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

Abstract

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

Description

Technical Field

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

[0002] Compared with liquid crystal display (LCD), organic light-emitting diode (OLED) has technical advantages such as being lighter and thinner, having a high color contrast ratio, low power consumption, fast response, high clarity, and being flexible, and is considered to dominate future display terminal products. With the advent of the 5G era, the new information display industry urgently needs iterative development. The early lower color gamut standards (BT.709 and DCIP3) can no longer meet the high-quality technical development requirements of display products. To achieve the performance requirements of ultra-high definition and higher picture quality for display products, the new generation of display standard (BT.2020) drives OLED luminescent materials to develop towards high color purity, which requires the core luminescent materials to have a narrower emission spectrum. Among the current commercial OLED red, green, and blue color display technologies, the blue light uses the triplet-triplet conversion (TTF) technology of traditional fluorescence. Although this technology has low efficiency, it has high color purity and basically meets the BT.2020 display index; the green and red lights use phosphorescent emission technology. This technology has high efficiency, and the red light is close to the BT.2020 display index. However, the green light is limited by the relatively wide emission spectrum of phosphorescence and has a large difference from the requirements of the high-definition display index. Therefore, it is very crucial to develop high-color-purity green OLED materials.

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

[0004] In addition, the sensitization technology combines triplet exciton sensitizing materials (including but not limited to TADF materials and phosphorescent materials) with fluorescent doping materials. Using the triplet exciton sensitizing materials as the exciton sensitizing medium, it makes full use of triplet excitons and transfers the energy to the fluorescent doping materials through energy transfer, which can also achieve a 100% internal quantum efficiency of the device. This technology can make up for the deficiency of the exciton utilization rate of fluorescent doping materials and effectively utilize the characteristics of high fluorescence quantum yield, high device stability, high color purity and low cost of fluorescent doping materials, showing broad prospects in the application of OLEDs. For example, in CN 107507921 A and CN110492006 A, a light-emitting layer combination technology is disclosed with a TADF material having a lowest singlet and lowest triplet energy level difference less than or equal to 0.2 eV as the main body and a boron-containing material as the dopant; in CN 110492005 A and CN 110492009A, a light-emitting layer combination scheme with an exciplex as the main body and a boron-containing material as the dopant is disclosed, both of which can achieve efficiency comparable to that of phosphorescence and a relatively narrow full width at half maximum. Therefore, developing a sensitization technology based on boron-containing luminescent materials with a narrow full width at half maximum has unique advantages and strong potential for meeting the BT.2020 display index. Summary of the Invention

[0005] In view of the above problems existing in the prior art, the present invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention can achieve green light emission.

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

[0007]

[0008] In the general formula (1), R 1 -R 10 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 2 ~C 10 alkynyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C2 ~C 30 one of heteroaryl, substituted or unsubstituted boranyl, and substituted or unsubstituted silyl;

[0009] X represents O, S, N-R 11 , C-(R 12 R 13 ), Si-(R 14 R 15 );

[0010] R 11 represents one of substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted C 2 ~C 30 heteroaryl;

[0011] R 12 -R 15 each independently represents a deuterium atom, a halogen atom, a cyano group, substituted or unsubstituted C 1 ~C 10 alkyl, substituted or unsubstituted C 3 ~C 10 cycloalkyl, substituted or unsubstituted C 2 ~C 10 alkenyl, substituted or unsubstituted C 1 ~C 10 alkoxy, substituted or unsubstituted C 6 ~C 30 aryloxy, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted C 2 ~C 30 heteroaryl;

[0012] The M ring represents one of an aromatic ring of one or more R-substituted or unsubstituted C 6 ~C 30 and a heteroaromatic ring of one or more R-substituted or unsubstituted C 2 ~C 30 ;

[0013] Each occurrence of R, which may be the same or different, represents a deuterium atom, a halogen atom, a cyano group, substituted or unsubstituted C 1 ~C 10 alkyl, substituted or unsubstituted C 3 ~C 10 cycloalkyl, substituted or unsubstituted C 2 ~C 10 alkenyl, substituted or unsubstituted C 2 ~C 10 alkynyl, substituted or unsubstituted C1 ~C 10 alkoxy, substituted or unsubstituted C 6 ~C 10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted C 2 ~C 30 heteroaryl, substituted or unsubstituted boranyl, substituted or unsubstituted silyl;

[0014] Said R 1 , R 2 are not connected to each other or are connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)-, -Si(RdRe)- or -C(Rp)=C(Rq)-;

[0015] Said R 6 -R 10 Any two adjacent groups among them are not connected to each other or are connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)--Si(RdRe)- or -C(Rp)=C(Rq)-;

[0016] Said R 11 and the M ring are not connected to each other or are connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)--Si(RdRe)- or -C(Rp)=C(Rq)-;

[0017] Said R 11 and R 5 are not connected to each other or are connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)--Si(RdRe)- or -C(Rp)=C(Rq)-;

[0018] Said Rb and Rc, Rd and Re are not connected to each other or are connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)-, -Si(RdRe)- or -C(Rp)=C(Rq)-;

[0019] Said R 12 and R 13 , R 14 and R 15 are not connected to each other or are connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)-, -Si(RdRe)- or -C(Rp)=C(Rq)-;

[0020] Said Ra, Rb, Rc, Rd, Re, Rp, Rq each independently represent a deuterium atom, a halogen atom, a cyano group, substituted or unsubstituted C1 ~C 10 alkyl, substituted or unsubstituted C 3 ~C 10 cycloalkyl, substituted or unsubstituted C 2 ~C 10 alkenyl, substituted or unsubstituted C 1 ~C 10 alkoxy, substituted or unsubstituted C 6 ~C 30 aryloxy, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted C 2 ~C 30 one of heteroaryl;

[0021] When R 1 and R 2 are connected by a single bond to form a benzene ring, and R 11 and R 5 are not connected by -O- or -S-;

[0022] The substituents for substituting the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, C 1 ~C 10 alkyl, deuterium-substituted C 1 ~C 10 alkyl, fluorine-substituted C 1 ~C 10 alkyl, C 3 ~C 10 cycloalkyl, deuterium-substituted C 3 ~C 10 cycloalkyl, C 6 ~C 30 aryl, deuterium-substituted C 6 ~C 30 aryl, C 5 ~C 30 heteroaryl, deuterium-substituted C 2 ~C 30 heteroaryl, C 2 ~C 10 alkenyl, C 2 ~C 10 alkynyl, C 1 ~C 10 alkoxy, C 6 ~C 10 aryloxy, arylamino, or any one or more of them;

[0023] The heteroatoms in the heteroaryl are each independently selected from O, S, N, Si, B.

[0024] Further, the structure of the boron-containing organic compound is as shown in any one of General Formulas (2-1) to (2-3):

[0025]

[0026] In General Formulas (2-1) to (2-3), Y represents O, S, N-R 11 , C-(R 12 R 13 ), Si-(R 14 R 15 );

[0027] R 1 -R 15 , and the meanings of X are the same as the definitions in General Formula (1);

[0028] R 16 -R 21 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group, or a substituted or unsubstituted silyl group;

[0029] The substituents for substituting the above-mentioned groups that can be substituted are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C 1 ~C 10 alkyl group, a deuterium-substituted C 1 ~C 10 alkyl group, a fluorine-substituted C 1 ~C 10 alkyl group, a C 3 ~C 10 cycloalkyl group, a deuterium-substituted C 3 ~C 10 cycloalkyl group, a C 6 ~C 30 aryl group, a deuterium-substituted C 6 ~C 30 aryl group, a C 5 ~C 30Heteroaryl, deuterium-substituted C 2 ~C 30 Heteroaryl, C 2 ~C 10 Alkenyl, C 2 ~C 10 Alkynyl, C 1 ~C 10 Alkoxy, C 6 ~C 10 Aryloxy, arylamino, or one or more of them;

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

[0031] Furthermore, the structure of the boron-containing organic compound is as shown in any one of General Formulas (3-1) to (3-5):

[0032]

[0033]

[0034] In General Formulas (3-1) to (3-5), the meanings of R 1 -R 15 and X are the same as those defined in General Formula (1);

[0035] R 16 -R 19 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group, or a substituted or unsubstituted silyl group;

[0036] The substituents used to replace the above-mentioned groups that can be substituted are optionally selected from a deuterium atom, a halogen atom, a cyano group, a C 1 ~C 10 alkyl group, a deuterium-substituted C 1 ~C 10 alkyl group, a fluorine-substituted C 1 ~C10 alkyl, C 3 -C 10 cycloalkyl, deuterium-substituted C 3 -C 10 cycloalkyl, C 6 -C 30 aryl, deuterium-substituted C 6 -C 30 aryl, C 5 -C 30 heteroaryl, deuterium-substituted C 2 -C 30 heteroaryl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 10 alkoxy, C 6 -C 10 aryloxy, arylamino, or one or more of them;

[0037] The heteroatom in the heteroaryl is optionally selected from one of O, S, N, Si, and B.

[0038] Furthermore, the structure of the boron-containing organic compound is represented by any one of general formula (4-1) to general formula (4-2):

[0039]

[0040] In general formula (4-1) to general formula (4-2), the meanings of R 3 -R 15 and X are the same as those defined in general formula (1);

[0041] R 16 -R 19 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 10 alkyl, a substituted or unsubstituted C 3 -C 10 cycloalkyl, a substituted or unsubstituted C 2 -C 10 alkenyl, a substituted or unsubstituted C 1 -C 10 alkoxy, a substituted or unsubstituted C 6 -C 10 aryloxy, a substituted or unsubstituted arylamino, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 2 -C 30 heteroaryl, or a substituted or unsubstituted silyl group;

[0042] Each occurrence of Z, the same or different, is represented as C-(H) or C-(R 0 ); R 0 is represented as a deuterium atom, a halogen atom, a cyano group, C 1 ~C 10 alkyl, deuterium-substituted C 1 ~C 10 alkyl, fluorine-substituted C 1 ~C 10 alkyl, C 3 ~C 10 cycloalkyl, deuterium-substituted C 3 ~C 10 cycloalkyl, C 6 ~C 30 aryl, deuterium-substituted C 6 ~C 30 aryl, C 5 ~C 30 heteroaryl, deuterium-substituted C 2 ~C 30 heteroaryl, C 2 ~C 10 alkenyl, C 2 ~C 10 alkynyl, C 1 ~C 10 alkoxy, C 6 ~C 10 aryloxy, arylamino, or one of them;

[0043] The substituents for substituting the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, C 1 ~C 10 alkyl, deuterium-substituted C 1 ~C 10 alkyl, fluorine-substituted C 1 ~C 10 alkyl, C 3 ~C 10 cycloalkyl, deuterium-substituted C 3 ~C 10 cycloalkyl, C 6 ~C 30 aryl, deuterium-substituted C 6 ~C 30 aryl, C 5 ~C 30 heteroaryl, deuterium-substituted C 2 ~C 30 heteroaryl, C 2 ~C 10 alkenyl, C 2 ~C 10 alkynyl, C 1 ~C10 Alkoxy, C 6 ~C 10 One or more of aryloxy, arylamino;

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

[0045] Furthermore, the structure of the boron-containing organic compound is represented by any one of general formulas (5-1) to (5-6):

[0046]

[0047] In general formulas (5-1) to (5-6), Z, R 1 -R 10 has the same meaning as defined in general formula (1);

[0048] R 16 -R 35 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group, a substituted or unsubstituted silyl group;

[0049] X 1 represents one of a carbon atom or a silicon atom;

[0050] The substituents for substituting the above-mentioned substituable groups are optionally selected from a deuterium atom, a halogen atom, a cyano group, C 1 ~C 10 alkyl group, a deuterium-substituted C 1 ~C 10 alkyl group, a fluorine-substituted C 1 ~C 10 alkyl group, C 3 ~C 10 cycloalkyl group, a deuterium-substituted C 3 ~C 10 cycloalkyl group, C 6 ~C30 Aryl, deuterium-substituted C 6 -C 30 Aryl, C 5 -C 30 Heteroaryl, deuterium-substituted C 2 -C 30 Heteroaryl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl, C 1 -C 10 Alkoxy, C 6 -C 10 One or more of aryloxy, arylamino;

[0051] The heteroatom in the heteroaryl is optionally selected from one of O, S, N, Si, B.

[0052] Furthermore, the structure of the boron-containing organic compound is shown in any one of general formulas (6-1) to (6-6):

[0053]

[0054] In general formulas (6-1) to (6-6), the meanings of Z, R 4 , R 7 , R 8 , R 17 , R 23 , R 27 , R 34 , X 1 are the same as defined above;

[0055] Preferably, the structure of the boron-containing organic compound is shown in any one of general formulas (7-1) to (7-4):

[0056]

[0057]

[0058] In general formulas (7-1) to (7-4), the meanings of Z, R 4 , R 7 , R 8 , R 17 , R 23 , R 27 , R 34 are the same as defined above.

[0059] Further, M is represented by any of the following groups which may be substituted or unsubstituted by R: phenyl, naphthyl, anthryl, phenanthryl, pyridyl, quinolinyl, furyl, thienyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, indolo[3,2,1-jk]carbazolyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, spirofluorene;

[0060] Each occurrence of R, which may be the same or different, is represented by any of the following: deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorene, substituted or unsubstituted amino group, substituted or unsubstituted triazinyl;

[0061] Said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31, R 32 , R 33 , R 34 , R 35 are each independently represented by any one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, and a substituted or unsubstituted triazinyl group;

[0062] wherein the R 11 is represented by any one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted indolo[3,2,1-jk]carbazolyl group, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted spirofluorene group, and a substituted or unsubstituted arylamino group;

[0063] wherein the R 0Represented by any one of a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, and a substituted or unsubstituted triazinyl group;

[0064] The substituents for the substituent groups are each independently selected from a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuryl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group;

[0065] Preferably, the M ring is represented by the following groups:

[0066]

[0067] any one of;

[0068] Z, each occurrence being the same or different, is represented by C-(H) or C-(R 0 );

[0069] R 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 12 、R 13 、R 14 、R15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 are each independently represented as a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, a phenyl group, any one of;

[0070] The said R 11 is represented as any one of.

[0071] Furthermore, the specific structure of the boron-containing organic compound is any one of the following structures:

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086] The present invention also provides an organic electroluminescent device, which sequentially includes a substrate, a first electrode, an organic light-emitting functional layer, and a second electrode. The organic light-emitting functional layer is located between the first electrode and the second electrode. The organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound described above.

[0087] Preferably, the light-emitting layer includes a host material and a doping material, and the doping material contains the boron-containing organic compound.

[0088] Preferably, the light-emitting layer includes a first host material, a second host material, and a doping material. At least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound described above.

[0089] In a preferred embodiment, the light-emitting layer includes a host material, an exciton sensitizing material, and a doping material. The exciton sensitizing material is a metal element-containing complex, and the doping material is the boron-containing organic compound described above.

[0090] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0091] (1) The compound of the present invention can be used as a doping material for the light-emitting layer material when applied to an OLED device, and can emit green fluorescence under the action of an electric field, and can be applied to the fields of OLED lighting or OLED display.

[0092] (2) As a doping material, the compound of the present invention introduces a phosphorus photosensitizer, which can effectively improve the device lifetime.

[0093] (3) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the device color gamut. BRIEF DESCRIPTION OF THE DRAWINGS

[0094] Figure 1 It is a schematic structural diagram of the materials listed in the present invention applied to an OLED device.

[0095] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0096] The present invention will be specifically described below with reference to the drawings and embodiments.

[0097] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms indicating orientation such as "upper", "lower", "top", and "bottom" only represent the orientation in a specific state, and do not mean that the related structures can only exist in the stated orientation; on the contrary, if the structure can change its position, for example, be inverted, the orientation of the structure will change accordingly. Specifically, in the present invention, the "bottom" and "lower" sides of the electrode refer to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" and "upper" sides.

[0098] In the present invention, the substituted or unsubstituted arylamino group referred to in the present invention means where Q 1 , Q 2 represents a substituted or unsubstituted aromatic group, and Q 4 , Q 5 is preferably represented as a substituted or unsubstituted C 6 -C 30 aryl or a substituted or unsubstituted C 2 ~C 30 heteroaryl.

[0099] In the present invention, the substituted or unsubstituted C 6 -C 30 aryl refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms, still more preferably an aryl group having 8 to 10 carbon atoms, and is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group, a substituted or unsubstituted di-p-terphenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a combination thereof, or a fused ring of the foregoing group combinations, but not limited thereto.

[0100] In the present invention, the substituted or unsubstituted C 2 ~C 30Heteroaryl refers to heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 4 to 20 carbon atoms, preferably heteroaryl having 5 to 20 carbon atoms, preferably heteroaryl having 4 to 10 carbon atoms, preferably heteroaryl having 5 to 10 carbon atoms, preferably substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, combinations thereof or fused rings of combinations of the foregoing groups, but not limited thereto.

[0101] In the present invention, the substituted or unsubstituted C 2 ~C 30 The number of heteroatoms in the heteroaryl is 1 - 5, preferably 1 - 4. Preferably 1 - 3, preferably 1 - 2.

[0102] The C 1 -C 10 alkyl (including straight-chain alkyl and branched-chain alkyl) refers to alkyl having 1 to 10 carbon atoms, preferably alkyl having 1 to 5 carbon atoms, preferably alkyl having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but not limited thereto.

[0103] The C 3 -C 10 cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms as ring-forming atoms. In this context, C 4 -C 9 cycloalkyl is preferably used, more preferably C 5 -C 8 cycloalkyl, particularly preferably C 5 -C 7Cycloalkyl. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, cycloheptyl, etc., but are not limited thereto.

[0104] The halogen atom in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0105] The C in the present invention 1 -C 10 The alkoxy group refers to methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, isopropoxy, etc., but is not limited thereto.

[0106] The C in the present invention 2 -C 10 The alkenyl group refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylethylene, 1,2-diphenylethylene, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, etc., but is not limited thereto.

[0107] The organic electroluminescent device of the present invention may be a bottom-emitting organic electroluminescent device, a top-emitting organic electroluminescent device or a stacked organic electroluminescent device, and no specific limitation is made thereto.

[0108] The organic electroluminescent device of the present invention includes a substrate, a first electrode, a multilayer organic thin film layer and a second electrode. Among them, the multilayer organic thin film layer includes a hole transport region, a light-emitting layer and an electron transport region. The hole transport region includes a hole injection layer, a hole transport layer and an electron blocking layer. The electron transport region includes a hole blocking layer, an electron transport layer and an electron injection layer. In addition, a CPL layer may be provided on the second electrode.

[0109] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent PI film substrates; opaque substrates such as silicon substrates. Different substrates have different mechanical strengths, thermal stabilities, transparencies, surface smoothnesses, water resistances. Depending on the nature of the substrate, its usage direction is different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0110] A first electrode is formed on a substrate, and the first electrode and the second electrode can face each other. The first electrode can be an anode. The first electrode can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it can 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), etc. When the first electrode is a semi-transmissive electrode or a reflective electrode, it can include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, or Cr, and can also be an alloy of several metals, or a combination of a metal, a metal oxide, and a metal alloy. The thickness of the first electrode layer depends on the material used, usually being 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0111] The organic functional material layer disposed between the first electrode and the second electrode sequentially includes a hole transport region, a light-emitting layer, and an electron transport region from bottom to top.

[0112] In the present invention, examples of the hole transport region constituting the organic electroluminescent device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0113] As the materials for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials for organic electroluminescent devices for use.

[0114] The hole injection layer contains a host organic material that can conduct holes, and also contains a P-type doping material with a deep HOMO energy level (the corresponding LUMO energy level will also be deep). Based on empirical summaries, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the host organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doping material, so as to expect the occurrence of a charge transfer state between the host material and the doping material, achieve Ohmic contact between the buffer layer and the anode, and achieve efficient injection from the electrode to hole injection conduction.

[0115] In view of the above empirical summaries, for hole-type host organic materials with different HOMO energy levels, different P-doping materials need to be selected to match them in order to achieve Ohmic contact at the interface and improve the hole injection effect.

[0116] Preferably, as the host organic material of the hole injection layer of the present invention, any compound disclosed in the following prior arts can be optionally selected: JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN105439999A or CN103108859A.

[0117] Preferably, the P-type doping material is a compound having charge conductivity selected from those disclosed in the prior art, and the P-type dopant can be selected from the compounds disclosed in any one of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE102007031220A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but not limited thereto.

[0118] In one embodiment of the present invention, the hole injection layer comprises a P-type doping material having charge conductivity selected from the following: quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanomethanylylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0119] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material used is 99:1 - 95:5, preferably 99:1 - 97:3, by mass.

[0120] 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.

[0121] Preferably, as the hole transport layer material of the present invention, any compound disclosed in the following prior arts can be optionally selected:

[0122]

[0123]

[0124] Preferably, the hole transport layer material of the present invention and the main organic material in the hole injection layer are selected from the same compound.

[0125] 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.

[0126] In one embodiment of the present invention, as the electron blocking layer material of the present invention, any compound disclosed in the following prior art can be optionally selected:

[0127]

[0128] 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.

[0129] After forming the hole injection layer, the hole transport layer and the electron blocking layer, a corresponding light-emitting layer is formed on the electron blocking layer.

[0130] The light-emitting layer may include a host material and a doping material. The host material can use a common green host material in the art, and the doping material uses a boron-containing organic compound represented by the general formula (1) of the present invention.

[0131] The light-emitting layer may include a single host material or a dual host material;

[0132] The dual host material includes a first host material and a second host material. At least one of the first host material and the second host material is preferably a TADF material;

[0133] The TADF material refers to a material with thermally activated delayed fluorescence properties, characterized by having a small energy level difference between the first singlet excited state and the first triplet excited state. Therefore, singlet excitons and triplet excitons generated can be simultaneously utilized in the device, enabling the utilization rate of excitons generated electro-optically inside the device to be as close as possible to 100%. Compared with traditional fluorescent materials, the TADF material has a higher exciton utilization rate.

[0134] The light-emitting layer may include a host material, an exciton sensitizing material, and a doping material;

[0135] An exciton-sensitizing material refers to a material that can enable the luminescent material in the light-emitting layer to make full use of electro-generated excitons, so that the light-emitting layer finally generates the emission spectrum of the sensitized material. The exciton sensitizer may perform functions such as exciton capture, exciton conversion, and exciton transfer in the electroluminescent device. The boron-containing organic compound represented by the general formula (1) of the present invention is used in combination with the exciton-sensitizing material, which has an obvious improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0136] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material used is 99:1 - 70:30, preferably 99:1 - 85:15, and more preferably 97:3 - 87:13, based on mass.

[0137] The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, further preferably 10 - 50 nm, and more preferably 15 - 40 nm, but the thickness is not limited to this range.

[0138] In the present invention, the electron transport region may sequentially include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer provided above the light-emitting layer, but is not limited thereto.

[0139] The hole blocking layer is a layer that blocks the holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby prolonging the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be provided above the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds known in the prior art with hole blocking effects can be used, for example:

[0140]

[0141] The thickness of the hole blocking layer of the present invention can be 2 - 200 nm, preferably 5 - 150 nm, and more preferably 5 - 50 nm, but the thickness is not limited to this range.

[0142] The electron transport layer can be provided above the light-emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that can easily receive electrons from the cathode and transfer the received electrons to the light-emitting layer. A material with a high electron mobility is preferred. As the electron transport layer material 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:

[0143]

[0144]

[0145] In a preferred embodiment of the present invention, the electron transport layer further includes other compounds conventionally used in the electron transport layer, for example, Alq3 , LiQ, preferably LiQ.

[0146] 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.

[0147] The electron injection layer can be disposed on the electron transport layer. The electron injection layer material is generally preferably a material with a low work function, so that electrons can be easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer materials for organic electroluminescent devices disclosed in the prior art can be used, such as: LiF, Cs 2 CO 3 , CsF, Csq, NaF, MgF 2 , CaF 2 , Al 2 O 3 , Yb, etc.

[0148] 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.

[0149] The second electrode can be disposed on the electron transport region. The second electrode can be a cathode. The second electrode can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode can include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode can include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0150] The organic electroluminescent device of the present invention may further include a packaging structure. The packaging structure can be a protective structure for preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The packaging structure can be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.

[0151] A method for preparing the organic electroluminescent device of the present invention, which includes successively laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer and a cathode on a substrate, and optionally a covering layer. 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 each of the layers. Those skilled in the art can conventionally select various process conditions in the vacuum evaporation method according to actual needs.

[0152] Synthesis Example

[0153] The raw materials involved in the synthesis examples of the present invention can all be purchased from the market or prepared by conventional preparation methods in the art;

[0154] Synthesis of Compound 5 in Example 1:

[0155]

[0156]

[0157] Preparation of Intermediate a-1:

[0158] Raw material A-1 (1.68 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) were added to a two-necked flask. Under nitrogen protection, 50 mL of anhydrous DMF was added, and the mixture was stirred at room temperature for 30 min. Under nitrogen protection, raw material B-1 (1.4 g, 5 mmol) was added, and the mixture was stirred at 140 °C for 12 hours under nitrogen protection. After filtration, washing with water, drying, and column chromatography with PE:EA = 20:1, Intermediate a-1 was obtained.

[0159] Preparation of Intermediate b-1:

[0160] Intermediate a-1 (3.03 g, 5.1 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen passing at 0 °C, 3.8 mL of a 1.6 M n-butyllithium solution in n-hexane was slowly added; after stirring at 0 °C for 2 hours, 10 mL of a THF solution of raw material C-1 (0.99 g, 5.5 mmol) was slowly added. Then the reaction mixture was slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water and ethyl acetate were added to the reaction mixture, and 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 quenched slowly with an aqueous NaHCO 3 aqueous solution. Then the aqueous layer was separated and extracted with dichloromethane. Dried over sodium sulfate, filtered, and evaporated by rotary evaporation, and column chromatography was carried out to obtain Intermediate b-1.

[0161] Preparation of Intermediate c-1:

[0162] Add raw material E-1 (4.46 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) into a two-necked flask. Under nitrogen protection, add 100 mL of anhydrous DMF, stir at room temperature for 30 min, add raw material D-1 (6.72 g, 25 mmol) under nitrogen protection, stir at 140 °C for 12 hours under nitrogen protection, filter, wash with water, dry, and column chromatograph with PE:EA = 20:1 to obtain Intermediate c-1.

[0163] Preparation of Intermediate d-1:

[0164] Under nitrogen protection, add 6.3 g (10 mmol) of Intermediate b-1, 3.8 g (12 mmol) of Intermediate c-1, 2.1 g (15 mmol) of potassium carbonate, 0.1 g (0.5 mmol) of palladium acetate, 0.4 g (1.5 mmol) of tetrabutylphosphonium tetrafluoroborate and 100 mL of DMAC into a three-necked flask, and reflux for 18 hours. After the reaction is completed, reduce the pressure and concentrate the organic layer, and then purify by silica gel column chromatography to obtain Intermediate d-1.

[0165] Preparation of Compound 5:

[0166] In a sealed pressure-resistant tube, under nitrogen protection, add 8.7 g (10 mmol) of Intermediate d-1 and 75 mL of anhydrous o-dichlorobenzene. After cooling to -78 °C, dropwise add 4.8 mL of 2.5 M sec-butyllithium-n-hexane solution. Transfer to 60 °C and react for 6 hours. After the reaction is cooled to -42 °C, dropwise add 1.4 mL (15 mmol) of boron tribromide. Slowly warm to room temperature and react for 3 hours. After cooling to 0 °C, dropwise add 2.6 mL (20 mmol) of ultra-dry N,N-diisopropylethylamine. Heat the reaction solution to 180 °C and react for 15 hours. Cool to room temperature, distill off the low-boiling solvent under reduced pressure, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate and filter to collect the filtrate. Concentrate and purify by column chromatography to obtain Compound 5. The half-peak width of Compound 5 in toluene solution (1×10 -5 M) is 22 nm, which is measured by a Fluorolog-3 series fluorescence spectrometer from Horiba.

[0167] Synthesis of Compound 28 in Example 2:

[0168]

[0169] Preparation of Intermediate c-2:

[0170] Add raw material E-2 (7.26 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol) and palladium acetate (0.09 g, 0.4 mmol) into a two-necked flask, add 100 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material D-1 (6.72 g, 25 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA=20:1 to obtain intermediate c-2.

[0171] Preparation of intermediate d-2:

[0172] Under nitrogen protection, 6.3g (10mmol) of intermediate b-1, 5.2g (12mmol) of intermediate c-2, 2.1g (15mmol) of potassium carbonate, 0.1g (0.5mmol) of palladium acetate, 0.4g (1.5mmol) of tri-tert-butylphosphine tetrafluoroborate and 100mL of DMAC were added to a three-necked flask and refluxed for 18 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate d-2.

[0173] Preparation of compound 28:

[0174] In a sealed pressure tube, under nitrogen protection, 9.8 g (10 mmol) of intermediate d-2 and 75 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 ° C, 4.8 mL of 2.5 M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60 ° C for reaction for 6 hours, the reaction was cooled to -42 ° C, 1.4 mL (15 mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 3 hours. After cooling to 0 ° C, 2.6 mL (20 mmol) of ultra-dry N, N-diisopropylethylamine was added dropwise, and the reaction solution was heated to 180 ° C for 15 hours. Cool to room temperature, remove low boiling point solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate and separate and purify with column chromatography to obtain compound 28. Compound 28 in toluene solution (1×10 -5 M) The half-peak width is 21 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0175] Example 3 Synthesis of Compound 56:

[0176]

[0177]

[0178] Preparation of raw material E-3:

[0179] Pd(PPh 3 ) 2 Cl 2 (0.2g, 0.3mmol) and raw material C-3 (0.3g, 4mmol), the mixture was stirred at 100°C for 24h, cooled, filtered, rinsed with 30ml DMF, and the solvent was removed from the filtrate in vacuo. The solution was then washed 5 times with 100ml of water and once with 100ml of saturated sodium chloride solution, and the organic phase was dried over magnesium sulfate. After removing ethyl acetate in vacuo, the raw material E-3 was obtained by passing through a silica gel (n-heptane: ethyl acetate = 99:1) column.

[0180] Preparation of intermediate c-3:

[0181] Add raw material E-3 (9.97 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) into a two-necked flask, add 100 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material D-1 (6.72 g, 25 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA=20:1 to obtain intermediate c-3.

[0182] Preparation of intermediate d-3:

[0183] Under nitrogen protection, 6.3g (10mmol) of intermediate b-1, 6.5g (12mmol) of intermediate c-3, 2.1g (15mmol) of potassium carbonate, 0.1g (0.5mmol) of palladium acetate, 0.4g (1.5mmol) of tri-tert-butylphosphine tetrafluoroborate and 100mL of DMAC were added to a three-necked flask and refluxed for 18 hours. After the reaction, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate d-3.

[0184] Preparation of compound 56:

[0185] In a sealed pressure tube, under nitrogen protection, 10.9 g (10 mmol) of intermediate d-3 and 75 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 ° C, 4.8 mL of 2.5 M sec-butyl lithium-n-hexane solution was added dropwise. After transferring to 60 ° C for reaction for 6 hours, the reaction was cooled to -42 ° C, 1.4 mL (15 mmol) of boron tribromide was added dropwise, and the reaction was slowly restored to room temperature for 3 hours. After cooling to 0 ° C, 2.6 mL (20 mmol) of ultra-dry N, N-diisopropylethylamine was added dropwise, and the reaction solution was heated to 180 ° C for 15 hours. Cool to room temperature, remove low boiling point solvents by vacuum distillation, dissolve with dichloromethane, filter, dry with anhydrous sodium sulfate, collect the filtrate by filtration, concentrate and separate and purify with column chromatography to obtain compound 56. Compound 56 in toluene solution (1×10 -5 M) The half-peak width is 20 nm, which is measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, deuterated chloroform) δ 8.98–8.86 (d, 1H), 8.30–8.21 (m, 1H), 7.81–7.70 (d, 3H), 7.67–7.51 (m, 3H), 7.49–7.17 (m, 12H), 7.16–6.96 (m, 3H), 6.88–6.71 (m, 2H), 1.50–1.42 (d, 8H), 1.39–1.22 (m, 42H).

[0186] Example 4 Synthesis of Compound 147:

[0187]

[0188] Preparation of intermediate d-4:

[0189] Under nitrogen protection, 6.3g (10mmol) of intermediate b-1, 2.6g (12mmol) of raw material D-4, 2.1g (15mmol) of potassium carbonate, 0.1g (0.5mmol) of palladium acetate, 0.4g (1.5mmol) of tri-tert-butylphosphine tetrafluoroborate and 100mL of DMAC were added to a three-necked flask and refluxed for 18 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate d-4.

[0190] Preparation of compound 147:

[0191] In a sealed pressure-resistant tube, under nitrogen protection, 7.7 g (10 mmol) of intermediate d-4 and 75 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 °C, 4.8 mL of a 2.5 M sec-butyllithium-n-hexane solution was added dropwise. After transferring to 60 °C and reacting for 6 hours, the reaction was cooled to -42 °C, and 1.4 mL (15 mmol) of boron tribromide was added dropwise. After slowly returning to room temperature, the reaction was carried out for 3 hours. Under the condition of cooling to 0 °C, 2.6 mL (20 mmol) of ultra-dry N,N-diisopropylethylamine was added dropwise, and the reaction solution was heated to 180 °C and reacted for 15 hours. After cooling to room temperature, the low-boiling solvent was removed by distillation under reduced pressure. It was dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate and filtered to collect the filtrate. The concentrate was separated and purified by column chromatography to obtain compound 147. The half-peak width of compound 147 in a toluene solution (1×10 -5 M) was 23 nm, which was measured by a Horiba Fluorolog-3 series fluorescence spectrometer. 1 1H NMR (400 MHz, chloroform-d) δ 8.96–8.89 (d, 1H), 8.36–8.15 (m, 2H), 7.84–7.68 (d, 3H), 7.64–7.58 (d, 2H), 7.55–7.17 (m, 10H), 7.15–6.95 (m, 3H), 6.88–6.73 (m, 2H), 1.41–1.21 (d, 18H).

[0192] Synthesis of compound 244 in Example 5:

[0193]

[0194] Preparation of intermediate b-5:

[0195] Under nitrogen protection, 2.8 g (10 mmol) of raw material B-1, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask. The reaction was stirred at room temperature for 0.5 hour, and 2.7 g (10 mmol) of raw material A-5 dissolved in 25 mL of anhydrous DMF was added dropwise. The reaction was carried out at 80 °C for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction. The mixture was concentrated and separated and purified by silica gel column chromatography to obtain intermediate b-5.

[0196] Preparation of intermediate d-5:

[0197] Under nitrogen protection, 4.3 g (10 mmol) of intermediate c-2, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask. The reaction was stirred at room temperature for 0.5 h, and 5.3 g (10 mmol) of intermediate b-5 dissolved in 25 mL of anhydrous DMF was added dropwise. The reaction was carried out at 80 °C for 5 h. After cooling to room temperature, 1 mL of water was added to quench the reaction. The reaction mixture was concentrated and purified by silica gel column chromatography to obtain intermediate d-5.

[0198] Preparation of Compound 244:

[0199] In a sealed pressure-resistant tube, under nitrogen protection, 9.4 g (10 mmol) of intermediate d-5 and 75 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 °C, 4.8 mL of 2.5 M n-butyllithium-n-hexane solution was added dropwise. After transferring to 60 °C and reacting for 6 h, the reaction was cooled to -42 °C, and 1.4 mL (15 mmol) of boron tribromide was added dropwise. After slowly returning to room temperature, the reaction was carried out for 3 h. After cooling to 0 °C, 2.6 mL (20 mmol) of ultra-dry N,N-diisopropylethylamine was added dropwise. The reaction solution was heated to 180 °C and reacted for 15 h. After cooling to room temperature, the low-boiling solvent was removed by distillation under reduced pressure. The residue was dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate and filtered to collect the filtrate. The filtrate was concentrated and purified by column chromatography to obtain Compound 244. The half-peak width of Compound 244 in toluene solution (1×10 -5 M) is 22 nm, which was measured by a Horiba Fluorolog-3 series fluorescence spectrometer. 1 1H NMR (400 MHz, CDCl3) δ 8.95–8.90 (d, 1H), 8.46–8.27 (m, 1H), 8.05–7.68 (m, 7H), 7.67–7.24 (m, 11H), 7.19–6.96 (m, 5H), 1.46–1.24 (m, 36H).

[0200] Synthesis of Compound 286 in Example 6:

[0201]

[0202] Preparation of Raw Material B-6:

[0203] Under nitrogen protection, 2.6 g (10 mmol) of raw material C-6, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask. The mixture was stirred at room temperature for 0.5 h, and 1.5 g (10 mmol) of raw material D-6 dissolved in 25 mL of anhydrous DMF was added dropwise. The reaction was carried out at 80 °C for 5 h. After cooling to room temperature, 1 mL of water was added to quench the reaction. The mixture was concentrated and purified by silica gel column chromatography to obtain raw material B-6.

[0204] Preparation of intermediate b-6:

[0205] Under nitrogen protection, 3.9 g (10 mmol) of raw material B-6, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask. The mixture was stirred at room temperature for 0.5 h, and 2.5 g (10 mmol) of raw material A-6 dissolved in 25 mL of anhydrous DMF was added dropwise. The reaction was carried out at 80 °C for 5 h. After cooling to room temperature, 1 mL of water was added to quench the reaction. The mixture was concentrated and purified by silica gel column chromatography to obtain intermediate b-6.

[0206] Preparation of intermediate d-6:

[0207] Under nitrogen protection, 4.3 g (10 mmol) of intermediate c-2, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask. The mixture was stirred at room temperature for 0.5 h, and

[0208] 6.2 g (10 mmol) of intermediate b-6 dissolved in 25 mL of anhydrous DMF was added dropwise. The reaction was carried out at 80 °C for 5 h. After cooling to room temperature, 1 mL of water was added to quench the reaction. The mixture was concentrated and purified by silica gel column chromatography to obtain intermediate d-6.

[0209] Preparation of compound 286:

[0210] In a sealed pressure-resistant tube, under nitrogen protection, 10.3 g (10 mmol) of intermediate d-6 and 75 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 °C, 4.8 mL of 2.5 M n-butyllithium-n-hexane solution was added dropwise. After transferring to 60 °C and reacting for 6 hours, the reaction was cooled to -42 °C, and 1.4 mL (15 mmol) of boron tribromide was added dropwise. After slowly returning to room temperature, the reaction was carried out for 3 hours. After cooling to 0 °C, 2.6 mL (20 mmol) of ultra-dry N,N-diisopropylethylamine was added dropwise, and the reaction solution was heated to 180 °C and reacted for 15 hours. After cooling to room temperature, the low-boiling solvent was removed by distillation under reduced pressure. It was dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate and filtered to collect the filtrate. The concentrate was separated and purified by column chromatography to obtain compound 286. The half-peak width of compound 286 in toluene solution (1×10 -5 M) was 19 nm, which was measured by a Horiba Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, chloroform-d) δ 7.97–7.81 (m, 6H), 7.80–7.70 (m, 1H), 7.68–

[0211] 7.50 (m, 5H), 7.49–7.36 (m, 5H), 7.35–7.24 (m, 4H), 7.23–7.15 (m, 3H), 7.14–6.99 (m, 3H), 6.96–6.85 (d, 1H), 1.52–1.22 (m, 36H).

[0212] Example 7 Synthesis of Compound 287:

[0213]

[0214] Preparation of Raw Material B-7:

[0215] Under nitrogen protection, 4.6 g (10 mmol) of raw material C-7, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask. The reaction was stirred at room temperature for 0.5 hour, and 1.5 g (10 mmol) of raw material D-6 dissolved in 25 mL of anhydrous DMF was added dropwise. The reaction was carried out at 80 °C for 5 hours. After cooling to room temperature, 1 mL of water was added to quench the reaction. It was concentrated and separated and purified by silica gel column chromatography to obtain raw material B-7.

[0216] Preparation of Intermediate b-7:

[0217] Under nitrogen protection, 5.9 g (10 mmol) of raw material B-7, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask. The mixture was stirred at room temperature for 0.5 h, and 2.5 g (10 mmol) of raw material A-6 dissolved in 25 mL of anhydrous DMF was added dropwise. The reaction was carried out at 80 °C for 5 h. After cooling to room temperature, 1 mL of water was added to quench the reaction. The mixture was concentrated and purified by silica gel column chromatography to obtain intermediate b-7.

[0218] Preparation of intermediate d-7:

[0219] Under nitrogen protection, 4.3 g (10 mmol) of intermediate c-2, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF were added to a three-necked flask. The mixture was stirred at room temperature for 0.5 h, and 8.2 g (10 mmol) of intermediate b-7 dissolved in 25 mL of anhydrous DMF was added dropwise. The reaction was carried out at 80 °C for 5 h. After cooling to room temperature, 1 mL of water was added to quench the reaction. The mixture was concentrated and purified by silica gel column chromatography to obtain intermediate d-7.

[0220] Preparation of compound 287:

[0221] In a sealed pressure-resistant tube, under nitrogen protection, 12.3 g (10 mmol) of intermediate d-7 and 75 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 °C, 4.8 mL of 2.5 M n-butyllithium-n-hexane solution was added dropwise. The mixture was transferred to 60 °C and reacted for 6 h. Then the reaction was cooled to -42 °C, and 1.4 mL (15 mmol) of boron tribromide was added dropwise. After slowly returning to room temperature, the reaction was carried out for 3 h. After cooling to 0 °C, 2.6 mL (20 mmol) of ultra-dry N,N-diisopropylethylamine was added dropwise. The reaction solution was heated to 180 °C and reacted for 15 h. After cooling to room temperature, the low-boiling solvent was removed by distillation under reduced pressure. The residue was dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate and filtered to collect the filtrate. The filtrate was concentrated and purified by column chromatography to obtain compound 287. The half-peak width of compound 287 in toluene solution (1×10 -5 M) is 22 nm, which was measured by a Fluorolog-3 series fluorescence spectrometer from Horiba. 1 1H NMR (400 MHz, chloroform-d) δ 7.95–7.80 (m, 4H), 7.79–7.71 (m, 1H), 7.69–7.25 (m, 30H), 7.24–7.20 (d, 1H), 7.19–7.14 (s, 1H), 7.13–7.01 (m, 2H), 6.96–6.57 (d, 1H), 1.45–1.28 (m, 36H).

[0222] Synthesis of Compound 330 in Example 8:

[0223]

[0224]

[0225] Preparation of Raw Material C-8-1:

[0226] Under nitrogen protection, 50 g of raw material C-8 (0.335 mol) was dissolved in anhydrous ACN (500 mL). The reaction system was cooled to 0 °C, and 59.63 g of NBS (0.335 mmol) was slowly added. After the addition was complete, the temperature was maintained and stirring continued for 3 hours. Subsequently, the reaction was quenched with water, extracted with ethyl acetate successively, washed with saturated brine, and dried over anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure, and column chromatography (petroleum ether / ethyl acetate = 20 / 1) was used to obtain raw material C-8-1.

[0227] Preparation of Raw Material C-8-2:

[0228] Under nitrogen protection, 31.03 g of raw material C-8-1 (0.136 mol), 16.58 g of raw material D-8-1 (0.136 mol), and 56.39 g of K 2 CO 3 (0.408 mol) were dissolved in 1,4-dioxane (310 mL) and water (100 mL). Then, 1.98 g of Pd(dppf)Cl 2 (2.71 mmol) was added. The reaction system was reacted at 80 °C for 16 hours. After the reaction was completed, the mixture was filtered while hot, extracted with ethyl acetate successively, washed with saturated brine, and dried over anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure, and column chromatography (petroleum ether / ethyl acetate = 20 / 1) was used to obtain raw material C-8-2.

[0229] Preparation of Raw Material C-8-3:

[0230] Under nitrogen protection, 40.11 g of raw material C-8-2 (0.178 mol) was dissolved in anhydrous THF (400 mL). The reaction system was cooled to 0 °C, and a solution of concentrated hydrochloric acid (81.7 mL) in water (235 mL) was slowly added dropwise. After the addition was complete, 18.42 g of NaNO 2(0.267 mol) aqueous solution of water (90 mL), keep the reaction temperature below 5 °C. After the dropping is completed, the reaction system is stirred for another 15 minutes. Aqueous solution of 58.93 g KI (0.355 mol) in water (371.5 mL) is added dropwise to the reaction system, keeping the reaction temperature below 5 °C. After the dropping is completed, stir at this temperature for 2 hours. Subsequently, the reaction is quenched with saturated sodium sulfite solution, extracted with ethyl acetate successively and washed with saturated brine, anhydrous Na 2 SO 4 dried, the solvent is rotary evaporated, and column chromatography (petroleum ether = 100%) gives the starting material C-8-3.

[0231] Preparation of starting material D-8-3:

[0232] Under nitrogen protection and anhydrous and anaerobic conditions, 70.10 g of starting material D-8-2 (0.337 mol), 93.96 g of B 2 Pin 2 (0.370 mol) and 99.12 g of KOAc (1.01 mol) are dissolved in anhydrous DMF (500 mL), 4.92 g of Pd(dppf)Cl 2 is added (6.73 mmol), and the reaction system is reacted at 100 °C for 16 hours. After the reaction is completed, filter while it is hot, and most of the DMF is concentrated with an oil pump. Dissolve with ethyl acetate, wash successively with water and saturated brine, anhydrous Na 2 SO 4 dried, the solvent is rotary evaporated, and column chromatography (petroleum ether / ethyl acetate = 20 / 1) gives the starting material D-8-3.

[0233] Preparation of starting material C-8-4:

[0234] Under nitrogen protection and anhydrous and anaerobic conditions, 129.11 g of starting material C-8-3 (0.384 mol), 97.95 g of starting material D-8-3 (0.384 mol) and 76.15 g of K 2 CO 3 (0.551 mol) are dissolved in 1,4-dioxane (720 mL) and water (150 mL), 2.69 g of Pd(dppf)Cl 2 is added (3.67 mmol), and the reaction system is reacted at 60 °C for 16 hours. After the reaction is completed, filter while it is hot, extract with ethyl acetate successively and wash with saturated brine, anhydrous Na 2 SO 4 dried, the solvent is rotary evaporated, and column chromatography (petroleum ether / ethyl acetate = 50 / 1) gives the starting material C-8-4.

[0235] Preparation of starting material A-8:

[0236] To 8.57 g of raw material C-8-4 (25.4 mmol) and 28.37 g of CuBr 2 (127 mmol), add acetonitrile (300 mL). Cool the reaction system to 0 °C and slowly add Isoamyl nitrite (10.24 mL) dropwise. After reacting for 16 hours, quench the reaction with aqueous ammonia solution, extract with ethyl acetate and wash with saturated brine in sequence, and dry with anhydrous Na 2 SO 4 Dry, evaporate the solvent, and obtain raw material A-8 by column chromatography (petroleum ether).

[0237] Preparation of intermediate b-8:

[0238] Under nitrogen protection, add 2.8 g (10 mmol) of raw material B-1, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF to a three-necked flask, stir and react at room temperature for 0.5 hour, and gradually add dropwise 4.0 g (10 mmol) of raw material A-8 dissolved in 25 mL of anhydrous DMF, and react at 80 °C for 5 hours. After cooling to room temperature, add 1 mL of water to quench the reaction, concentrate and purify by silica gel column chromatography to obtain intermediate b-8.

[0239] Preparation of intermediate d-8:

[0240] Under nitrogen protection, add 2.2 g (10 mmol) of raw material D-4, 0.4 g (11 mmol) of NaH dissolved in mineral oil (60%) and 50 mL of anhydrous DMF to a three-necked flask, stir and react at room temperature for 0.5 hour, and gradually add dropwise 6.6 g (10 mmol) of intermediate b-8 dissolved in 25 mL of anhydrous DMF, and react at 80 °C for 5 hours. After cooling to room temperature, add 1 mL of water to quench the reaction, concentrate and purify by silica gel column chromatography to obtain intermediate d-8.

[0241] Preparation of compound 330:

[0242] In a sealed pressure-resistant tube, under nitrogen protection, 8.6 g (10 mmol) of intermediate d-8 and 75 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 °C, 4.8 mL of 2.5 M n-butyllithium-n-hexane solution was added dropwise. After transferring to 60 °C and reacting for 6 hours, the reaction was cooled to -42 °C, and 1.4 mL (15 mmol) of boron tribromide was added dropwise. After slowly returning to room temperature, the reaction was carried out for 3 hours. After cooling to 0 °C, 3.5 mL (20 mmol) of ultra-dry N,N-diisopropylethylamine was added dropwise, and the reaction solution was heated to 180 °C and reacted for 15 hours. After cooling to room temperature, the low-boiling solvent was removed by distillation under reduced pressure. It was dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate and filtered to collect the filtrate. The concentrate was separated and purified by column chromatography to obtain compound 330. The half-peak width of compound 330 in toluene solution (1×10 -5 M) is 23 nm, which was measured by a Fluorolog-3 series fluorescence spectrometer from Horiba. 1 1H NMR (400 MHz, chloroform-d) δ 8.97–8.90 (dd, 1H), 8.47–8.16 (m, 2H), 8.03–7.72 (m, 5H), 7.71–7.18 (m, 13H), 7.16–6.95 (m, 3H), 1.49–1.38 (d, 18H), 1.32–1.25 (s, 9H).

[0243] The structural characterizations of the compounds obtained in each example are shown in Table 1

[0244] Table 1

[0245]

[0246]

[0247] The application effects of the OLED materials synthesized by the present invention in the devices are described in detail below through Device Examples 1-8 and Device Comparative Examples 1-3. The manufacturing processes of the devices in Device Examples 2-8 and Device Comparative Examples 1-3 are exactly the same as those in Device Example 1, and the same substrate materials and electrode materials are used. The film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Tables 2-1 and 3 respectively:

[0248] Device Example 1

[0249] As Figure 1As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using GH-1 and GH-2 as the host materials and compound 5 as the doping material, and the mass ratio of GH-1, GH-2, and compound 5 is 69:30:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously vacuum-evaporated with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, and the film thickness is 30 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0250] The application effects of the OLED materials synthesized by the present invention in the device are described in detail below through device examples 9-16 and device comparative examples 4-6. The device fabrication processes of device examples 10-16 and device comparative examples 4-6 of the present invention are exactly the same as those of device example 9, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the device are replaced. The layer structures and test results of each device example are shown in Tables 2-2 and 3 respectively:

[0251] Device Example 9

[0252] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first doping material, and compound 5 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and compound 5 is 66.5:30:3:0.5, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously vacuum-evaporated with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0253] The molecular structural formulas of the related materials are as follows:

[0254]

[0255] After the OLED light-emitting device is completed as described above, the anode and the cathode are connected by a known driving circuit, and the current efficiency, emission peak, and lifetime of the device are measured. The device examples and comparative examples prepared by the same method are shown in Tables 2-1 and 2-2; the test results of the current efficiency, emission peak, and lifetime of the obtained devices are shown in Table 3.

[0256] Table 2-1

[0257]

[0258]

[0259] Table 2-2

[0260]

[0261]

[0262] Table 3

[0263]

[0264] Note: The current efficiency and emission peak are measured using an IVL (current-voltage-brightness) test system (Suzhou FushiDa Scientific Instrument Co., Ltd.); the lifetime test system is the EAS-62C type OLED device lifetime tester from System Technology Research Co., Ltd. in Japan; LT95 refers to the time when the device brightness decays to 95%; all data are measured at 10 mA / cm 2 below.

[0265] It can be seen from the device data results in Table 3 that compared with the comparative compounds ref-1, ref-2, and ref-3, the emission peak of the compound of the present invention is between 510 and 550 nm, and the effect of green emission can be well achieved; compared with device comparative examples 1-6, for the organic light-emitting device of the present invention, whether in a single-doping system or a double-doping system, the current efficiency and lifetime of the device are improved compared to the OLED devices of known materials; when using an exciton sensitizing material as the first dopant, the device efficiency is significantly improved compared to the single-doping case.

[0266] In summary, the above are only the preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention shall 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 the general formula (1): In general formula (1), R 1 -R 10 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 6 -C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted silyl group; X is represented by O, S, N-R 11 , C-(R 12 R 13 ), Si-(R 14 R 15 ); R 11 represents a substituted or unsubstituted C 6 ~C 30 aryl, a substituted or unsubstituted C 2 ~C 30 heteroaryl; R 12 -R 15 are each independently represented by a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 30 aryloxy group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group; The M ring is represented as one or more R-substituted or unsubstituted C 6 ~C 30 aromatic ring, one or more R-substituted or unsubstituted C 2 ~C 30 heteroaromatic ring; Each occurrence of R, which may be the same or different, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 2 ~C 10 alkynyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted silyl group; The R 1 and R 2 are not connected or are connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)-, -Si(RdRe)- or -C(Rp)=C(Rq)-; The R 6 -R 10 There is no connection or connection through a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)--Si(RdRe)- or -C(Rp)=C(Rq)- between any two adjacent groups; The R 11 is not connected to the M ring or is connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)--Si(RdRe)- or -C(Rp)=C(Rq); The R 11 and R 5 are not connected or are connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)--Si(RdRe)- or -C(Rp)=C(Rq); there is no connection between Rb and Rc, Rd and Re, or they are connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)-, -Si(RdRe)- or -C(Rp)=C(Rq)-; Said R 12 and R 13 , R 14 and R 15 are not connected to each other or are connected by a single bond, -O-, -S-, -N(Ra)-, -C(RbRc)-, -Si(RdRe)- or -C(Rp)=C(Rq)-; Ra, Rb, Rc, Rd, Re, Rp, and Rq each independently represent a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 30 aryloxy group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group; When R 1 and R 2 are connected to form a benzene ring through a single bond, and R 11 and R 5 are not connected through -O- or -S-; The substituents for replacing the above-mentioned replaceable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C 1 -C 10 alkyl group, a deuterium-substituted C 1 -C 10 alkyl group, a fluorine-substituted C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterium-substituted C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a deuterium-substituted C 6 -C 30 aryl group, a C 5 -C 30 heteroaryl group, a deuterium-substituted C 2 -C 30 heteroaryl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 1 -C 10 alkoxy group, a C 6 -C 10 aryloxy group, an arylamino group, or any one or more thereof; the heteroatom in the heteroaryl is arbitrarily selected from one of O, S, N, Si, 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 the general formulas (2-1) to (2-3): In General Formulas (2-1) to (2-3), Y represents O, S, N-R 11 , C-(R 12 R 13 ), Si-(R 14 R 15 ); R 1 -R 15 The meaning of X is the same as defined in the general formula (1); R 16 -R 21 are each independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group, or a substituted or unsubstituted silyl group; The substituents for replacing the above-mentioned replaceable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C 1 -C 10 alkyl group, a deuterium-substituted C 1 -C 10 alkyl group, a fluorine-substituted C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterium-substituted C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a deuterium-substituted C 6 -C 30 aryl group, a C 5 -C 30 heteroaryl group, a deuterium-substituted C 2 -C 30 heteroaryl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 1 -C 10 alkoxy group, a C 6 -C 10 aryloxy group, an arylamino group, or one or more of them; the heteroatom in the heteroaryl is arbitrarily selected from one of O, S, N, Si, 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 any one of the general formulas (3-1) to (3-5): In General Formulas (3-1) to (3-5), R 1 -R 15 and X have the same meanings as defined in Claim 1; R 16 -R 19 are each independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group, or a substituted or unsubstituted silyl group; The substituents used to replace the above-mentioned replaceable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C 1 -C 10 alkyl group, a deuterium-substituted C 1 -C 10 alkyl group, a fluorine-substituted C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterium-substituted C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a deuterium-substituted C 6 -C 30 aryl group, a C 5 -C 30 heteroaryl group, a deuterium-substituted C 2 -C 30 heteroaryl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 1 -C 10 alkoxy group, a C 6 -C 10 aryloxy group, an arylamino group, or one or more of them; the heteroatom in the heteroaryl is arbitrarily selected from one of O, S, N, Si, B.

4. The boron-containing organic compound according to claim 1, characterized in that, the structure of the boron-containing organic compound is shown in any one of the general formulas (4-1) to (4-2): In General Formulas (4-1) to (4-2), R 3 -R 15 and X have the same meanings as defined in Claim 1; R 16 -R 19 are each independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group, or a substituted or unsubstituted silyl group; Each occurrence of Z, whether the same or different, is represented as C-(H) or C-(R 0 ); R 0 is represented as a deuterium atom, a halogen atom, a cyano group, C 1 ~C 10 alkyl, deuterium-substituted C 1 ~C 10 alkyl, fluorine-substituted C 1 ~C 10 alkyl, C 3 ~C 10 cycloalkyl, deuterium-substituted C 3 ~C 10 cycloalkyl, C 6 ~C 30 aryl, deuterium-substituted C 6 ~C 30 aryl, C 5 ~C 30 heteroaryl, deuterium-substituted C 2 ~C 30 heteroaryl, C 2 ~C 10 alkenyl, C 2 ~C 10 alkynyl, C 1 ~C 10 alkoxy, C 6 ~C 10 aryloxy, arylamino, or one of them; The substituents used to replace the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C 1 -C 10 alkyl group, a deuterium-substituted C 1 -C 10 alkyl group, a fluorine-substituted C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterium-substituted C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a deuterium-substituted C 6 -C 30 aryl group, a C 5 -C 30 heteroaryl group, a deuterium-substituted C 2 -C 30 heteroaryl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 1 -C 10 alkoxy group, a C 6 -C 10 aryloxy group, an arylamino group, or one or more of them; the heteroatom in the heteroaryl is arbitrarily selected from one of O, S, N, Si, B.

5. The boron-containing organic compound according to claim 1, characterized in that, the structure of the boron-containing organic compound is shown in any one of the general formulas (5-1) to (5-6): In General Formulas (5-1) to (5-6), Z and R 1 -R 10 have the same meanings as defined in Claim 1; R 16 -R 35 are each independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 2 to C 10 alkenyl group, a substituted or unsubstituted C 1 to C 10 alkoxy group, a substituted or unsubstituted C 6 to C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, or a substituted or unsubstituted silyl group; X 1 is represented by one of a carbon atom or a silicon atom; The substituents for replacing the above replaceable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C 1 -C 10 alkyl group, a deuterium-substituted C 1 -C 10 alkyl group, a fluorine-substituted C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterium-substituted C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a deuterium-substituted C 6 -C 30 aryl group, a C 5 -C 30 heteroaryl group, a deuterium-substituted C 2 -C 30 heteroaryl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 1 -C 10 alkoxy group, a C 6 -C 10 aryloxy group, an arylamino group, or one or more of them; the heteroatom in the heteroaryl is arbitrarily selected from one of O, S, N, Si, B.

6. The boron-containing organic compound according to claim 5, characterized in that, the structure of the boron-containing organic compound is shown in any one of the general formulas (6-1) to (6-6): In General Formula (6-1) to General Formula (6-6), the meanings of Z, R 4 , R 7 , R 8 , R 17 , R 23 , R 27 , R 34 , X 1 are the same as the definitions in Claim 5; Preferably, the structure of the boron-containing organic compound is shown in any one of the general formulas (7-1) to (7-4): In General Formulas (7-1) to (7-4), Z, R 4 , R 7 , R 8 , R 17 , R 23 , R 27 , R 34 have the same meanings as defined in Claim 5.

7. The boron-containing organic compound according to any one of claims 1-6, characterized in that, M represents the following groups substituted or unsubstituted by R: phenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolinyl, furyl, thienyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, indolo[3,2,1-jk]carbazolyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, spirofluorene, etc. Each occurrence of R is the same or different and represents any one of a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, a substituted or unsubstituted triazine group; Said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 、R 34 、R 35 are each independently represented by any one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, and a substituted or unsubstituted triazinyl group; Said R 11 represents any one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted indolo[3,2,1-jk]carbazolyl group, a substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, a substituted or unsubstituted spirofluorene group, and a substituted or unsubstituted arylamine group; The R 0 represents any one of a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, and a substituted or unsubstituted triazinyl group; The substituents for the substituent groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuryl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group; Preferably, the M ring is represented by the following group: any one of; Each occurrence of Z, whether the same or different, is represented as C-(H) or C-(R 0 ); R 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 、R 34 、R 35 are each independently represented by a hydrogen atom, a deuterium atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, a phenyl group, any one of; The R 11 is represented as any one of.

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

9. An organic electroluminescent device, sequentially comprising 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, wherein, the light-emitting layer contains the boron-containing organic compound according to any one of claims 1-8; Preferably, the light-emitting layer comprises a host material and a doping material, and the doping material contains the boron-containing organic compound according to any one of claims 1-8; Preferably, the light-emitting layer comprises a first host material, a second host material, and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1-8.

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

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