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

Abstract

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

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) offer significant advantages over liquid crystal displays (LCDs), including being lighter and thinner, having higher color contrast, lower power consumption, faster response times, higher resolution, and greater flexibility. They are considered poised to dominate future display terminal products. With the advent of the 5G era, the new information display industry urgently needs iterative development. Early color gamut standards (BT.709 and DCIP3) are no longer sufficient to meet the high-quality technological demands of display products. To achieve ultra-high definition and higher image quality performance requirements, the new generation display standard (BT.2020) is driving the development of organic electroluminescent materials towards higher color purity, which necessitates that the core light-emitting material have a narrower emission spectrum. Currently, among the three commercially available OLED color display technologies (red, green, and blue), blue light uses traditional fluorescent triplet-triplet transition (TTF) technology. This technology has lower efficiency but higher color purity, and it has basically met the BT.2020 display specifications. Green and red light use phosphorescence technology, which has high efficiency. Red light is close to the BT.2020 display specifications, while green light is limited by the wider emission spectrum of phosphorescence, which is significantly different from the requirements of high-definition display specifications. In addition, green phosphorescence naturally has a high shoulder peak, making it relatively difficult to improve the color gamut display under traditional device structures. Therefore, developing a new generation of high color purity green organic electroluminescent materials is crucial.

[0003] Since 2020, green light materials with narrow half-width at half-maximum (WHM < 30nm) based on boron-nitrogen resonant structures have been reported successively. Furthermore, several papers on green boron-nitrogen narrow-emission materials and device effects were reported in 2022 and 2023, such as: DOI: 10.1002 / anie.202301930, DOI: 10.1038 / s41566-022-01106-8, DOI: 10.1002 / anie.202313254, DOI: 10.1038 / s41566-022-01083-y, DOI: 10.1002 / anie.202202380, etc., demonstrating the high color purity and efficiency of these materials, which have great potential as a new generation of green organic electroluminescent display materials. However, there are still many technical challenges in the development of green ultra-high color purity materials with boron-nitrogen structures. Existing materials also have the drawbacks of insufficient efficiency and lifespan to meet the needs of mass production. Developing narrow half-peak width green light materials based on boron-nitrogen resonant structures that can meet practical applications is a key technology for the next generation of display devices with high color purity, high color gamut coverage, high efficiency and high immersion.

[0004] In addition, sensitization technology combines triplet exciton sensitizing materials (including but not limited to TADF materials and phosphorescent materials) with fluorescent doping materials. By using triplet exciton sensitizing materials as exciton sensitization media, it fully utilizes triplet excitons and transfers energy to fluorescent doping materials through energy transfer, achieving 100% in-device quantum efficiency (DOI: 10.1038 / ncomms5016, DOI: 10.1038 / s41566-022-00958-4). This technology can compensate for the insufficient exciton utilization of fluorescent doping materials and effectively leverage the high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects for OLED applications. For example, CN 107507921A and CN 110492006A disclose a light-emitting layer combination technology using TADF materials with a minimum singlet and triplet energy level difference of less than or equal to 0.2 eV as the main body and boron-containing materials as dopants; CN 110492005A and CN 110492009A disclose a light-emitting layer combination scheme using excitocomplexes as the main body and boron-containing materials as dopants; both can achieve efficiencies comparable to phosphorescence and relatively narrow half-peak widths (HWHM). Therefore, developing sensitization technologies based on narrow HWHM boron-based light-emitting materials has unique advantages and strong potential for improving BT.2020 display performance. Summary of the Invention

[0005] To address the aforementioned problems in the existing technology, this application provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of this invention can achieve green light emission 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 general formula (1), Y1 represents N or C-Ar1;

[0009] Z1, Z2, Z3, and Z4 are independently represented as N or C-Ar. a C-Ar b C-Ar c C-Ar d ;

[0010] R1, R2, Ar1, Ar2, Ar a Ar b Ar c Ar d Independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C.10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane or One of them;

[0011] M1, M2, and M3 are independently represented as being composed of one or more R... m Substituted or unsubstituted C6-C 30 Aromatic rings, composed of one or more R m One of the substituted or unsubstituted 5- to 30-membered heteroaryl rings;

[0012] The R m The replacement method is either a single-key connection or a parallel-loop connection;

[0013] N1 represents a combination of one or more R n Substituted or unsubstituted C5-C 30 cycloalkyl groups;

[0014] The R n The replacement method is either a single-key connection or a parallel-loop connection;

[0015] R m R n Independently represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane;

[0016] R1 and R2 are not connected or are connected by a single bond, double bond, -O-, -S-, or -N(R). a)-、-C(R b R c )-、-Si(R d R e - or -C(R) p )=C(R q )-connect;

[0017] Ar1 and Ar2 are not connected or are connected by a single bond, double bond, -O-, -S-, or -N(R). a )-、-C(R b R c )-、-Si(R d R e - or -C(R) p )=C(R q )-connect;

[0018] The R a R b R c R d R e R p R q R s R k Independently represented as substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5- to 30-membered heteroaryl groups;

[0019] X represents C and Si;

[0020] The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups;

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

[0022] Furthermore, the structure of the boron-containing organic compound is shown in any one of general formulas (2-1) to (2-6):

[0023]

[0024] In general formulas (2-1) to (2-6), the meanings of X, R1, R2, Y1, Ar2, M1, M2, M3, Z1, Z2, Z3 and Z4 are the same as those defined in general formula (1);

[0025] M4 represents a combination of one or more R t Substituted or unsubstituted C6-C 30 Aromatic rings, composed of one or more R t One of the substituted or unsubstituted 5- to 30-membered heteroaryl rings;

[0026] R t Independently represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane;

[0027] The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups;

[0028] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0029] Furthermore, the structure of the boron-containing organic compound is shown in any one of general formulas (3-1) to (3-2):

[0030]

[0031] In general formulas (3-1) to (3-2), the meanings of X, R1, R2, Y1, Ar2, M1, N1, Z1, Z2, Z3 and Z4 are the same as those defined in general formula (1);

[0032] M4 represents a combination of one or more R t Substituted or unsubstituted C6-C 30 Aromatic rings, composed of one or more Rt One of the substituted or unsubstituted 5- to 30-membered heteroaryl rings;

[0033] R t Independently represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane;

[0034] R6-R 11 Independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane;

[0035] The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups;

[0036] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0037] Furthermore, the structure of the boron-containing organic compound is shown in any one of general formulas (4-1) to (4-10):

[0038]

[0039]

[0040] In general formulas (4-1) to (4-10), the meanings of X, R1, R2, Y1, Ar2, M1, N1, Z1, Z2, Z3 and Z4 are the same as those defined in general formula (1);

[0041] M4 represents a combination of one or more R t Substituted or unsubstituted C6-C 30 Aromatic rings, composed of one or more R t One of the substituted or unsubstituted 5- to 30-membered heteroaryl rings;

[0042] R t Independently represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane;

[0043] R3-R 18 Independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane;

[0044] The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups;

[0045] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0046] Furthermore, the structure of the boron-containing organic compound is shown in any one of general formulas (5-1) to (5-10):

[0047]

[0048]

[0049] In general formulas (5-1) to (5-10), the meanings of R1, R2, Y1, Ar2, Z1, Z2, Z3 and Z4 are the same as those defined in general formula (1);

[0050] R3-R 18 Independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane;

[0051] The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups;

[0052] The heteroatom in the heteroaryl group is 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 any one of general formulas (6-1) to (6-3):

[0054]

[0055]

[0056] In general formulas (6-1) to (6-3), the meanings of R1, R2, Z1, Z2, Z3 and Z4 are the same as those defined in general formula (1);

[0057] X1 is independently represented as -O-, -S-, -N(R) a )-、-C(R b R c )-、-Si(R d R e );

[0058] The R a R b R c R d R e Independently represented as substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5- to 30-membered heteroaryl groups;

[0059] R b With R c They are either not connected to each other or are linked into a ring through single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene;

[0060] R d With R e They are either not connected to each other or are linked into a ring through single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene;

[0061] R3-R 12 Independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C5-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane;

[0062] The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups;

[0063] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0064] Furthermore, M1, M2, M3, and M4 are independently represented as being composed of one or more R... m Substituted or unsubstituted benzene ring, composed of one or more R m Substituted or unsubstituted naphthalene ring, composed of one or more R m Substituted or unsubstituted anthracene ring, composed of one or more R m Substituted or unsubstituted phenanthrene rings, composed of one or more R m Substituted or unsubstituted pyridine ring, composed of one or more R m Substituted or unsubstituted quinoline ring, composed of one or more R m Substituted or unsubstituted furan ring, composed of one or more R m Substituted or unsubstituted thiophene ring, composed of one or more R m Substituted or unsubstituted benzofuran ring, composed of one or more R m Substituted or unsubstituted benzothiophene ring, composed of one or more R m Substituted or unsubstituted dibenzofuran ring, composed of one or more R m Substituted or unsubstituted dibenzothiophene ring, composed of one or more R m Substituted or unsubstituted N-phenylcarbazole ring, composed of one or more R m Substituted or unsubstituted 9,9-dimethylfluorene ring, composed of one or more R m Substituted or unsubstituted indole[3,2,1-jk]carbazole ring, consisting of one or more R m Substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene ring, composed of one or more R m Any of the substituted or unsubstituted spirofluorene rings;

[0065] The R1, R2, Ar1, Ar2, Ar a Ar b Ar c Ar d, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, or substituted or unsubstituted quinolinyl group. The following are all of the following: substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted aromatic aminoyl, and substituted or unsubstituted triazineyl.

[0066] The R m R n R t Represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthraquinyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted... The substituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted aromatic aminoyl, substituted or unsubstituted triazineyl;

[0067] The R a R b R c Rd R e R p R q R s R k Each of the following can be independently represented as substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted... Any one of the following: furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted aromatic aminoyl, substituted or unsubstituted triazineyl;

[0068] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, fluorine atom, adamantyl, cyano, methyl, ethyl, n-propyl, isopropyl, tert-amyl, tert-butyl, n-butyl, isobutyl, sec-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheninyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, aziphenanthryl, and diphenylamino.

[0069] Preferably, M1, M2, and M3 are independently represented by any one of the following groups:

[0070]

[0071]

[0072] M4 can be independently represented by any of the following groups:

[0073]

[0074] N1 can be independently represented by any of the following groups:

[0075]

[0076] The asterisk (*) indicates the bonding location.

[0077] Z is represented as C-R0, where R0 can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, or substituted or unsubstituted group. The quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted aromatic amino, substituted or unsubstituted triazineyl;

[0078] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, fluorine atom, adamantyl, cyano, methyl, ethyl, n-propyl, isopropyl, tert-amyl, tert-butyl, n-butyl, isobutyl, sec-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheninyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, azirphenanthreneyl, and diphenylamino.

[0079] Preferably, R1, R2, Ar1, Ar2, Ar a Ar b Ar c Ar d , R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 Each of these can be independently represented as a hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-tert-butyl group, iso-tert-butyl group, trifluoromethyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated n-tert-butyl group, phenyl group, etc.

[0080]

[0081] Any one of them;

[0082] The R m R n R t These can be independently represented as cyano, deuterium, methyl, ethyl, n-propyl, isopropyl, n-tert-butyl, iso-tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated n-tert-butyl, phenyl,

[0083]

[0084] Any one of them; the * indicates the bonding position.

[0085] Furthermore, the specific structure of the boron-containing organic compound is any one of the following structures:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] 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 includes a light-emitting layer containing the boron-containing organic compound described above.

[0102] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material contains the boron-containing organic compound;

[0103] Preferably, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a thermally activated delayed fluorescence material, and the dopant material is the boron-containing organic compound.

[0104] Furthermore, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material. The exciton-sensitizing material is a complex containing a metal element, and the dopant material is the boron-containing organic compound.

[0105] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0106] (1) The compound of the present invention can be used in organic electroluminescent devices as a doping material for the light-emitting layer. It can emit green fluorescence under the action of an electric field and can be applied in the fields of OLED lighting or OLED display.

[0107] (2) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device.

[0108] (3) The compound of the present invention, as a green light doping material, can significantly improve device efficiency and device lifetime. Attached Figure Description

[0109] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device using the materials listed in this invention;

[0110] Wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. Detailed Implementation

[0111] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0112] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.

[0113] In this invention, the substituted or unsubstituted aromatic amino group refers to... Q a Q b Q represents substituted or unsubstituted aromatic groups. a Q b Preferably represented as substituted or unsubstituted C6-C 30 Aryl or substituted or unsubstituted 5-30 heteroaryl groups.

[0114] In this invention, C6 to C6 are substituted or unsubstituted. 30 Aryl refers to an aryl group with 6 to 30 carbon atoms, substituted or unsubstituted, preferably an aryl group with 6 to 20 carbon atoms, preferably an aryl group with 6 to 10 carbon atoms, preferably substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted para-triphenyl, substituted or unsubstituted meta-triphenyl, substituted or unsubstituted The group may include, but is not limited to, a triphenylene group substituted or unsubstituted with a substituent, a perylene group substituted or unsubstituted with a substituent, an indene group substituted or unsubstituted with a substituent, a combination thereof, or a fused ring of the aforementioned groups.

[0115] In this invention, C6~C 30 Aryl refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and even more preferably an aryl group having 6 to 10 carbon atoms. Other preferred aryl groups include phenyl, naphthyl, anthraceneyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, phenanthrene, tetraphenyl, pyrene, biphenyl, para-triphenyl, and meta-triphenyl. Fused rings of alkyl, triphenylene, perylene, indene, or combinations thereof, but not limited to these groups.

[0116] In this invention, C6 to C are deuterated. 30 The aryl group refers to an aryl group with 6 to 30 deuterated carbon atoms, preferably an aryl group with 6 to 20 deuterated carbon atoms, more preferably an aryl group with 6 to 10 deuterated carbon atoms, and preferably deuterated phenyl, deuterated naphthyl, deuterated anthracene, deuterated fluorenyl, deuterated dimethyl fluorenyl, deuterated diphenyl fluorenyl, deuterated spirofluorenyl, deuterated phenanthrene, deuterated fused tetraphenyl, deuterated pyrene, deuterated biphenyl, deuterated para-triphenyl, deuterated meta-triphenyl, and deuterated... Fused rings of alkyl, deuterated triphenylene, deuterated perylyl, deuterated indene, or combinations thereof, but not limited to these.

[0117] In this invention, the 5-30 membered heteroaryl group, whether substituted or unsubstituted, refers to a heteroaryl group with 5 to 30 cyclic atoms, preferably a heteroaryl group with 5 to 20 cyclic atoms, preferably a heteroaryl group with 5 to 10 cyclic atoms, preferably a furanyl group, a thiophene group, a pyrrole group, or a group with a substituted or unsubstituted cyclic atom. Substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazine group, substituted or unsubstituted Benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), benzimidazolyl (substituted or unsubstituted), indolyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), isoquinolinyl (substituted or unsubstituted), quinazolinyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), naphthidyl (substituted or unsubstituted), benzoxazinyl (substituted or unsubstituted), and others. The following are fused rings, including but not limited to: benzothiazinyl (substituted or unsubstituted), acridineyl (substituted or unsubstituted), phenazinyl (substituted or unsubstituted), phenoxazinyl (substituted or unsubstituted), phenoxazinyl (substituted or unsubstituted), fumonyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiophenyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), combinations thereof, or combinations of the foregoing groups.

[0118] In this invention, 5-30 membered heteroaryl refers to a heteroaryl group with 5 to 30 cyclic atoms, preferably a heteroaryl group with 5 to 20 cyclic atoms, more preferably a heteroaryl group with 5 to 10 cyclic atoms, preferably furanyl, thiopheneyl, pyrroleyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiazolyl, pyridinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiopheneyl, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, acridineyl, benazinoyl, benazinothiazinyl, benazinoyloxazinyl, fumonyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, or combinations thereof or fused rings of the aforementioned groups, but not limited thereto.

[0119] In this invention, deuterated 5-30-membered heteroaryl refers to a heteroaryl group with 5 to 30 deuterated cyclic atoms, preferably a heteroaryl group with 5 to 20 deuterated cyclic atoms, preferably a heteroaryl group with 5 to 10 deuterated cyclic atoms, preferably deuterated furanyl, deuterated thiopheneyl, deuterated pyrroleyl, deuterated pyrazolyl, deuterated imidazolyl, deuterated triazolyl, deuterated oxazolyl, deuterated thiazolyl, deuterated oxadiazolyl, deuterated thiazolyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyrazinyl, deuterated pyridyl The following are fused rings: triazinyl, deuterated benzofuranyl, deuterated benzothiophenyl, deuterated benzimidazolyl, deuterated indolyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated quinazolinyl, deuterated quinolinyl, deuterated naphthidyl, deuterated benzoxazinyl, deuterated benzothiazinyl, deuterated acridineyl, deuterated benziazinyl, deuterated benzithiazinyl, deuterated benzioxazinyl, deuterated fumonyl, deuterated dibenzofuranyl, deuterated dibenzothiaphenyl, deuterated carbazoyl, combinations thereof, or combinations of the foregoing groups, but not limited to these.

[0120] In this invention, the number of heteroatoms in the 5-30 member heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.

[0121] The C1-C1 components of this invention, whether substituted or unsubstituted, are... 10Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to an alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted, preferably an alkyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, etc., substituted or unsubstituted. Substituted isobutyl, sec-butyl substituted or unsubstituted, neopentyl substituted or unsubstituted, n-pentyl substituted or unsubstituted, isopentyl substituted or unsubstituted, octyl substituted or unsubstituted, heptyl substituted or unsubstituted, n-decyl substituted or unsubstituted, 1-methylpentyl substituted or unsubstituted, 2-methylpentyl substituted or unsubstituted, 3-methylpentyl substituted or unsubstituted, 1-butylpentyl substituted or unsubstituted, etc., but not limited to these.

[0122] The C1 to C of this invention 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but not limited to these.

[0123] The deuterated C1-C of this invention 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to alkyl with 1 to 10 deuterated carbon atoms, preferably alkyl with 1 to 5 deuterated carbon atoms, preferably alkyl with 1 to 4 deuterated carbon atoms, preferably deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated tert-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated neopentyl, deuterated n-pentyl, deuterated isopentyl, deuterated octyl, deuterated heptyl, deuterated n-decyl, deuterated 1-methylpentyl, deuterated 2-methylpentyl, deuterated 3-methylpentyl, deuterated 1-butylpentyl, etc., but not limited to these.

[0124] The substituted or unsubstituted C3-C of this invention 10Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl is preferred, C5-C8 cycloalkyl is more preferred, and C5-C7 cycloalkyl is particularly preferred. Non-limiting examples may include, but are not limited to, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted 4-methylcyclohexyl, substituted or unsubstituted 4,4-dimethylcyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted cycloheptyl, etc.

[0125] The C3~C of this invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups are preferred, C5-C8 cycloalkyl groups are more preferred, and C5-C7 cycloalkyl groups are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0126] The deuterated C3-C of this invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, deuterated C4-C9 cycloalkyl groups are preferred, more preferably deuterated C5-C8 cycloalkyl groups, and particularly preferably deuterated C5-C7 cycloalkyl groups. Non-limiting examples may include, but are not limited to, deuterated cyclopropyl, deuterated cyclobutyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated 4-methylcyclohexyl, deuterated 4,4-dimethylcyclohexyl, deuterated adamantyl, and deuterated cycloheptyl.

[0127] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0128] The C1 to C of this invention 10 Alkoxy groups include, but are not limited to, alkoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or isopropoxy.

[0129] The C2 to C of this invention 10 Alkenyl refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl, etc., but is not limited to these.

[0130] The substituents described in this invention are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

[0131] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent PI film substrates; and opaque substrates, such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent glass substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0132] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, or Cr, or it may be an alloy of several metals, or a combination of metals, metal oxides, or metal alloys. The thickness of the first electrode layer depends on the material used, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0133] 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.

[0134] In this invention, the hole transport region constituting the organic electroluminescent device can be exemplified as a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0135] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer, any material can be selected from known materials used in organic electroluminescent devices.

[0136] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

[0137] Based on the above empirical summary, for hole-based host organic materials with different HOMO energy levels, it is necessary to select different P-doped materials to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0138] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from the following prior art:

[0139] The compounds disclosed in JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, and CN105439999A, but not limited thereto.

[0140] Preferably, the p-type doped material is a charge-conducting compound disclosed in the prior art. The p-type dopant can be selected from compounds disclosed in any of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE10200703122. 0A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but not limited to these.

[0141] In one embodiment of the invention, the hole injection layer comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0142] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass meter.

[0143] The thickness of the hole injection layer of the present invention can be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0144] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0145]

[0146] Preferably, the main organic material used as the hole transport layer material and the hole injection layer of the present invention is selected from the same compound.

[0147] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0148] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0149]

[0150] The thickness of the electron blocking layer of the present invention can be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0151] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.

[0152] The light-emitting layer may include a host material and a dopant material. The host material may be a green light host material commonly used in the art, and the dopant material may be a boron-containing organic compound represented by the general formula (1) of this invention.

[0153] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0154] The dual-body material comprises a first body material and a second body material, wherein preferably at least one of the first body material and the second body material is a TADF material;

[0155] TADF materials refer to materials with thermally activated delayed fluorescence properties. They are characterized by a small energy difference between the first excited singlet and triplet states, allowing for the simultaneous utilization of both singlet and triplet excitons generated within the device, thus enabling the exciton utilization rate of electrogenerated excitons within the device to approach 100%. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0156] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0157] Exciton-sensitized materials refer to materials that enable the luminescent material in the luminescent layer to fully utilize electroexcitons, thereby allowing the luminescent layer to ultimately produce the emission spectrum of the sensitized material. Exciton sensitizers may perform functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron-containing organic compound shown in the general formula (1) of this invention, when used in combination with the exciton-sensitized material, has a significant improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0158] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material is 99:1-70:30, preferably 99:1-85:15, and more preferably 97:3-87:13, based on mass.

[0159] The thickness of the light-emitting layer can be adjusted to optimize luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and even more preferably 15-40 nm, but the thickness is not limited to this range.

[0160] In this invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light-emitting layer, but is not limited thereto.

[0161] A hole-blocking layer is a layer that prevents holes injected from the anode from penetrating the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its performance. The hole-blocking layer of this invention can be disposed on top of the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, for example:

[0162]

[0163] The thickness of the hole blocking layer of the present invention can be 2-200nm, preferably 5-150nm, more preferably 5-50nm, but the thickness is not limited to this range.

[0164] An electron transport layer may be disposed above the light-emitting layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers these received electrons to the light-emitting layer. Preferably, a material with high electron mobility is used. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials disclosed in the prior art for organic electroluminescent devices can be used, for example:

[0165]

[0166] In a preferred embodiment of the invention, the electron transport layer further includes other compounds conventionally used in electron transport layers, such as Alq3, Liq, preferably Liq.

[0167] The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm and more preferably 25-45 nm, but the thickness is not limited to this range.

[0168] An electron injection layer can be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, which facilitates electron injection into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of this invention, electron injection layer materials disclosed in the prior art for organic electroluminescent devices can be used, such as LiF, Cs₂CO₃, CsF, Csq, NaF, MgF₂, CaF₂, Al₂O₃, Yb, etc.

[0169] The thickness of the electron injection layer of the present invention can be 0.1-5 nm, preferably 0.5-3 nm and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[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 transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF2, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0171] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.

[0172] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0173] Synthesis Examples

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

[0175] Synthesis of intermediate Y1

[0176]

[0177] Under nitrogen protection, raw material K1 (30 mmol, 8.71 g), potassium carbonate (72 mmol, 9.95 g), tricyclohexylphosphine (1.5 mmol, 0.42 g), and palladium acetate (0.5 mmol, 0.11 g) were added to a flask. 100 mL of anhydrous DMF was added, the mixture was brought to room temperature, and the reaction was stirred for 30 min. Under nitrogen protection, raw material J1 (30.2 mmol, 8.13 g) was added, and the mixture was stirred at 140 °C for 12 h under nitrogen protection. The mixture was filtered, washed with water, dried, and column-flushed at a PE:EA ratio of 20:1 to obtain intermediate Y1.

[0178] The following intermediate Y was prepared using the same method as intermediate Y1. The raw materials J and K used in the synthesis process are shown in Table 1-1 below.

[0179] Table 1-1

[0180]

[0181]

[0182] Synthesis of intermediate Y4

[0183]

[0184] Under nitrogen protection, starting material A1 (320 mmol, 66.33 g) and sodium hydride (850 mmol, 34.00 g) dispersed in mineral oil (60% concentration) were dissolved in 1.2 L of anhydrous tetrahydrofuran in a flask, and the mixture was refluxed for 5 hours. After cooling to room temperature, 1.6 L of 1 M glacial hydrochloric acid solution was slowly added dropwise to the reaction mixture. The mixture was filtered, washed, and intermediate X1 was obtained.

[0185] Under nitrogen protection, intermediate X1 (160 mmol, 56.07 g) was dissolved in 1.3 L of chloroform in a flask. Phosphorus pentachloride (400 mmol, 83.30 g) was added in an ice-water bath. The mixture was gradually heated to room temperature, then refluxed overnight. After cooling, filtration, and solvent removal by rotary evaporation, intermediate X2 was obtained by column chromatography.

[0186] Under nitrogen protection, intermediate X2 (58 mmol, 22.47 g) was dissolved in 300 mL of tetrahydrofuran in a flask, and zinc powder (590 mmol, 38.57 g) was added. 50 mL of trifluoroacetic acid was slowly added in an ice bath, and the mixture was then brought to room temperature and reacted for 15.5 hours. The mixture was filtered, extracted, evaporated to dryness, and washed to obtain intermediate X3.

[0187] Under nitrogen protection, raw material B1 (20 mmol, 4.62 g) and cesium carbonate (60 mmol, 19.55 g) were added to a flask. Under nitrogen protection, 130 mL of anhydrous DMF was added, and the mixture was stirred at room temperature for 35 minutes. Under nitrogen protection, intermediate X3 (22 mmol, 7.01 g) was added. The solution was refluxed for 25 hours with magnetic stirring. After cooling, filtration, washing with water, and drying, intermediate X4 was obtained by column chromatography.

[0188] Intermediate X4 (18 mmol, 9.53 g), tetra-n-butylammonium bromide (nBu4NBr) (1 mmol, 0.32 g), triphenylphosphine (0.5 mmol, 0.13 g), palladium acetate (0.2 mmol, 0.04 g), potassium carbonate (22 mmol, 3.04 g), and DMAc (60 mL) were added sequentially to a sealed pressure-resistant tube. The mixture was then heated under reflux and stirred for 50 hours under nitrogen protection. After cooling, the organic phase was separated and collected, dried over anhydrous sodium sulfate, filtered, concentrated, and the compound was separated by silica gel column chromatography to obtain intermediate Y4.

[0189] Synthesis of intermediates Y2 and Y3

[0190]

[0191] Under nitrogen protection, raw material K2 (25 mmol, 4.46 g), potassium carbonate (63 mmol, 8.71 g), tricyclohexylphosphine (1.5 mmol, 0.42 g), and palladium acetate (0.6 mmol, 0.13 g) were added to a flask. Under nitrogen protection, 100 mL of anhydrous DMF was added, and the mixture was stirred at room temperature for 1 hour. Under nitrogen protection, raw material J2 (28 mmol, 9.28 g) was added, and the mixture was stirred at 140 °C for 15 hours. The mixture was filtered, washed with water, dried, and passed through a column to obtain intermediates Y2 and Y3.

[0192] Synthesis of intermediate N1

[0193]

[0194] Under nitrogen protection, raw material D1 (12 mmol, 4.02 g), cesium carbonate (15 mmol, 4.89 g), and 50 mL of anhydrous DMF were added to a flask. The mixture was stirred at room temperature for 40 min, and raw material C1 (12.2 mmol, 3.41 g) was slowly added. The mixture was heated to 140 °C and stirred for 12 h. The mixture was then filtered, washed with water, dried, and passed through a column using PE:EA = 20:1 to obtain intermediate M1.

[0195] Under a nitrogen atmosphere, intermediate M1 (10 mmol, 5.95 g) was dissolved in 45 mL of tetrahydrofuran (THF) solution. The mixture was cooled to 0 °C, and 3.8 mL of n-butyllithium (1.6 M) n-hexane solution was slowly added. After stirring for 2 hours, 10 mL of tetrahydrofuran solution of starting material E1 (8 mmol, 1.91 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with NaHCO3 aqueous solution. The aqueous layer was then separated and extracted with dichloromethane. The product was dried over sodium sulfate, filtered, and evaporated by rotary evaporation. The solution was then column-purified to obtain intermediate N1.

[0196] The following intermediates N were prepared using the same method as intermediate N1, using the same intermediate M1, but with different raw material E. The raw material E used in the synthesis process is shown in Table 1-2 below.

[0197] Table 1-2

[0198]

[0199]

[0200] Synthesis Example 1

[0201] Synthesis of Compound 5

[0202]

[0203] Under nitrogen protection, intermediates N1 (10.5 mmol, 7.24 g), Y1 (10 mmol, 4.32 g), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (110 mL) were added sequentially to a three-necked flask. The mixture was heated to reflux for 24 hours. After the reaction system cooled to room temperature, the reaction mixture was filtered and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate T1.

[0204] Under nitrogen protection, intermediate T1 (5 mmol, 5.20 g) and 80 mL of tert-butylbenzene were added sequentially to a three-necked flask. The mixture was cooled to -40 °C, and a 1.6 M tert-butyllithium solution in pentane (6.4 mmol, 4 mL) was slowly added dropwise. After the addition was complete, the temperature was raised to 60 °C and the reaction was continued for 6 hours. Then, boron tribromide (5 mmol, 0.5 mL) was added at -40 °C, and the mixture was slowly raised to room temperature and the reaction continued for 6 hours. Subsequently, N,N-diisopropylethylamine (5 mmol, 0.9 mL) was added to the system at 0 °C, and the mixture was heated to 120 °C and the reaction continued for 12 hours. After the reaction was completed, the reaction system was cooled to room temperature, the reaction was quenched with methanol, the organic layer was concentrated under reduced pressure, and then purified by silica gel column chromatography. After vacuum drying, compound 5 was obtained. In toluene solution (1 × 10⁻⁶ g / mL) -5 The half-width at half maximum (WHM) is 21 nm.

[0205] The compounds in the following examples were prepared using the same method as compound 5. Intermediates Y and N used in the synthesis are shown in Tables 1-3 below.

[0206] Table 1-3

[0207]

[0208]

[0209] Note: Half-width at half-maximum (HWHM) is for toluene solution (1×10⁻⁶). -5 The half-peak width (WHM) of the toluene solution.

[0210] Synthesis Example 2

[0211] Synthesis of Compound 13

[0212]

[0213] Starting materials F1 (25 mmol, 6.80 g) and G1 (25 mmol, 4.30 g) were added to a three-necked flask and dissolved in a mixed solvent (110 mL toluene, 50 mL ethanol). Then, Pd(PPh3)4 (0.20 mmol, 0.23 g) and 30 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux under nitrogen protection for 12 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as eluent to give intermediate P1.

[0214] Intermediate P1 (12 mmol, 3.83 g) and cesium carbonate (25 mmol, 8.15 g) were added to a two-necked flask. Under nitrogen protection, 40 mL of anhydrous DMF was added and the mixture was stirred at room temperature for 35 minutes. Under nitrogen protection, starting material C1 (24 mmol, 6.71 g) was added. The solution was refluxed for 22 hours with magnetic stirring. After cooling, filtration, washing with water, drying, and column chromatography, intermediate Q1 was obtained.

[0215] Intermediate Q1 (12 mmol, 10.06 g) was dissolved in 100 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, a 2.5 M n-butyllithium (11 mmol, 4.4 mL) hexane solution was slowly added. After stirring at -78 °C for 2.5 hours, a tetrahydrofuran solution of starting material E1 (14 mmol, 3.34 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 40 mL of 1 M dilute hydrochloric acid solution, distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with an aqueous solution of NaHCO3. The aqueous layer was then separated and extracted with dichloromethane. The product was dried over sodium sulfate, filtered, and evaporated by rotary evaporation. The resulting product was then column-purified to give intermediate S1.

[0216] Intermediate S1 (12 mmol, 11.75 g) was added sequentially to a three-necked flask, followed by 100 mL of glacial acetic acid. The mixture was then cooled to 0°C under nitrogen protection and strictly protected from light. NBS (15 mmol, 2.67 g) was added in portions, and the mixture was stirred at 0°C for 12.5 hours. The reaction solution was concentrated and purified by silica gel column chromatography to obtain intermediate T2.

[0217] In a sealed, pressure-resistant tube under nitrogen protection, intermediate T2 (12 mmol, 12.70 g) and 120 mL of tert-butylbenzene were added. A 2.5 M solution of n-butyllithium in n-hexane (14 mmol, 5.6 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 5.5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 165 °C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 13. In toluene solution (1 × 10⁻⁶ g / mL) -5 The half-width at half maximum (WHM) is 24 nm.

[0218] The structural characterization of the compounds obtained in each embodiment is shown in Table 2:

[0219] Table 2

[0220]

[0221] The following details the application effects of the organic electroluminescent materials synthesized in this invention in devices through Device Examples 1-8 and Comparative Examples 1-3. Device Examples 2-8 and Comparative Examples 1-3 of this invention have the same fabrication process as Device Example 1, and use the same substrate and electrode materials, with consistent electrode film thickness. The only difference is the replacement of the light-emitting layer material. The layer structures and test results of each device example are shown in Tables 3-1 and 4, respectively.

[0222] Device Example 1

[0223] like Figure 1As shown, the transparent substrate layer 1 is transparent glass. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, HT-1 and HI-1 with a thickness of 10nm are deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the organic electroluminescent device is fabricated, using GH-1 and GH-2 as the host materials and compound 5 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 5 of 69:30:1. The light-emitting layer film thickness is 30nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.

[0224] The application effects of the organic electroluminescent materials synthesized in this invention in devices are described in detail below through device examples 9-16 and device comparative examples 4-6. The fabrication processes of device examples 10-16 and device comparative examples 4-6 are exactly the same as those of device example 9, and the same substrate and electrode materials are used. The film thickness of the electrode materials is also kept consistent. The only difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device example are shown in Tables 3-2 and 4, respectively.

[0225] Device Example 9

[0226] The transparent substrate layer 1 is transparent glass. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the light-emitting layer 6 of the organic electroluminescent device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 as the first dopant, and compound 5 as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 5 is 66.5:30:3:0.5, and the thickness of the light-emitting layer is 30 nm. After the light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1, with a thickness of 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated by vacuum evaporation device, with a Mg:Ag mass ratio of 1:9. This layer is used as the cathode layer 10.

[0227] The molecular structural formulas of the relevant materials are shown below:

[0228]

[0229]

[0230] After completing the organic electroluminescent device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency, peak emission, and lifetime of the device are measured. Examples and comparisons of devices prepared using the same method are shown in Tables 3-1 and 3-2; the test results of the current efficiency, peak emission, and lifetime of the obtained devices are shown in Table 4.

[0231] Table 3-1

[0232]

[0233]

[0234] Table 3-2

[0235]

[0236]

[0237] Table 4

[0238]

[0239] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0240] As can be seen from the device data results in Table 4, compared with the comparative compounds ref-1 and ref-3, the compound of the present invention can achieve green light emission effect well and has higher current efficiency; compared with the comparative compound ref-2, the current efficiency and lifetime of the device are significantly improved.

[0241] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A boron-containing organic compound, characterized by, The structure of the boron-containing organic compound is represented by any one of general formulae (1) to (6-3): In general formula (1), Y1represents N or C-Ar1; Z1, Z2, Z3, Z4 independently represent N or C-Ar a , C-Ar b , C-Ar c , C-Ar d ; R1, R2, Ar1, Ar2, Ar a Ar b Ar c Ar d Independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted borane or One of them; M1, M2, and M3 are independently represented as being composed of one or more R... m Substituted or unsubstituted C6-C 30 Aromatic rings, composed of one or more R m One of the substituted or unsubstituted 5- to 30-membered heteroaryl rings; The R m substituted in a manner which is either a single bond or a fused ring; N1represents a group selected from one or more of R n substituted or unsubstituted C5-C 30 substituted or unsubstituted C5-C The R n substituted in a manner which is either a single bond or a fused ring; R m R n Independently represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane; R1 and R2 are not connected or are connected by a single bond, double bond, -O-, -S-, or -N(R). a )-、-C(R b R c )-、-Si(R d R e - or -C(R) p )=C(R q )-connect; Ar1 and Ar2 are not connected or are connected by a single bond, double bond, -O-, -S-, or -N(R). a )-、-C(R b R c )-、-Si(R d R e - or -C(R) p )=C(R q )-connect; R a , R b , R c , R d , R e , R p , R q , R s , R k independently represent one of substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C2-C 10 alkynyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl; X represents C, Si; The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups; The heteroatom in the heteroaryl group is optionally one or more selected from O, S, N, Si, and B.

2. The boron-containing organic compound according to claim 1, characterized in that, The structure of the boron-containing organic compound is represented by any one of general formulae (1) to (6-3): In general formulae (2-1) to (2-6), the meanings of X, R1, R2, Y1, Ar2, M1, M2, M3, Z1, Z2, Z3, and Z4are the same as defined in general formula (1) of claim 1. M4 represents a combination of one or more R t Substituted or unsubstituted C6-C 30 Aromatic rings, composed of one or more R t One of the substituted or unsubstituted 5- to 30-membered heteroaryl rings; R t Independently represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane; The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups; The heteroatom in the heteroaryl group is optionally one or more selected from O, S, N, Si, and B.

3. The boron-containing organic compound according to claim 1, wherein The structure of the boron-containing organic compound is represented by any one of general formulae (1) to (6-3): In general formulae (3-1) to (3-2), the meanings of X, R1, R2, Y1, Ar2, M1, N1, Z1, Z2, Z3, and Z4are the same as defined in general formula (1) of claim 1. M4 represents a combination of one or more R t Substituted or unsubstituted C6-C 30 Aromatic rings, composed of one or more R t One of the substituted or unsubstituted 5- to 30-membered heteroaryl rings; R t Independently represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane; R6-R 11 Independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane; The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups; The heteroatom in the heteroaryl group is optionally one or more selected from O, S, N, Si, and B.

4. The boron-containing organic compound according to claim 1, wherein The structure of the boron-containing organic compound is represented by any one of general formulae (1) to (6-3): In general formulae (4-1) to (4-10), the meanings of X, R1, R2, Y1, Ar2, M1, N1, Z1, Z2, Z3, and Z4are the same as defined in general formula (1) of claim 1. M4 represents a combination of one or more R t Substituted or unsubstituted C6-C 30 Aromatic rings, composed of one or more R t One of the substituted or unsubstituted 5- to 30-membered heteroaryl rings; R t Independently represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane; R3-R 18 Independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane; The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups; The heteroatom in the heteroaryl group is optionally one or more selected from O, S, N, Si, and B.

5. The boron-containing organic compound of claim 1, wherein The structure of the boron-containing organic compound is represented by any one of general formulae (1) to (6-3): In general formulae (5-1) to (5-10), the meanings of R1, R2, Y1, Ar2, Z1, Z2, Z3, and Z4are the same as defined in general formula (1) of claim 1. R3-R 18 Independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane; The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups; The heteroatom in the heteroaryl group is optionally one or more selected from O, S, N, Si, and B.

6. The boron-containing organic compound of claim 1, wherein The structure of the boron-containing organic compound is represented by any one of general formulae (1) to (6-3): In general formulae (6-1) to (6-3), the meanings of R1, R2, Z1, Z2, Z3, and Z4are the same as defined in general formula (1) of claim 1. X1independently represents -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e ); R a , R b , R c , R d , R e independently represent one of substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C2-C 10 alkynyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl; R b With R c They are either not connected to each other or are linked into a ring through single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; R d With R e They are either not connected to each other or are linked into a ring through single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene; R3-R 12 Independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C5-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane; The substituents used for the substituent groups are optionally selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, C6-C 30 Aryl, 5-30 heteroaryl, deuterated C1-C 10 Alkyl, deuterated C6-C 30 Any one or more of aryl and deuterated 5-30 heteroaryl groups; The heteroatom in the heteroaryl group is optionally one or more selected from O, S, N, Si, and B.

7. The boron-containing organic compound according to any one of claims 1 to 6, wherein The M1, M2, M3, and M4 are independently represented by one or more R... m Substituted or unsubstituted benzene ring, composed of one or more R m Substituted or unsubstituted naphthalene ring, composed of one or more R m Substituted or unsubstituted anthracene ring, composed of one or more R m Substituted or unsubstituted phenanthrene rings, composed of one or more R m Substituted or unsubstituted pyridine ring, composed of one or more R m Substituted or unsubstituted quinoline ring, composed of one or more R m Substituted or unsubstituted furan ring, composed of one or more R m Substituted or unsubstituted thiophene ring, composed of one or more R m Substituted or unsubstituted benzofuran ring, composed of one or more R m Substituted or unsubstituted benzothiophene ring, composed of one or more R m Substituted or unsubstituted dibenzofuran ring, composed of one or more R m Substituted or unsubstituted dibenzothiophene ring, composed of one or more R m Substituted or unsubstituted N-phenylcarbazole ring, composed of one or more R m Substituted or unsubstituted 9,9-dimethylfluorene ring, composed of one or more R m Substituted or unsubstituted indole[3,2,1-jk]carbazole ring, consisting of one or more R m Substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene ring, composed of one or more R m Any of the substituted or unsubstituted spirofluorene rings; R1, R2, Ar1, Ar2, Ar a , Ar b , Ar c , Ar d , R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 each independently represents any one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted triazinyl group; R m , R n , R t represents any one of a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted triazinyl group; R a , R b , R c , R d , R e , R p , R q , R s , R k each independently represents any one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted arylamine, substituted or unsubstituted triazinyl; The substituents for the substituent group are optionally one or more selected from a deuterium atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a t-amyl group, a t-butyl group, a n-butyl group, an i-butyl group, a sec-butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalyl 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, a phenanthrolinyl group, a diphenylamine group.

8. The boron-containing organic compound of claim 1, wherein The specific structure of the boron-containing organic compound is any one of the following structures:

9. An organic electroluminescent device comprising, in this order, a substrate, a first electrode, an organic luminescent functional layer, and a second electrode, the organic luminescent functional layer being located between the first electrode and the second electrode, the organic luminescent functional layer including a luminescent layer, characterized by, The light-emitting layer contains the boron-containing organic compound according to any one of claims 1 to 8; 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 dopant material, the dopant material comprising the boron-containing organic compound according to any one of claims 1-8. Preferably, the light-emitting layer comprises a first host material, a second host material, and a dopant material, at least one of the first host material and the second host material being a thermally activated delayed fluorescence material, the dopant material being the boron-containing organic compound according to any one of claims 1-8.

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

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