in the general formula (1);

[0041] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane;

[0042] The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine;

[0043] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

[0044] Furthermore, the structure of the boron-containing organic compound is shown in any one of general formulas (1-13) to (1-16):

[0045]

[0046] In the general formulas (1-13) to (1-16), Ra, Rb, Rc, Ar 1 , Q 1 , Q 2The meaning of is the same as that defined in general formula (1);

[0047] X represents O, S, -N (Q 0 )-、-C(Q 3 )(Q 4 )-、-Si(Q 5 )(Q 6 )-one of;

[0048] Q 0 , Q 3 -Q 6 The meaning of is the same as that defined in general formula (1);

[0049] Z is represented by CH or CR;

[0050] Each occurrence of R is the same or different and represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane;

[0051] The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine;

[0052] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

[0053] Furthermore, the structure of the boron-containing organic compound is shown in general formula (2):

[0054]

[0055] In the general formula (2), Ra, Rb, Rc, Ar 1 , Q 1 , Q 2 has the same meaning as defined above;

[0056] M 1 Expressed as Asterisks indicate junction sites;

[0057] Z is represented by CH or CR;

[0058] Z at the attachment site is represented by a carbon atom;

[0059] Each occurrence of R is the same or different and represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane;

[0060] The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine;

[0061] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si, and B;

[0062] Preferably, the structure of the boron-containing organic compound is as shown in any one of the general formulas (2-1) to (2-4):

[0063]

[0064] In the general formula (2-1) to the general formula (2-4), Z, Rb, Rc, Ar 1 , Q 1 , Q 2 The meaning of is the same as that defined in general formula (2);

[0065] Preferably, the structure of the boron-containing organic compound is as shown in any one of the general formulas (3) to (11):

[0066]

[0067] In the general formula (3) to the general formula (11), Z, Ar 1 , Rb, Rc, Q 1 , Q 2 The meaning is the same as that defined in general formula (2); preferably, the structure of the boron-containing organic compound is as shown in any one of general formulas (12) to (19):

[0068]

[0069]

[0070] In general formulae (12) to (19), Z and Rb have the same meanings as defined in general formula (2);

[0071] X 2 Indicated as O, S, NQ 7 , C(Q 8 )(Q 9 )、Si(Q 10 )(Q 11 )

[0072] Q 7 Indicated as substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0073] Q 8 , Q 9 , Q 10 , Q 11 Each independently represents a substituted or unsubstituted C 1 ~C10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 one of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane,

[0074] Q 8 With Q 9 , Q 10 With Q 11 Can be connected into rings by single bonds;

[0075] The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine;

[0076] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

[0077] Furthermore, the R, Ra, Rb, Rc, Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 , Q 8 , Q 9 , Q 10 , Q 11 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R18 , R 19 , R 20 , R 21 , R 22 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group , isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazine, phenyl-substituted boryl, methoxy, tert-butoxy, diphenylamine;

[0078] The Ar 1 It is represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, and xanthone;

[0079] The M 1 dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, tert-butyl-substituted dibenzofuranyl, One of;

[0080] The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group, and a diphenylamine group;

[0081] Preferably, the M 1 Each independently represents any of the following ring structures:

[0082]

[0083] * indicates the connection site;

[0084] Z is represented by CH or CR;

[0085] R, Ra, Rb, Rc, Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 , Q 8 , Q 9 , Q 10 , Q 11 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 are independently represented by the following groups: hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, trifluoromethyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, phenyl group, Any of;

[0086] The Ar 1 The independent representations are as follows:

[0087] Any of .

[0088] Furthermore, the specific structure of the boron-containing organic compound is any one of the following structures:

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] The present invention also provides an organic electroluminescent device, comprising a substrate, a first electrode, an organic light-emitting functional layer and a second electrode in sequence, wherein the organic light-emitting functional layer is located between the first electrode and the second electrode, and the organic light-emitting functional layer comprises a light-emitting layer, wherein the light-emitting layer contains the boron-containing organic compound of the present invention;

[0106] Preferably, the light-emitting layer comprises a main material and a doping material, and the doping material comprises the boron-containing organic compound described in the present invention;

[0107] Preferably, the light-emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound described in the present invention.

[0108] Preferably, the light-emitting layer comprises a host material, an exciton-sensitizing material and a doping material, the exciton-sensitizing material is a complex containing a metal element, and the doping material is the boron-containing organic compound described in the present invention.

[0109] Compared with the prior art, the beneficial technical effects of the present invention are:

[0110] (1) The compounds of the present invention are applied to OLED devices and can be used as doping materials for light-emitting layer materials. They can emit green fluorescence under the action of an electric field and can be applied to OLED lighting or OLED display fields;

[0111] (2) The compounds of the present invention have excellent structural stability, which helps to improve the life of the device;

[0112] (3) The compound of the present invention is used as a doping material, and the TADF sensitizer is introduced as a second host, which can effectively improve the device efficiency;

[0113] (4) The compound of the present invention is used as a doping material to introduce a phosphorescent sensitizer, which can effectively improve the efficiency and life of the device;

[0114] (5) The spectral FWHM of the compounds of the present invention is relatively narrow, which can effectively improve the color gamut of the device; BRIEF DESCRIPTION OF THE DRAWINGS

[0115] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0116] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. DETAILED DESCRIPTION

[0117] The present invention is described in detail below in conjunction with the accompanying drawings and embodiments.

[0118] In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, the words "upper", "lower", "top" and "bottom" used to indicate orientation only indicate the orientation in a certain state, and do not mean that the related structure can only exist in the orientation described; on the contrary, if the structure can change its position, such as inverted, the orientation of the structure will be changed accordingly. Specifically, in the present invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" or "upper" side.

[0119] In the present invention, the substituted or unsubstituted aromatic amine group described in the present invention refers to Where Q a , Q b represents a substituted or unsubstituted aromatic group, Q 4 , Q 5 Preferably, it is represented by substituted or unsubstituted C 6 -C 30 aryl or substituted or unsubstituted 5-30 membered heteroaryl.

[0120] In the present invention, substituted or unsubstituted C 6 -C 30 The aryl group refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 10 carbon atoms, preferably an aryl group having 8 to 10 carbon atoms, preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted The invention also includes, but is not limited to, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a combination thereof, or a condensed ring of a combination of the foregoing groups.

[0121] In the present invention, the substituted or unsubstituted 5-30 membered heteroaryl group refers to a substituted or unsubstituted furyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzo imidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, combinations thereof, or condensed rings of combinations of the foregoing groups, but are not limited thereto.

[0122] In the present invention, the number of heteroatoms in the substituted or unsubstituted 5-30 membered heteroaryl group is 1-5, preferably 1-4, preferably 1-3, and preferably 1-2.

[0123] The C of the present invention 1 -C 10 Alkyl (including straight-chain alkyl and branched alkyl) refers to an alkyl group having 1 to 10 carbon atoms, 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, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but are not limited thereto.

[0124] The C of the present invention 3 -C 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group containing 3 to 10 carbon atoms as ring atoms. 4 -C 9 Cycloalkyl, more preferably C 5 -C 8 Cycloalkyl, particularly preferably C 5 -C 7 Cycloalkyl. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, cycloheptyl, and the like, but are not limited thereto.

[0125] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0126] The C of the present invention 1 -C 10 The alkoxy group refers to a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an isopropoxy group or the like, but is not limited thereto.

[0127] The C of the present invention 2 -C 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 thereto.

[0128] The organic electroluminescent device of the present invention may be a bottom-emitting organic electroluminescent device, a top-emitting organic electroluminescent device, or a stacked organic electroluminescent device, without any particular limitation.

[0129] The organic electroluminescent device of the present invention comprises a substrate, a first electrode, a multi-layer organic thin film layer and a second electrode. The multi-layer organic thin film layer comprises a hole transport region, a light-emitting layer and an electron transport region, the hole transport region comprises a hole injection layer, a hole transport layer and an electron blocking layer, the electron transport region comprises a hole blocking layer, an electron transport layer and an electron injection layer, and in addition, a CPL layer may be arranged on the second electrode.

[0130] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent plastic substrates; opaque substrates such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its use direction is different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0131] A first electrode is formed on a substrate, and the first electrode and the second electrode may be opposite to 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 Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr or a metal mixture. The thickness of the first electrode layer depends on the material used, and is typically 50-500nm, preferably 70-300nm and more preferably 100-200nm.

[0132] 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.

[0133] In the present 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, and the like.

[0134] As the material for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials used for OLED devices.

[0135] The hole injection layer contains a main organic material that can conduct holes, and also contains a P-type dopant material with a deep HOMO energy level (the corresponding LUMO energy level will also be very deep). Based on empirical summary, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the main organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doped material, so that the charge transfer state between the main material and the dopant material can be realized, the ohmic contact between the buffer layer and the anode can be achieved, and the efficient injection from the electrode to the hole injection conduction can be achieved.

[0136] In view of the above empirical summary, for hole-type host organic materials with different HOMO energy levels, different P-doped materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0137] Preferably, the main organic material of the hole injection layer of the present invention can be selected from the compounds disclosed in the following prior arts: JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN105439999A or CN103108859A.

[0138] Preferably, the P-type doping material is selected from the compounds with charge conductivity disclosed in the prior art, and the P-type dopant can be selected from the compounds disclosed in any one of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE10200703122 0A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but are not limited thereto.

[0139] In one embodiment of the present invention, the hole injection layer comprises a P-type dopant material with charge conductivity selected from the following: quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited to these.

[0140] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material used is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0141] The thickness of the hole injection layer of the present invention may be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0142] Preferably, the hole transport layer material of the present invention may be selected from the following compounds disclosed in the prior art:

[0143]

[0144]

[0145] Preferably, the hole transport layer material and the host organic material in the hole injection layer of the present invention are selected from the same compound.

[0146] The thickness of the hole transport layer of the present invention may be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0147] In one embodiment of the present invention, the electron blocking layer material of the present invention may be selected from the following compounds disclosed in the prior art:

[0148]

[0149] The thickness of the electron blocking layer of the present invention may be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0150] After forming the hole injection layer, the hole transport layer and the electron blocking layer, a corresponding light emitting layer is formed on the electron blocking layer.

[0151] The light-emitting layer may include a host material and a dopant material. The host material may be a common green light host material in the art, and the dopant material may be a boron-containing organic compound represented by the general formula (1) of the present invention.

[0152] The light-emitting layer may contain a single host material or a dual host material;

[0153] The dual-host material comprises a first host material and a second host material, and preferably at least one of the first host material and the second host material is a TADF material;

[0154] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by a small energy level difference between the first excited singlet state and the first excited triplet state, so that the singlet excitons and triplet excitons generated can be used simultaneously in the device, making the utilization rate of the excitons generated by the device as close to 100% as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0155] The light-emitting layer may include a host material, an exciton-sensitizing material, and a doping material;

[0156] Exciton sensitizing materials refer to materials that can make the luminescent material in the luminescent layer fully utilize the electroexcitons, so that the luminescent layer finally produces the emission spectrum of the sensitized material. Exciton sensitizers may undertake functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron-containing organic compound represented by the general formula (1) of the present invention and the exciton sensitizing material are used in combination, which has a significant improvement effect on the problems of device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0157] In the light-emitting layer of the present invention, the ratio of the host material to the doping material used is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0158] The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and the driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and more preferably 15-40 nm, but the thickness is not limited to this range.

[0159] In the present 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.

[0160] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be arranged on the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds with hole blocking function known in the prior art can be used, for example:

[0161]

[0162] The thickness of the hole blocking layer of the present invention may be 2-200 nm, preferably 5-150 nm, more preferably 5-50 nm, but the thickness is not limited to this range.

[0163] The electron transport layer may be disposed on the light-emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. A material having a high electron mobility is preferred. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer materials for organic electroluminescent devices disclosed in the prior art can be used, for example:

[0164]

[0165] In a preferred embodiment of the present invention, the electron transport layer further comprises other compounds conventionally used in electron transport layers, for example, Alq3, LiQ, preferably LiQ.

[0166] The thickness of the electron transport layer of the present invention may be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm, but the thickness is not limited to this range.

[0167] The electron injection layer may be disposed on the electron transport layer. The electron injection layer material is generally preferably a material having a low work function, so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer material for organic electroluminescent devices disclosed in the prior art can be used, for example:

[0168]

[0169] The thickness of the electron injection layer of the present invention may 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.

[0170] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF2, Ba, Ag, or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0171] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign 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 can or a metal can; or a thin film covering the entire surface of the organic layer.

[0172] The method for preparing the organic electroluminescent device of the present invention comprises laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer and a cathode successively on a substrate, and optionally a covering layer. In this regard, vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI methods can be used, but are not limited thereto. In the present invention, it is preferred to use a vacuum evaporation method to form the various layers. Those skilled in the art can conventionally select various process conditions in the vacuum evaporation method according to actual needs.

[0173] Synthesis Example

[0174] The raw materials involved in the synthesis examples of the present invention can be purchased from the market or prepared by conventional preparation methods in the art;

[0175] Synthesis of intermediate 1:

[0176]

[0177]

[0178] Synthesis of intermediate a-1:

[0179] In a three-necked flask, under nitrogen protection, add 3.6g (10mmol) of raw material B-1, 0.4g (60%) NaH dissolved in mineral oil and 80mL anhydrous DMF, and react for 0.5 hours at room temperature. Add 1.9g (10mmol) of raw material A-1 dissolved in 10mL DMF dropwise, heat to 80°C and react for 5 hours. After cooling to room temperature, add 1mL of water to quench the reaction, concentrate and purify by silica gel column chromatography to obtain intermediate a-1.

[0180] Synthesis of intermediate b-1:

[0181] Dissolve the intermediate a-1 (3.9 g, 7.5 mmol) in N, N-dimethylacetamide (50 mL), and add tricyclohexylphosphine (0.63 g, 2.25 mmol), palladium acetate (0.25 g, 1.13 mmol), and cesium carbonate (4.9 g, 15.0 mmol) in sequence. Under nitrogen protection, heat to 160 ° C and stir for 13 h. After the reaction, cool to room temperature. Then pour into water, extract with ethyl acetate, wash the organic phase with saturated brine, and anhydrous Na 2 SO 4 The residue was dried, concentrated under reduced pressure and purified by column chromatography to obtain intermediate b-1.

[0182] Synthesis of intermediate c-1:

[0183] Dissolve the intermediate b-1 (4.4 g, 10 mmol) in 100 mL of ethanol, add 0.56 g (10 mmol) of iron powder and 1.1 g (20 mmol) of ammonium chloride, heat under reflux for 12 hours, filter out the insoluble solid, dry the organic phase over anhydrous sodium sulfate, filter, concentrate and purify by column chromatography to obtain the intermediate c-1.

[0184] Synthesis of intermediate 1:

[0185] Dissolve the raw material C-1 (0.5 g, 5.0 mmol) in a solution of N, N-dimethylformamide (50 mL) and water (10 mL), and add the intermediate c-1 (1.9 g, 5 mmol). Heat to 80 ° C and stir for 48 hours. After the reaction is completed, concentrate the reaction solution until about 5 mL of N, N-dimethylformamide remains. Slowly add the concentrated reaction solution dropwise to water to obtain an insoluble yellow solid precipitate. After filtration, the filter cake is slurried with methanol and water (30 mL, 1:1) overnight, and then filtered to obtain a filter cake. The filter cake is spin-dried, slurried with petroleum ether and dichloromethane overnight, and filtered to obtain intermediate 1.

[0186] Synthesis of intermediate 2:

[0187]

[0188] Synthesis of intermediate a-2:

[0189] In a three-necked flask, under nitrogen protection, add 3.6g (10mmol) of raw material B-1, 0.4g (60%) NaH dissolved in mineral oil and 80mL anhydrous DMF, and react for 0.5 hours at room temperature. Add 1.9g (10mmol) of raw material A-2 dissolved in 10mL DMF dropwise, heat to 80°C and react for 3 hours. After cooling to room temperature, add 1mL of water to quench the reaction, concentrate and purify by silica gel column chromatography to obtain intermediate a-2.

[0190] Synthesis of intermediate b-2:

[0191] Dissolve the intermediate a-2 (3.9 g, 7.5 mmol) in N, N-dimethylacetamide (50 mL), and add tricyclohexylphosphine (0.6 g, 2.25 mmol), palladium acetate (0.3 g, 1.13 mmol), and cesium carbonate (4.9 g, 15.0 mmol) in sequence. Under nitrogen protection, heat to 160 ° C and stir for 13 h. After the reaction, cool to room temperature. Then pour into water, extract with ethyl acetate, wash the organic phase with saturated brine, and anhydrous Na 2 SO 4 Dry, concentrate under reduced pressure and purify by column chromatography to obtain intermediate b-2.

[0192] Synthesis of intermediate c-2:

[0193] Dissolve the intermediate b-2 (4.4 g, 10 mmol) in 100 mL of ethanol, add 0.6 g (10 mmol) of iron powder and 1.1 g (20 mmol) of ammonium chloride, heat under reflux for 12 hours, filter out the insoluble solid, dry the organic phase over anhydrous sodium sulfate, filter, concentrate and purify by column chromatography to obtain the intermediate c-2.

[0194] Synthesis of intermediate 2:

[0195] Dissolve the raw material C-1 (0.5 g, 5.0 mmol) in a solution of N, N-dimethylformamide (50 mL) and water (10 mL), and add the intermediate c-2 (1.9 g, 5 mmol). Heat to 80 ° C and stir for 33 hours. After the reaction is completed, concentrate the reaction solution until about 5 mL of N, N-dimethylformamide remains. Slowly add the concentrated reaction solution dropwise to water to obtain an insoluble yellow solid precipitate. After filtration, the filter cake is slurried with methanol and water (32 mL, 1:1) overnight, and then filtered to obtain a filter cake. The filter cake is spin-dried, slurried with petroleum ether and dichloromethane overnight, and filtered to obtain intermediate 2.

[0196] Synthesis of intermediate 3:

[0197]

[0198] Synthesis of intermediate 3:

[0199] The raw material C-2 (1.0 g, 5.0 mmol) was dissolved in a solution of N, N-dimethylformamide (50 mL) and water (10 mL), and the intermediate c-2 (1.9 g, 5 mmol) was added. The temperature was raised to 80 ° C and stirred for 72 hours. After the reaction was completed, the reaction solution was concentrated until about 5 mL of N, N-dimethylformamide remained. The concentrated reaction solution was slowly added dropwise to water to obtain an insoluble yellow solid precipitate. After filtration, the filter cake was slurried with methanol and water (40 mL, 1:1) overnight, and then filtered to obtain a filter cake. The filter cake was spin-dried, slurried with petroleum ether and dichloromethane overnight, and filtered to obtain intermediate 3.

[0200] Synthesis of intermediate G1:

[0201]

[0202] Under nitrogen protection, raw material R1 (4.46 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), palladium acetate (0.09 g, 0.4 mmol) were added to a two-necked bottle, 100 mL of anhydrous DMF was added under nitrogen protection, and the mixture was stirred at room temperature for 30 min. Raw material P1 (6.73 g, 25 mmol) was added under nitrogen protection, and the mixture was stirred at 140 ° C for 12 h under nitrogen protection. The mixture was filtered, washed with water, dried, and passed through a column with PE:EA=20:1 to obtain intermediate G1.

[0203] Synthesis of intermediate G2:

[0204]

[0205] Add raw material R2 (7.26 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask, add 100 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material P1 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA=20:1 to obtain intermediate G2.

[0206] Synthesis of intermediate G3:

[0207]

[0208] Add raw material R2 (7.26 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask, add 100 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material P2 (6.73 g, 25 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA=20:1 to obtain intermediate G3.

[0209] Example 1 Synthesis of Compound 21:

[0210]

[0211] Preparation of intermediate d-1:

[0212] Add raw material D-1 (1.68 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) into a two-necked flask, add 50 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material B-2 (1.4 g, 5 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA = 20:1 to obtain intermediate d-1.

[0213] Preparation of intermediate e-1:

[0214] The intermediate d-1 (3.03 g, 5.1 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen gas at 0°C, 3.8 mL of n-butyl lithium (1.6 M) n-hexane solution was slowly added; after stirring at 0°C for 2 hours, 10 mL of tetrahydrofuran solution of raw material E-1 (0.99 g, 5.5 mmol) was slowly added. Then the reaction mixture was slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water and ethyl acetate were added to the reaction mixture, the water layer was separated, and extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and treated with NaHCO 3 The aqueous solution was slowly quenched. The aqueous layer was then separated and extracted with dichloromethane. It was dried over sodium sulfate, filtered, and evaporated by rotary concentrator and passed through a column to obtain intermediate e-1.

[0215] Preparation of intermediate f-1:

[0216] The intermediate e-1 (1.58 g, 2.5 mmol) was dissolved in 50 mL of toluene solution, and the intermediate 1 (1.2 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 22 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, the ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring and filtered to obtain the intermediate f-1.

[0217] Preparation of compound 21:

[0218] Dissolve the intermediate f-1 (12.75 g, 12.5 mmol) in 300 mL of tert-butylbenzene, slowly add 10 mL of tert-butyl lithium (1.6 M) in n-pentane under a nitrogen atmosphere at 0°C, stir at 60°C for 1 hour, add boron tribromide (6.26 g, 25 mmol) at 0°C, and stir the reaction mixture at room temperature for 2 hours. Add N,N-diisopropylethylamine (DIPEA) (3.27 g, 25.2 mmol) at 0°C and wait for the reaction mixture to reach room temperature. After stirring at 130°C for 4 hours, cool the reaction mixture to room temperature. Add methanol to the reaction mixture to remove residual BBr 3 The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed in a vacuum and passed through a column to obtain compound 21. The half peak width of compound 21 in toluene solution was 23 nm (1×10 -5 M, toluene solution). 1 H NMR (400 MHz, deuterated chloroform) δ8.82–8.77 (m, 1H), 8.39–8.33 (m, 1H), 8.28 (d, 1H), 8.26–8.13 (m, 2H), 7.91 (d, 1H), 7.85 (m, 2H), 7.66–7.48 (m, 4H), 7.46–7.30 (m, 7H), 7.25 (m, 2H), 7.11 (dd, 2H), 7.05–6.98 (m, 2H), 1.39 (s, 9H), 1.37–1.26 (m, 27H).

[0219] Example 2 Synthesis of Compound 36:

[0220]

[0221] Preparation of intermediate e-2:

[0222] Under nitrogen protection, 4.7 g (10 mmol) of intermediate 1, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 2.5 g (10 mmol) of raw material D-2 dissolved in 25 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate e-2.

[0223] Preparation of intermediate f-2:

[0224] Under nitrogen protection, 3.2 g (10 mmol) of intermediate G1, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 7.0 g (10 mmol) of intermediate e-2 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate f-2.

[0225] Preparation of compound 36:

[0226] Dissolve the intermediate f-2 (12.5 g, 12.5 mmol) in 300 mL of tert-butylbenzene, slowly add 10 mL of n-butyllithium (1.6 M) in n-pentane under a nitrogen atmosphere at 0°C, stir at 60°C for 3 hours, add boron tribromide (6.26 g, 25 mmol) at 0°C, and stir the reaction mixture at room temperature for 2 hours. Add N,N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) at 0°C and wait for the reaction mixture to reach room temperature. After stirring at 130°C for 4 hours, cool the reaction mixture to room temperature. Add methanol to the reaction mixture to remove residual BBr 3 The mixture was separated and extracted with water and dichloromethane. The combined organic layer was condensed in a vacuum and passed through a column to obtain compound 36. The half peak width of compound 36 in toluene solution was 20 nm (1×10 -5 M, toluene solution).

[0227] Example 3 Synthesis of Compound 41:

[0228]

[0229] Preparation of intermediate e-3:

[0230] Under nitrogen protection, 4.7 g (10 mmol) of intermediate 1, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 2.7 g (10 mmol) of raw material D-3 dissolved in 25 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate e-3.

[0231] Preparation of intermediate f-3:

[0232] Under nitrogen protection, 2.8 g (10 mmol) of raw material B-2, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 7.2 g (10 mmol) of intermediate e-3 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80°C for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate f-3.

[0233] Preparation of compound 41:

[0234] Dissolve the intermediate f-3 (12.2 g, 12.5 mmol) in 300 mL of tert-butylbenzene, slowly add 10 mL of n-butyllithium (1.6 M) in n-pentane under a nitrogen atmosphere at 0°C, stir at 60°C for 2 hours, add boron tribromide (6.26 g, 25 mmol) at 0°C, and stir the reaction mixture at room temperature for 2 hours. Add N,N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) at 0°C and wait for the reaction mixture to reach room temperature. After stirring at 130°C for 5 hours, cool the reaction mixture to room temperature. Add methanol to the reaction mixture to remove residual BBr 3 The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed in a vacuum and passed through a column to obtain compound 41. The half peak width of compound 41 in toluene solution was 24 nm (1×10 -5 M, toluene solution). 1 H NMR (400 MHz, deuterated chloroform) δ 8.74–8.59 (m, 1H), 8.37 (d, 1H), 8.34 (dd, 2H), 8.25–8.16 (m, 2H), 7.94 (t, 2H), 7.78 (d, 1H), 7.69 (d, 1H), 7.64–7.51 (m, 3H), 7.43–7.27 (m, 9H), 7.10 (d, 1H), 1.42 (d, 18H), 1.36 (d, 18H).

[0235] Example 4 Synthesis of Compound 79:

[0236]

[0237] Preparation of intermediate e-4:

[0238] Under nitrogen protection, 4.7 g (10 mmol) of intermediate 2, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 2.5 g (10 mmol) of raw material D-2 dissolved in 25 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate e-4.

[0239] Preparation of intermediate f-4:

[0240] Under nitrogen protection, 4.3 g (10 mmol) of intermediate G2, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 7.0 g (10 mmol) of intermediate e-4 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate f-4.

[0241] Preparation of compound 79:

[0242] Dissolve the intermediate f-4 (13.9 g, 12.5 mmol) in 300 mL of tert-butylbenzene, slowly add 10 mL of n-butyllithium (1.6 M) in n-pentane under a nitrogen atmosphere at 0°C, stir at 60°C for 3 hours, add boron tribromide (6.26 g, 25 mmol) at 0°C, and stir the reaction mixture at room temperature for 2 hours. Add N,N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) at 0°C and wait for the reaction mixture to reach room temperature. After stirring at 130°C for 3 hours, cool the reaction mixture to room temperature. Add methanol to the reaction mixture to remove residual BBr 3 The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed in a vacuum and passed through a column to obtain compound 79. The half peak width of compound 79 in toluene solution was 19 nm (1×10 -5 M, toluene solution).

[0243] Example 5 Preparation of Compound 80:

[0244]

[0245] Preparation of intermediate f-5:

[0246] Under nitrogen protection, 4.3 g (10 mmol) of intermediate G3, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 7.0 g (10 mmol) of intermediate e-2 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate f-5.

[0247] Preparation of compound 80:

[0248] Dissolve the intermediate f-5 (13.9 g, 12.5 mmol) in 300 mL of tert-butylbenzene, slowly add 10 mL of n-butyllithium (1.6 M) in n-pentane under a nitrogen atmosphere at 0°C, stir at 60°C for 3 hours, add boron tribromide (6.26 g, 25 mmol) at 0°C, and stir the reaction mixture at room temperature for 2 hours. Add N,N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) at 0°C and wait for the reaction mixture to reach room temperature. After stirring at 130°C for 5 hours, cool the reaction mixture to room temperature. Add methanol to the reaction mixture to remove residual BBr 3 The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed in a vacuum and passed through a column to obtain compound 80. The half peak width of compound 80 in toluene solution was 22 nm (1×10 -5 M, toluene solution). 1 H NMR(400MHz,Chloroform-d)δ8.37–8.32(m,1H),8.22–8.09(m,2H),7.91(d,2H),7.80(m,2H),7.69–7.66(m,2H ),7.65–7.63(m,2H),7.62–7.55(m,3H),7.48–7.43(m,6H),7.36–7.22(m,4H),7.17(d,2H),1.45–1.33(m,45H).

[0249] Example 6 Synthesis of Compound 142:

[0250]

[0251]

[0252] Preparation of intermediate e-5:

[0253] Under nitrogen protection, 5.6 g (10 mmol) of intermediate 3, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 2.5 g (10 mmol) of raw material D-2 dissolved in 25 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate e-5.

[0254] Preparation of intermediate f-6:

[0255] Under nitrogen protection, 3.2 g (10 mmol) of intermediate G1, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 7.9 g (10 mmol) of intermediate e-5 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate f-6.

[0256] Preparation of compound 142:

[0257] Dissolve the intermediate f-6 (13.6 g, 12.5 mmol) in 300 mL of tert-butylbenzene, slowly add 10 mL of n-butyllithium (1.6 M) in n-pentane under a nitrogen atmosphere at 0°C, stir at 60°C for 2 hours, add boron tribromide (6.26 g, 25 mmol) at 0°C, and stir the reaction mixture at room temperature for 2 hours. Add N,N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) at 0°C and wait for the reaction mixture to reach room temperature. After stirring at 130°C for 8 hours, cool the reaction mixture to room temperature. Add methanol to the reaction mixture to remove residual BBr 3 The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed in a vacuum and passed through a column to obtain compound 142. The half peak width of compound 142 in toluene solution was 21 nm (1×10 -5 M, toluene solution).

[0258] Example 7 Synthesis of Compound 174:

[0259]

[0260] Preparation of intermediate f-7:

[0261] Under nitrogen protection, 4.3 g (10 mmol) of intermediate G1, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask, stirred and reacted for 0.5 hours at room temperature, and 7.9 g (10 mmol) of intermediate e-5 dissolved in 35 mL of anhydrous DMF was added dropwise, and reacted at 80° C. for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction, concentrated and separated and purified by silica gel column chromatography to obtain intermediate f-7.

[0262] Preparation of compound 174:

[0263] Dissolve the intermediate f-7 (15.0 g, 12.5 mmol) in 300 mL of tert-butylbenzene, slowly add 10 mL of n-butyllithium (1.6 M) in n-pentane under a nitrogen atmosphere at 0°C, stir at 60°C for 3 hours, add boron tribromide (6.26 g, 25 mmol) at 0°C, and stir the reaction mixture at room temperature for 3 hours. Add N,N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) at 0°C and wait for the reaction mixture to reach room temperature. After stirring at 130°C for 6 hours, cool the reaction mixture to room temperature. Add methanol to the reaction mixture to remove residual BBr 3 The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed in a vacuum and passed through a column to obtain compound 174. The half peak width of compound 174 in toluene solution was 21 nm (1×10 -5 M, toluene solution).

[0264] Example 8 Synthesis of Compound 280:

[0265]

[0266] Preparation of intermediate f-8:

[0267] The intermediate e-1 (1.58 g, 2.5 mmol) was dissolved in 50 mL of toluene solution, and the intermediate 2 (1.2 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 22 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, the ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring and filtered to obtain the intermediate f-8.

[0268] Preparation of compound 280:

[0269] Dissolve the intermediate f-8 (12.75 g, 12.5 mmol) in 300 mL of tert-butylbenzene, slowly add 10 mL of tert-butyl lithium (1.6 M) in n-pentane under a nitrogen atmosphere at 0°C, stir at 60°C for 2 hours, add boron tribromide (6.26 g, 25 mmol) at 0°C, and stir the reaction mixture at room temperature for 1 hour. Add N,N-diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) at 0°C and wait for the reaction mixture to reach room temperature. After stirring at 130°C for 7 hours, cool the reaction mixture to room temperature. Add methanol to the reaction mixture to remove residual BBr 3 The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed in a vacuum and passed through a column to obtain compound 280. The half peak width of compound 280 in toluene solution was 22 nm (1×10 -5 M, toluene solution).

[0270] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0271] Table 1

[0272]

[0273]

[0274] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 1-8 and device comparative examples 1-6. The device manufacturing process of device embodiments 2-8 and device comparative examples 1-6 of the present invention is exactly the same as that of device embodiment 1, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 2-1 and Table 3 respectively:

[0275] Device Example 1

[0276] The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as a hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then evaporate HT-1 with a thickness of 60nm as a hole transport layer 4. Then evaporate EB-1 with a thickness of 30nm as an electron blocking layer 5. After the above electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, compound 21 as the doping material, the mass ratio of GH-1, GH-2 and compound 21 is 69:30:1, and the film thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm, which was the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq were vacuum-deposited to a thickness of 30 nm, with a mass ratio of ET-1 to Liq of 1:1. On the electron transport layer 8, a LiF layer with a thickness of 1 nm was made by vacuum evaporation, which was the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm was made by vacuum evaporation, with a mass ratio of Mg to Ag of 1:9, which was used as the cathode layer 10.

[0277] The following device embodiments 9-16 are used to explain in detail the application effect of the OLED material synthesized by the present invention in the device. The device embodiments 10-16 of the present invention are completely identical in manufacturing process to the device embodiment 9, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also consistent. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 2-2 and Table 3 respectively:

[0278] Device Example 9

[0279] The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as the hole injection layer 3, and the mass ratio of HT-1 to HI-1 is 97:3. Then, HT-1 with a thickness of 60nm is evaporated as the hole transport layer 4. Then, EB-1 with a thickness of 30nm is evaporated as the electron blocking layer 5. After the above-mentioned electron blocking material is deposited, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, GD-1 as the first doping material, and compound 21 as the second doping material. The mass ratio of GH-1, GH-2, GD-1 and compound 21 is 66.5:30:3:0.5, and the thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 is vacuum-deposited with a film thickness of 5nm. This layer is the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq are vacuum-deposited. The mass ratio of ET-1 and Liq is 1:1, and the film thickness is 30nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1nm is prepared by a vacuum evaporation device. This layer is the electron injection layer 9. On the electron injection layer 9 , a Mg:Ag electrode layer with a film thickness of 80 nm was produced by a vacuum evaporation device. The mass ratio of Mg to Ag was 1:9. This layer was used as the cathode layer 10 .

[0280] The molecular structure formula of the relevant materials is shown below:

[0281]

[0282] After the OLED light-emitting device is completed as described above, the anode and cathode are connected by a known driving circuit, and the current efficiency, luminous peak value and life of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 2-1 and Table 2-2; the test results of the current efficiency, luminous peak value and life of the obtained device are shown in Table 3.

[0283] Table 2-1

[0284]

[0285]

[0286] Table 2-2

[0287]

[0288]

[0289] Table 3

[0290]

[0291] Note: Current efficiency and luminescence peak are tested using IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); life test system is EAS-62C OLED device life tester from Japan System Technology Co., Ltd.; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are at 10mA / cm 2 Next test.

[0292] It can be seen from the device data results in Table 3 that, compared with the comparative compounds ref-1, ref-2, ref-3, ref-4, ref-5 and ref-6, the luminescence peak of the compound of the present invention is between 510 and 550 nm, and the green luminescence effect can be well achieved; the current efficiency and life of the organic light-emitting device of the present invention are greatly improved compared with the OLED device of the known materials; when the exciton-sensitizing material is used as the first doping, the device efficiency is significantly improved compared with the single doping.

[0293] In summary, the above are only 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 in the protection scope of the present invention.

Claims

1. A boron-containing organic compound, It is characterized in that The structure of the boron-containing organic compound is shown in general formula (1): In the general formula (1), M 2 Represented by one or more R substituted or unsubstituted C 6 ~C 30 aromatic ring, one or more R substituted or unsubstituted 5-30 membered heteroaromatic ring, one or more R substituted or unsubstituted C 6 ~C 30 One of the aliphatic rings; Ar 1 Represented by R substituted or unsubstituted C 6 ~C 30 Aryl, or a 5-30 membered heteroaryl group which may be substituted by R; M 1 Expressed as Where X represents O, S, -N(Q 0 )-、-C(Q 3 )(Q 4 )-、-Si(Q 5 )(Q 6 )-one of; c 1 、c 2 、c 3 、c 4 Indicates M 1 The connection site on Each occurrence of R is the same or different and represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane; R 1 , R 2 , R 3 , R 4 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane; Ra, Rb, Rc, Q 1 , Q 2 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane; Q 0 Represented by R substituted or unsubstituted C 1 ~C 10 Alkyl, R-substituted or unsubstituted C 3 ~C 10 Cycloalkyl, R-substituted or unsubstituted C 6 ~C 30 Aryl, 5-30 membered heteroaryl substituted or unsubstituted by R; Q 3 , Q 4 , Q 5 , Q 6 Each independently represents a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane; When there are multiple Rs, any two adjacent Rs are not connected or connected by a single bond, double bond, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect; R 1 and Q 0 They are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect; Q 0 and c 1 The sites are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect; Rc and Q 1 They are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect; Q 1 With Q 2 They are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )connect; Q 3 With Q 4 They are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect; Q 5 With Q 6 They are not connected or connected by single bonds, double bonds, -O-, -S-, -N(Q 0 )-、-C(Q 3 )(Q 4 )-or-Si(Q 5 )(Q 6 )-connect; The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

2. The boron-containing organic compound according to claim 1, It is characterized in that The M 1 Expressed as c 1 、c 2 、c 3 、c 4 represents the junction site; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane; The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

3. The boron-containing organic compound according to claim 1, It is characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (1-1) to (1-6): M 1 、M 2 、Ra、Rb、Rc、Q 1 , Q 2 ,Ar 1 has the meaning defined in the general formula (1); R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane; The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

4. The boron-containing organic compound according to claim 1, It is characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (1-7) to (1-12): Ra, Rb, Rc, Q 1 , Q 2 ,Ar 1 has the meaning defined in the general formula (1); R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane; The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

5. The boron-containing organic compound according to claim 1, It is characterized in that The structure of the boron-containing organic compound is shown in any one of the general formulas (1-13) to (1-16): In the general formulas (1-13) to (1-16), Ra, Rb, Rc, Ar 1 , Q 1 , Q 2 The meaning of is the same as that defined in general formula (1); X represents O, S, -N (Q 0 )-、-C(Q 3 )(Q 4 )-、-Si(Q 5 )(Q 6 )-one of; Q 0 , Q 3 -Q 6 The meaning of is the same as that defined in general formula (1); Z is represented by CH or CR; Each occurrence of R is the same or different and represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane; The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

6. The boron-containing organic compound according to claim 1, It is characterized in that The structure of the boron-containing organic compound is shown in general formula (2): In the general formula (2), Ra, Rb, Rc, Ar 1 , Q 1 , Q 2 has the same meaning as defined in claim 1; M 1 Expressed as Asterisks indicate junction sites; Z is represented by CH or CR; Z at the attachment site is represented by a carbon atom; Each occurrence of R is the same or different and represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 2 ~C 20 Alkynyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane, and substituted or unsubstituted silane; The substituent for substituting the substitutable group may be selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si, and B; Preferably, the structure of the boron-containing organic compound is as shown in any one of the general formulas (2-1) to (2-4): In the general formula (2-1) to the general formula (2-4), Z, Rb, Rc, Ar 1 , Q 1 , Q 2 The meaning of is the same as that defined in general formula (2); Preferably, the structure of the boron-containing organic compound is as shown in any one of the general formulas (3) to (11): In the general formula (3) to the general formula (11), Z, Ar 1 , Rb, Rc, Q 1 , Q 2 The meaning of is the same as that defined in general formula (2); Preferably, the structure of the boron-containing organic compound is as shown in any one of the general formulas (12) to (19): In general formulae (12) to (19), Z and Rb have the same meanings as defined in general formula (2); X 2 Indicated as O, S, NQ 7 , C(Q 8 )(Q 9 )、Si(Q 10 )(Q 11 ) Q 7 Indicated as substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; Q 8 , Q 9 , Q 10 , Q 11 Each independently represents a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C 6 ~C 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl, and borane, Q 8 With Q 9 , Q 10 With Q 11 Can be connected into rings by single bonds; The substituents for the substituent groups are selected from deuterium atoms, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 One or more of aryl, 5-30 membered heteroaryl, and arylamine; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si and B.

7. The boron-containing organic compound according to any one of claims 1 to 6, It is characterized in that R, Ra, Rb, Rc, Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 , Q 8 , Q 9 , Q 10 , Q 11 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group , isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazine, phenyl-substituted boryl, methoxy, tert-butoxy, diphenylamine; The Ar 1 It is represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, and xanthone; The M 1 dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, tert-butyl-substituted dibenzofuranyl, One of; The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group, and a diphenylamine group; Preferably, the M 1 Each independently represents any of the following ring structures: * indicates the connection site; Z is represented by CH or CR; R, Ra, Rb, Rc, Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 , Q 8 , Q 9 , Q 10 , Q 11 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 are independently represented by the following groups: hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, trifluoromethyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, phenyl group, Any of; The Ar 1 The independent representations are as follows: Any of .

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

9. An organic electroluminescent device, comprising a substrate, a first electrode, an organic light-emitting functional layer and a second electrode in sequence, wherein the organic light-emitting functional layer is located between the first electrode and the second electrode, and the organic light-emitting functional layer comprises a light-emitting layer, It is characterized in that The light-emitting layer contains the boron-containing organic compound according to any one of claims 1 to 8; Preferably, the light-emitting layer comprises a host material and a doping material, and the doping material comprises the boron-containing organic compound according to any one of claims 1 to 8; Preferably, the light-emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1-8.

10. The organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises a host material, an exciton sensitizing material and a doping material. Features: The exciton sensitizing material is a complex containing a metal element, and the doping material is a boron-containing organic compound according to any one of claims 1 to 8.

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