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

Description

TECHNICAL FIELD

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

[0002] Compared with liquid crystal display (LCD), organic light-emitting diode (OLED) has the technical advantages of lighter and thinner, high color contrast, low power consumption, fast response, high definition, and flexibility, and is considered to dominate the future display terminal products. With the advent of the 5G era, the new information display industry urgently needs to develop iteratively. The early lower color gamut standards (BT.709 and DCIP3) have been unable to meet the high-quality technical development needs of display products. To achieve the performance requirements of ultra-high definition and higher picture quality of display products, the new generation of display standards (BT.2020) drive the development of organic electroluminescent materials towards high color purity, which requires the core light-emitting materials to have a narrower emission spectrum. Among the three color display technologies of commercially available OLEDs, blue light uses the traditional fluorescent three triplet-three triplet conversion (TTF) technology, which has a low efficiency but a high color purity and has basically met the BT.2020 display index; green light and red light use phosphorescent light-emitting technology, which has a high efficiency, and the red light has approached the BT.2020 display index. However, the green light is limited by the relatively wide emission spectrum of phosphorescent light, which is quite different from the high-definition display index requirement. Moreover, green phosphorescent light naturally has a high shoulder peak, and it is relatively difficult to improve the color gamut display under the traditional device structure. Therefore, it is very crucial to develop a new generation of high-color-purity green organic electroluminescent material.

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

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

[0005] In view of the above problems existing in the prior art, the present application provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present application can simultaneously realize green light emission and can be used as a green light dopant material for the light-emitting layer of an organic electroluminescent device.

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

[0007]

[0008] In general formula (1), A ring and B ring are represented by R-substituted or unsubstituted C6-C 30 aryl;

[0009] Z is represented by C-R0;

[0010] R0 is represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl, a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C2-C 10 alkenyl, a substituted or unsubstituted C2-C 10 alkynyl, a substituted or unsubstituted silyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 30 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 30 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 30 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and

[0011] adjacent R0are not linked to form a ring or linked to form a benzene ring substituted or unsubstituted by R, a cyclohexane ring substituted or unsubstituted by R;

[0012] Ar1, Ar2are independently represented by one of R-substituted or unsubstituted C1-C6alkyl, R-substituted or unsubstituted C3-Ci0cycloalkyl, R-substituted or unsubstituted C6-Ci0aryl, R-substituted or unsubstituted C2-Ci0heteroaryl, and 10 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 10 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 30 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 30 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and

[0013] Z1, Z2, Z3are independently represented by C-Ra, C-Rb, C-Rc;

[0014] Ra, Rb, Rcare independently represented by hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 10 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 10 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 30 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 30 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and

[0015] said Raand Rb, Rband Rcare not linked to form a ring or linked to form a benzene ring substituted or unsubstituted by R, a cyclohexane ring substituted or unsubstituted by R;

[0016] Y1is represented by R-substituted or unsubstituted C1-C6alkyl, R-substituted or unsubstituted C3-Ci0cycloalkyl, R-substituted or unsubstituted C6-Ci0aryl, R-substituted or unsubstituted C2-Ci0heteroaryl, and 10 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 10 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 10 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 30 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and 30 alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and

[0017] Y1is not linked to the A ring to form a ring or linked to form a ring through a single bond or a double bond;

[0018] Ar2is not linked to the B ring to form a ring or linked to form a ring through a single bond or a double bond;

[0019] said R, which is the same or different for each occurrence, is represented by deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C3-Ci0cycloalkyl, substituted or unsubstituted C6-Ci0aryl, substituted or unsubstituted C2-Ci0heteroaryl, and10 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 boronyl, substituted or unsubstituted C1-C 10 alkoxy, substituted or unsubstituted C6-C 30 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl, one of the following;

[0020] the substituent for the substituent group is optionally selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl, deuterium-substituted C1-C 10 alkyl, C6-C 30 aryl, deuterium-substituted C6-C 30 aryl, C1-C 10 alkyl-substituted C6-C 30 aryl, C2-C 30 heteroaryl, deuterium-substituted C2-C 30 one or more of the following; any of the heteroatoms in the heteroaryl group;

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

[0022] Further, the structure of the boron-containing organic compound is as shown in any one of general formula (1-1) to general formula (1-8):

[0023]

[0024] In general formula (1-1) to general formula (1-8), the meanings of the A ring, the B ring, Ar1, Ar2, Y1, Z1, Z2, Z3, Z are the same as those in general formula (1);

[0025] Ar3, Ar4 are independently represented by a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl, one of the following;

[0026] the substituent for the substituent group is optionally selected from a deuterium atom, a cyano group, a C1-C 10 alkyl, deuterium-substituted C1-C 10Alkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0027] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0028] Furthermore, the structure of the boron-containing organic compound is shown in general formula (1-9):

[0029]

[0030] In general formula (1-9), Z is represented as C-R0;

[0031] 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;

[0032] Adjacent R0s are not connected to form a ring or are connected to form a benzene ring substituted or unsubstituted by R, or a cyclohexane substituted or unsubstituted by R;

[0033] Ar1 and Ar2 are independently represented as C1 to C2, with or without R substitution. 10 Alkyl groups, C3-C6 groups substituted with R or unsubstituted with R. 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl group, C2-C substituted or unsubstituted with R 30 One of the heteroaryl groups;

[0034] Z1, Z2, Z3, and Z4 are represented as C-Ra, C-Rb, C-Rc, and C-Rd, respectively.

[0035] Ra, Rb, Rc, Rd each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0036] Y1represents one of a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0037] Y1and Rdare not connected to form a ring or are connected to form a ring through a single bond or a double bond;

[0038] Ar2and the nearest R0are not connected to form a ring or are connected to form a ring through a single bond or a double bond;

[0039] each occurrence of the R, which is the same or different, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 alkenyl group, a substituted or unsubstituted C2-C 10 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 30 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0040] the substituents for the substituents are optionally selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C1-C 10 alkyl-substituted C6-C 30 aryl group, a C2-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group;

[0041] The heteroatom in the heteroaryl group is optionally one or more of O, S, N, Si, B.

[0042] Further, the boron-containing organic compound has a structure as shown in any one of general formula (2) or general formula (3):

[0043]

[0044] In general formula (2) to (3), Z, Z1, Z2, Z3 have the same meaning as defined in general formula (1).

[0045] Preferably, the boron-containing organic compound has a structure as shown in any one of general formula (2-1) to (2-5):

[0046]

[0047] In general formula (2-1) to (2-5), Z, Z1 have the same meaning as defined in general formula (1).

[0048] Preferably, the boron-containing organic compound has a structure as shown in any one of general formula (3-1) to (3-11):

[0049]

[0050]

[0051] In general formula (3-1) to (3-11), Z, Z1 have the same meaning as defined in general formula (1).

[0052] Further, the boron-containing organic compound has a structure as shown in any one of general formula (4-1) to (4-8):

[0053]

[0054] In general formula (4-1) to (4-8), Ar1, Ar2, Z1 have the same meaning as defined in general formula (1).

[0055] Ar3, Ar4 are independently hydrogen atom, deuterium atom, cyano group, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted C3-C6 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C10 aryl group, substituted or unsubstituted C2-C10 heteroaryl group, or a group represented by general formula (4-1) to (4-8). 10 alkyl group, substituted or unsubstituted C3-C6 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C10 aryl group, substituted or unsubstituted C2-C10 heteroaryl group, or a group represented by general formula (4-1) to (4-8). 10 alkyl group, substituted or unsubstituted C3-C6 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C10 aryl group, substituted or unsubstituted C2-C10 heteroaryl group, or a group represented by general formula (4-1) to (4-8). 30 alkyl group, substituted or unsubstituted C3-C6 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C10 aryl group, substituted or unsubstituted C2-C10 heteroaryl group, or a group represented by general formula (4-1) to (4-8). 30 alkyl group, substituted or unsubstituted C3-C6 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C10 aryl group, substituted or unsubstituted C2-C10 heteroaryl group, or a group represented by general formula (4-1) to (4-8).

[0056] R1, R2, R3, R4, R5, R6, R7, R8, R9 represent one of hydrogen atom, deuterium atom, cyano group, substituted or unsubstituted C1-C 10 alkyl group, substituted or unsubstituted C3-C 10 cycloalkyl group, substituted or unsubstituted C2-C 10 alkenyl group, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C 10 alkoxy group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C2-C 30 heteroaryl group;

[0057] m1, m4, m5, m6, m7 each independently represent 0, 1, 2, 3 or 4;

[0058] m2 represents 0, 1, 2 or 3;

[0059] m3, m9 each independently represent 0, 1, 2, 3, 4 or 5;

[0060] m8, each independently represent 0, 1 or 2;

[0061] the substituent group for the substituent group is optionally selected from deuterium atom, halogen atom, cyano group, C1-C 10 alkyl group, deuterium-substituted C1-C 10 alkyl group, C6-C 30 aryl group, deuterium-substituted C6-C 30 aryl group, C1-C 10 alkyl-substituted C6-C 30 aryl group, C2-C 30 heteroaryl group, deuterium-substituted C2-C 30 heteroaryl group, any one or more of them;

[0062] the heteroatom in the heteroaryl group is optionally selected from one or more of O, S, N, Si, B.

[0063] Further, the structure of the boron-containing organic compound is represented by any one of general formulae (5-1) to (5-8):

[0064]

[0065]

[0066] In general formulae (5-1) to (5-8), the meanings of Ar1, Ar2, Z1 are the same as defined in general formula (1).

[0067] Ar3, Ar4 independently represent hydrogen atom, deuterium atom, cyano group, substituted or unsubstituted C1-C 10 alkyl group, substituted or unsubstituted C3-C 10 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C2-C 30 heteroaryl group;

[0068] R1, R2, R3, R4, R7 represent hydrogen atom, deuterium atom, cyano group, substituted or unsubstituted C1-C 10 alkyl group, substituted or unsubstituted C3-C 10 cycloalkyl group, substituted or unsubstituted C2-C 10 alkenyl group, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C 10 alkoxy group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C2-C 30 heteroaryl group;

[0069] the substituent group for the substituent group is optionally selected from deuterium atom, halogen atom, cyano group, C1-C 10 alkyl group, deuterium-substituted C1-C 10 alkyl group, C6-C 30 aryl group, deuterium-substituted C6-C 30 aryl group, C1-C 10 alkyl-substituted C6-C 30 aryl group, C2-C 30 heteroaryl group, deuterium-substituted C2-C 30 any one or more of the heteroaryl groups;

[0070] the heteroatom in the heteroaryl group is optionally selected from one or more of O, S, N, Si, B.

[0071] Further, the boron-containing organic compound has a structure as represented by any one of general formulae (4) to (11):

[0072]

[0073]

[0074] In general formulae (4) to (11), Z1 has the same meaning as in general formula (1).

[0075] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11, R 12 , R 13 represents any one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0076] m, n represent 0, 1 or 2;

[0077] o represents 0, 1, 2, 3, 4 or 5;

[0078] p represents 0 or 1;

[0079] the substituents for the substituents are optionally selected from a deuterium atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a deuterium-substituted C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a C1-C 10 alkyl-substituted C6-C 30 aryl group, a C2-C 30 heteroaryl group, a deuterium-substituted C2-C 30 heteroaryl group;

[0080] the heteroatom in the heteroaryl group is optionally selected from one or more of O, S, N, Si, B.

[0081] Further, the A ring and the B ring represent a benzene ring substituted or unsubstituted by R, a naphthalene ring substituted or unsubstituted by R;

[0082] the R0, Ra, Rb, Rc, Rd, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13Each of the following can be independently represented as a hydrogen atom, a deuterium atom, 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 anthraquinyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, or a substituted or unsubstituted diphenylamino group.

[0083] The R represents any one of the following: deuterium atom, cyano, 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 phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and substituted or unsubstituted diphenylamino.

[0084] Y1 represents any one of the following: substituted or unsubstituted vinyl, 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 dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and substituted or unsubstituted diphenylamino.

[0085] Ar1, Ar2, Ar3, and Ar4 are each independently represented as any one of the following: 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 phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, and substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl.

[0086] The substituents used for the substituent groups are selected from deuterium, cyano, adamantyl, methyl, ethyl, n-propyl, isopropyl, tert-amyl, tert-butyl, n-butyl, isobutyl, sec-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, furanyl, thiophene, indole, pyrrole, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazole, N-phenylcarbazole, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, methyl-substituted phenyl, ethyl One or more of the following: alkyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, and deuterated tert-butyl-substituted diphenyl.

[0087] Furthermore, the specific structure of the boron-containing organic compound is any one of the following structures:

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[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 described above.

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

[0106] (2) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device.

[0107] (3) The compound of the present invention, as a green light doping material, can significantly improve device efficiency and device lifetime. Attached Figure Description

[0108] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device using the materials listed in this invention;

[0109] Wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. Detailed Implementation

[0110] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0111] 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.

[0112] 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.

[0113] In this invention, C6 to C are substituted or unsubstituted. 30 Aryl refers to an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, preferably an aryl group with 6 to 20 substituted or unsubstituted carbon atoms, preferably an aryl group with 6 to 10 substituted or unsubstituted carbon atoms, preferably an aryl group with 8 to 10 substituted or unsubstituted carbon atoms, preferably substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrene, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted The group may contain, but is not limited to, a fused ring consisting of a substituted or unsubstituted triphenyl group, a substituted or unsubstituted peryl group, a substituted or unsubstituted indole group, a combination thereof, or a combination of the aforementioned groups.

[0114] In this invention, C6~C 30 Aryl refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and even more preferably an aryl group having 6 to 10 carbon atoms. Other preferred aryl groups include phenyl, naphthyl, anthraceneyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, phenanthryl, tetraphenyl, pyrene, diphenyl, and terphenyl. Fused rings of alkyl, triphenylene, perylene, indene, or combinations thereof, but not limited to these groups.

[0115] In this invention, deuterium-substituted C6-C 30 Aryl refers to a deuterated aryl group having 6 to 30 carbon atoms, preferably a deuterated aryl group having 6 to 20 carbon atoms, more preferably a deuterated aryl group having 6 to 10 carbon atoms, and preferably deuterated phenyl, deuterated naphthyl, deuterated anthracene, deuterated fluorenyl, deuterated dimethylfluorenyl, deuterated diphenylfluorenyl, deuterated spirofluorenyl, deuterated phenanthrene, deuterated tetraphenyl, deuterated pyrene, deuterated diphenyl, deuterated terphenyl, and deuterated... The group may include, but is not limited to, fused rings of alkyl, deuterated triphenylene, deuterated peryl, deuterated indene, combinations thereof, or combinations of the aforementioned groups.

[0116] In this invention, C2 to C are substituted or unsubstituted. 30 Heteroaryl refers to a heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms, preferably a heteroaryl group with 2 to 20 substituted or unsubstituted carbon atoms, preferably a heteroaryl group with 4 to 20 substituted or unsubstituted carbon atoms, preferably a heteroaryl group with 4 to 10 substituted or unsubstituted carbon atoms, preferably a heteroaryl group with 5 to 10 substituted or unsubstituted carbon atoms, preferably a furanyl group, a thiophene group, a pyrrole group, a pyrazolyl group, a pyrazolyl group, a substituted imidazolyl group, a triazolyl group, a substituted oxazolyl group, a substituted thiazolyl group, a substituted oxadiazolyl group, a substituted thiadiazolyl group, a substituted pyridyl group, a substituted pyrimidinyl group, a substituted pyrimidinyl group, a substituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrid ... The substituted triazine group, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted benzimidazol group, substituted or unsubstituted indol group, substituted or unsubstituted quinolino group, substituted or unsubstituted isoquinolino group, substituted or unsubstituted quinazolino group, substituted or unsubstituted quinolino group, substituted or unsubstituted naphridinyl group, substituted or unsubstituted benzooxazinyl group, substituted or unsubstituted benzothiazinyl group, substituted or unsubstituted acridine group, substituted or unsubstituted benzazinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted tyloyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiapheneyl group, substituted or unsubstituted carbazoyl group, substituted or unsubstituted N-phenylcarbazoyl group, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0117] In this invention, C2~C 30The term "heteroaryl" refers to a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 20 carbon atoms, preferably a heteroaryl group having 4 to 20 carbon atoms, preferably a heteroaryl group having 4 to 10 carbon atoms, and preferably a furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiazolyl, pyridinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiophene, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, acridineyl, benazinoyl, benazinothiazinyl, benazinoyl, fumonyl, dibenzofuranyl, dibenzothiophene, carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, combinations thereof, or fused rings of the aforementioned groups, but not limited thereto.

[0118] In this invention, deuterium-substituted C2-C 30 The heteroaryl group refers to a heteroaryl group with 5 to 30 deuterated carbon atoms, preferably a heteroaryl group with 5 to 20 deuterated carbon atoms, preferably a heteroaryl group with 5 to 10 deuterated carbon atoms, preferably deuterated furanyl, deuterated thiophene, deuterated pyrrole, deuterated pyrazolyl, deuterated imidazolyl, deuterated triazolyl, deuterated oxazolyl, deuterated thiazolyl, deuterated oxadiazolyl, deuterated thiadiazolyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated triazine, deuterated benzofuranyl, deuterated... The substituted benzothiophene group, deuterated benzimidazolyl group, deuterated indolyl group, deuterated quinolinyl group, deuterated isoquinolinyl group, deuterated quinazolinyl group, deuterated quinolinyl group, deuterated naphridyl group, deuterated benzoxazinyl group, deuterated benzothiazinyl group, deuterated acridineyl group, deuterated benziazinyl group, deuterated benziazinyl group, deuterated benziazinyl group, deuterated benziazinyl group, deuterated fumonyl group, deuterated dibenzofuranyl group, deuterated dibenzothiophene group, deuterated carbazoyl group, deuterated N-phenylcarbazoyl group, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0119] 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.

[0120] The substituted or unsubstituted C1-C of this invention 10Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to alkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, preferably alkyl groups with 1 to 5 substituted or unsubstituted carbon atoms, preferably alkyl groups with 1 to 4 substituted or unsubstituted carbon atoms, preferably substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted neopentyl, substituted or unsubstituted n-pentyl, substituted or unsubstituted isopentyl, substituted or unsubstituted octyl, substituted or unsubstituted heptyl, substituted or unsubstituted n-decyl, substituted or unsubstituted 1-methylpentyl, substituted or unsubstituted 2-methylpentyl, substituted or unsubstituted 3-methylpentyl, substituted or unsubstituted 1-butylpentyl, etc., but not limited to these.

[0121] 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.

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

[0123] The substituted or unsubstituted C3-C of this invention 10The cycloalkyl group preferably uses substituted or unsubstituted C4-C9 cycloalkyl groups, more preferably substituted or unsubstituted C5-C8 cycloalkyl groups, and particularly preferably substituted or unsubstituted C5-C7 cycloalkyl groups. Non-limiting examples may include, but are not limited to, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted 4-methylcyclohexyl, substituted or unsubstituted 4,4-dimethylcyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted cycloheptyl.

[0124] The C3~C of this invention 10 The cycloalkyl group is preferably C4-C9 cycloalkyl, more preferably C5-C8 cycloalkyl, and particularly preferably C5-C7 cycloalkyl. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0125] The deuterium-substituted C3-C of the present invention 10 The cycloalkyl group is preferably a deuterated C4-C9 cycloalkyl group, more preferably a deuterated C5-C8 cycloalkyl group, and particularly preferably a deuterated C5-C7 cycloalkyl group. Non-limiting examples may include, but are not limited to, deuterated cyclopropyl, deuterated cyclobutyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated 4-methylcyclohexyl, deuterated 4,4-dimethylcyclohexyl, deuterated adamantyl, and deuterated cycloheptyl.

[0126] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0127] The C1 to C of this invention 10 Alkoxy groups include, but are not limited to, alkoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or isopropoxy.

[0128] The C2 to C of this invention 10 Alkenyl refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl, etc., but is not limited to these.

[0129] In this invention, the substituents used for the substituent groups are selected from deuterium, cyano, adamantyl, methyl, ethyl, n-propyl, isopropyl, tert-amyl, tert-butyl, n-butyl, isobutyl, sec-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, furanyl, thiophene, indole, pyrrole, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazole, N-phenylcarbazole, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and methyl-substituted benzene. One or more of the following: methyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, and deuterated tert-butyl-substituted diphenyl.

[0130] 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.

[0131] 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.

[0132] The organic functional material layer disposed between the first electrode and the second electrode includes, from bottom to top, a hole transport region, a light-emitting layer, and an electron transport region.

[0133] In 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.

[0134] 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.

[0135] 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.

[0136] 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.

[0137] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from the following prior art:

[0138] The compounds disclosed in JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, and CN105439999A, but not limited thereto.

[0139] 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.

[0140] 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.

[0141] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass meter.

[0142] 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.

[0143] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0144]

[0145]

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

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

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

[0149]

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

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

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

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

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

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

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

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

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

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

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

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

[0162]

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

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

[0165]

[0166]

[0167] 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.

[0168] 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.

[0169] 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.

[0170] 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.

[0171] 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.

[0172] 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.

[0173] 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.

[0174] Synthesis Examples

[0175] 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;

[0176]

[0177] Synthesis of intermediate a-1:

[0178] Add raw material A-3 (0.66 g, 2.5 mmol) and cesium carbonate (2.61 g, 8 mmol) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 min. Add raw material B-2 (1.08 g, 2.5 mmol) under nitrogen protection and stir at 140 °C for 5 h under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate a-1.

[0179] Synthesis of intermediate b-1:

[0180] Intermediate a-1 (1.69 g, 2.5 mmol) was dissolved in 50 mL of toluene solution. Starting material C-1 (0.37 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 10 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 overnight 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 b-1.

[0181]

[0182] Synthesis of intermediate d-1:

[0183] Add raw material A-2 (0.52 g, 2.5 mmol) and cesium carbonate (2.61 g, 8 mmol) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 min. Add raw material B-1 (1.01 g, 2.5 mmol) under nitrogen protection and stir at 140 °C for 3 h under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate d-1.

[0184]

[0185] Synthesis of intermediate e-1:

[0186] In a three-necked flask under nitrogen protection, 2.5 g (10 mmol) of starting material B-4, 3.4 g (10 mmol) of starting material A-4, 5.6 g (25 mmol) of zinc bromide, and 180 mL of anhydrous toluene were added, and the mixture was heated to 110 °C and reacted for 14 hours. After cooling to room temperature, the mixture was concentrated and purified by silica gel column chromatography to obtain intermediate e-1.

[0187] Synthesis of intermediate f-1:

[0188] Intermediate e-1 (1.2 g, 2.5 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at 0 °C, 1.6 mL of n-butyllithium (1.6 M) n-hexane solution was slowly added. After stirring at 0 °C for 2 hours, 5 mL of tetrahydrofuran solution of starting material D-1 (0.5 g, 2.8 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 passed through a column to obtain intermediate f-1.

[0189]

[0190] Synthesis of intermediate a-2:

[0191] Add raw material A-3 (0.66 g, 2.5 mmol) and cesium carbonate (2.61 g, 8 mmol) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 min. Add intermediate f-1 (1.36 g, 2.5 mmol) under nitrogen protection and stir at 140 °C for 5 h under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate a-2.

[0192] Synthesis of intermediate b-2:

[0193] Intermediate a-2 (1.97 g, 2.5 mmol) was dissolved in 100 mL of toluene solution. Starting material C-1 (0.37 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C 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 overnight 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 b-2.

[0194]

[0195] Synthesis of intermediate d-2:

[0196] Add raw material A-2 (0.52 g, 2.5 mmol) and cesium carbonate (2.61 g, 8 mmol) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 min. Add intermediate f-1 (1.36 g, 2.5 mmol) under nitrogen protection and stir at 140 °C for 4 h under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate d-2.

[0197]

[0198] Synthesis of intermediate d-3:

[0199] Add raw material A-2 (0.52 g, 2.5 mmol) and cesium carbonate (2.61 g, 8 mmol) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 min. Add raw material B-2 (1.09 g, 2.5 mmol) under nitrogen protection and stir at 140 °C for 12 h under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate d-3.

[0200]

[0201] Synthesis of intermediate d-4:

[0202] Add raw material A-2 (0.52 g, 2.5 mmol) and cesium carbonate (2.61 g, 8 mmol) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 min. Add raw material B-3 (1.08 g, 2.5 mmol) under nitrogen protection and stir at 140 °C for 8 h under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate d-4.

[0203]

[0204] Synthesis of intermediate a-3:

[0205] Add raw material A-3 (0.66 g, 2.5 mmol) and cesium carbonate (2.61 g, 8 mmol) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 min. Add raw material B-3 (1.08 g, 2.5 mmol) under nitrogen protection and stir at 140 °C for 9 h under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate a-3.

[0206] Synthesis of intermediate b-3:

[0207] Intermediate a-3 (1.69 g, 2.5 mmol) was dissolved in 80 mL of toluene solution. Starting material C-1 (0.37 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 4 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 overnight 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 b-3.

[0208]

[0209] Synthesis of intermediate G5: In a two-necked flask, starter R2 (10.07 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) were added. Under nitrogen protection, 100 mL of anhydrous DMF was added, and the mixture was stirred at room temperature for 30 min. Then, under nitrogen protection, starter P3 (6.73 g, 25 mmol) was added, and the mixture was stirred at 140 °C for 14 h under nitrogen protection. The mixture was filtered, washed with water, dried, and column filtered to obtain intermediate G5.

[0210]

[0211] Synthesis of intermediate a-4:

[0212] Add raw material A-3 (0.66 g, 2.5 mmol) and cesium carbonate (2.61 g, 8 mmol) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 min. Add intermediate G5 (1.36 g, 2.5 mmol) under nitrogen protection and stir at 140 °C for 4 h under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate a-4.

[0213] Synthesis of intermediate b-5:

[0214] Intermediate a-4 (1.97 g, 2.5 mmol) was dissolved in 60 mL of toluene solution. Starting material C-1 (0.37 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 10 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 overnight 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 b-5.

[0215] Example 1: Synthesis of Compound 145:

[0216]

[0217] Preparation of intermediate c-1:

[0218] Intermediate b-1 (1.86 g, 2.5 mmol) was dissolved in 200 mL of toluene solution. Starting material A-1 (1.17 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 10 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 overnight 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.

[0219] Preparation of compound 145:

[0220] Intermediate c-1 (14.17 g, 12.5 mmol) was dissolved in 350 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 4 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 3 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 14 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 chromatography to give compound 145. The full width at half maximum (FWHM) of compound 145 in toluene solution was 16 nm (1 × 10⁻⁶).-5 M, toluene solution). LC-MS: Measured value: 1080.90 ([M+H]). + Precision quality: 1079.65.

[0221] Example 2: Synthesis of Compound 151:

[0222]

[0223] Preparation of intermediate c-2:

[0224] Intermediate b-1 (1.86 g, 2.5 mmol) was dissolved in 60 mL of toluene solution. Intermediate d-1 (1.49 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C 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). After drying overnight with anhydrous magnesium sulfate, 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.

[0225] Preparation of compound 151:

[0226] Intermediate c-2 (15.74 g, 12.5 mmol) was dissolved in 360 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 4 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 3 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 14 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 chromatography to give compound 151. The full width at half maximum (FWHM) of compound 151 in toluene solution was 15 nm (1 × 10⁻⁶). -5 M (toluene solution). LC-MS: Measured value: 1206.72 ([M+H)). + Precision quality: 1205.60.

[0227] Example 3: Synthesis of Compound 157:

[0228]

[0229] Preparation of intermediate c-3:

[0230] Intermediate b-2 (2.14 g, 2.5 mmol) was dissolved in 70 mL of toluene solution. Starting material A-1 (1.17 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 4 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 overnight with anhydrous magnesium sulfate, the ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether with stirring, and filtered to obtain intermediate c-3.

[0231] Preparation of compound 157:

[0232] Intermediate c-3 (15.57 g, 12.5 mmol) was dissolved in 360 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 3 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 12 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 chromatography to give compound 157. The full width at half maximum (FWHM) of compound 157 in toluene solution was 15 nm (1 × 10⁻⁶). -5 M (toluene solution). LC-MS: Measured value: 1192.83 ([M+H]). + Precision mass: 1191.68.

[0233] Example 4: Synthesis of compound 174:

[0234]

[0235] Preparation of intermediate c-4:

[0236] Intermediate b-1 (1.86 g, 2.5 mmol) was dissolved in 80 mL of toluene solution. Intermediate d-2 (1.83 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 4 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 overnight with anhydrous magnesium sulfate, 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-4.

[0237] Preparation of compound 174:

[0238] Intermediate C-4 (17.47 g, 12.5 mmol) was dissolved in 400 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 3 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 3 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 10 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 chromatography to give compound 174. The full width at half maximum (FWHM) of compound 174 in toluene solution was 16 nm (1 × 10⁻⁶). -5 M (toluene solution). LC-MS: Measured value: 1344.57 ([M+H)). + ), Precision quality: 1343.74.

[0239] Example 5: Preparation of compound 181:

[0240]

[0241] Preparation of intermediate c-5:

[0242] Intermediate b-2 (2.14 g, 2.5 mmol) was dissolved in 80 mL of toluene solution. Intermediate d-3 (1.55 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 5 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 overnight with anhydrous magnesium sulfate, 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-5.

[0243] Preparation of compound 181:

[0244] Intermediate C-5 (17.47 g, 12.5 mmol) was dissolved in 400 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 4 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 4 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 18 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 chromatography to give compound 181. The full width at half maximum (FWHM) of compound 181 in toluene solution was 18 nm (1 × 10⁻⁶). -5 M (toluene solution). LC-MS: Measured value: 1344.94 ([M+H)). + ), Precision quality: 1343.74.

[0245] Example 6: Synthesis of Compound 188:

[0246]

[0247] Preparation of intermediate c-6:

[0248] Intermediate b-1 (1.86 g, 2.5 mmol) was dissolved in 80 mL of toluene solution. Intermediate d-3 (1.55 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 4 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 overnight with anhydrous magnesium sulfate, 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-6.

[0249] Preparation of compound 188:

[0250] Intermediate C-6 (16.07 g, 12.5 mmol) was dissolved in 350 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 2 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 8 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 chromatography to give compound 188. The full width at half maximum (FWHM) of compound 188 in toluene solution was 15 nm (1 × 10⁻⁶). -5 M (toluene solution). LC-MS: Measured value: 1232.94 ([M+H)). + ), Precision quality: 1231.71.

[0251] Example 7: Synthesis of Compound 193:

[0252]

[0253] Preparation of intermediate c-7:

[0254] Intermediate b-1 (1.86 g, 2.5 mmol) was dissolved in 80 mL of toluene solution. Intermediate d-4 (1.55 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C 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 overnight with anhydrous magnesium sulfate, 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-7.

[0255] Preparation of compound 193:

[0256] Intermediate C-7 (16.07 g, 12.5 mmol) was dissolved in 350 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 3 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 4 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 20 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 chromatography to give compound 193. The full width at half maximum (FWHM) of compound 193 in toluene solution was 19 nm (1 × 10⁻⁶). -5 M (toluene solution). LC-MS: Measured value: 1232.79 ([M+H)). + ), Precision quality: 1231.71.

[0257] Example 8: Synthesis of Compound 198:

[0258]

[0259] Preparation of intermediate c-8:

[0260] Intermediate b-3 (1.86 g, 2.5 mmol) was dissolved in 80 mL of toluene solution. Intermediate d-3 (1.55 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 7 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 overnight with anhydrous magnesium sulfate, 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-8.

[0261] Preparation of compound 198:

[0262] Intermediate C-8 (16.07 g, 12.5 mmol) was dissolved in 350 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 3 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 5 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 mmol) was added at 0 °C, and the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 20 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 chromatography to give compound 198. The full width at half maximum (FWHM) of compound 198 in toluene solution was 18 nm (1 × 10⁻⁶). -5 M (toluene solution). LC-MS: Measured value: 1232.98 ([M+H)). + ), Precision quality: 1231.71.

[0263] Example 9: Synthesis of Compound 147:

[0264]

[0265] Preparation of intermediate c-9:

[0266] Intermediate b-5 (2.14 g, 2.5 mmol) was dissolved in 80 mL of toluene solution. Starting material A-1 (1.17 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 (0.009 g, 0.04 mmol) were added, and the mixture was stirred vigorously. The resulting mixture was refluxed at 105 °C for 5 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 overnight 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-9.

[0267] Preparation of compound 147:

[0268] Intermediate C-9 (15.57 g, 12.5 mmol) was dissolved in 350 mL of tert-butylbenzene. Under a nitrogen atmosphere at 0 °C, 12.5 mL of a 2.5 M tert-butyllithium solution in n-pentane was slowly added. After stirring at 60 °C for 2 hours, boron tribromide (9.39 g, 37.5 mmol) was added at 0 °C, and the reaction mixture was stirred at room temperature for 2 hours. N,N-diisopropylethylamine (DIPEA) (8.08 g, 62.5 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 chromatography to give compound 147. The full width at half maximum (FWHM) of compound 147 in toluene solution was 16 nm (1 × 10⁻⁶). -5 M (toluene solution). LC-MS: Measured value: 1192.69 ([M+H)). + ), Precision quality: 1191.77.

[0269] The following details the application effects of the OLED materials synthesized in this invention in devices through device examples 1-9 and device comparative examples 1-2. Device examples 2-9 and device comparative examples 1-2 of this invention have the same fabrication process as device example 1, and use the same substrate and electrode materials, with consistent electrode film thickness. The only difference is the replacement of the light-emitting layer material. The layer structures and test results of each device example are shown in Tables 2-1 and 3, respectively.

[0270] Device Example 1

[0271] like Figure 1As shown, the transparent substrate layer 1 is transparent glass. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet light and ozone to remove organic residues from the transparent ITO surface. After the above washing, HT-1 and HI-1 with a film thickness of 10nm are deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the organic electroluminescent device is fabricated, using GH-1 and GH-2 as the host materials and compound 145 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 145 of 69:30:1, and a film thickness of 30nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.

[0272] The application effects of the OLED material synthesized in this invention in devices are described in detail below through device examples 10-18 and device comparative examples 3-4. Device examples 11-18 and device comparative examples 3-4 of this invention have the same fabrication process as device example 10, and use the same substrate material and electrode material, with the same electrode film thickness. The only difference is the replacement of the light-emitting layer material in the device. The layer structure and test results of each device example are shown in Tables 2-2 and 3, respectively.

[0273] Device Example 10

[0274] The transparent substrate layer 1 is transparent glass. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the light-emitting layer 6 of the organic electroluminescent device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 as the first dopant, and compound 145 as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 145 is 66.5:30:3:0.5, and the thickness of the light-emitting layer is 30 nm. After the light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1, with a thickness of 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated by vacuum evaporation device, with a Mg:Ag mass ratio of 1:9. This layer is used as the cathode layer 10.

[0275] The molecular structural formulas of the relevant materials are shown below:

[0276]

[0277]

[0278] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency, peak emission, and lifetime of the device are measured. Examples and comparisons of devices prepared using the same method are shown in Tables 2-1 and 2-2; the test results for the current efficiency, peak emission, and lifetime of the obtained devices are shown in Table 3.

[0279] Table 2-1

[0280]

[0281]

[0282] Table 2-2

[0283]

[0284]

[0285] Table 3

[0286]

[0287] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0288] As can be seen from the device data results in Table 3, compared with the comparative compounds ref-1 and ref-2, the emission peak of the compound of the present invention is between 510 and 550 nm, which can achieve the effect of green light emission very well; the current efficiency and lifetime of the organic light-emitting device of the present invention are significantly improved compared with the organic electroluminescent devices of known materials; when using exciton-sensitized material as the first dopant, the device efficiency is significantly improved compared with single doping.

[0289] 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), rings A and B are represented as C6-C6 rings substituted with or unsubstituted with R. 30 Aryl; 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 not connected to form a ring or are connected to form a benzene ring substituted or unsubstituted by R, or a cyclohexane substituted or unsubstituted by R; Ar1 and Ar2 are independently represented as C1 to C2, with or without R substitution. 10 Alkyl groups, C3-C6 groups substituted with R or unsubstituted 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl group, C2-C substituted or unsubstituted with R 30 One of the heteroaryl groups; Z1, Z2, and Z3 are represented as C-Ra, C-Rb, and C-Rc, respectively. Ra, Rb, and Rc are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, and substituted or unsubstituted C1-C1 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Ra and Rb, Rb and Rc are not connected to form a ring or are connected to form a benzene ring substituted or unsubstituted by R, or a cyclohexane substituted or unsubstituted by R; Y1 represents C1 to C1, with or without R substitution. 10 Alkyl groups, C3-C6 groups substituted with R or unsubstituted 10 Cycloalkyl, C2-C substituted or unsubstituted 10 Alkenyl, C6-C substituted or unsubstituted with R 30 Aryl group, C2-C substituted or unsubstituted with R 30 One of the heteroaryl groups; Y1 is not connected to ring A to form a ring, or is connected to ring A by a single bond or double bond; Ar2 and B ring are not connected to form a ring, or are connected to form a ring through a single bond or double bond; 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; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

2. The 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 (1-1) to (1-8): In general formulas (1-1) to (1-8), the meanings of ring A, ring B, Ar1, Ar2, Y1, Z1, Z2, Z3, and Z are the same as those in general formula (1); Ar3 and Ar4 are represented independently as hydrogen atoms, deuterium atoms, and substituted or unsubstituted C1 to C1 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aromatic amino, 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, cyano groups, C1 to C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

3. The boron-containing organic compound according to claim 1, characterized in that, The structure of the boron-containing organic compound is shown in general formula (1-9): In general formula (1-9), 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 not connected to form a ring or are connected to form a benzene ring substituted or unsubstituted by R, or a cyclohexane substituted or unsubstituted by R; Ar1 and Ar2 are independently represented as C1 to C2, with or without R substitution. 10 Alkyl groups, C3-C6 groups substituted with R or unsubstituted 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl group, C2-C substituted or unsubstituted with R 30 One of the heteroaryl groups; Z1, Z2, Z3, and Z4 are represented as C-Ra, C-Rb, C-Rc, and C-Rd, respectively. Ra, Rb, Rc, and Rd are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, and substituted or unsubstituted C1-C1 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Y1 represents C1 to C1, with or without R substitution. 10 Alkyl groups, C3-C6 groups substituted with R or unsubstituted 10 Cycloalkyl, C2-C substituted or unsubstituted 10 Alkenyl, C6-C substituted or unsubstituted with R 30 Aryl group, C2-C substituted or unsubstituted with R 30 One of the heteroaryl groups; Y1 and Rd are not connected to form a loop, or are connected to form a loop through a single bond or double bond; Ar2 is not connected to the nearest R0 in a loop, or is connected to it in a loop via a single or double bond; 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; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

4. 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) to (3), the meanings of Z, Z1, Z2, and Z3 are the same as those in general formula (1); Preferably, the structure of the boron-containing organic compound is shown in any one of general formulas (2-1) to (2-5): In general formulas (2-1) to (2-5), the meanings of Z and Z1 are the same as those in general formula (1); Preferably, the structure of the boron-containing organic compound is shown in any one of general formulas (3-1) to (3-11): In general formulas (3-1) to (3-11), the meanings of Z and Z1 are the same as those in general formula (1).

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 (4-1) to (4-8): In general formulas (4-1) to (4-8), the meanings of Ar1, Ar2, and Z1 are the same as those in general formula (1); Ar3 and Ar4 are independently represented as hydrogen atom, deuterium atom, cyano group, and substituted or unsubstituted C1-C1 groups, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aromatic amino, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R1, R2, R3, R4, R5, R6, R7, R8, and R9 represent hydrogen atom, deuterium atom, cyano group, and substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; m1, m4, m5, m6, and m7 are each independently represented as 0, 1, 2, 3, or 4; m2 can be represented as 0, 1, 2, or 3; m3 and m9 can be independently represented as 0, 1, 2, 3, 4 or 5 respectively; m8, each can be represented independently as 0, 1, or 2; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

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 (4) to (11): In general formulas (4) to (11), the meaning of Z1 is the same as that in general formula (1); R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 Represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted silyl, 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, or 2; o represents 0, 1, 2, 3, 4 or 5; p represents 0 or 1; The substituents used for the substituent groups are optionally selected from deuterium atoms, cyano groups, C1 to 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, C1-C 10 Alkyl-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

7. The boron-containing organic compound according to any one of claims 1-6, characterized in that, The A ring and B ring are represented as benzene rings substituted or unsubstituted with R, and naphthalene rings substituted or unsubstituted with R; The values ​​R0, Ra, Rb, Rc, Rd, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 Each of the following can be independently represented as a hydrogen atom, a deuterium atom, 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 anthraquinyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, or a substituted or unsubstituted diphenylamino group. The R represents any one of the following: deuterium atom, cyano, 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 phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and substituted or unsubstituted diphenylamino. Y1 represents any one of the following: substituted or unsubstituted vinyl, 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 dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and substituted or unsubstituted diphenylamino. Ar1, Ar2, Ar3, and Ar4 are each independently represented as any one of the following: 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 phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, and substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl. The substituents used for the substituent groups are selected from deuterium, cyano, adamantyl, methyl, ethyl, n-propyl, isopropyl, tert-amyl, tert-butyl, n-butyl, isobutyl, sec-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, furanyl, thiophene, indole, pyrrole, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazole, N-phenylcarbazole, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, methyl-substituted phenyl, ethyl One or more of the following: alkyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, and deuterated tert-butyl-substituted diphenyl.

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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