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

Abstract

The invention discloses a boron-containing organic compound and an organic electroluminescent device prepared from the same, and belongs to the technical field of semiconductors. The structure of the organic compound is as shown in a general formula (1), the boron-containing organic compound is narrower in half-peak width, has a certain degree of blue shift on a light-emitting peak value, can be used as a light-emitting layer wide-color-gamut green light doping material of an organic electroluminescent device, is more excellent in color purity and higher in CIEy value, and can be used as a light-emitting layer wide-color-gamut green light doping material of the organic electroluminescent device. And the color gamut display color point requirements of display indexes of a new-generation OLED can be better met.

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.

[0005] Currently, most mainstream phosphorescent devices are in the P3 color gamut, with CIE coordinates for green light at (0.24, 0.72). Next-generation OLED display specifications have higher requirements for green light color points. Adobe RGB color gamut displays require green light devices to meet color point requirements of (0.21, 0.75), while the BT.2020 color gamut requires green light color points to meet (0.170, 0.797). This necessitates a higher CIEy value (>0.77) for next-generation green light materials compared to P3 color gamut luminescent materials, along with a narrower half-width, to achieve the higher coverage required for BT.2020 displays.

[0006] The boron-containing compounds in WO2024125652A1 all have a single-boron structure, and their emission peak value and half-width at half-maximum (WHM) values ​​are relatively large (the WHM values ​​of the compounds in the examples in toluene solution are all ≥24nm). Wide color gamut (Adobe RGB and BT.2020 color gamut) display technology requires relatively small emission peak values ​​and extremely high WHM requirements for luminescent materials, which the compounds in WO2024125652A1 cannot yet meet. Summary of the Invention

[0007] To address the aforementioned problems in the existing technology, this invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The boron-containing organic compound of this invention has a narrower full width at half maximum (FWHM) and a certain degree of blue shift in its emission peak value, making it suitable as a wide-gamut green doping material for the emitting layer of an organic electroluminescent device.

[0008] 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):

[0009]

[0010] In general formula (1), Z is represented as C-R0;

[0011] R0 represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0012] Adjacent R0s are either not connected or connected in a loop;

[0013] Each occurrence of the same or different Y1-Y8 indicates that C6-C6 is substituted or not substituted by R. 30 Aryl group, C2-C substituted or unsubstituted with R 30 Heteroaryl, C1-C substituted or unsubstituted 10 Alkyl groups, C3-C6 groups substituted with R or unsubstituted with R. 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, or one of R-substituted or unsubstituted boronyl groups;

[0014] M1 represents C6-C6 with or without R substitution. 30 Aryl group, C2-C substituted or unsubstituted with R 30 One of the heteroaryl groups;

[0015] Y3 and Y4 are either not connected or connected in a loop;

[0016] Y6 and Y5 are either not connected or connected in a loop;

[0017] Y2 and M1 are either not connected or connected in a loop;

[0018] The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0019] Z1 is denoted as C-Ra;

[0020] Ra represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0021] The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0022] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0023] Furthermore, "linking into rings" refers to linking into aromatic rings, heteroaromatic rings, or aliphatic rings;

[0024] Preferably, adjacent R0s are not connected or are connected to form C6-C6 groups that are either substituted or unsubstituted by R. 30 Aromatic rings, C2-C2 with or without R substitution 30 heteroaryl rings, C6-C6 substituted or unsubstituted with R. 30 Aliphatic rings;

[0025] Preferably, Y3 and Y4 are not connected or are connected in the form of C6 to C6 with or without R substitution. 30 Aromatic rings, C2-C2 with or without R substitution 30 heteroaryl rings, C6-C6 substituted or unsubstituted with R. 30 Aliphatic rings;

[0026] Preferably, Y6 and Y5 are not connected or are connected in the form of C6 to C6, which are either substituted or unsubstituted by R. 30 Aromatic rings, C2-C2 with or without R substitution 30 heteroaryl rings, C6-C6 substituted or unsubstituted with R. 30 Aliphatic rings;

[0027] Preferably, Y2 and M1 are not connected or are connected in the form of C6 to C6 with or without R substitution. 30 Aromatic rings, C2-C2 with or without R substitution 30 heteroaryl rings, C6-C6 substituted or unsubstituted with R. 30 Aliphatic rings;

[0028] The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0029] The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0030] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0031] Furthermore, linking into a ring refers to linking into a ring through single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)-, or -C(R'6)=C(R'7)-.

[0032] Preferably, adjacent R0s are not connected or are connected in a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-;

[0033] Preferably, Y3 and Y4 are not connected or are connected in a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-;

[0034] Preferably, Y6 and Y5 are not connected or are connected in a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-;

[0035] Preferably, Y2 and M1 are not connected or are connected in a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-;

[0036] R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1 to C1 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0037] The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0038] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0039] Furthermore, R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are independently represented as substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted... Or any one of the following: unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 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.

[0040] Furthermore, 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.

[0041] Furthermore, the structure of the boron-containing organic compound is shown in general formula (1-1) or general formula (1-2):

[0042]

[0043] In general formulas (1-1) and (1-2), the meanings of Z, Z1, Y1, Y2, Y7, and Y8 are the same as those in general formula (1);

[0044] X is represented as one of O, S, N-Rb, C(Rc)(Rd);

[0045] Rb, Rc, and Rd represent substituted or unsubstituted C1 to C2. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0046] The Rc and Rd are not connected to each other or are linked in a ring by single bonds, double bonds, oxygen atoms, sulfur atoms, dimethyl-substituted methylene, diphenyl-substituted methylene or -N(Ph)-.

[0047] The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0048] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0049] Furthermore, the structure of the boron-containing organic compound is shown in general formula (2) or general formula (3):

[0050]

[0051] In general formulas (2) and (3), the meanings of Z and Z1 are the same as those in general formula (1);

[0052] X is represented as one of O, S, N-Rb, C(Rc)(Rd);

[0053] Rb, Rc, and Rd represent substituted or unsubstituted C1 to C2. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C30 One of the heteroaryl groups;

[0054] The Rc and Rd are not connected to each other or are linked in a ring by single bonds, double bonds, oxygen atoms, sulfur atoms, dimethyl-substituted methylene, diphenyl-substituted methylene or -N(Ph)-.

[0055] The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0056] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0057] Furthermore, the structure of the boron-containing organic compound is shown in any one of general formulas (2-1) to (2-2) and (3-1) to (3-4):

[0058]

[0059]

[0060] In general formulas (2-1) to (2-2) and general formulas (3-1) to (3-4), the meanings of Z and Z1 are the same as those in general formula (1);

[0061] Rb represents C1 to C2 with or without substitution. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0062] The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C30 Any one or more of the heteroaryl groups;

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

[0064] Furthermore, the structure of the boron-containing organic compound is shown in any one of general formulas (4) to (5):

[0065]

[0066] In general formulas (4) to (5), the meaning of Z is the same as that in general formula (1).

[0067] Furthermore, the structure of the boron-containing organic compound is shown in any one of general formulas (6) to (7):

[0068]

[0069] In general formulas (6) to (7), the meanings of Z1, Y1, Y2, Y7, and Y8 are the same as those in general formula (1);

[0070] R1, R2, R3, R4, and R5 represent hydrogen atom, deuterium atom, halogen atom, cyano group, and substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0071] m and n represent 0, 1, 2 or 3;

[0072] p and q represent 0, 1, 2, 3 or 4;

[0073] k can be 0, 1, 2, 3, 4 or 5;

[0074] The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0075] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0076] Furthermore, R0, Ra, R1, R2, R3, R4, and R5 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted 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 pyridine group, etc. The following are all of the following: pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 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, and substituted or unsubstituted triazineyl.

[0077] The R represents 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 diphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, or a substituted... Or any one of the following: 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, substituted or unsubstituted triazineyl;

[0078] Rb, Rc, and Rd are independently represented as substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted... Or any one of the following: 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, substituted or unsubstituted triazineyl;

[0079] The Y1-Y8 represent any one of the following: substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted aromatic amino, and substituted or unsubstituted triazineyl.

[0080] The M1 represents any one of the following: substituted or unsubstituted benzene ring, substituted or unsubstituted naphthyl ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted phenanthrene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted furan ring, substituted or unsubstituted thiophene ring, substituted or unsubstituted benzofuran ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted dibenzofuran ring, substituted or unsubstituted dibenzothiophene ring, substituted or unsubstituted N-phenylcarbazole ring, substituted or unsubstituted 9,9-dimethylfluorene ring, substituted or unsubstituted indole[3,2,1-jk]carbazole ring, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl ring, and substituted or unsubstituted spirofluorene ring.

[0081] 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.

[0082] Furthermore, R0, Ra, R1, R2, R3, R4, and R5 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, and ethyl. The substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boraneyl, methoxy, tert-butoxy, diphenylamino;

[0083] The R represents a deuterium atom, a halogen atom, a cyano group, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl... The following is a list of butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boraneyl, methoxy, tert-butoxy, and diphenylamino.

[0084] Rb, Rc, and Rd are independently represented as adamantyl, methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, and methyl-substituted benzyl. One of the following: methyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuranyl, and phenyl-substituted tert-butyl.

[0085] Y1-Y8 represents one of the following: phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, and tert-butyl-substituted diphenyl.

[0086] M1 represents phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl One of the following: biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tert-butyl-substituted dibenzofuranyl, and phenyl-substituted tert-butyl.

[0087] 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.

[0088] Preferably, R0, Ra, R1, R2, R3, R4, and R5 are independently represented by the following groups: hydrogen atom, cyano, deuterium atom, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl. Any one of them;

[0089] Preferably, R represents the following groups: cyano, deuterium, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl. Any one of them;

[0090] Rb, Rc, and Rd are independently represented by the following groups: deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, Any one of them; the Y1-Y8 are each independently represented by the following structural features:

[0091]

[0092] any one of them;

[0093] M1 is represented by the following structural features:

[0094] Any one of the following. Furthermore, the specific structure of the boron-containing organic compound is any one of the following structures:

[0095]

[0096]

[0097]

[0098]

[0099]

[0100] 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.

[0101] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material contains the boron-containing organic compound.

[0102] Preferably, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing organic compound.

[0103] 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.

[0104] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0105] The boron-containing organic compound of this invention has a narrower half-width at half-maximum (WHM) and a certain degree of blue shift in the emission peak value. When used as a dopant material in the emitting layer of organic electroluminescent devices, it can be used as a green dopant material in the emitting layer of organic electroluminescent devices. Compared with the currently mainstream P3 color gamut emitting materials (0.24, 0.72), it has a better WHM and color purity, and a higher CIEy value, which can better meet the color point requirements of the next-generation OLED display indicators Adobe RGB color gamut (0.21, 0.75) or BT.2020 (0.170, 0.797) color gamut. Attached Figure Description

[0106] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0107] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a light extraction layer. Detailed Implementation

[0108] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0109] 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.

[0110] 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 C2-C 30 Mixed aromatic compounds.

[0111] In this invention, C6 to C are substituted or unsubstituted. 30 The aryl group refers to an aryl group with 6 to 30 carbon atoms, preferably an aryl group with 6 to 20 carbon atoms, more preferably an aryl group with 6 to 10 carbon atoms, and more preferably an aryl group with 8 to 10 carbon atoms. It is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted tetraphenyl group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted para-triphenyl group, a substituted or unsubstituted meta-triphenyl group, or a substituted or unsubstituted phenyl group. The group may contain, but is not limited to, a fused ring consisting of a substituted or unsubstituted triphenyl group, a substituted or unsubstituted peryl group, a substituted or unsubstituted indole group, a combination thereof, or a combination of the aforementioned groups.

[0112] 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, more preferably an aryl group having 6 to 10 carbon atoms, and more preferably an aryl group having 8 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.

[0113] In this invention, C2 to C are substituted or unsubstituted. 30Heteroaryl refers to heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 20 carbon atoms, preferably heteroaryl groups with 4 to 20 carbon atoms, preferably heteroaryl groups with 4 to 10 carbon atoms, preferably heteroaryl groups with 5 to 10 carbon atoms, preferably substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or Unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphthinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted tyloyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiaphenyl, substituted or unsubstituted carbazoyl, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0114] In this invention, C2 to C are substituted or unsubstituted. 30 The number of heteroatoms in the heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.

[0115] In this invention, C2~C 30 Heteroaryl refers to a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 20 carbon atoms, more preferably a heteroaryl group having 4 to 20 carbon atoms, more preferably a heteroaryl group having 4 to 10 carbon atoms, more preferably a heteroaryl group having 5 to 10 carbon atoms, and preferably furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, or pyridine. Fused rings of pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiopheneyl, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, acridineyl, benzazinyl, benzthiazinyl, benzoxazinyl, fumonyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, or combinations thereof or combinations of the foregoing groups, but not limited thereto.

[0116] In this invention, C2~C 30 The number of heteroatoms in the heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.

[0117] The substituted or unsubstituted C1-C of the present 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, preferably substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted neopentyl, substituted or unsubstituted n-pentyl, substituted or unsubstituted isopentyl, substituted or unsubstituted octyl, substituted or unsubstituted heptyl, substituted or unsubstituted n-decyl, substituted or unsubstituted 1-methylpentyl, substituted or unsubstituted 2-methylpentyl, substituted or unsubstituted 3-methylpentyl, substituted or unsubstituted 1-butylpentyl, etc., but not limited thereto.

[0118] 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.

[0119] The substituted or unsubstituted 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, substituted or unsubstituted C4-C9 cycloalkyl groups are preferred, more preferably substituted or unsubstituted C5-C8 cycloalkyl groups, and particularly preferably substituted or unsubstituted C5-C7 cycloalkyl groups. Non-limiting examples may include, but are not limited to, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted 4-methylcyclohexyl, substituted or unsubstituted 4,4-dimethylcyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted cycloheptyl.

[0120] 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.

[0121] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0122] The C1 to C of this invention 10 Alkoxy groups include, but are not limited to, alkoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or isopropoxy.

[0123] The C2~C of this invention 10 Alkenyl refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl, etc., but is not limited to these.

[0124] 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, and the thickness of the substrate is not particularly limited.

[0125] 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.

[0126] 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.

[0127] In this invention, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from the following prior art:

[0132] The compounds disclosed in JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, and CN105439999A, but not limited thereto.

[0133] 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.

[0134] 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.

[0135] 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.

[0136] 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.

[0137] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0138]

[0139] 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.

[0140] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm, but the thickness is not limited to this range.

[0141] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0142]

[0143]

[0144] 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.

[0145] 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.

[0146] 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.

[0147] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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:

[0152]

[0153] 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.

[0154] 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:

[0155]

[0156]

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] To improve the light extraction efficiency of organic electroluminescent devices, a light extraction layer (i.e., a capping layer, also known as a CPL layer) can be added to the cathode of the device. Compounds disclosed in existing technologies CN103828485A, CN106946859A, KR1020170116927A, CN109206420A, CN112310292A, CN110229145A, KR1020210052171A, CN111869326A, TW201920606A, and CN110256358A can be used as light extraction layer materials.

[0163] The thickness of the light extraction layer is typically 5-300 nm, preferably 20-100 nm, and more preferably 40-80 nm.

[0164] 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.

[0165] 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.

[0166] Synthesis Examples

[0167] 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;

[0168]

[0169] Synthesis of raw material B-1:

[0170] In a three-necked flask under N2 protection, 290 ml of toluene was added. While stirring, raw material 2 (8.8 g, 22.5 mmol), BocNH2 (3.4 g, 29.3 mmol), BINAP (0.42 g, 0.68 mmol), cesium carbonate (11 g, 33.8 mmol), and palladium acetate (0.13 g, 0.56 mmol) were added sequentially. After the addition was completed, the mixture was purged with nitrogen three times and then heated to 100 °C for about 15 hours. After cooling to room temperature, the mixture was filtered, concentrated, and column filtered to obtain intermediate 3.

[0171] In a three-necked flask, intermediate 3 (4.3 g, 12 mmol), ethanol (25 ml), tetrahydrofuran (25 ml), and sodium hydroxide aqueous solution (1.2 g / 5 ml, 30.1 mmol) were added. After the addition was complete, the temperature was raised to 70 °C and the reaction was carried out for 15 h. The reaction solution was then cooled to room temperature, filtered, and evaporated to dryness before recrystallization with ethanol to obtain intermediate 4.

[0172] In a three-necked flask, intermediate 4 (4.0 g, 11.6 mmol) and 2.5 M ethyl hydrochloride (20 ml) were added. After the addition was complete, the system was reacted at room temperature for 4 hours. The reaction system was filtered, concentrated, and recrystallized with ethanol to obtain intermediate 5.

[0173] In a three-necked flask, toluene (100 ml), intermediate 5 (2.46 g, 10.1 mmol), phthalic anhydride (1.94 g, 13.1 mmol), and triethylamine (2.55 g, 25.2 mmol) were added. After the addition was complete, the system was heated to 105 °C and reacted for about 15 hours. After returning to room temperature, the mixture was concentrated under reduced pressure and recrystallized from ethanol to obtain intermediate 6.

[0174] In a three-necked flask, intermediate 6 (1.45 g, 3.88 mmol), THF (50 ml), DPPA (1.39 g, 5.05 mmol), and TEA (0.59 g, 5.83 mmol) were added. After the addition was complete, the system was heated to 70 °C and reacted for 3 hours. The reaction system was then cooled to room temperature, concentrated under reduced pressure to remove THF, extracted with ethyl acetate, washed with water and salt, dried over anhydrous sodium sulfate, filtered, concentrated, and then subjected to column chromatography to obtain intermediate 7.

[0175] In a three-necked flask, acetonitrile (15 ml), isoamyl nitrite (0.85 g, 7.26 mmol), and diiodomethane (3.88 g, 14.5 mmol) were added. The system was heated to 50 °C, and intermediate 7 / acetonitrile solution (0.50 g / 10 ml, 1.45 mmol) was slowly added dropwise at 50 °C. After the addition was complete, the system was reacted at 50 °C for 30 min, concentrated under reduced pressure, and column chromatography to obtain intermediate 8.

[0176] In a three-necked flask, intermediate 8 (3.8 g, 8.35 mmol), ethanol (38 ml), and hydrazine hydrate (19 ml) were added. After the addition was complete, the system was heated to 50 °C and reacted for 1 hour. The system was then cooled to room temperature, concentrated under reduced pressure, and passed through a column to obtain starting material B-1.

[0177]

[0178] Synthesis of intermediate b-1:

[0179] Add raw material C-1 (7.26 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 min. Add raw material B-1 (8.13 g, 25 mmol) under nitrogen protection and stir at 140 °C for 20 h under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate b-1.

[0180]

[0181] Synthesis of intermediate c-1:

[0182] Under nitrogen protection, starting material D-1 (1.86 g, 2.5 mmol) was dissolved in 50 mL of toluene solution. Intermediate b-1 (1.22 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.01 g, 0.05 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed for 6 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed three times with deionized water (100 mL). After drying with anhydrous magnesium sulfate, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring, and filtered to obtain intermediate c-1.

[0183] Synthesis of intermediate d-1:

[0184] Intermediate c-1 (14.38 g, 12.5 mmol) was dissolved in 270 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 10 mL of a 1.6 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 3 hours, boron tribromide (6.25 g, 25 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 1 hour. N,N-diisopropylethylamine (DIPEA) (3.26 g, 25.2 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 5 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed under vacuum and column filtered to obtain intermediate d-1.

[0185]

[0186] Synthesis of intermediate e-1:

[0187] Starting material E-1 (3.03 g, 5.1 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at 0 °C, 3.8 mL of n-butyllithium (1.6 M) n-hexane solution was slowly added. After stirring at 0 °C for 4 hours, 10 mL of tetrahydrofuran solution of starting material F-1 (1.30 g, 5.5 mmol) 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 and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with NaHCO3 aqueous solution. 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 give intermediate e-1.

[0188] Synthesis of intermediate c-2:

[0189] Under nitrogen protection, intermediate e-1 (1.72 g, 2.5 mmol) was dissolved in 50 mL of toluene solution. Starting material G-1 (1.08 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.01 g, 0.05 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed for 8 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed three times with deionized water (100 mL). It was dried over anhydrous magnesium sulfate, and the ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring, and filtered to give intermediate c-2.

[0190]

[0191] Synthesis of intermediate d-2:

[0192] Intermediate c-2 (12.97 g, 12.5 mmol) was dissolved in 250 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 10 mL of a 1.6 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 2 hours, boron tribromide (6.25 g, 25 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (DIPEA) (3.26 g, 25.2 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 6 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed under vacuum and column filtered to obtain intermediate d-2.

[0193] Synthesis of intermediate e-2:

[0194] In a three-necked flask under nitrogen protection, 5.06 g (5 mmol) of intermediate d-2 and 100 mL of dry chloroform were added. Then, NBS (1.07 g, 6 mmol) dissolved in 20 mL of dry chloroform was slowly added dropwise at 0 °C. The reaction mixture was stirred at room temperature for 6 hours, concentrated, and purified by silica gel column chromatography to obtain intermediate e-2.

[0195] Example 1: Synthesis of Compound 12:

[0196]

[0197] Preparation of intermediate a-1:

[0198] In a three-necked flask under nitrogen protection, 4.21 g (5 mmol) of starting material A-1 and 90 mL of dry chloroform were added. NBS (1.07 g, 6 mmol) dissolved in 20 mL of dry chloroform was slowly added dropwise at 0 °C. The reaction mixture was stirred at room temperature for 6 hours, concentrated, and purified by silica gel column chromatography to obtain intermediate a-1.

[0199] Preparation of compound 12:

[0200] Intermediate a-1 (11.52 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene. Under a nitrogen atmosphere at -78 °C, 10 mL of a pentane solution of n-butyllithium (1.6 M) was slowly added. After stirring at 60 °C for 2 hours, 4.29 g, 16 mmol of di(1,3,5-trimethylyl)fluoride dissolved in tetrahydrofuran was added at -78 °C. The reaction mixture was then stirred at -78 °C for 0.5 hours, followed by stirring at room temperature for 5 hours. After the reaction was complete, the mixture was extracted with water and dichloromethane. The combined organic layers were concentrated and column-sected to give compound 12. The full width at half maximum (FWHM) of compound 12 in toluene solution was 21 nm (1 × 10⁻⁶). -5 M, toluene solution).

[0201] Example 2: Synthesis of compound 35:

[0202]

[0203] Preparation of intermediate a-2:

[0204] In a three-necked flask under nitrogen protection, 5.34 g (5 mmol) of starting material A-2 and 100 mL of dry chloroform were added. NBS (1.07 g, 6 mmol) dissolved in 20 mL of dry chloroform was slowly added dropwise at 0 °C. The reaction mixture was stirred at room temperature for 5 hours, concentrated, and purified by silica gel column chromatography to obtain intermediate a-2.

[0205] Preparation of compound 35:

[0206] Intermediate a-2 (14.33 g, 12.5 mmol) was dissolved in 330 mL of tert-butylbenzene. Under a nitrogen atmosphere at -78 °C, 10 mL of a 1.6 M n-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 1.5 hours, 4.29 g, 16 mmol of di(1,3,5-trimethylyl)fluoride dissolved in tetrahydrofuran was added at -78 °C. The reaction mixture was then stirred at -78 °C for 1 hour, followed by stirring at room temperature for 5 hours. After the reaction was complete, the mixture was extracted with water and dichloromethane. The combined organic layers were concentrated and column-sected to give compound 35. The full width at half maximum (FWHM) of compound 35 in toluene solution was 21 nm (1 × 10⁻⁶). -5 M, toluene solution).

[0207] Example 3: Synthesis of compound 36:

[0208]

[0209] Preparation of intermediate a-3:

[0210] In a three-necked flask under nitrogen protection, 5.34 g (5 mmol) of starting material A-3 and 100 mL of dry chloroform were added. NBS (1.07 g, 6 mmol) dissolved in 20 mL of dry chloroform was slowly added dropwise at 0 °C. The reaction mixture was stirred at room temperature for 8 hours, concentrated, and purified by silica gel column chromatography to obtain intermediate a-3.

[0211] Preparation of compound 36:

[0212] Intermediate a-3 (14.33 g, 12.5 mmol) was dissolved in 330 mL of tert-butylbenzene. Under a nitrogen atmosphere at -78 °C, 10 mL of a 1.6 M n-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 1 hour, 4.29 g (16 mmol) of di(1,3,5-trimethylyl)fluoride dissolved in tetrahydrofuran was added at -78 °C. The reaction mixture was then stirred at -78 °C for 1.5 hours, followed by stirring at room temperature for 6 hours. After the reaction was complete, the mixture was extracted with water and dichloromethane. The combined organic layers were concentrated and column-sected to give compound 36. The full width at half maximum (FWHM) of compound 36 in toluene solution was 21 nm (1 × 10⁻⁶). -5 M, toluene solution).

[0213] Example 4: Synthesis of compound 38:

[0214]

[0215] Preparation of intermediate a-4:

[0216] In a three-necked flask under nitrogen protection, 5.62 g (5 mmol) of intermediate d-1 and 100 mL of dry chloroform were added. NBS (1.07 g, 6 mmol) dissolved in 20 mL of dry chloroform was then slowly added dropwise at 0 °C. The reaction mixture was stirred at room temperature for 4 hours, concentrated, and purified by silica gel column chromatography to obtain intermediate a-4.

[0217] Preparation of compound 38:

[0218] Intermediate a-4 (15.03 g, 12.5 mmol) was dissolved in 340 mL of tert-butylbenzene. Under a nitrogen atmosphere at -78 °C, 10 mL of a pentane solution of n-butyllithium (1.6 M) was slowly added. After stirring at 60 °C for 2 hours, 4.29 g, 16 mmol of di(1,3,5-trimethylyl)fluoride dissolved in tetrahydrofuran was added at -78 °C. The reaction mixture was then stirred at -78 °C for 1.5 hours, followed by stirring at room temperature for 5 hours. After the reaction was complete, the mixture was extracted with water and dichloromethane. The combined organic layers were concentrated and column-sected to give compound 38. The full width at half maximum (FWHM) of compound 38 in toluene solution was 21 nm (1 × 10⁻⁶). -5 M, toluene solution).

[0219] Preparation of compound 51 in Example 5:

[0220]

[0221] Preparation of compound 51:

[0222] Intermediate e-2 (13.63 g, 12.5 mmol) was dissolved in 280 mL of tert-butylbenzene. Under a nitrogen atmosphere at -78 °C, 10 mL of a pentane solution of n-butyllithium (1.6 M) was slowly added. After stirring at 60 °C for 1 hour, 4.29 g, 16 mmol of boron fluoride dissolved in tetrahydrofuran was added at -78 °C. The reaction mixture was then stirred at -78 °C for 1 hour, and then stirred at room temperature for 3 hours. After the reaction was complete, the mixture was extracted with water and dichloromethane. The combined organic layers were concentrated and column-sected to give compound 51. The full width at half maximum (FWHM) of compound 51 in toluene solution was 20 nm (1 × 10⁻⁶). -5 M, toluene solution).

[0223] Example 6: Synthesis of Compound 56:

[0224]

[0225] Preparation of compound 56:

[0226] Intermediate a-2 (14.33 g, 12.5 mmol) was dissolved in 310 mL of tert-butylbenzene. Under a nitrogen atmosphere at -78 °C, 10 mL of a pentane solution of n-butyllithium (1.6 M) was slowly added. After stirring at 60 °C for 1.5 hours, 6.98 g, 16 mmol of boron fluoride dissolved in tetrahydrofuran was added at -78 °C. The reaction mixture was then stirred at -78 °C for 1 hour, followed by stirring at room temperature for 4 hours. After the reaction was complete, the mixture was extracted with water and dichloromethane. The combined organic layers were concentrated and column-sected to give compound 56. The full width at half maximum (FWHM) of compound 56 in toluene solution was 20 nm (1 × 10⁻⁶). -5 M, toluene solution).

[0227] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0228] Table 1

[0229]

[0230] The following details the application effects of the organic electroluminescent materials synthesized in this invention in devices through device examples 1-6 and device comparative examples 1-4. Device examples 2-6 and device comparative examples 1-4 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 structure and test results of each device example are shown in Tables 2-1 and 3 and 4, respectively.

[0231] Device Example 1

[0232] like Figure 1As shown, the transparent substrate layer 1 is transparent glass. Ag (100nm) is deposited as the anode layer 2. On the anode layer 2, HT-1 and HI-1 with a thickness of 10nm are deposited using a vacuum evaporation apparatus as the hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, HT-1 with a thickness of 120nm is deposited as the hole transport layer 4. Subsequently, EB-1 with a thickness of 5nm is deposited as the 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 12 as the dopant material, with a mass ratio of GH-1, GH-2 and compound 12 of 69:30:1, and a film thickness of 30nm. After the light-emitting layer 6, HB-1 is deposited with a thickness of 5nm as the hole blocking layer 7. On the hole blocking layer 7, ET-1 and Liq are deposited with a mass ratio of ET-1 to Liq of 1:1. The vacuum-deposited film of this material is 30 nm thick, and this layer is the electron transport layer 8. On the electron transport layer 8, a 1 nm thick LiF layer is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a 16 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg to Ag mass ratio of 1:9; this layer is used as the cathode layer 10. On the cathode layer 10, a 65 nm thick CP-1 layer is vacuum-deposited as the light extraction layer 11.

[0233] The application effects of the organic electroluminescent materials synthesized in this invention in devices are described in detail below through device examples 7-12 and device comparative examples 5-8. The fabrication processes of device examples 8-12 and device comparative examples 5-8 are exactly the same as those of device example 7, and the same substrate and electrode materials are used. The film thickness of the electrode materials is also kept consistent. The only difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device example are shown in Tables 2-2 and 3 and 4, respectively.

[0234] Device Example 7

[0235] like Figure 1As shown, the transparent substrate layer 1 is transparent glass. Ag (100nm) is deposited as the anode layer 2. On the anode layer 2, HT-1 and HI-1 with a thickness of 10nm are deposited using a vacuum evaporation apparatus as the hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, HT-1 with a thickness of 120nm is deposited as the hole transport layer 4. Subsequently, EB-1 with a thickness of 5nm is deposited as the electron blocking layer 5. After the above 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, GD-1 as the first dopant, and compound 12 as the second dopant, with a mass ratio of GH-1, GH-2, GD-1, and compound 12 of 66.5:30:3:0.5, and a light-emitting layer thickness of 30nm. After the above light-emitting layer 6, HB-1 is deposited with a thickness of 5nm as the hole blocking layer 7. On top of the hole-blocking layer 7, ET-1 and Liq are further deposited by vacuum evaporation, with an ET-1 to Liq mass ratio of 1:1. The vacuum-deposited film thickness of this material is 30 nm, and 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, a Mg:Ag electrode layer with a thickness of 16 nm is fabricated using a vacuum evaporation apparatus, with a Mg to Ag mass ratio of 1:9; this layer serves as the cathode layer 10. On the cathode layer 10, CP-1 with a thickness of 65 nm is vacuum-deposited as the light extraction layer 11. The molecular structure formula of the relevant materials is shown below:

[0236]

[0237]

[0238] After completing the organic electroluminescent device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency, emission peak, and lifetime of the device are measured. Examples and comparisons of devices prepared using the same method are shown in Tables 2-1 and 2-2; the test results for the color coordinates and emission peak of the obtained devices are shown in Table 3, and the test results for the current efficiency and lifetime of the obtained devices are shown in Table 4.

[0239] Table 2-1

[0240]

[0241]

[0242] Table 2-2

[0243]

[0244]

[0245] Table 3

[0246] Device Examples CIEy Emission peak Device Examples CIEy Emission peak Example 1 0.772 524 Example 7 0.771 525 Example 2 0.775 524 Example 8 0.779 525 Example 3 0.786 518 Example 9 0.781 519 Example 4 0.783 524 Example 10 0.784 525 Example 5 0.790 523 Example 11 0.786 524 Example 6 0.787 524 Example 12 0.789 524 Comparative Example 1 0.733 535 Comparative Example 5 0.724 536 Comparative Example 2 0.730 536 Comparative Example 6 0.718 536 Comparative Example 3 0.120 470 Comparative Example 7 0.135 472 Comparative Example 4 0.750 518 Comparative Example 8 0.749 519

[0247] Note: CIEy and luminescence peak values ​​were measured using an IVL (current-voltage-luminance) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); all data are within 10 mA / cm². 2 Next test.

[0248] As can be seen from the device data results in Table 3, compared with the comparative compounds ref-1, ref-2, ref-3, and ref-4, the boron-containing organic compound of the present invention has an emission peak value between 515 and 525 nm and a CIEy value > 0.77, which can better meet the display requirements of wide color gamut Adobe RGB (0.21, 0.75) and achieve a better BT.2020 color gamut coverage effect (0.17, 0.797). The CIEy and emission peak value of the organic light-emitting device of the boron-containing organic compound of the present invention are more in line with the requirements of wide color gamut display standards, especially the requirements of BT.2020 display indicators, compared with the comparative compounds ref-1, ref-2, ref-3, and ref-4.

[0249] Table 4

[0250]

[0251] Note: Current efficiency was tested using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); lifetime testing was conducted using 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.

[0252] As can be seen from the device data results in Table 4, compared with the comparative compound ref-3, the current efficiency and lifetime of the organic light-emitting device with boron-containing organic compound of the present invention are significantly improved compared with the organic electroluminescent device with known materials; when using exciton-sensitized material as the first dopant, the device efficiency is significantly improved compared with single dopant.

[0253] 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 in that, The structure of the boron-containing organic compound is shown in general formula (1): In general formula (1), Z is represented as C-R0; R0 represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Adjacent R0s are either not connected or connected in a loop; Each occurrence of the same or different Y1-Y8 indicates that C6-C6 is substituted or not substituted by R. 30 Aryl group, C2-C substituted or unsubstituted with R 30 Heteroaryl, C1-C substituted or unsubstituted 10 Alkyl groups, C3-C6 groups substituted with R or unsubstituted with R. 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, or one of R-substituted or unsubstituted boronyl groups; M1 represents C6-C6 with or without R substitution. 30 Aryl group, C2-C substituted or unsubstituted with R 30 One of the heteroaryl groups; Y3 and Y4 are either not connected or connected in a loop; Y6 and Y5 are either not connected or connected in a loop; Y2 and M1 are either not connected or connected in a loop; The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Z1 is denoted as C-Ra; Ra represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

2. The boron-containing organic compound according to claim 1, characterized in that, The structures of the boron-containing organic compounds are shown in general formula (1-1) or general formula (1-2): In general formulas (1-1) and (1-2), the meanings of Z, Z1, Y1, Y2, Y7, and Y8 are the same as those in general formula (1); X is represented as one of O, S, N-Rb, C(Rc)(Rd); Rb, Rc, and Rd represent substituted or unsubstituted C1 to C2. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The Rc and Rd are not connected to each other or are linked in a ring by single bonds, double bonds, oxygen atoms, sulfur atoms, dimethyl-substituted methylene, diphenyl-substituted methylene or -N(Ph)-. The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

3. The boron-containing organic compound according to claim 1, characterized in that, The structure of the boron-containing organic compound is shown in general formula (2) or general formula (3): In general formulas (2) and (3), the meanings of Z and Z1 are the same as those in general formula (1); X is represented as one of O, S, N-Rb, C(Rc)(Rd); Rb, Rc, and Rd represent substituted or unsubstituted C1 to C2. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The Rc and Rd are not connected to each other or are linked in a ring by single bonds, double bonds, oxygen atoms, sulfur atoms, dimethyl-substituted methylene, diphenyl-substituted methylene or -N(Ph)-. The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

4. The boron-containing organic compound according to claim 1, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formulas (2-1) to (2-2) and (3-1) to (3-4): In general formulas (2-1) to (2-2) and general formulas (3-1) to (3-4), the meanings of Z and Z1 are the same as those in general formula (1); Rb represents C1 to C2 with or without substitution. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

5. The boron-containing organic compound according to claim 1, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formulas (4) to (5): In general formulas (4) to (5), the meaning of Z is the same as that in general formula (1).

6. The boron-containing organic compound according to claim 1, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formulas (6) to (7): In general formulas (6) to (7), the meanings of Z1, Y1, Y2, Y7, and Y8 are the same as those in general formula (1); R1, R2, R3, R4, and R5 represent hydrogen atom, deuterium atom, halogen atom, cyano group, and substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; m and n represent 0, 1, 2 or 3; p and q represent 0, 1, 2, 3 or 4; k can be 0, 1, 2, 3, 4 or 5; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

7. The boron-containing organic compound according to any one of claims 1-4, characterized in that, R0, Ra, R1, R2, R3, R4, and R5 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted 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, and substituted or unsubstituted pyridyl group. The following are substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 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, and substituted or unsubstituted triazineyl. The R represents 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 diphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, or a substituted... Or any one of the following: 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, substituted or unsubstituted triazineyl; Rb, Rc, and Rd are independently represented as substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted... Or any one of the following: 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, substituted or unsubstituted triazineyl; The Y1-Y8 represent any one of the following: substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted aromatic amino, and substituted or unsubstituted triazineyl. The M1 represents any one of the following: substituted or unsubstituted benzene ring, substituted or unsubstituted naphthyl ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted phenanthrene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted furan ring, substituted or unsubstituted thiophene ring, substituted or unsubstituted benzofuran ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted dibenzofuran ring, substituted or unsubstituted dibenzothiophene ring, substituted or unsubstituted N-phenylcarbazole ring, substituted or unsubstituted 9,9-dimethylfluorene ring, substituted or unsubstituted indole[3,2,1-jk]carbazole ring, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl ring, and substituted or unsubstituted spirofluorene ring. 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.

8. The boron-containing organic compound according to claim 1, characterized in that, The boron-containing organic compound has any of the following structures:

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

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

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