Boron-containing organic compounds and organic electroluminescent devices prepared therefrom

Abstract

The present invention relates to the field of semiconductor technology, and provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom.The structure of the organic compound in the present invention is shown in general formula (A-1).The compound in the present invention can be used as a green light doping material in the light-emitting layer of an organic electroluminescent device, and can improve the life of the device.

Description

[Technical Field]

[0001] The present invention relates to the field of semiconductor technology, and in particular to boron-containing organic compounds and organic electroluminescent devices prepared therefrom. [Background technology]

[0002] Limited by early technology, conventional fluorescent doping materials only utilize 25% of the singlet excitons formed upon excitation during light emission. This results in low internal quantum efficiency (maximum 25%) and external quantum efficiency (typically less than 5%), a significant efficiency gap compared to phosphorescent devices. Phosphorescent materials, thanks to intersystem crossing enhanced by strong spin-orbit coupling at the heavy atom center, can efficiently utilize the singlet and triplet excitons formed upon excitation to emit light, achieving 100% internal quantum efficiency. However, most phosphorescence-resistant materials are expensive, suffer from low material stability, low color purity, and a significant drop in device efficiency, among other issues, limiting the use of phosphorescent materials in OLEDs.

[0003] With the advent of the 5G era, higher requirements will be placed on color rendering standards. In addition to high efficiency and stability, emitting materials are also required to have narrow FWHMs to improve the color purity of device emission. Molecular engineering of fluorescent doping materials can achieve high fluorescence quantum yields and narrow FWHMs. A breakthrough has been achieved in blue fluorescent doping materials, with the FWHM of boron-based materials reaching 30 nm or less. Research into the green light region, where the human eye is more sensitive, has primarily focused on phosphorescent doping materials. However, it is difficult to narrow the emission peak shape of photoluminescent doping materials using simple methods. Therefore, research into highly efficient green fluorescent doping materials with narrow FWHMs is crucial to meet higher color rendering standards.

[0004] In addition, triplet exciton-sensitized materials and fluorescent doping materials are combined using sensitization technology. The triplet exciton-sensitized material used as the exciton-sensitizing medium transfers energy to the fluorescent doping material through energy transfer by fully utilizing triplet excitons. This method can also achieve 100% internal quantum efficiency of the device. This technology overcomes the shortcomings of insufficient exciton utilization in fluorescent doping materials and effectively achieves the advantages of fluorescent doping materials, such as high fluorescent quantum yield, high device stability, high color purity, and low price, providing the prospect of widespread application in OLEDs.

[0005] Boron-based compounds with resonant structures can more easily achieve emission with narrow full width at half maximum. The use of these materials in sensitization techniques allows for the preparation of highly efficient light-emitting devices with narrow full width at half maximum. For example, Chinese Patent Application Publication Nos. CN107507921A and CN110492006A disclose a technique for combining a TADF material as a host material, with an energy gap between the lowest singlet state and the lowest triplet state of 0.2 eV or less, and a boron-containing material as a doping material in an emission layer. Chinese Patent Application Publication Nos. CN110492005A and CN110492009A also disclose solutions for combining an exciplex as a host material and a boron-containing material as a doping material in an emission layer. Both solutions can achieve efficiencies comparable to those of phosphorescent materials and relatively narrow full width at half maximum. The development of sensitization technology based on boron-based luminescent materials with narrow full width at half maximum offers unique advantages and strong potential for the BT.2020 display standard. Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention has been made in view of the above-mentioned problems of the prior art, and provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention can be used as a green light doping material in the light-emitting layer of an organic electroluminescent device. [Means for solving the problem]

[0007] The present invention provides the following technical solutions: A boron-containing organic compound is provided, the structure of which is shown in general formula (A-1):

[0008] [ka] General formula (A-1) In general formula (A-1), R to R 19 each represents one of the following, which may be the same or different: a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkenyl, a substituted or unsubstituted C1-C10 alkynyl, a substituted or unsubstituted silanyl, a substituted or unsubstituted boranyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C6-C30 aryloxy, a substituted or unsubstituted arylamido, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; R1 to R 17 Any two adjacent groups can be linked to form a ring, R 18 and R 19 can be linked to form a ring, Ar1 and Ar2 are the same or different and each represent one of a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkenyl, a substituted or unsubstituted C1-C10 alkynyl, a substituted or unsubstituted silanyl, a substituted or unsubstituted boranyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C6-C30 aryloxy, a substituted or unsubstituted arylamide, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; M1, M2, M3, M4, and M5 each independently represent one of a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted 5 to 30-membered heteroaromatic ring, and a substituted or unsubstituted C6 to C10 aliphatic ring; X represents C or Si; The substituent substituting the group is optionally selected from any one of deuterium, tritium, a halogen atom, cyano, C1-C10 alkyl, deuterium- or tritium-substituted C1-C10 alkyl, C6-C30 aryl, deuterium- or tritium-substituted C6-C30 aryl, C2-C30 heteroaryl, and deuterium- or tritium-substituted C2-C30 heteroaryl.

[0009] In a preferred solution, in the general formula (A-1), R1 to R 17 Any two adjacent rings may be bonded to form a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted C2 to C30 heteroaromatic ring, or a substituted or unsubstituted C6 to C30 aliphatic ring.

[0010] In a preferred solution, in the general formula (A-1), R1 to R 19 are the same or different, and are a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl,

[0011] [ka] or phenyl, Ar1 and Ar2 are the same or different, methyl,

[0012] [ka] represents one of the following: M1, M2, and M3 are the following ring structures:

[0013] [ka] represents one of the following: M4 and M5 each represent the following ring structure:

[0014] [ka] represents Z is CR a represents R a each independently represents a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl,

[0015] [ka] or phenyl, X represents C or Si.

[0016] In a preferred solution, the structure of the boron-containing organic compound is represented by the following general formula (A):

[0017] [ka] is expressed as In general formula (A), R to R 19 each represents one of the following, which may be the same or different: a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C1-C10 aryloxy, a substituted or unsubstituted arylamide, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; R1 to R 14 Any two adjacent groups can be linked to form a ring, R 18 and R 19 can be linked to form a ring, Ar1 and Ar2 are the same or different and each represent one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; M1 represents a substituted or unsubstituted C6 to C30 aromatic ring or a substituted or unsubstituted 5 to 30-membered heteroaromatic ring; X represents C or Si; The substituent substituting the group is optionally selected from any one of deuterium, tritium, a halogen atom, cyano, C1 to C10 alkyl, deuterium- or tritium-substituted C1 to C10 alkyl, C6 to C30 aryl, deuterium- or tritium-substituted C6 to C30 aryl, C5 to C30 heteroaryl, and deuterium- or tritium-substituted C2 to C30 heteroaryl.

[0018] In a preferred solution, in the general formula (A), R to R 14Any two adjacent groups may be bonded to form a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted C2 to C30 heteroaromatic ring, or a substituted or unsubstituted C6 to C30 aliphatic ring.

[0019] In a preferred solution, in the general formula (A), R1 to R19 are each the same or different and are a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl,

[0020] [ka] or phenyl, Ar1 and Ar2 are the same or different, methyl,

[0021] [ka] represents one of the following: M1 is one of the following ring structures:

[0022] [ka] represents one of the following: Z is CR a represents R a each independently represents a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl,

[0023] [ka] or phenyl, X represents C or Si.

[0024] In a preferred solution, the structure of the boron-containing organic compound is represented by general formula (1-1) or general formula (1-2):

[0025] [ka] In the general formula (1-1) and the general formula (1-2), R1 to R 21 each represents, the same or different, any of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C1-C10 aryloxy, a substituted or unsubstituted arylamide, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; R1 to R 21 Any two adjacent groups can be linked to form a ring, Ar1 and Ar2 are the same or different and each represent one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; X represents C or Si; The substituents for substituting the group may be, as needed, deuterium, tritium, a halogen atom, cyano, C1 to C 10 alkyl, deuterium- or tritium-substituted C1-C10 alkyl, C6-C30 aryl, deuterium- or tritium-substituted C6-C30 aryl, C5-C30 heteroaryl, and deuterium- or tritium-substituted C2-C30 heteroaryl.

[0026] In a preferred solution, in the general formula (1-1) and the general formula (1-2), R1 to R21 Any two adjacent groups may be bonded to form a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted C2 to C30 heteroaromatic ring, or a substituted or unsubstituted C6 to C30 aliphatic ring.

[0027] In a preferred solution, in the general formula (1-1) and the general formula (1-2), R1 to R 21 are the same or different, and are a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl,

[0028] [ka] or phenyl, Ar1 and Ar2 are the same or different, methyl,

[0029] [ka] represents one of the following: X represents C or Si.

[0030] In a preferred solution, the structure of the boron-containing organic compound is represented by general formula (1-3) or general formula (1-4):

[0031] [ka] In the general formula (1-3) and the general formula (1-4), R to R 19each represent, the same or different, any of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkenyl, a substituted or unsubstituted C1-C10 alkynyl, a substituted or unsubstituted silanyl, a substituted or unsubstituted boranyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C6-C30 aryloxy, a substituted or unsubstituted arylamide, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; R1 to R 19 Any two adjacent groups can be linked to form a ring, Ar1 and Ar2 are the same or different and each represent one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkenyl, substituted or unsubstituted C1-C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted boranyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; X represents C or Si; The substituents for substituting the group may be, as needed, deuterium, tritium, a halogen atom, cyano, C1 to C 10 Alkyl, deuterium- or tritium-substituted C1-C 10 Alkyl, C6-C 30 Aryl, deuterium- or tritium-substituted C6-C 30 Aryl, C2-C 30 Heteroaryl, deuterium- or tritium-substituted C2-C 30 and the heteroaryl is selected from any one of the following:

[0032] In a preferred solution, in the general formula (1-3) and the general formula (1-4), R1 to R 19Any two adjacent groups may be bonded to form a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted C2 to C30 heteroaromatic ring, or a substituted or unsubstituted C6 to C30 aliphatic ring.

[0033] In a preferred solution, in the general formula (1-3) and the general formula (1-4), R1 to R 19 are the same or different, and are a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl,

[0034] [ka] or phenyl, Ar1 and Ar2 are the same or different, methyl,

[0035] [ka] represents one of the following: X represents C or Si.

[0036] In a preferred solution, the structure of the boron-containing organic compound is represented by the following general formula (2):

[0037] [ka] In general formula (2), R2, R7, R 10 , R 13 , R 16 , R 18 The meanings of Ar1, Ar2, and X are the same as those in general formula (A).

[0038] In a preferred solution, in the general formula (2), R2, R7, R 10 , R 13 , R 16, and R 18 each independently represents a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl,

[0039] [ka] or phenyl, Ar1 and Ar2 are the same or different, methyl,

[0040] [ka] represents one of the following: X represents C or Si.

[0041] In a preferred solution, the structure of the boron-containing organic compound is represented by general formula (2-1) or general formula (2-2):

[0042] [ka] In the general formula (2-1) and the general formula (2-2), R2, R7, R 10 , R 13 , R 18 The meanings of Ar1, Ar2 and X are the same as those in general formula (A).

[0043] In a preferred solution, in the general formula (2-1) and the general formula (2-2), R2, R7, R 10 , R 13 and R 18 each independently represents a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl,

[0044] [ka] or phenyl, Ar1 and Ar2 are the same or different, methyl,

[0045] [ka] represents one of the following: X represents C or Si.

[0046] In a preferred solution, the structure of the boron-containing organic compound is represented by the following general formula (3-1):

[0047] [ka] In general formula (3-1), R's are the same or different and represent any one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C1-C10 aryloxy, a substituted or unsubstituted arylamide, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; X represents C or Si; The substituent substituting the group is optionally selected from any one of deuterium, tritium, a halogen atom, cyano, C1-C10 alkyl, deuterium- or tritium-substituted C1-C10 alkyl, C6-C30 aryl, deuterium- or tritium-substituted C6-C30 aryl, C5-C30 heteroaryl, and deuterium- or tritium-substituted C2-C30 heteroaryl.

[0048] In a preferred solution, in the general formula (3-1), R are each the same or different and independently represent a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl,

[0049] [ka] or phenyl.

[0050] In the preferred solution, R and R1 to R 21each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a fluorine atom, cyano, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzo furyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy.

[0051] Ar1 and Ar2 each independently represent phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl and tert-butylsubstituted diphenyl, phenyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy.

[0052] M1, M2, M3, M4, and M5 represent one of phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuryl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, and xanthone.

[0053] Substituents replacing a substitutable group are optionally selected from one or more of deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-pentyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthryl, phenanthryl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolyl, isoquinolyl, furyl, thienyl, indolyl, pyrrolyl, dibenzofuryl, dibenzothienyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, and azaphenanthryl.

[0054] In the preferred solution, R and R1 to R 21 each independently represents a hydrogen atom, a cyano,

[0055] [ka] represents one of the following: Ar1 and Ar2 are

[0056] [ka] represents one of the following: M1, M2, and M3 are the following ring structures:

[0057] [ka] represents one of the following: M4 and M5 are the following ring structures:

[0058] [ka] represents one of the following: Z is CR arepresents R a are each independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzyl, and n-phenyl-, ...

[0059] In a preferred solution, R and R1 to R21 are each independently a hydrogen atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl,

[0060] [ka] represents one of the following: Ar1 and Ar2 are methyl,

[0061] [ka] represents one of the following: M1, M2, and M3 are the following ring structures:

[0062] [ka] represents M4 and M5 are the following ring structures:

[0063] [ka] represents Z is CR a represents R a each independently represents a hydrogen atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl,

[0064] [ka] represents one of the following:

[0065] In a preferred solution, the specific structural formula of the boron-containing organic compound is:

[0066] [ka] TIFF2026500514000037.tif236170 TIFF2026500514000038.tif251170 TIFF2026500514000039.tif245170 TIFF2026500514000040.tif249170 TIFF2026500514000041.tif245170 TIFF2026500514000042.tif192128 TIFF2026500514000043.tif229170 TIFF2026500514000044.tif255170 TIFF2026500514000045.tif234170 TIFF2026500514000046.tif230170 TIFF2026500514000047.tif231170 TIFF2026500514000048.tif240170 TIFF2026500514000049.tif236170 TIFF2026500514000050.tif238170 TIFF2026500514000051.tif226170 TIFF2026500514000052.tif243170 TIFF2026500514000053.tif249170 TIFF2026500514000054.tif253170 TIFF2026500514000055.tif255170 TIFF2026500514000056.tif242170 TIFF2026500514000057.tif219170 It is one of the following.

[0067] In a preferred solution, the specific structural formula of the boron-containing organic compound is:

[0068] [ka] TIFF2026500514000059.tif220170.

[0069] The present invention provides an organic electroluminescent device having a cathode, an anode, and an organic light-emitting functional layer between the cathode and the anode, An organic electroluminescent device is provided, wherein the organic light-emitting functional layer comprises a light-emitting layer, the light-emitting layer comprising a boron-containing organic compound.

[0070] In a preferred solution, the organic electroluminescent device comprises, in this order, a substrate, an anode, an organic light-emitting functional layer, and a cathode, wherein the organic light-emitting functional layer comprises a light-emitting layer, the light-emitting layer comprising a boron-containing organic compound.

[0071] In a preferred solution, the organic electroluminescent device comprises, in this order, a substrate, a cathode, an organic light-emitting functional layer, and an anode, wherein the organic light-emitting functional layer comprises a light-emitting layer, the light-emitting layer comprising a boron-containing organic compound.

[0072] In a preferred solution, the light-emitting layer comprises a host material and a doping material, and the doping material comprises a boron-containing organic compound.

[0073] In a preferred solution, the light-emitting layer comprises a first host material, a second host material, and a doping material, wherein at least one of the first host material and the second host material is a TADF material, and the doping material is a boron-containing organic compound.

[0074] In a preferred solution, the light-emitting layer comprises a host material, an exciton-sensitized material, and a doping material, wherein the exciton-sensitized material is a complex containing a metal element, and the doping material is a boron-containing organic compound.

[0075] The present invention provides a material for an organic electroluminescent device, which comprises the above-described boron-containing organic compound.

[0076] The present invention provides the use of said boron-containing organic compounds in organic electroluminescent devices.

[0077] In a preferred solution, the organic light-emitting functional layer comprises a light-emitting layer, and the light-emitting layer uses the boron-containing organic compound of the present invention.

[0078] A display member is provided comprising an organic electroluminescent device according to the present invention.

[0079] A lighting device is provided that includes an organic electroluminescent device according to the present invention.

[0080] An electronic device carrying an organic electroluminescent device according to the present invention is provided.

[0081] The present invention has the following significant technical effects: (1) When the compound of the present invention is used in an OLED device, it can be used as a doping material for the light-emitting layer material, and can exhibit green fluorescence under the influence of an electric field, and can be used in the field of OLED lighting or OLED display; (2) As a doping material, the compounds of the present invention can significantly improve the lifetime of devices. [Brief explanation of the drawings]

[0082] [Figure 1] 1 is a diagram of the structure of materials used in an OLED device according to the present invention, showing 1 a transparent substrate layer, 2 an anode layer, 3 a hole injection layer, 4 a hole transport layer, 5 an electron blocking layer, 6 an emissive layer, 7 a hole blocking layer, 8 an electron transport layer, 9 an electron injection layer, and 10 a cathode layer. [Figure 2] FIG. 1 shows the spectrum of compound 222. [Figure 3] FIG. 1 shows the nuclear magnetic resonance spectrum of compound 222. [Figure 4] FIG. 1 shows the spectrum of compound 186. [Figure 5] FIG. 1 shows the nuclear magnetic resonance spectrum of Compound 186. [Figure 6] FIG. 1 shows the spectrum of compound 226. [Figure 7] FIG. 1 shows the nuclear magnetic resonance spectrum of Compound 226. [Figure 8] FIG. 1 shows the nuclear magnetic resonance spectrum of Compound 273. [Figure 9] FIG. 1 shows the mass spectrum of compound 273. [Figure 10] FIG. 1 shows the nuclear magnetic resonance spectrum of Compound 116. [Figure 11] FIG. 1 shows the nuclear magnetic resonance spectrum of compound 190. [Figure 12] FIG. 1 shows the nuclear magnetic resonance spectrum of compound 275. [Figure 13] FIG. 1 shows the nuclear magnetic resonance spectrum of compound 331. [Figure 14] FIG. 1 shows the nuclear magnetic resonance spectrum of Compound 367. DETAILED DESCRIPTION OF THE INVENTION

[0083] The technical solutions in the embodiments of the present invention will be clearly and fully described below with reference to the accompanying drawings in the embodiments of the present invention. The embodiments of the present invention and the features in the embodiments may be combined with each other if not contradictory. The present invention will be further described below with reference to the accompanying drawings and specific embodiments, which are not intended to limit the present invention.

[0084] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms such as "upper," "lower," "top," and "bottom" used to indicate orientation simply indicate an orientation in a specific state, and do not mean that the associated structure can only exist according to that orientation. Conversely, when the position of a structure changes, for example, when it is inverted, the orientation of the structure changes accordingly. In particular, in the present invention, the "bottom" or "lower" of an electrode refers to the side of the electrode that is closer to the substrate in the preparation process, and the opposite side that is farther from the substrate is the "top" or "upper" side.

[0085] In the present invention, substituted or unsubstituted C6 to C 30 The aryl in the formula (I) is, but is not limited to, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted diphenylphenyl, substituted or unsubstituted perylenyl, or substituted or unsubstituted indenyl.

[0086] In the present invention, substituted or unsubstituted C2 to C 30Heteroaryl in the formula (I) is 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 pyridinyl, 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 quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted 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 ring combinations of the foregoing groups.

[0087] C1 to C in the present invention 10 The alkyl (including straight chain alkyl and branched alkyl) is, but is not limited to, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, or 1-butylpentyl.

[0088] C3 to C in the present invention 10The cycloalkyl in the formula (I) is a monovalent, monocyclic, saturated hydrocarbyl group containing 3 to 10 carbon atoms as ring-forming atoms. Herein, C4 to C9 cycloalkyl is preferred, C5 to C8 cycloalkyl is more preferred, and C5 to C7 cycloalkyl is particularly preferred. Non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0089] In the present invention, substituted or unsubstituted C5-C 30 Heteroaryl in the formula (I) is substituted or unsubstituted pyridinyl, 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 quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyl, The radicals include, but are not limited to, 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 ring combinations of the foregoing groups.

[0090] In the present invention, the C1-C10 alkenyl is preferably a C2-C8 alkenyl, more preferably a C2-C5 alkenyl, non-limiting examples of which include ethenyl, propenyl, isobutenyl, n-pentenyl, isopentenyl, neo-pentenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylethenyl, styryl, 2,2-diphenylethenyl, 1,2-diphenylethenyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl.

[0091] In the present invention, the C1-C10 alkynyl is preferably a C2-C8 alkynyl, more preferably a C2-C5 alkynyl, non-limiting examples of which include, but are not limited to, ethynyl, propynyl, n-butynyl, isobutynyl, n-pentynyl, isopentynyl, and neopentynyl.

[0092] In the present invention, the phrase "capable of being linked to form a ring" means that two adjacent groups do not form a ring, or can be linked to each other to form a ring.

[0093] Preferably, two adjacent groups may be linked to form a substituted or unsubstituted 6- to 30-membered aromatic ring, a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, or a substituted or unsubstituted 5- to 30-membered aliphatic ring.

[0094] In the present invention, the substituted or unsubstituted arylamide is

[0095] [ka] wherein Q4 and Q5 each represent a substituted or unsubstituted aromatic group, and Q4 and Q5 are preferably substituted or unsubstituted C-C 30aryl or substituted or unsubstituted C2-C 30 represents a heteroaryl of the formula:

[0096] The halogen atom in the present invention is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0097] In the present invention, C1 to C10 alkoxy includes, but is not limited to, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, and isopropoxy.

[0098] In the present invention, substituted or unsubstituted C6 to C 30 The aromatic ring in the formula (I) is, but is not limited to, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted diphenylphenyl, substituted or unsubstituted perylenyl, or substituted or unsubstituted indenyl.

[0099] In the present invention, the substituted or unsubstituted 5- to 30-membered heteroaromatic ring is 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 pyridinyl, 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 quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted 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 ring combinations of the foregoing groups.

[0100] The present invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention can be used as a green light doping material in the light-emitting layer of an organic electroluminescent device, thereby significantly improving the life of the device.

[0101] The organic electroluminescent device in the present invention may be a bottom-emission organic electroluminescent device, a top-emission organic electroluminescent device, or a tandem organic electroluminescent device, but is not particularly limited thereto.

[0102] The organic electroluminescent device of the present invention comprises a substrate, a first electrode, an organic light-emitting functional layer, and a second electrode. The organic light-emitting functional layer comprises a hole transport region, an emitting layer, and an electron transport region. The hole transport region comprises a hole injection layer, a hole transport layer, and an electron blocking layer. The electron transport region comprises a hole blocking layer, an electron transport layer, and an electron injection layer. A CPL layer may also be provided on the second electrode.

[0103] The substrate of the organic electroluminescent device of the present invention may be a substrate commonly used in organic electroluminescent devices, such as a transparent substrate such as a glass or transparent plastic substrate, or an opaque substrate such as a silicon substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and waterproof properties. The direction in which the substrate is used varies depending on the different properties of the substrate. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0104] The first electrode is formed on the substrate. The first electrode and the second electrode may face each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may contain Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a metal mixture. The thickness of the first electrode depends on the material used, but is usually 50 nm to 500 nm, preferably 70 nm to 300 nm, and more preferably 100 nm to 200 nm.

[0105] The organic functional material layer provided between the first electrode and the second electrode includes, in order from the bottom, a hole transport region, a light emitting layer, and an electron transport region.

[0106] Herein, the hole transport region of the organic electroluminescent device may be exemplified as a hole injection layer, a hole transport layer, an electron blocking layer, and the like.

[0107] The materials for the hole injection layer, hole transport layer, and electron blocking layer can be selected from any of the conventional materials used in OLED devices.

[0108] Examples of such materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinoxalinol derivatives, styrene compounds such as styrylanthracene derivatives or styrylamine derivatives, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylenevinylene and its derivatives, polythiophene and its derivatives, poly(N-vinylcarbazole) derivatives, thiophene oligomers, and other conductive macromolecular oligomers, aromatic derivatives, These include tertiary amine compounds, styrylamine compounds, triamines, tetramines, benzidine, aminomethylacetylene derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamine)biphenyl, bis[4-(diarylamino)phenyl]methane, 4,4'-bis(diarylamino)terphenyl, 4,4'-bis(diarylamino)quaterphenyl, 4,4'-bis(diarylamino)diphenyl ether, 4,4'-bis(diarylamino)diphenylsulfane, bis[4-(diarylamino)phenyl]dimethylmethane, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methane, and 2,2-diphenylethenyl compounds.

[0109] In addition, depending on the device matching requirements, the hole transport layer between the electron blocking layer and the hole injection layer of the organic electroluminescent device may be a single layer or a laminate structure of multiple hole transport materials. In this specification, the thicknesses of the aforementioned hole carrier conductive layers with different functions are not particularly limited.

[0110] The hole injection layer contains a host organic material capable of conducting holes, and also contains a P-type doping material with a deep HOMO energy level (with a corresponding extremely deep LUMO energy level). Experimental results have shown that, to ensure smooth hole injection from the anode into the organic film layer, as long as the HOMO energy level of the host organic material used in the hole-conducting buffer layer on the anode interface has specific characteristics with the P-type doping material, a charge transfer state can be established between the host material and the doping material, forming an ohmic contact between the buffer layer and the anode, enabling efficient hole injection from the electrode into the hole injection conductive layer.

[0111] Considering the above empirical summary, different P-type doping materials are required to match the hole host materials with different HOMO energy levels, which can form an ohmic contact at the interface and improve the hole injection effect.

[0112] Therefore, in an embodiment of the present invention, for better hole injection, the hole injection layer further comprises a charge-conducting P-type doping material selected from, but not limited to, 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 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)-malononitrile; or metal oxides such as tungsten oxide and molybdenum oxide.

[0113] In the hole injection layer of the present invention, the mass ratio of the hole transport material to the P-type doping material is 99:1 to 95:5, and preferably 99:1 to 97:3.

[0114] The thickness of the hole injection layer of the present invention is 5 nm to 100 nm, preferably 5 nm to 50 nm, and more preferably 5 nm to 20 nm, but is not limited to this range.

[0115] The thickness of the hole transport layer of the present invention is 5 nm to 200 nm, preferably 10 nm to 150 nm, and more preferably 20 nm to 100 nm, but is not limited to this range.

[0116] The thickness of the electron blocking layer of the present invention is 1 nm to 50 nm, preferably 5 nm to 40 nm, but is not limited to this range.

[0117] After the hole injection layer, hole transport layer, and electron blocking layer are formed, a corresponding light-emitting layer is formed on the electron blocking layer.

[0118] The light-emitting layer may include a host material and a doping material. The host material may be a general green-emitting host material. The doping material may be a boron-containing organic compound represented by general formula (1) of the present invention.

[0119] The light-emitting layer may include a single host material or dual host materials.

[0120] The dual host material includes a first host material and a second host material, and preferably, at least one of the first host material and the second host material is a TADF material.

[0121] TADF materials are thermally activated delayed fluorescent materials characterized by a small energy gap between the first excited singlet state and the first excited triplet state. In this case, both the generated singlet and triplet excitons can be used in the device, and the utilization rate of the excitons generated by excitation within the device can be as close to 100% as possible. Compared to conventional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0122] The light-emitting layer may include a host material, an exciton-sensitized material, and a doping material.

[0123] An exciton-sensitized material is a material that allows the light-emitting material in the light-emitting layer to fully utilize excitons, so that the light-emitting layer exhibits the emission spectrum of the sensitized material. The exciton sensitizer may provide functions such as exciton capture, exciton conversion, and exciton transfer in an electroluminescent device. The combination of the boron-containing organic compound represented by general formula (1) of the present invention with an exciton-sensitized material significantly improves device efficiency and solves problems such as exciton quenching and efficiency loss in the device.

[0124] In the light-emitting layer of the present invention, the ratio of the host material to the doping material is 99:1 to 70:30, preferably 99:1 to 85:15, and more preferably 97:3 to 87:13, by mass.

[0125] The thickness of the light-emitting layer may be adjusted to optimize the light-emitting efficiency and driving voltage. The thickness is preferably in the range of 5 nm to 50 nm, more preferably 10 nm to 50 nm, and even more preferably 15 nm to 40 nm, but is not limited to these ranges.

[0126] In the present invention, the electron transport region may have, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer provided on the light emitting layer, but is not limited thereto.

[0127] The hole-blocking layer blocks holes injected from the anode through the light-emitting layer to the cathode, thereby improving the device's lifetime and efficiency. The hole-blocking layer of the present invention may be provided on the light-emitting layer. The hole-blocking layer of the organic electroluminescent device of the present invention may be formed from compounds known in the art that have hole-blocking properties, such as bathocuproine (BCP) and other phenanthroline derivatives, metal complexes of aluminum(III) bis(2-methyl-8-quinoline)-4-phenylphenolate (BAlq) and other hydroxyquinoline derivatives, various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole) and other pyrimidine derivatives. The thickness of the hole blocking layer of the present invention is 2 nm to 200 nm, preferably 5 nm to 150 nm, but is not limited to this range.

[0128] The electron transport layer may be provided on the light-emitting layer or on the hole-blocking layer (if present). The material of the electron transport layer is a material that can easily accept electrons from the cathode and transport the accepted electrons to the light-emitting layer. A material with high electron mobility is preferred. The charge transport layer of the organic electroluminescent device of the present invention may be made of conventional materials for the charge transport layer of an organic electroluminescent device, such as metal complexes of hydroxyquinoline derivatives, such as Alq3, BAlq, and Liq, various rare earth metal complexes, triazole derivatives, 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(2-naphthalenyl)-1,3,5-triazine (CAS number: 1459162-51-6) and other triazine derivatives, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS number: 561064-11-7, LG201) and other imidazole derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, and silicon-based compound derivatives. The thickness of the electron transport layer of the present invention is 10 nm to 80 nm, preferably 20 nm to 60 nm, and more preferably 25 nm to 45 nm, but is not limited to this range.

[0129] The electron injection layer may be provided on the electron transport layer. Typically, materials with a low work function are preferred for the electron injection layer, so as to facilitate electron injection into the organic functional material layer. The electron injection layer of the organic electroluminescent device of the present invention may be made of materials known as materials for electron injection layers of conventional organic electroluminescent devices, such as lithium; lithium salts such as 8-hydroxyquinolinolato-lithium, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts such as cesium fluoride, cesium carbonate, or cesium azide. The thickness of the electron injection layer of the present invention is 0.1 nm to 5 nm, preferably 0.5 nm to 3 nm, and more preferably 0.8 nm to 1.5 nm, but is not limited to this range.

[0130] A second electrode may be provided on the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the second electrode is a transmissive electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof. If the second electrode is a semi-transmissive or reflective electrode, it may include, but is not limited to, 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. The thickness of the cathode depends on the material used.

[0131] The organic electroluminescent device of the present invention may further have a packaging structure. The packaging structure is a protective structure and may prevent external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The packaging structure may be, for example, a can such as a glass can or a metal can; or a film that covers the entire surface of the organic layer.

[0132] The method for manufacturing an organic electroluminescent device of the present invention includes sequentially stacking 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, a cathode, and an optional cover layer on a substrate. This method may be performed using, but is not limited to, vacuum deposition, vacuum evaporation, spin coating, casting, LB printing, inkjet printing, laser printing, LITI, or other methods. In the present invention, each layer is preferably formed using vacuum evaporation. Those skilled in the art can generally select the processing conditions for vacuum evaporation according to actual requirements.

[0133] In the synthesis embodiment of the present invention, all raw materials may be purchased from the market or prepared using conventional, conventional preparation methods.

[0134] Synthesis of intermediates: Synthesis of Intermediate A Series:

[0135] [ka] Synthesis of Intermediate A2: In a two-neck flask, raw material N1 (2.05 g, 6.31 mmol), raw material M1 (1.54 g, 13.25 mmol), tetrakis(triphenylphosphine)palladium (0.22 g, 0.19 mmol), tri-tert-butylphosphine (0.12 g, 0.57 mmol), potassium carbonate (0.17 g, 1.23 mmol), toluene (50 mL), and water (10 mL) were added. The mixture was reacted at 110 °C for 24 hours under a nitrogen atmosphere, then cooled. The mixture was extracted with ethyl acetate, washed with saturated brine, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate A2.

[0136] [ka] Synthesis of Intermediate A3: A two-neck flask was charged with Raw Material N1 (2.05 g, 6.31 mmol), Raw Material M2 (1.54 g, 13.25 mmol), tetrakis(triphenylphosphine)palladium (0.22 g, 0.19 mmol), tri-tert-butylphosphine (0.12 g, 0.57 mmol), potassium carbonate (0.17 g, 1.23 mmol), toluene (50 mL), and water (10 mL). The mixture was reacted at 110 °C for 24 hours under a nitrogen atmosphere and then cooled. The mixture was then extracted with ethyl acetate, washed with saturated brine, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate A3.

[0137] [ka] Synthesis of intermediate A7: See the synthesis of intermediate A2, except that raw material M1 is replaced with raw material M3.

[0138] Synthesis of R series intermediates:

[0139] [ka] Synthesis of Intermediate R5: Starting material S1 (0.76 g, 3.6 mmol) and starting material S2 (1.15 g, 4.3 mmol) were dissolved in THF (80 mL), and PdCl2(PPh3)2 (0.11 g, 0.15 mmol), CuI (0.07 g, 0.36 mmol), and triethylamine (40 mL) were added sequentially. The mixture was purged with nitrogen three times, then slowly heated to 80 °C and maintained at that temperature for 12 h. The reaction mixture was then cooled to room temperature, filtered to remove inorganic salts, and then rotary evaporated to remove triethylamine. The product was poured into acidified water. The precipitate was washed five times with deionized water and dried overnight under vacuum at 80 °C. The crude product was subjected to silica gel column chromatography using petroleum ether as the eluent to obtain the crude product. The crude product was recrystallized to obtain Intermediate R5.

[0140] [ka] Synthesis of Intermediate S5: Raw material S3 (10 mmol, 3.39 g) and raw material S4 (10 mmol, 3.16 g) were placed in a three-neck flask and dissolved in a mixed solvent (70 mL of 1,4-dioxane / water (volume ratio: 4:1), 35 mL of ethanol). Pd(dppf)Cl2 (0.10 mmol, 0.07 g) and 15 mL of 3 mol / L aqueous K2CO3 solution were then added. The mixture was heated to reflux under nitrogen protection and reacted for 4 hours. A sample of the reaction mixture was taken and spotted on a plate to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth pad and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / toluene as an eluent to obtain Intermediate S5.

[0141] [ka] Synthesis of Intermediate R6: For the preparation and synthesis of Intermediate R6, refer to the preparation and synthesis of Intermediate R5 using the same reaction conditions and the same reactant equivalents, except that the reactants S1 and S2 were replaced with S6 and S5, respectively.

[0142] Synthesis of G series intermediates:

[0143] [ka] Synthesis of Intermediate G1: In a two-neck flask, add starting material R1 (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). Under nitrogen protection, add 100 mL of anhydrous DMF. Stir the mixture at room temperature for 30 minutes. Under nitrogen protection, add starting material P1 (5.54 g, 25 mmol). Stir the mixture at 140 °C for 12 hours under nitrogen protection, then filter, wash, dry, and subject to column chromatography (PE:EA = 20:1) to obtain Intermediate G1.

[0144] [ka] Synthesis of Intermediate G2: In a two-neck flask, add starting material R2 (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). Under nitrogen protection, add 100 mL of anhydrous DMF. The mixture is stirred at room temperature for 30 minutes. Starting material P1 (5.54 g, 25 mmol) is added under nitrogen protection. The mixture is stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate G2.

[0145] [ka] Synthesis of Intermediate P2-1: A two-neck flask was charged with raw material P2 (8.69 g, 30.80 mmol), copper iodide (0.29 g, 1.54 mmol), diethylenetriamine (0.32 g, 3.08 mmol), sodium iodide (9.02 g, 60.16 mmol), and 300 mL of anhydrous acetonitrile, and the mixture was heated to reflux for 24 hours. After cooling, the mixture was extracted with ethyl acetate and washed with saturated brine to remove the acetonitrile. The organic phase was dried over anhydrous sodium sulfate. The solvent was removed by spin drying, and then triturated with methanol. The solid was recrystallized from dichloromethane-methanol to obtain Intermediate P2-1.

[0146] Synthesis of Intermediate G3: Raw material R2 (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) were added to a two-neck flask, and 100 mL of anhydrous DMF was added under nitrogen protection. The mixture was stirred at room temperature for 30 minutes. Under nitrogen protection, intermediate P2-1 (8.23 g, 25 mmol) was added. The mixture was stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain intermediate G3.

[0147] [ka] Synthesis of Intermediate G4: In a two-neck flask, add starting material R1 (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). Under nitrogen protection, add 100 mL of anhydrous DMF. The mixture is stirred at room temperature for 30 minutes. Starting material P3 (6.73 g, 25 mmol) is added under nitrogen protection. The mixture is stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate G4.

[0148] [ka] Synthesis of Intermediate G5: A two-neck flask was charged with starting material R2 (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). Under nitrogen protection, 100 mL of anhydrous DMF was added. The mixture was stirred at room temperature for 30 minutes. Starting material P3 (6.73 g, 25 mmol) was added under nitrogen protection. The mixture was stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate G5.

[0149] [ka] Synthesis of Intermediate G6: In a two-neck flask, add starting material R3 (1.35 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). Under nitrogen protection, add 100 mL of anhydrous DMF. The mixture is stirred at room temperature for 30 minutes. Under nitrogen protection, add starting material P3 (6.73 g, 25 mmol). The mixture is stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate G6.

[0150] [ka] Synthesis of Intermediate G7: In a two-neck flask, add starting material R1 (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). Under nitrogen protection, add 100 mL of anhydrous DMF. The mixture is stirred at room temperature for 30 minutes. Starting material P4 (6.73 g, 25 mmol) is added under nitrogen protection. The mixture is stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate G7.

[0151] [ka] Synthesis of Intermediate G8: In a two-neck flask, add starting material R2 (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). Under nitrogen protection, add 100 mL of anhydrous DMF. The mixture is stirred at room temperature for 30 minutes. Starting material P4 (6.73 g, 25 mmol) is added under nitrogen protection. The mixture is stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate G8.

[0152] [ka] Synthesis of Intermediate G10: In a two-neck flask, add starting material R4 (5.16 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). Under nitrogen protection, add 100 mL of anhydrous DMF. The mixture is stirred at room temperature for 30 minutes. Starting material P3 (6.73 g, 25 mmol) is added under nitrogen protection. The mixture is stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate G10.

[0153] [ka] Synthesis of Intermediate G11: In a two-neck flask, add starting material R4 (5.16 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). Under nitrogen protection, add 100 mL of anhydrous DMF. The mixture is stirred at room temperature for 30 minutes. Starting material P4 (6.73 g, 25 mmol) is added under nitrogen protection. The mixture is stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate G11.

[0154] [ka] Synthesis of Intermediate G12: Add Intermediate R5 (9.9 g, 25 mmol), potassium carbonate (8.64 g, 62.5 mmol), tricyclohexylphosphine (0.35 g, 1.25 mmol), and palladium acetate (0.09 g, 0.4 mmol) to a two-neck flask and add 100 mL of anhydrous DMF under nitrogen protection. Stir the mixture at room temperature for 30 minutes. Add raw material P3 (6.73 g, 25 mmol) under nitrogen protection. Stir the mixture at 140 °C for 12 hours under nitrogen protection, then filter, wash, dry, and subject to column chromatography (PE:EA = 20:1) to obtain Intermediate G12.

[0155] [ka] Synthesis of Intermediate G13: Add Intermediate R5 (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) to a two-neck flask and add 100 mL of anhydrous DMF under nitrogen protection. Stir the mixture at room temperature for 30 minutes. Add raw material P4 (6.73 g, 25 mmol) under nitrogen protection. Stir the mixture at 140 °C for 12 hours under nitrogen protection, then filter, wash, dry, and subject to column chromatography (PE:EA = 20:1) to obtain Intermediate G13.

[0156] [ka] Synthesis of Intermediate G14: Intermediate R6 (11.97 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) were placed in a two-neck flask, and 100 mL of anhydrous DMF was added under nitrogen protection. The mixture was stirred at room temperature for 30 minutes. Raw material P3 (6.73 g, 25 mmol) was added under nitrogen protection. The mixture was stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain Intermediate G14.

[0157] Example 1: Synthesis of Compound 5:

[0158] [ka] Synthesis of intermediate B1: Raw material E1 (1.68 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) are placed in a two-neck flask, and 50 mL of anhydrous DMF is added under nitrogen protection. The mixture is stirred at room temperature for 30 minutes. Under nitrogen protection, intermediate A1 (1.4 g, 5 mmol) is added. The mixture is stirred at 140 °C for 12 hours under nitrogen protection, then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain intermediate B1.

[0159] Synthesis of Intermediate C1: Intermediate B1 (3.03 g, 5.1 mmol) is dissolved in 50 mL of tetrahydrofuran (THF) solution. 3.8 mL of n-butyllithium (1.6 M) is slowly added to n-hexane at 0 °C under nitrogen. The mixture is stirred at 0 °C for 2 hours. Next, 10 mL of a solution of starting material F1 (0.99 g, 5.5 mmol) is slowly added to tetrahydrofuran. The reaction mixture is then slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water, and ethyl acetate are added to the reaction mixture. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. 47% boron trifluoride-diethyl ether is then slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO3 solution. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to give intermediate C1.

[0160] Synthesis of Intermediate D1: Under nitrogen protection, dissolve Intermediate C1 (1.58 g, 2.5 mmol) in 50 mL of toluene and add Intermediate G1 (0.67 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol), and palladium acetate (0.01 g, 0.04 mmol). Stir the mixture vigorously. Reflux the resulting mixture at 105 °C for 10 hours and then cool to room temperature. Add ethyl acetate (100 mL). Wash the mixture three times with deionized water (100 mL) and dry it over anhydrous magnesium sulfate overnight. Ethyl acetate is then evaporated under reduced pressure. While stirring, pour the remaining mixture into 100 mL of petroleum ether. Filter the mixture to obtain Intermediate D1.

[0161] Synthesis of Compound 5: Intermediate D1 (10.24 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene, and 10 mL of a solution of tert-butyllithium (1.6 M) in n-pentane was slowly added at 0°C under a nitrogen atmosphere. The mixture was stirred at 60°C for 2 hours. Boron tribromide (6.26 g, 25 mmol) was then added at 0°C. The reaction mixture was then stirred at room temperature for 1 hour. N,N-Diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was then added at 0°C. After reaching room temperature, the reaction mixture was stirred at 130°C for 6 hours. The reaction mixture was then cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The organic layers were combined, concentrated under vacuum, and subjected to column chromatography to obtain Compound 5.

[0162] Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, and 17: Synthesis of the corresponding compounds 17, 41, 154, 182, 183, 186, 188, 204, 222, 268, 280, 327, 331, 343, 367, and 321: The following target compounds were synthesized using the same reaction conditions and the same starting material E1 as in Example 1, with reference to the preparation method of compound 5. The difference is that intermediates / starting materials A, F, and G shown in Table 2-1 were used.

[0163] [Table 2-1] TIFF2026500514000082.tif235170 TIFF2026500514000083.tif228170 Example 18: Synthesis of Compound 320:

[0164] [ka] Synthesis of intermediate B2: Raw material E2 (1.22 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) were placed in a two-neck flask, and 50 mL of anhydrous DMF was added under nitrogen protection. The mixture was stirred at room temperature for 30 minutes. Under nitrogen protection, intermediate A6 (1.79 g, 5 mmol) was added. The mixture was stirred at 140 °C for 12 hours under nitrogen protection, and then filtered, washed, dried, and subjected to column chromatography (PE:EA = 20:1) to obtain intermediate B2.

[0165] Synthesis of Intermediate C2: Intermediate B2 (4.19 g, 7.2 mmol) is dissolved in 30 mL of anhydrous ether, and 10 mL of a solution of n-butyllithium (1.6 M) in hexane is added dropwise at 0 °C under a N2 atmosphere. The mixture is stirred at 0 °C for 1 h. Then, 100 mL of a solution of starting material F3 (2.91 g, 8.00 mmol) in anhydrous toluene is added dropwise. The reaction mixture is stirred at 35 °C for 2 h and then cooled to room temperature. Water is added, and the reaction mixture is extracted with ethyl acetate to obtain the product. The organic layers are combined, washed with brine, dried over anhydrous Na2SO4, filtered, evaporated, and subjected to column chromatography to obtain Intermediate C2.

[0166] Synthesis of Intermediate D2: Under nitrogen protection, dissolve Intermediate C2 (3.50 g, 4.9 mmol) in 50 mL of toluene and add Intermediate G4 (1.60 g, 5 mmol), tri-tert-butylphosphine (0.051 g, 0.25 mmol), sodium tert-butoxide (1.25 g, 13 mmol), and palladium acetate (0.018 g, 0.08 mmol). Stir the mixture vigorously. Reflux the resulting mixture at 105 °C for 9 hours and then cool to room temperature. Add ethyl acetate (100 mL). Wash with deionized water (100 mL) three times and dry over anhydrous magnesium sulfate overnight. Ethyl acetate is then evaporated under reduced pressure. While stirring, pour the remaining mixture into 100 mL of petroleum ether. Filter the mixture to obtain Intermediate D2.

[0167] Synthesis of Compound 320: Intermediate D2 (12.47 g, 12.5 mmol) was dissolved in 300 mL of tert-butylbenzene, and 9 mL of a solution of tert-butyllithium (1.6 M) in n-pentane was slowly added at 0 °C under a nitrogen atmosphere. The mixture was stirred at 60 °C for 2 hours. Boron tribromide (6.26 g, 25 mmol) was then added at 0 °C. The reaction mixture was then stirred at room temperature for 1 hour. N,N-Diisopropylethylamine (DIPEA) (3.25 g, 25.2 mmol) was then added at 0 °C. After reaching room temperature, the reaction mixture was stirred at 130 °C for 6 hours. The reaction mixture was then cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr3. The mixture was separated and extracted with water and dichloromethane. The organic layers were combined, concentrated under vacuum, and subjected to column chromatography to obtain Compound 320.

[0168] Example 19: Synthesis of Compound 324:

[0169] [ka] Synthesis of intermediate B2: Add raw material E2 (1.22 g, 5 mmol or more) and cesium carbonate (4.07 g, 12.5 mmol) to a two-neck flask, and add 50 mL of anhydrous DMF under nitrogen protection. Stir the mixture at room temperature for 30 minutes. Add intermediate A6 (1.79 g, 5 mmol) under nitrogen protection. Stir the mixture at 140 °C for 12 hours under nitrogen protection, then filter, wash, dry, and subject to column chromatography (PE:EA = 20:1) to obtain intermediate B2.

[0170] Synthesis of Intermediate C3: To 30 mL of a solution of Intermediate B2 (4.19 g, 7.2 mmol) in anhydrous ether under N2 atmosphere at 0 °C, 10 mL of a solution of n-butyllithium in hexane (1.6 M) is added dropwise with stirring. The mixture is stirred at 0 °C for 1 hour. Then, 10 mL of a solution of Raw Material F5 (2.01 g, 8.00 mmol) in anhydrous toluene is added dropwise. The reaction mixture is stirred at 35 °C for 2 hours and then cooled to room temperature. Water is added, and the reaction mixture is extracted with ethyl acetate to obtain the product. The organic layers are combined, washed with brine, dried over anhydrous Na2SO4, filtered, evaporated, and subjected to column chromatography to obtain Intermediate C3.

[0171] Synthesis of Intermediate D3: Under nitrogen protection, dissolve Intermediate C3 (2.95 g, 4.9 mmol) in 50 mL of toluene and add Intermediate G4 (1.60 g, 5 mmol), tri-tert-butylphosphine (0.051 g, 0.25 mmol), sodium tert-butoxide (1.25 g, 13 mmol), and palladium acetate (0.018 g, 0.08 mmol). Stir the mixture vigorously. Reflux the resulting mixture at 105 °C for 9 hours and then cool to room temperature. Add ethyl acetate (100 mL). Wash the mixture three times with deionized water (100 mL) and dry it over anhydrous magnesium sulfate overnight. Ethyl acetate is then evaporated under reduced pressure. While stirring, pour the remaining mixture into 100 mL of petroleum ether. Filter the mixture to obtain Intermediate D3.

[0172] Synthesis of Compound 324: Under a nitrogen atmosphere, 9 mL of a solution of tert-butyllithium (1.6 M) in n-pentane is slowly added to 300 mL of a solution of intermediate D3 (11.07 g, 12.5 mmol) in tert-butylbenzene at 0 °C. The mixture is stirred at 60 °C for 2 hours. Then, n-pentane is removed under vacuum. Boron tribromide (6.26 g, 25 mmol) is added at 0 °C. The reaction mixture is then stirred at room temperature for 1 hour. N,N-Diisopropylethylamine (DIEA) (3.25 g, 25.2 mmol) is added at 0 °C. After reaching room temperature, the reaction mixture is stirred at 130 °C for 6 hours. Then, the reaction mixture is cooled to room temperature. Methanol is added to the reaction mixture to remove residual BBr3. The mixture is separated and extracted with water and dichloromethane. The organic layers are combined, concentrated under vacuum, and subjected to column chromatography to obtain Compound 324.

[0173] Examples 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30: Synthesis of the corresponding compounds 83, 116, 190, 212, 226, 264, 273, 275, 409, 417, and 481: The following target compounds were synthesized using the same reaction conditions and the same starting material E1 as in Example 1, with reference to the preparation method of compound 5. The difference is that intermediates / starting materials A, F, and G shown in Table 2-2 were used.

[0174] [Table 2-2] TIFF2026500514000087.tif216170 The test results of the structural characteristics, mass analysis and physicochemical properties of the compounds obtained in the examples are as follows:

[0175] The structural formula of compound 5 (C 59 H 45 BN2): Theoretical: C = 89.38, H = 5.72, N = 3.53, Test: C = 89.41, H = 5.64, N = 3.54. LC-MS: Found: 793.25 ([M+H] +), exact mass: 792.37. PLQY is 98% and FWHM is 25 nm.

[0176] The structural formula of compound 17 (C 61 H 49 BN2): Calculated: C = 89.25, H = 6.02, N = 3.41; Tested: C = 89.23, H = 6.09, N = 3.37. LC-MS: Found: 821.42 ([M+H] + ), exact mass: 820.40. PLQY was 96% and FWHM was 27 nm.

[0177] The structural formula of compound 41 (C 67 H 61 BN2): Calculated: C = 88.92, H = 6.79, N = 3.10; Tested: C = 88.99, H = 6.86, N = 3.00. LC-MS: Found: 905.46 ([M+H] + ), exact mass: 904.49. PLQY is 97% and FWHM is 28 nm.

[0178] The structural formula of compound 154 (C 77 H 79 BN2): Calculated: C = 88.65, H = 7.63, N = 2.69; Tested: C = 88.57, H = 7.58, N = 2.72. LC-MS: Found: 1043.86 ([M+H] + ), exact mass: 1042.63. PLQY is 94% and FWHM is 26 nm.

[0179] The structural formula of compound 182 (C 55 H 31 BN2): Calculated: C = 90.41, H = 4.28, N = 3.83; Tested: C = 90.44, H = 4.20, N = 3.92. LC-MS: Found: 731.16 ([M+H] + ), exact mass: 730.26. PLQY is 98% and FWHM is 27 nm.

[0180] The structural formula of compound 183 (C 57 H 35BN2): Calculated: C = 90.23, H = 4.65, N = 3.69; Tested: C = 90.19, H = 4.59, N = 3.74. LC-MS: Found: 759.40 ([M+H] + ), exact mass: 758.29. PLQY is 96% and FWHM is 24 nm.

[0181] The structural formula of compound 186 (C 63 H 47 BN2): Calculated: C = 89.77, H = 5.62, N = 3.32; Tested: C = 89.75, H = 5.52, N = 3.33. LC-MS: Found: 843.30 ([M+H] + ), exact mass: 842.38. PLQY is 94% and FWHM is 24 nm.

[0182] Figure 4 shows the spectrum of compound 186. Test conditions (toluene solution, 5 × 10 -5 M). Test equipment: Horiba Fluorolog-3 research fluorescence spectrometer.

[0183] FIG. 5 shows the nuclear magnetic resonance spectrum of compound 186.

[0184] The structural formula of compound 188 (C 65 H 51 BN2): Calculated: C = 89.64, H = 5.90, N = 3.22; Tested: C = 89.61, H = 5.80, N = 3.18. LC-MS: Found: 871.29 ([M+H] + ), exact mass: 870.41. PLQY is 97% and FWHM is 26 nm.

[0185] The structural formula of compound 204 (C 65 H 51 BN2): Calculated: C = 89.64, H = 5.90, N = 3.22; Tested: C = 89.60, H = 5.86, N = 3.13. LC-MS: Found: 871.62 ([M+H] + ), exact mass: 870.41. PLQY is 93% and FWHM is 25 nm.

[0186] The structural formula of compound 222 (C 71 H 63 BN2): Calculated: C = 89.29, H = 6.65, N = 2.93, Tested: C = 89.38, H = 6.75, N = 2.98. LC-MS: Found: 955.30 ([M+H] + ), exact mass: 954.51. PLQY is 97% and FWHM is 26 nm.

[0187] Figure 2 shows the spectrum of compound 222. Test conditions (toluene solution, 5 × 10 -5 M). Test equipment: Horiba Fluorolog-3 research fluorescence spectrometer.

[0188] FIG. 3 shows the nuclear magnetic resonance spectrum of compound 222.

[0189] The structural formula of compound 268 (C 71 H 63 BN2): Calculated: C = 89.29, H = 6.65, N = 2.93, Tested: C = 89.30, H = 6.67, N = 2.98. LC-MS: Found: 955.77 ([M+H] + ), exact mass: 954.51. PLQY is 98% and FWHM is 27 nm.

[0190] The structural formula of compound 280 (C 53 H 43 BN2): Calculated: C = 88.57, H = 6.03, N = 3.90; Tested: C = 88.53, H = 6.11, N = 3.98. LC-MS: Found: 719.40 ([M+H] + ), exact mass: 718.35. PLQY is 97% and FWHM is 28 nm.

[0191] The structural formula of compound 320 (C 70 H 63 BN2Si): ​​Theoretical: C = 86.57, H = 6.54, N = 2.88; Tested: C = 86.48, H = 6.58, N = 2.87. LC-MS: Found: 971.48 ([M+H] + ), exact mass: 970.49. PLQY is 93% and FWHM is 25 nm.

[0192] The structural formula of compound 324 (C 62 H 47 BN2Si): ​​Theoretical: C = 86.70, H = 5.52, N = 3.26, Si = 3.27; Tested: C = 86.67, H = 5.43, N = 3.30, Si = 3.26. LC-MS: Found: 859.54 ([M+H] + ), exact mass: 858.36. PLQY is 97% and FWHM is 29 nm.

[0193] The structural formula of compound 327 (C 55 H 31 BN2): Calculated: C = 90.41, H = 4.28, N = 3.83, Tested: C = 90.47, H = 4.25, N = 3.86. LC-MS: Found: 731.15 ([M+H] + ), exact mass: 730.26. PLQY is 97% and FWHM is 28 nm.

[0194] The structural formula of compound 331 (C 63 H 47 BN2): Theoretical: C = 89.77, H = 5.62, N = 3.32; Test: C = 89.83, H = 5.56, N = 3.37. LC-MS: Found: 843.63 ([M+H] + ), exact mass: 842.38. PLQY is 94% and FWHM is 25 nm.

[0195] FIG. 13 shows the nuclear magnetic resonance spectrum of compound 331.

[0196] The structural formula of compound 343 (C 65 H 51 BN2): Calculated: C=89.64, H=5.90, N=3.22, Tested: C=89.60, H=5.84, N=3.24. LC-MS: Found: 871.38 ([M+H]+), Exact Mass: 870.41. PLQY is 97% and FWHM is 25 nm.

[0197] The structural formula of compound 367 (C 71 H 63BN2): Calculated: C=89.29, H=6.65, N=2.93, Tested: C=89.27, H=6.72, N=3.01. LC-MS: Found: 955.67 ([M+H]+), Exact Mass: 954.51. PLQY is 97% and FWHM is 24 nm.

[0198] FIG. 14 shows the nuclear magnetic resonance spectrum of compound 367.

[0199] The structural formula of compound 321 (C 79 H 79 BN2): Calculated: C = 88.90, H = 7.46, N = 2.62, Tested: C = 88.88, H = 7.36, N = 2.56. LC-MS: Found: 1067.61 ([M+H] + ), exact mass: 1066.63. PLQY is 96% and FWHM is 28 nm.

[0200] The structural formula of compound 83 (C 56 H 39 BN2): Theoretical: C=89.59, H=5.24, N=3.73, Tested: C=89.56, H=5.23, N=3.74. LC-MS: Found: 751.41 ([M+H]+), Exact mass: 750.32.

[0201] The structural formula of compound 116 (C 71 H 69 BN2): Theoretical: C=88.72, H=7.24, N=2.91, Tested: C=88.71, H=7.22, N=2.89. LC-MS: Found: 961.72 ([M+H]+), Exact mass: 960.56.

[0202] FIG. 10 shows the nuclear magnetic resonance spectrum of compound 116.

[0203] The structural formula of compound 190 (C 65 H 51 BN2): Theoretical: C=89.64, H=5.90, N=3.22, Tested: C=89.60, H=5.89, N=3.17. LC-MS: Found: 871.28 ([M+H]+), Exact mass: 870.41.

[0204] FIG. 11 shows the nuclear magnetic resonance spectrum of compound 190.

[0205] The structural formula of compound 212 (C 58 H 37 BN2): Theoretical: C=90.15, H=4.83, N=3.63, Tested: C=90.21, H=4.79, N=3.61. LC-MS: Found: 773.33 ([M+H]+), Exact mass: 772.30.

[0206] The structural formula of compound 226 (C 73 H 67 BN2): Theoretical: C=89.18, H=6.87, N=2.85, Tested: C=89.24, H=6.86, N=2.86. LC-MS: Found: 983.66 ([M+H]+), Exact mass: 982.54.

[0207] Figure 6 shows the spectrum of compound 226. Test conditions (toluene solution, 5 × 10 -5 M). Test equipment: Horiba Fluorolog-3 research fluorescence spectrometer.

[0208] FIG. 7 shows the nuclear magnetic resonance spectrum of compound 226.

[0209] The structural formula of compound 264 (C 60 H 41 BN2): Theoretical: C=89.99, H=5.16, N=3.50, Tested: C=89.96, H=5.18, N=3.52. LC-MS: Found: 801.20 ([M+H]+), Exact mass: 800.34.

[0210] The structural formula of compound 273 (C 79 H 75 BN2): Theoretical: C=89.24, H=7.11, N=2.63, Tested: C=89.23, H=7.08, N=2.73. LC-MS: Found: 1063.74 ([M+H]+), Exact mass: 1062.60.

[0211] FIG. 8 shows the nuclear magnetic resonance spectrum of compound 273.

[0212] The mass spectrum of compound 273 is shown in FIG.

[0213] The structural formula of compound 275 (C 79 H 79 BN2): Theoretical: C=88.90, H=7.46, N=2.62, Tested: C=88.86, H=7.49, N=2.58. LC-MS: Found: 1067.81 ([M+H]+), Exact mass: 1066.63.

[0214] FIG. 12 shows the nuclear magnetic resonance spectrum of compound 275.

[0215] The structural formula of compound 409 (C 60 H 41 BN2): Theoretical: C=89.99, H=5.16, N=3.50, Tested: C=89.98, H=5.22, N=3.51. LC-MS: Found: 801.43 ([M+H]+), Exact mass: 800.34.

[0216] The structural formula of compound 417 (C 79 H 75 BN2): Theoretical: C=89.24, H=7.11, N=2.63, Tested: C=89.14, H=7.14, N=2.64. LC-MS: Found: 1063.90 ([M+H]+), Exact mass: 1062.60.

[0217] The structural formula of compound 481 (C 85 H 83 BN2): Theoretical: C=89.29, H=7.32, N=2.45, Tested: C=89.33, H=7.29, N=2.38. LC-MS: Found: 1143.54 ([M+H]+), Exact mass: 1142.66.

[0218] NOTE: PLQY (fluorescence quantum yield) and FWHM (full width at half maximum) are measured in the film state by a Horiba Fluorolog-3 series fluorescence spectrometer.

[0219] From the above compound data, it can be seen that the compound of the present invention, as a doping material, has a high fluorescence quantum yield, the fluorescence quantum yield of the material is close to 100%, the material has a narrow spectral FWHM, and can effectively improve the color gamut of the device and the luminous efficiency of the device.

[0220] The following describes in detail the effects of using the OLED materials synthesized in the present invention in devices using Device Examples 1 to 30 and Device Comparative Examples 1 to 5. Throughout Device Examples 1 to 30 of the present invention and Device Comparative Examples 1 to 5, the device fabrication process is identical, and the substrate material, electrode material, and electrode material thickness are all the same. The only difference is that the light-emitting layer material in the device has been changed. Tables 3 and 4 show the layer structures and test results of device embodiments, respectively.

[0221] Device Example 1 As shown in Figure 1, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (150 nm thick) is sequentially washed with a cleaner (Semiclean M-L20) and pure water. After drying, it is cleaned with ultraviolet ozone to remove organic residues from the transparent ITO surface. Using a vacuum deposition system, 10 nm thick films of HT-1 and HI-1, which will be used as the hole injection layer 3, are deposited on the cleaned ITO anode layer 2. The mass ratio of HT-1 to HI-1 is 97:3. Next, a 60 nm thick film of HT-1 is deposited as the hole transport layer 4. Next, a 30 nm thick film of EB-1 is deposited as the electron blocking layer 5. After the electron blocking material is deposited, the light-emitting layer 6 of the OLED light-emitting device is prepared using GH-1 and GH-2 as host materials and compound 5 as a doping material. Here, the mass ratio of GH-1 to GH-2 to compound 5 is 69:30:1, and the thickness of the light-emitting layer is 30 nm. Further, under vacuum, a 5 nm thick film of HB-1 is formed on the light-emitting layer 6 to form a hole-blocking layer 7. Further, under vacuum, a 30 nm thick film of ET-1 and Liq is formed on the hole-blocking layer 7 to form an electron-transporting layer 8. Here, the mass ratio of ET-1 to Liq is 1:1. Using a vacuum evaporation system, a 1 nm thick LiF layer is prepared on the electron-transporting layer 8 to form an electron-injecting layer 9. Using a vacuum evaporation system, an 80 nm thick Mg:Ag electrode layer is prepared on the electron-injecting layer 9 to form a cathode layer 10. The mass ratio of Mg to Ag is 1:9.

[0222] The following describes in detail the effects of using the OLED materials synthesized in the present invention in devices using Device Examples 31-60 and Device Comparative Examples 6-10. In comparing Device Examples 31-60 of the present invention with Device Comparative Examples 6-10, the device fabrication process is identical, the substrate material, electrode material, and electrode material thickness are all the same. The only difference is that the light-emitting layer material in the device has been changed. Tables 3 and 4 show the layer structures and test results of device embodiments, respectively.

[0223] Device Example 31 The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (150 nm thick) is sequentially washed with a cleaner (Semiclean M-L20) and pure water. After drying, it is cleaned with ultraviolet ozone to remove organic residues from the transparent ITO surface. Using a vacuum deposition system, 10 nm thick films of HT-1 and HI-1, which will be used as the hole injection layer 3, are deposited on the cleaned ITO anode layer 2. The mass ratio of HT-1 to HI-1 is 97:3. Next, a 60 nm thick film of HT-1 is deposited as the hole transport layer 4. Next, a 30 nm thick film of EB-1 is deposited as the electron blocking layer 5. After the electron blocking material is deposited, the light-emitting layer 6 of the OLED light-emitting device is prepared using GH-1 and GH-2 as the host material, GD-1 as the first doping material, and compound 5 as the second doping material. Here, the mass ratio of GH-1 to GH-2 to GD-1 to compound 5 is 66:30:3:1, and the thickness of the light-emitting layer is 30 nm. A 5 nm thick film of HB-1 is then formed on the light-emitting layer 6 under vacuum to form a hole-blocking layer 7. A 30 nm thick film of ET-1 and Liq is then formed on the hole-blocking layer 7 under vacuum to form an electron-transporting layer 8. The mass ratio of ET-1 to Liq is 1:1. Next, a 1 nm thick LiF layer is formed on the electron-transporting layer 8 using a vacuum evaporation system to form an electron-injecting layer 9. An 80 nm thick Mg:Ag electrode layer is then formed on the electron-injecting layer 9 using a vacuum evaporation system to form a cathode layer 10. The mass ratio of Mg to Ag is 1:9.

[0224] The molecular structures of the relevant materials are shown below.

[0225] [ka] Comparative compounds ref-1, ref-2, ref-3, ref-4, and ref-5 are prepared with reference to methods described in the prior art.

[0226] After fabricating the above-described OLED light-emitting device, the anode and cathode are connected by a well-known driving circuit, and the current efficiency and lifetime of the device are measured. Table 3 shows examples and comparative examples of devices prepared by the same method. Table 4 shows the test results of the current efficiency and lifetime of the obtained devices.

[0227] [Table 3] TIFF2026500514000090.tif250170 TIFF2026500514000091.tif253170 TIFF2026500514000092.tif252170 TIFF2026500514000093.tif252170 TIFF2026500514000094.tif251170 TIFF2026500514000095.tif247170 TIFF2026500514000096.tif253170 TIFF2026500514000097.tif250170 TIFF2026500514000098.tif254170 TIFF2026500514000099.tif253170 TIFF2026500514000100.tif253170

[0228] [Table 4] TIFF2026500514000102.tif173170 Note: The current efficiency and peak luminance were measured using an IVL (current-voltage-luminance) measurement device (Suzhou Fstar Scientific Instruments). The life test device was a Nippon Giken Kogyo EAS-62C OLED device life tester. LT95 is the time required for the device luminance to decay to 95%. All data are based on a current of 10 mA / cm. 2 was measured.

[0229] The device data results in Table 4 show that the device lifetime of the single-doped device with the compounds of the present invention is longer than that of Comparative Device Examples 1-5, and the device efficiency of the single-doped device is also better. Compared to Comparative Device Examples 1-5, the current efficiency and device lifetime of the double-doped device with the compounds of the present invention, which uses an exciton-sensitized material as the first doping material, are significantly improved compared to OLED devices made with known materials. Also, the device efficiency of the double-doped device is significantly improved compared to the single-doped device.

[0230] The above description is merely a preferred embodiment of the present invention, and does not limit the present invention. It should be noted that any modifications, equivalent replacements, and improvements made within the spirit and principle of the present invention shall fall within the protection scope of the present invention.

Claims

1. A boron-containing organic compound, The structure of the boron-containing organic compound is represented by the following general formula (A-1): 【Chemistry 1】 In general formula (A-1), R 1 ~R 19 each represents, the same or different, one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkenyl, a substituted or unsubstituted C1-C10 alkynyl, a substituted or unsubstituted silanyl, a substituted or unsubstituted boranyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C6-C30 aryloxy, a substituted or unsubstituted arylamido, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; R 1 ~R 17 Any two adjacent groups can be linked to form a ring, R 18 and R 19 can be linked to form a ring, Ar 1 and Ar 2 each represents the same or different one of a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkenyl, a substituted or unsubstituted C1-C10 alkynyl, a substituted or unsubstituted silanyl, a substituted or unsubstituted boranyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C6-C30 aryloxy, a substituted or unsubstituted arylamido, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; M 1 , M 2 , M 3 , M 4 , and M 5 each independently represents one of a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted 5 to 30-membered heteroaromatic ring, and a substituted or unsubstituted C6 to C10 aliphatic ring; X represents C or Si; A boron-containing organic compound, wherein the substituents substituting the group are optionally selected from any one of deuterium, tritium, a halogen atom, cyano, C1-C10 alkyl, deuterium- or tritium-substituted C1-C10 alkyl, C6-C30 aryl, deuterium- or tritium-substituted C6-C30 aryl, C2-C30 heteroaryl, and deuterium- or tritium-substituted C2-C30 heteroaryl.

2. The structure of the boron-containing organic compound is represented by the following general formula (A): 【Chemistry 2】 is expressed as In general formula (A), R 1 ~R 19 each represents one of the following, which may be the same or different: a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C1-C10 aryloxy, a substituted or unsubstituted arylamide, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; R 1 ~R 14 Any two adjacent groups can be linked to form a ring, R 18 and R 19 can be linked to form a ring, Ar 1 and Ar 2 each represents one of the following, which may be the same or different: substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 aryloxy, substituted or unsubstituted arylamido, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; M 1 is a substituted or unsubstituted C 6 ~C 30 or a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, X represents C or Si; The substituents for the group may be, as needed, deuterium, tritium, a halogen atom, cyano, C 1 ~C 10 Alkyl, deuterium- or tritium-substituted C 1 ~C 10 Alkyl, C 6 ~C 30 Aryl, deuterium- or tritium-substituted C 6 ~C 30 Aryl, C 5 ~C 30 Heteroaryl, deuterium- or tritium-substituted C 2 ~C 30 2. The boron-containing organic compound of claim 1, wherein the heteroaryl is selected from any one of the following:

3. The structure of the boron-containing organic compound is represented by general formula (1-1) or general formula (1-2): 【Transformation 3】 In the general formula (1-1) and the general formula (1-2), R 1 ~R 21 each represents, the same or different, any of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C1-C10 aryloxy, a substituted or unsubstituted arylamide, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; R 1 ~R 21 Any two adjacent groups can be linked to form a ring, Ar 1 and Ar 2 each represents one of the following, which may be the same or different: substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 aryloxy, substituted or unsubstituted arylamido, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; X represents C or Si; The substituents for the group may be, as needed, deuterium, tritium, a halogen atom, cyano, C 1 ~C 10 Alkyl, deuterium- or tritium-substituted C 1 ~C 10 Alkyl, C 6 ~C 30 aryl, deuterium- or tritium-substituted C 6 ~C 30 Aryl, C 5 ~C 30 Heteroaryls of the formula: 2 ~C 30 3. The boron-containing organic compound of claim 2, wherein the heteroaryl is selected from any one of the following:

4. The structure of the boron-containing organic compound is represented by general formula (1-3) or general formula (1-4): 【Chemistry 4】 General formula (1-3) General formula (1-4) In the general formula (1-3) and the general formula (1-4), R 1 ~R 19 each represents, the same or different, a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkenyl, a substituted or unsubstituted C1-C10 alkynyl, a substituted or unsubstituted silanyl, a substituted or unsubstituted boranyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C6-C30 aryloxy, a substituted or unsubstituted arylamide, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; R 1 ~R 19 Any two adjacent groups can be linked to form a ring, Ar 1 and Ar 2 each represents the same or different one of substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C1 to C10 alkenyl, substituted or unsubstituted C1 to C10 alkynyl, substituted or unsubstituted silanyl, substituted or unsubstituted boranyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C30 aryloxy, substituted or unsubstituted arylamido, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C2 to C30 heteroaryl; X represents C or Si; The substituents for the group may be, as needed, deuterium, tritium, a halogen atom, cyano, C 1 ~C 10 Alkyl, deuterium- or tritium-substituted C 1 ~C 10 Alkyl, C 6 ~C 30 aryl, deuterium- or tritium-substituted C 6 ~C 30 Aryl, C 2 ~C 30 Heteroaryl, deuterium- or tritium-substituted C 2 ~C 30 2. The boron-containing organic compound of claim 1, wherein the heteroaryl is selected from any one of the following:

5. The structure of the boron-containing organic compound is represented by the following general formula (2): 【Transformation 5】 In general formula (2), R 2 , R 7 , R 10 , R 13 , R 16 , R 18 , Ar 1 , Ar 2 3. The boron-containing organic compound according to claim 2, wherein the meanings of X and X are the same as those described in claim 2.

6. The structure of the boron-containing organic compound is represented by general formula (2-1) or general formula (2-2): 【Transformation 6】 In the general formula (2-1) and the general formula (2-2), R 2 , R 7 , R 10 , R 13 , R 18 , Ar 1 , Ar 2 and X have the same meanings as those in claim 2. The boron-containing organic compound according to claim 2.

7. The structure of the boron-containing organic compound is represented by the following general formula (3-1): 【Transformation 7】 In general formula (3-1), R's are the same or different and represent any one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C1-C10 aryloxy, a substituted or unsubstituted arylamide, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; X represents C or Si; The substituents for the group may be, as needed, deuterium, tritium, a halogen atom, cyano, C 1 ~C 10 Alkyl, deuterium- or tritium-substituted C 1 ~C 10 Alkyl, C 6 ~C 30 aryl, deuterium- or tritium-substituted C 6 ~C 30 Aryl, C 5 ~C 30 Heteroaryl, deuterium- or tritium-substituted C 2 ~C 30 3. The boron-containing organic compound of claim 2, wherein the heteroaryl is selected from any one of the following:

8. R and R 1 ~R 21 each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a fluorine atom, cyano, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzo furyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy; Ar 1 and Ar 2 each independently represents phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl ether, phenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy; M 1 , M 2 , M 3 , M 4 , and M 5 represents one of phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuryl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, and xanthone; 8. The boron-containing organic compound of claim 1, wherein the substituent replacing the substitutable group is optionally selected from one or more of deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-pentyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthryl, phenanthryl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolyl, isoquinolyl, furyl, thienyl, indolyl, pyrrolyl, dibenzofuryl, dibenzothienyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, and azaphenanthryl.

9. R and R 1 ~R 21 each independently represents a hydrogen atom, a cyano, 【Transformation 8】 represents one of the following: Ar 1 and Ar 2 teeth, 【Chemistry 9】 represents one of the following: M 1 , M 2 , and M 3 is the following ring structure 【Chemistry 10】 represents one of the following: M 4 and M 5 is the following ring structure 【Chemistry 11】 represents one of the following: Z is CR a represents R a each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, 8. The boron-containing organic compound of claim 1, wherein the boron-containing organic compound is one of N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy.

10. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are the same or different, and are a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, 【Chemistry 12】 or phenyl, Ar 1 and Ar 2 are the same or different, methyl, 【Chemistry 13】 represents one of the following: M 1 , M 2 and M 3 is the following ring structure: 【Chemistry 14】 represents one of the following: M 4 and M 5 is the following ring structure: 【Chemistry 15】 represents Z is CR a represents R a each independently represents a hydrogen atom, a deuterium atom, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, 【Chemistry 16】 8. The boron-containing organic compound according to claim 1, wherein X represents C or Si.

11. The specific structural formula of the boron-containing organic compound is: 【Chemistry 17】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 2. The boron-containing organic compound according to claim 1, wherein the boron-containing organic compound is any one of the following:

12. 1. An organic electroluminescent device having a cathode, an anode, and an organic light-emitting functional layer between the cathode and the anode, the organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer includes the boron-containing organic compound according to any one of claims 1 to 11; Preferably, the light-emitting layer comprises a host material and a doping material, and the doping material comprises the boron-containing organic compound according to any one of claims 1 to 11.

13. the light-emitting layer comprises a first host material, a second host material, and a doping material; 13. The organic electroluminescent device according to claim 12, wherein at least one of the first host material and the second host material is a TADF material, and the doping material is a boron-containing organic compound according to any one of claims 1 to 11.

14. the light-emitting layer comprises a host material, an exciton-sensitized material, and a doping material; 13. The organic electroluminescent device according to claim 12, wherein the exciton-sensitized material is a complex containing a metal element, and the doping material is the boron-containing organic compound according to any one of claims 1 to 11.

15. 12. A material for an organic electroluminescent device, comprising a boron-containing organic compound according to any one of claims 1 to 11.

16. 12. Use of a boron-containing organic compound according to any one of claims 1 to 11 in an organic electroluminescent device.

17. the organic light-emitting functional layer has a light-emitting layer, 17. The use according to claim 16, wherein the light-emitting layer comprises a boron-containing organic compound according to any one of claims 1 to 11.

18. 15. A display member comprising an organic electroluminescent device according to any one of claims 12 to 14.

19. 15. A lighting device comprising an organic electroluminescent device according to any one of claims 12 to 14.

20. 15. An electronic device carrying an organic electroluminescent device according to any one of claims 12 to 14.

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