Organoboron compound and application thereof

Abstract

The invention provides an organoboron compound and application thereof. The organic boron compound has a structure as shown in a formula (0), a boron-carbon unit is adopted as a parent nucleus, and when the organic boron compound is used as a luminescent material, the relaxation degree of an excited state structure can be reduced by a large-plane parent nucleus unit, so that relatively narrow half-peak width is realized; different substituent groups are introduced into a rigid framework, so that the delayed fluorescence lifetime and the half-peak width can be further adjusted; the organic boron compound can be used for preparing an organic electroluminescent device, and the service life and the luminous efficiency of the device are improved. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the technical field of electroluminescence, and particularly relates to an organoboron compound and its application. Background Art

[0002] Due to the limitation of the spin quantum statistics law, traditional fluorescent materials can only utilize singlet excitons accounting for 25% of all excitons during electroluminescence, and the remaining 75% of triplet excitons are deactivated through non-radiative transitions. The theoretical limit value of the internal quantum efficiency of the device is 25%. In order to improve the exciton utilization rate, it is necessary to convert triplet excitons into photons to achieve 100% internal quantum efficiency. Phosphorescent metal complexes can convert triplet excitons into photons by using the spin-orbit coupling effect of heavy metal atoms, but this approach faces the problem of the high price of phosphorescent metal complexes. Another approach to utilize triplet excitons is to develop luminescent materials with thermally activated delayed fluorescence (TADF) properties, and use the thermally activated reverse intersystem crossing (RISC) process to transfer triplet excited states to singlet excited states to emit fluorescence, so as to achieve the full utilization of singlet and triplet excitons. Molecules with TADF properties generally need to meet two conditions: a small singlet-triplet energy level difference (ΔE ST ), and a high fluorescence quantum efficiency (PLQY). On the one hand, a small ΔE ST is beneficial to the occurrence of the thermally activated reverse intersystem crossing process, thus being beneficial to improving the utilization efficiency of triplet excitons; on the other hand, the material must have a high PLQY, so as to promote the decay of singlet excitons in the form of light and improve the device efficiency.

[0003] At present, the main way to develop TADF molecules is to introduce donor (D) and acceptor (A) groups, so that the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) are effectively separated in space, thus achieving a small ΔE ST . However, this D-A structure exhibits a large Stokes shift due to the vibrational relaxation of its excited state, and the emission spectrum is relatively wide, with the full width at half maximum (FWHM) generally being 70 nm to 100 nm. In practical applications, it is often necessary to use a filter or construct an optical microcavity to improve the color purity, but this will lead to a decrease in the external quantum efficiency of the device or the device structure becoming complex.

[0004] Therefore, how to develop a fluorescent material that not only has the TADF effect but also has a narrow spectral characteristic through appropriate chemical structure design to solve the defect of the relatively wide full width at half maximum of the above materials has become one of the problems that many forward-looking researchers in the field urgently need to solve.

[0005] In view of the above reasons, the present invention is proposed. Summary of the Invention

[0006] To solve the above problems existing in the prior art, the present invention provides an organic boron compound which emits deep blue to blue light and has high luminous efficiency when used as a luminescent material. The present invention also provides an organic luminescent material, an organic electroluminescent device and a consumer product containing the organic boron compound. In addition, the present invention also provides the use of the organic boron compound.

[0007] To achieve the above object, the present invention adopts the following technical solutions:

[0008] In a first aspect of the present invention, there is provided an organic boron compound having a structure represented by the following formula (0):

[0009]

[0010] Wherein, ring a, ring b, ring c and ring d are each independently selected from Provided that one of ring a and ring b is And one of ring c and ring d is Y is independently selected from O, S, Se, GeR'R”, SiR'R”, CR'R” or NAr 1 ;

[0011] Optionally, ring a and ring c are connected through L to form a fused ring structure, and L is selected from a single bond, O, S, S=O, SO2, Se, GeR 10 R 11 , SiR 10 R 11 , C=O, CR 10 R 11 Or NAr 2 ;

[0012] R a , R b , R c And R d Independently represent unsubstituted, mono-substituted or multi-substituted;

[0013] R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 , R', and R” are the same as or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C6-C 50 aryl, substituted or unsubstituted C3-C 30Cycloalkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 50 Aryloxy, substituted or unsubstituted C1-C 30 Alkylthio, substituted or unsubstituted C5-C 50 Arylthio, substituted or unsubstituted C1-C 30 Alkylamino, substituted or unsubstituted C5-C 50 Arylamino, substituted or unsubstituted C1-C 30 Alkylsilyl, substituted or unsubstituted C5-C 50 Aryl silyl, nitro, cyano and halogen atoms; optionally, R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 , R', and R", adjacent two or more groups are joined or fused to form a substituted or unsubstituted carbocyclic or heterocyclic ring, and the heteroatoms in the formed heterocyclic ring are selected from N, O, S, P, B, Si, and Se;

[0014] Ar 1 and Ar 2 each independently selected from substituted or unsubstituted C6-C 50 aryl, substituted or unsubstituted C 12 -C 50 condensed aryl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C6-C 50 arylamino group;

[0015] When R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 , R', R", Ar 1 and Ar 2 contains substituents, the substituents are one or more and each independently selected from the group consisting of the following groups: deuterium, halogen, C1-C 20 alkyl, C1-C 20 deuterated alkyl, C1-C 20 haloalkyl, C1-C20 Alkoxy, C6-C 30 Aryloxy, C3-C 20 Cycloalkyl, C2-C 20 Heterocycloalkyl, C6-C 30 Aryl, C2-C 30 Heteroaryl.

[0016] The organoboron compound of the present invention uses a boron-carbon unit as the core structure. When used as a luminescent material, the large planar core unit can reduce the degree of excited state structural relaxation, thereby achieving a narrower full width at half maximum; on the other hand, by introducing different substituents on the rigid skeleton, further adjustment of the delayed fluorescence lifetime and full width at half maximum can be achieved.

[0017] According to some embodiments of the present invention, in formula (0), ring a and ring c are each independently selected from Ring b and ring d are each independently selected from Y is defined as in the previous definition of the present invention.

[0018] According to some embodiments of the present invention, in formula (0), ring b and ring d are each independently selected from Ring a and ring c are each independently selected from Y is defined as in the previous definition of the present invention.

[0019] According to some embodiments of the present invention, in formula (0), ring a and ring d are each independently selected from Ring b and ring c are each independently selected from Y is defined as in the previous definition of the present invention.

[0020] According to some embodiments of the present invention, in formula (0), ring b and ring c are each independently selected from Ring a and ring d are each independently selected from Y is defined as in the previous definition of the present invention.

[0021] According to some embodiments of the present invention, in formula (0), Y is independently selected from O, S, Se, CR'R” or NAr 1 .

[0022] According to some embodiments of the present invention, in formula (0), each occurrence of R' and R” is the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C6-C 50 aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C2-C 50Groups consisting of heteroaryls; when R' and R” contain substituents, the substituents are one or more and each independently selected from the group consisting of the following groups: deuterium, halogen, C1-C 20 alkyls, C1-C 20 deuterated alkyls, C1-C 20 haloalkyls, C1-C 20 alkoxys, C6-C 20 aryloxys, C3-C 20 cycloalkyls, C2-C 20 heterocycloalkyls, C6-C 20 aryls, C2-C 20 heteroaryls.

[0023] According to some embodiments of the present invention, in formula (0), each occurrence of R' and R” is the same as or different from each other, and each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 10 alkyls, substituted or unsubstituted C6-C 20 aryls, substituted or unsubstituted C3-C 12 cycloalkyls, substituted or unsubstituted C2-C 20 heteroaryls, when R' and R” contain substituents, the substituents are one or more and each independently selected from the group consisting of the following groups: deuterium, halogen, C1-C 10 alkyls, C1-C 10 deuterated alkyls, C1-C 10 haloalkyls, C1-C 10 alkoxys, C6-C 15 aryloxys, C3-C 12 cycloalkyls, C2-C 15 heterocycloalkyls, C6-C 15 aryls, C2-C 15 heteroaryls.

[0024] According to some embodiments of the present invention, in formula (0), each occurrence of R' and R” is the same as or different from each other, and each independently selected from hydrogen, deuterium, C1-C6 alkyls, C1-C6 deuterated alkyls, C1-C6 haloalkyls, C1-C6 alkoxys, phenyl or deuterated phenyl.

[0025] According to some embodiments of the present invention, in formula (0), each occurrence of R' and R” is the same as or different from each other, and each independently selected from hydrogen, deuterium, methyl, ethyl or phenyl.

[0026] According to some embodiments of the present invention, in formula (0), R a 、R b 、R c 、R d 、R 4 、R5 , R 6 , R 10 , R 11 At each occurrence, each is the same as or different from one another and is independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 20 alkyl group, a substituted or unsubstituted C1-C 20 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C1-C 20 alkylsilyl group, a substituted or unsubstituted C5-C 30 arylsilyl group, a substituted or unsubstituted C3-C 20 cycloalkyl group, a substituted or unsubstituted C2-C 30 heteroaryl group; when R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 contains a substituent, the substituent is one or more and is independently selected from the group consisting of deuterium, halogen, C1-C 10 alkyl group, C1-C 10 deuterated alkyl group, C1-C 10 haloalkyl group, C1-C 10 alkoxy group, C6-C 20 aryloxy group, C3-C 12 cycloalkyl group, C2-C 12 heterocycloalkyl group, C6-C 20 aryl group, C2-C 20 heteroaryl group.

[0027] According to some embodiments of the present invention, in formula (0), R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 At each occurrence, each is the same as or different from one another and is independently selected from the group consisting of hydrogen, deuterium, a cyano group, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C6-C 20 aryl group, a substituted or unsubstituted C2-C 20 heteroaryl group; when R a , R b , Rc , R d , R 4 , R 5 , R 6 When there are substituents in, the substituents are one or more and each independently selected from the group consisting of the following groups: deuterium, halogen, C1-C 10 alkyl, C1-C 10 deuterated alkyl, C1-C 10 haloalkyl, C1-C 10 alkoxy, C6-C 20 aryloxy, C3-C 12 cycloalkyl, C2-C 12 heterocycloalkyl, C6-C 20 aryl, C2-C 20 heteroaryl.

[0028] According to some embodiments of the present invention, in formula (0), R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 Each time it appears, is the same as or different from each other and each independently selected from the group consisting of hydrogen, deuterium, cyano, halogen atom, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C 15 aryl, substituted or unsubstituted C5-C 15 heteroaryl; when R a , R b , R c , R d , R 4 , R 5 , R 6 contains substituents, the substituents are one or more and each independently selected from the group consisting of the following groups: deuterium, halogen, C1-C6 alkyl, C1-C6 deuterated alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C6-C 15 aryloxy, C3-C8 cycloalkyl, C2-C8 heterocycloalkyl, C6-C 15 aryl, C2-C 150 heteroaryl.

[0029] According to some embodiments of the present invention, in formula (0), R a , R b , R c , R d , R 4 , R 5 , R 6, R 10 , R 11 Each time it appears, it is the same as or different from each other and is independently selected from hydrogen, deuterium, cyano, halogen atom, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, phenyl, biphenyl, naphthyl, carbazolyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, deuterated carbazolyl, phenyl substituted with C1-C6 alkyl, biphenyl substituted with C1-C6 alkyl, naphthyl substituted with C1-C6 alkyl, carbazolyl substituted with C1-C6 alkyl.

[0030] According to some embodiments of the present invention, in formula (0), R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 Each time it appears, it is the same as or different from each other and is independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, methoxy, ethyl, ethoxy, propyl, propoxy, isopropyl, isopropoxy, butyl, butyloxy, isobutyl, isobutyloxy, tert-butyl, tert-butyloxy, trifluoromethyl, trifluoromethyloxy, pentafluoroethyl, pentafluoroethoxy, trimethylsilyl, substituted or unsubstituted phenyldimethylsilyl, cyclobutyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted benzanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted group, substituted or unsubstituted perylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl.

[0031] According to some embodiments of the present invention, in formula (0), R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11Each occurrence, which is the same as or different from each other and is independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, and the following groups:

[0032]

[0033] According to some embodiments of the present invention, the organoboron compound has a structure represented by formula (I), formula (II), or formula (III):

[0034]

[0035] In formula (I), formula (II), or formula (III): Y 1 , Y 2 are each independently selected from O, S, Se, GeR 10 R 11 , SiR 10 R 11 , CR 10 R 11 , or NAr 1 ;

[0036] L is absent or selected from O, S, S=O, SO2, Se, GeR 10 R 11 , SiR 10 R 11 , C=O, CR 10 R 11 , or NAr 2 ;

[0037] R 1 ~R 11 Each occurrence, which is the same as or different from each other, is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C6-C 50 aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted C6-C 50 aryloxy, substituted or unsubstituted C1-C 30 alkylthio, substituted or unsubstituted C5-C 50 arylthio, substituted or unsubstituted C1-C 30 alkylamino, substituted or unsubstituted C5-C 50 arylamino, substituted or unsubstituted C1-C 30 alkylsilyl, substituted or unsubstituted C5-C 50A group consisting of an arylsilyl, nitro, cyano or halogen atom, and any two or more adjacent Rs 1 ~R 11 may be optionally joined or fused to form a substituted or unsubstituted ring, which may or may not contain C or heteroatoms N, O, S, P, B, Si or Se;

[0038] Ar 1 、Ar 2 are the same as or different from each other and are each independently selected from the group consisting of substituted or unsubstituted C6-C 50 aryl, substituted or unsubstituted C6-C 50 condensed aryl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C6-C 50 arylamino.

[0039] According to some embodiments of the present invention, the organoboron compound is selected from the compounds represented by the following structures:

[0040]

[0041]

[0042] Wherein, the definitions of R a 、R b 、R c 、R d 、R 4 、R 5 、R 6 、L are the same as the definitions in formula (0) of the present invention; the definitions of Y1 and Y2 are the same as the definition of Y in formula (0).

[0043] In some embodiments, Y1 and Y2 are the same as or different from each other and are each independently selected from O, S, Se, CR 10 R 11 or NAr 1 。

[0044] In some embodiments, L is selected from O, S, Se, CR 10 R 11 or NAr 2 。In some embodiments, L is NAr 2 。

[0045] In some embodiments, Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C 12 ~C 30 condensed aryl, substituted or unsubstituted C5-C30 A group consisting of heteroaryl, substituted or unsubstituted C6-C 30 arylamino; when Ar 1 and Ar 2 contains substituents, the substituents are one or more and each independently selected from the group consisting of the following groups: deuterium, halogen, C1-C 10 alkyl, C1-C 10 deuterated alkyl, C1-C 10 haloalkyl, C1-C 10 alkoxy, C6-C 15 aryloxy, C3-C 12 cycloalkyl, C2-C 15 heterocycloalkyl, C6-C 15 aryl, C2-C 15 heteroaryl.

[0046] In some embodiments, Ar 1 and Ar 2 are each independently substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C 12 -C 30 fused aryl, substituted or unsubstituted C5-C 30 heteroaryl, when Ar 1 and Ar 2 contains substituents, the substituents are one or more and each independently selected from the group consisting of: deuterium, halogen, C1-C6 alkyl, C1-C6 deuterated alkyl, C1-C6 haloalkyl, phenyl.

[0047] In some embodiments, Ar 1 and Ar 2 are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted yl, substituted or unsubstituted perylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; when Ar 1 and Ar 2When having substituents, the substituents are one or more and each independently selected from the group consisting of the following groups: deuterium, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl.

[0048] In some embodiments, Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:

[0049]

[0050] According to some embodiments of the present invention, the organic boron compound is selected from any one of the following structures:

[0051]

[0052]

[0053]

[0054]

[0055] wherein, R 10 and R 11 can be joined to form L or may not be joined; the definition of L is the same as the foregoing definition of the present invention. Preferably, L is selected from O, S, Se, CR 10 R 11 or NAr 2 ;

[0056] The definitions of R' and R” are the same as the foregoing definitions of the present invention; further, each occurrence of R' and R” is the same as or different from each other and each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C6-C 50 aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C2-C 50 heteroaryl group. R' and R” can be joined or fused arbitrarily to form a substituted or unsubstituted ring, which contains or does not contain C or heteroatoms N, O, S, P, B, Si or Se. Further, R' and R” are each independently selected from methyl, phenyl or tert-butylphenyl; still further, R' and R” are each independently selected from methyl or phenyl;

[0057] R 4 ~R 6 、R10 , R 11 , Ar 1 , Ar 2 is defined as in the previous definition of the present invention, and R 1 to R 3 , R 7 to R 9 is defined as R in formula (0) of the present invention a , R b , R c , R d . In some embodiments, the R 1 to R 11 , each time it appears, is independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, methoxy, ethyl, ethoxy, propyl, propoxy, isopropyl, isopropoxy, butyl, butyloxy, isobutyl, isobutyloxy, tert-butyl, tert-butyloxy, trifluoromethyl, trifluoromethyloxy, pentafluoroethyl, pentafluoroethoxy, trimethylsilyl, substituted or unsubstituted phenyldimethylsilyl, cyclobutyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted group, substituted or unsubstituted perylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl. In some embodiments, R 10 , R 11 are each independently selected from methyl or phenyl. In some embodiments, the Ar 1 , Ar 2 are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted A group consisting of a base, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted indole group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzofuran group, and a substituted or unsubstituted dibenzothiophene group.

[0058] According to some embodiments of the present invention, the organoboron compound is selected from the compounds represented by B001 to B174 in Table 1 below, or is selected from one of the compounds represented by B001 to B174 substituted with one or more deuteriums:

[0059] Table 1

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069] In Table 1, Y, Y1, and Y2 are each independently selected from the group consisting of O, S, Se, C(CH3)2, or NAr; Ar is selected from the group consisting of the following groups:

[0070]

[0071] Cz is selected from the group consisting of the following groups:

[0072]

[0073] The second aspect of the present invention provides an organic electroluminescent material, and the organic electroluminescent material includes the above-mentioned organoboron compound.

[0074] According to some embodiments of the present invention, the organic electroluminescent material includes at least one host material and at least one dopant material, wherein the organoboron compound is contained in the host material or the dopant material.

[0075] According to some embodiments of the present invention, the host material includes the organic boron compound and / or a compound containing at least one of the following chemical groups: triphenylene, carbazolyl, dibenzothiophenyl, dibenzofuranyl, dibenzoselenophenyl, azatriphenylene, azacarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, azadibenzoselenophenyl, triazinyl, benzothiophenyl, benzofuranyl, and indolyl.

[0076] According to some embodiments of the present invention, in the organic electroluminescent material, the mass ratio of the doping material to the host material is 1:(1 - 99), for example, 1:1, 1:2, 1:5, 1:8, 1:10, 1:15, 1:20, 1:30, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90, 1:99, or any value therebetween. According to some embodiments of the present invention, in the organic electroluminescent material, the mass ratio of the doping material to the host material is 1:(1 - 20).

[0077] The third aspect of the present invention provides the use of the above-mentioned organic boron compound of the present invention or the above-mentioned organic electroluminescent material of the present invention in the preparation of an organic electroluminescent device.

[0078] In some embodiments, the organic boron compound or the organic electroluminescent material serves as the luminescent material of the organic light-emitting layer of the organic electroluminescent device.

[0079] The organic boron compound of the present invention can be used as the host material of the light-emitting layer of an organic electroluminescent element or as a doping material.

[0080] In some embodiments, the organic boron compound serves as the host material or the doping material of the organic light-emitting layer of the organic electroluminescent device.

[0081] In some embodiments, the organic light-emitting layer includes a host material and a doping material, and the mass ratio of the doping material to the host material is 1:(1 - 99), for example, 1:1, 1:2, 1:5, 1:8, 1:10, 1:15, 1:20, 1:30, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90, 1:99, or any value therebetween. According to some embodiments of the present invention, the mass ratio of the doping material to the host material is 1:(1 - 20).

[0082] The fourth aspect of the present invention provides an organic electroluminescent element, which includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains the above-mentioned organic boron compound of the present invention or the above-mentioned organic electroluminescent material of the present invention.

[0083] In some embodiments, the organic layer includes one or more light-emitting layers, and at least one of the light-emitting layers contains the above-mentioned organoboron compound of the present invention.

[0084] In some embodiments, the organic layer further contains at least one layer selected from an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, a hole blocking layer, and an electron blocking layer. In some embodiments, the organic layer contains one or more electron injection layers, electron transport layers, hole injection layers, hole transport layers, hole blocking layers, electron blocking layers, and light-emitting layers. Further, the light-emitting layer contains the organoboron compound or the above-mentioned organic electroluminescent material.

[0085] In some embodiments, the light-emitting layer includes a host material and a dopant material. The host material includes the organoboron compound of the present invention or a compound containing at least one of the following chemical groups: triphenylene, carbazolyl, dibenzothiophenyl, dibenzofuranyl, dibenzoselenophenyl, azatriphenylene, azacarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, azadibenzoselenophenyl, triazinyl, benzothiophenyl, benzofuranyl, and indolyl. In some embodiments, the dopant material includes the organoboron compound of the present invention. In some embodiments, any substituent in the host material can independently be a non-fused substituent selected from the group consisting of: C n H 2n+1 、OC n H 2n+1 、OAr 8 、N(C n H 2n+1 )2、N(Ar 8 )(Ar 9 )、CH=CH-C n H 2n+1 、C≡CC n H 2n+1 、Ar 8 、Ar 8 -Ar 9 、C n H 2n -Ar 8 or unsubstituted, where n is an integer from 1 to 10; and where Ar 8 and Ar 9 are independently selected from the group consisting of: phenyl, biphenyl, naphthyl, triphenylene, carbazolyl, and their heteroaromatic group analogs. Further, the host material is selected from one or more of the above-mentioned organoboron compounds of the present invention and the compounds represented by Formulas A1 to A90:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] In some embodiments, the mass ratio of the doping material to the host material is 1:(1-99), such as 1:1, 1:2, 1:5, 1:8, 1:10, 1:15, 1:20, 1:30, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90, 1:99 or any value therebetween.

[0092] The organic electroluminescent material described in the present invention may be composed of the organic boron compound of the present invention alone, or may contain other compounds at the same time.

[0093] Further, the host material includes the organic boron compound of the present invention as described above, or includes one or more doping materials used in combination with the organic boron compound of the present invention. Examples of other doping materials are not particularly limited, and any compound may be used as long as the compound is used as a luminescent material. Examples of suitable doping materials include, but are not limited to, compounds that can generate emission via phosphorescence, fluorescence, thermally activated delayed fluorescence (TADF), triplet-triplet annihilation, or a combination of these processes. Non-limiting examples of doping materials that can be combined with the organic boron compound of the present invention for use in an OLED may include the compounds represented by Formula IV, Formula V, Formula VI, and Formula VII:

[0094]

[0095]

[0096] wherein, ring A and ring B are each independently selected from a 5-membered, 6-membered, 7-membered carbocyclic or heterocyclic ring; Z 1 、Z 2 、Z 3 、Z 4 are each independently selected from C or N; L 1 、L 2 are each independently selected from a linking bond, BR’, NR’, PR’, O, S, Se, C=O, S=O, SO2, CR’R” or SiR’R”; L 3 is selected from BR’, NR’, PR’, O, S, Se, C=O, S=O, SO2, CR’R” or SiR’R”; M is selected from Pt or Pd; R A 、R B 、RC and R D and R E each represents mono - substitution, di - substitution or poly - substitution up to saturated substitution or no substitution, and two or more adjacent groups may form a ring through any bonding or fusion such as C, O, S, etc.; R A and R B and R C and R D and R E and R’, R” are each independently selected from hydrogen, deuterium, halogen atoms, alkyl groups, cycloalkyl groups, heteroalkyl groups, alkenyl groups, cycloalkenyl groups, heteroalkenyl groups, aryl groups, heteroaryl groups, aralkyl groups, alkoxy groups, aryloxy groups, alkylsilyl groups, nitrile groups, amino groups, arylamino groups, diarylamino groups, alkylamino groups, dialkylamino groups, germanium alkyl groups, arylalkylsilyl groups and combinations thereof; for example, in some instances, the compound represented by formula IV may be selected from the structures represented by formula IV - 1, and more specifically, for example, the structure represented by formula IV - 2,

[0097]

[0098] In formulae IV - 1 and IV - 2, adjacent R E and R D may bond to form a 5 - membered, 6 - membered, 7 - membered or 8 - membered ring; adjacent R C and R D may bond to form a 5 - membered, 6 - membered, 7 - membered or 8 - membered ring; adjacent R A and R B may bond to form a 5 - membered, 6 - membered, 7 - membered or 8 - membered ring; for example, the structures represented by formulae IV - 3 and IV - 4;

[0099]

[0100] In some instances, the compound represented by formula V may be selected from the structures represented by formula V - 1 or formula V - 2,

[0101]

[0102] In formulae V - 1 and V - 2, adjacent R B and R C may bond to form a 5 - membered, 6 - membered, 7 - membered or 8 - membered ring; adjacent R E and R D may bond to form a 5 - membered, 6 - membered, 7 - membered or 8 - membered ring; for example, the structures represented by formulae V - 3 and V - 4;

[0103]

[0104] In some instances, the compound represented by formula VI may be selected from the structures represented by formula VI - 1 or formula VI - 2,

[0105]

[0106] In Formulas VI-1 and VI-2, adjacent Rs A , Rs A and Rs B can join to form a 5-, 6-, 7- or 8-membered ring; adjacent Rs C , Rs D and Rs E can join to form a 5-, 6-, 7- or 8-membered ring, such as the structures shown in Formulas VI-3, VI-4, VI-5 and VI-6:

[0107]

[0108] wherein, T can be selected from N, B, CR", or P.

[0109] In some instances, the compound shown in Formula VII can be selected from the structures shown in Formula VII-1 or Formula VII-2,

[0110]

[0111] In Formulas VII-1 and VII-2, adjacent Rs B can join to form a 5-, 6-, 7- or 8-membered ring; adjacent Rs B , R" and Rs B can join to form a 5-, 6-, 7- or 8-membered ring, such as the structures shown in Formulas VII-3, VII-4, VII-5, VII-6:

[0112]

[0113] Furthermore, the Rs A , Rs B , Rs C , Rs D , Rs E , R', R" are each independently selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted C3-C 30 cycloalkoxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted di-C6-C 30 arylamino, substituted or unsubstituted C1-C 30 alkylsilyl, substituted or unsubstituted C6-C 30aryl-silyl, substituted or unsubstituted C1-C 30 alkyl-substituted or unsubstituted C6-C 30 aryl-silyl.

[0114] Furthermore, the mass ratio of the doping material to the host material is from 1:99 to 50:50.

[0115] In some embodiments, the organic electroluminescent element comprises a cathode, an anode and at least one light-emitting layer. In addition to these layers, it may also include other layers, for example, in each case, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and / or charge generation layers. An intermediate layer having, for example, an exciton blocking function can also be introduced between two light-emitting layers. However, it should be noted that not each of these layers must be present. The organic electroluminescent device described herein may include one light-emitting layer, or it may include multiple light-emitting layers. That is, a variety of light-emitting compounds capable of emitting light are used in the light-emitting layer. A system having three light-emitting layers is particularly preferred, wherein the three layers may exhibit blue, green and red light emission. If there are more than one light-emitting layer, then according to the present invention, at least one of these layers contains the compound of the present invention.

[0116] Furthermore, the organic electroluminescent element according to the present invention does not include a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, that is, the light-emitting layer is directly adjacent to the hole injection layer or the anode, and / or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.

[0117] In other layers of the organic electroluminescent element according to the present invention, especially in the hole injection and hole transport layers and in the electron injection and electron transport layers, all materials can be used in the manner commonly used according to the prior art. Those of ordinary skill in the art will thus be able to use all materials known about organic electroluminescent elements in combination with the light-emitting layer of the present invention without creative effort.

[0118] Furthermore, preferred is an organic electroluminescent element in which one or more layers can be applied by means of a sublimation method, wherein the material is deposited by vapor deposition in a vacuum sublimation apparatus at an initial pressure below 10 -5 Pa, preferably below 10 -6 Pa. However, the initial pressure may even be lower, for example, below 10 -7 Pa.

[0119] Also preferred is an organic electroluminescent element in which one or more layers can be applied by means of an organic vapor deposition method or by means of carrier gas sublimation, wherein, at 10 -5The material is applied under a pressure between Pa and 1 Pa. A particular example of the method is an organic vapor jet printing method, in which the material is applied directly through a nozzle and is thus structured.

[0120] Furthermore, preference is given to an organic electroluminescent element in which one or more layers are produced from a solution, for example by spin coating, or by means of any desired printing method such as screen printing, flexographic printing, lithographic printing, photothermographic imaging, thermal transfer printing, inkjet printing or nozzle printing. Soluble compounds are obtained, for example, by appropriately substituting and modifying the boron-nitrogen compound. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are feasible, in which, for example, one or more layers are applied from a solution and one or more further layers are applied by vapor deposition.

[0121] These methods are generally known to those skilled in the art and they can apply them to organic electroluminescent elements comprising the boron-nitrogen compounds of the invention without creative effort.

[0122] Accordingly, the invention also relates to a method for producing an organic electroluminescent element according to the invention, in which at least one layer can be applied by means of a sublimation method, and / or at least one layer can be applied by means of an organic vapor deposition method or by means of carrier gas sublimation, and / or at least one layer can be applied from a solution by spin coating or by means of a printing method.

[0123] In addition, the present invention relates to an organic boron compound of the present invention comprising at least one as indicated above. The same preferred cases as indicated above regarding the organic electroluminescent element apply to the organic boron compound of the present invention. In particular, the organic boron compound may preferably further comprise other compounds. Processing the organic boron compound of the present invention from the liquid phase, for example by spin coating or by printing methods, requires a formulation for processing the compound of the present invention. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, a mixture of two or more solvents may preferably be used. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenyltoluenes, especially 3-phenyltoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-methylcumene, phenetole, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or a mixture of these solvents.

[0124] The fifth aspect of the present invention provides a consumer product comprising the organic boron compound, the organic electroluminescent material or the organic electroluminescent element as described above in the present invention.

[0125] The organic electroluminescent device containing the compound of the present invention can be applied in planar light-emitting bodies such as wall-mounted TVs, flat panel displays, lighting, etc., light sources for copiers, printers, backlights of liquid crystal displays or measuring instruments, etc., display panels, indicator lights, etc.

[0126] The consumer products described in the present invention can be one of the following products: flat panel display, computer monitor, medical monitor, television, billboard, lamp for internal or external lighting and / or signaling, head-up display, fully transparent or partially transparent display, flexible display, laser printer, telephone, cellular phone, tablet computer, phablet, personal digital assistant (PDA), wearable device, laptop computer, digital camera, video camera, viewfinder, microdisplay with a diagonal less than 2 inches, 3-D display, virtual reality or augmented reality display, vehicle, video wall comprising a plurality of tiled-together displays, theater or stadium screen, light therapy device, and sign board.

[0127] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0128] The present invention uses a stable large π-conjugated carbon-boron-carbon parent nucleus compound formed by boron, five-membered heterocycle and strong donor as the light-emitting unit. On the one hand, the resonance effect between boron and heteroatoms such as oxygen and nitrogen can be utilized to achieve the separation of HOMO and LUMO, thereby realizing the TADF effect. At the same time, with the anchoring of the boron-carbon group, the degree of excited-state structural relaxation is reduced, resulting in a narrower full width at half maximum; on the other hand, by introducing different substituents on the rigid skeleton, the delayed fluorescence lifetime and full width at half maximum can be further adjusted, having a narrower emission peak width and higher efficiency compared with conventional compounds. At the same time, the organoboron compound has high thermal stability, thereby improving the lifespan of the organic electroluminescent device containing the compound; in addition, the organoboron compound improves the solubility of the solution, solving the productivity and cost problems of the processes of conventional blue light materials, and can be used in the solution process instead of the evaporation process in the original process to prepare the light-emitting layer. Description of the Drawings

[0129] Figure 1 It is a schematic diagram of an organic light-emitting device 100 according to a specific embodiment of the present invention.

[0130] Figure 2 It is a schematic diagram of an organic light-emitting device 200 according to another specific embodiment of the present invention.

[0131] The reference numerals are as follows:

[0132] 101: Substrate, 102: Anode layer, 103: Hole injection layer, 104: Hole transport layer, 105: Electron blocking layer, 106: Light-emitting layer, 107: Electron transport layer, 108: Electron injection layer, 109: Cathode layer, 110: Capping layer (CPL);

[0133] 201: Substrate, 202: Anode layer, 203: Hole injection layer, 204: Hole transport layer, 205: First light-emitting layer, 206: Electron transport layer, 207: Charge generation layer, 208: Hole injection layer, 209: Hole transport layer, 210: Second light-emitting layer, 211: Electron transport layer, 212: Electron injection layer, 213: Cathode layer. Detailed implementation mode

[0134] To make the objectives, technical solutions and advantages of the present invention clearer, the technical solutions of the present invention will be described in detail below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. All other implementation manners obtained by those of ordinary skill in the art based on the embodiments of the present invention without any creative effort fall within the scope protected by the present invention.

[0135] An aryl in the sense of the present invention contains 6 to 50 carbon atoms, and a heteroaryl in the sense of the present invention contains 2 to 50 carbon atoms and at least one heteroatom, provided that the sum of the carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. As non-limiting examples of aryl and heteroaryl, in particular, the following groups are selected: phenyl, naphthyl, anthracenyl, benzoanthracenyl, phenanthryl, pyrenyl, A group selected from the group consisting of a base, a perylene base, a fluoranthene base, a tetraphenyl group, a pentaphenyl group, a benzopyrene base, a biphenyl group, an azobenzene group, a terphenyl group, a triphenylphenyl group, a quaterphenyl group, a fluorene base, a spirobifluorene base, a dihydrophenanthrene base, a triphenylene base, a dihydropyrene base, a tetrahydropyrene base, a cis- or trans-indeno[1,2-b]fluorene base, a cis- or trans-indeno[2,1-b]carbazole base, an indolocarbazole base, a benzofurocarbazole base, a benzothienocarbazole base, a benzocarbazole base, a dibenzocarbazole base, aza-dibenzo[g,1,2-de]naphtho[2,1,8-cde]azulene, a trindene base, an isotrindene base, a spirotrindene base, a spiroisotrindene base, a furan base, a benzofuran base, an isobenzofuran base, a dibenzofuran base, a thiophene base, a benzothiophene base, an isobenzothiophene base, a dibenzothiophene base, a pyrrole base, an indole base, an isoindole base, a carbazole base, a pyridine base, a quinoline base, an isoquinoline base, an acridine base, a phenanthridine base, a benzo[5,6]quinoline base, a benzo[6,7]quinoline base, a benzo[7,8]quinoline base, a phenothiazine base, a phenoxazine base, a pyrazole base, an indazole base, an imidazole base, a benzimidazole base, a naphthimidazole base, a phenanthrimidazole base, a pyridinimidazole base, a pyrazinimidazole base, a quinoxalinimidazole base, an oxazole base, a benzoxazole base, a naphthoxazole base, an anthroxazole base, a phenanthroxazole base, an isoxazole base, a 1,2-thiazole base, a 1,3-thiazole base, a benzothiazole base, a pyridazine base, a hexaazapentacene base, a benzopyridazine base, a pyrimidine base, a benzopyrimidine base, a quinoxaline base, a 1,5-diazaanthracene base, a 2,7-diazapyrene base, a 2,3-diazapyrene base, a 1,6-diazapyrene base, a 1,8-diazapyrene base, a 4,5-diazapyrene base, a 4,5,9,10-tetraazaperylene base, a pyrazine base, a phenazine base, a phenoxazine base, a phenothiazine base, a fluoranthene ring group, a naphthyridine base, an azacarbazole base, a benzocarbazole base, a carbazole base, a phenanthroline base, a 1,2,3-triazole base, a 1,2,4-triazole base, a benzotriazole base, a 1,2,3-oxadiazole base, a 1,2,4-oxadiazole base, a 1,2,5-oxadiazole base, a 1,3,4-oxadiazole base, a 1,2,3-thiadiazole base, a 1,2,4-thiadiazole base, a 1,2,5-thiadiazole base, a 1,3,4-thiadiazole base, a 1,3,5-triazine base, a 1,2,4-triazine base, a 1,2,3-triazine base, a tetrazole base, a 1,2,4,5-tetrazine base, a 1,2,3,4-tetrazine base, a 1,2,3,5-tetrazine base, a purine base, a pteridine base, an indolizine base, a quinazoline base, a benzothiadiazole base, or a group derived from a combination of these systems.

[0136] The condensed aryl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from an aromatic hydrocarbon having 6 to 50 carbon atoms in which two or more rings are combined. At this time, the two or more rings may be simply attached to each other or attached in a condensed form. As non-limiting examples thereof, for example, there are a phenanthrene group, an anthracene group, a fluoranthene group, a pyrene group, a triphenylene group, a perylene group, groups, etc.

[0137] The arylamino group used in the present invention refers to an amine substituted by an aryl group having 6 to 50 carbon atoms. Non-limiting examples of the arylamino group include diphenylamino group, N-phenyl-1-naphthylamino group, N-(1-naphthyl)-2-naphthylamino group, etc. The heteroarylamino group refers to an amine substituted by an aryl group having 6 to 50 carbon atoms and a heteroaryl group having 2 to 50 carbon atoms. Non-limiting examples of the heteroarylamino group include N-phenylpyridin-3-ylamino group, N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-2-ylamino group, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-ylamino group, etc.

[0138] For the aliphatic hydrocarbon group or alkyl group containing 1 to 30 carbon atoms in the sense of the present invention, and in which a single hydrogen atom or -CH2- group may also be substituted by the above groups, it is preferably considered to refer to the following groups: methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-methylbutyl group, n-pentyl group, sec-pentyl group, neopentyl group, cyclopentyl group, n-hexyl group, neohexyl group, cyclohexyl group, n-heptyl group, cycloheptyl group, n-octyl group, cyclooctyl group, 2-ethylhexyl group, cyclohexenyl group, heptenyl group, cycloheptenyl group, octenyl group or cyclooctenyl group.

[0139] The alkoxy group preferably has an alkoxy group with 1 to 30 carbon atoms and is considered to be methoxy group, trifluoromethoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, n-pentyloxy group, sec-pentyloxy group, 2-methylbutoxy group, n-hexyloxy group, cyclohexyloxy group, n-heptyloxy group, cycloheptyloxy group, n-octyloxy group, cyclooctyloxy group, 2-ethylhexyloxy group, pentafluoroethoxy group and 2,2,2-trifluoroethoxy group.

[0140] The heteroalkyl group preferably has an alkyl group with 1 to 30 carbon atoms and refers to a group in which a single hydrogen atom or -CH2- group may be substituted by an oxygen atom, a sulfur atom or a halogen atom, and is considered to be an alkoxy group, an alkylthio group, a fluorinated alkoxy group, a fluorinated alkylthio group, especially methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, sec-butylthio group, tert-butylthio group, trifluoromethylthio group, trifluoromethoxy group, pentafluoroethoxy group, pentafluoroethylthio group, 2,2,2-trifluoroethoxy group, 2,2,2-trifluoroethylthio group, ethenyloxy group, ethenylthio group, propenyloxy group, propenylthio group, butenylthio group, butenyloxy group, pentenyloxy group, pentenylthio group, cyclopentenoxy group, cyclopentenylthio group, hexenyloxy group, hexenylthio group, cyclohexenyloxy group, cyclohexenylthio group, ethynyloxy group, ethynylthio group, propynyloxy group, propynylthio group, butynyloxy group, butynylthio group, pentynyloxy group, pentynylthio group, hexynyloxy group, hexynylthio group.

[0141] Generally speaking, the cycloalkyl group in the present invention can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, and one or more -CH2- groups can be replaced by the above groups; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms or nitrile groups.

[0142] The alkylamino group used in the present invention refers to an amine substituted by an alkyl group having 1 to 30 carbon atoms or a cycloalkyl group having 3 to 30 carbon atoms. As non-limiting examples of the alkylamino group, there are dimethylamino group, diethylamino group, dipropylamino group, diisopropylamino group, etc.

[0143] The alkenyl or alkynyl group in the present invention has 2 to 30 carbon atoms, and the alkenyl or alkynyl group in which a single hydrogen atom can be replaced by the above group R is preferably vinyl, propenyl, butenyl, isobutenyl, styryl, stilbenyl, ethynyl, propynyl, butynyl, phenylacetylenyl; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms or nitrile groups.

[0144] The aryloxy group used in the present invention refers to a monovalent functional group represented by R'O - wherein the above R' is an aryl group having 6 to 50 carbon atoms. As non-limiting examples of such aryloxy groups, there are phenoxy group, naphthyloxy group, biphenyloxy group, etc.

[0145] The arylthio group used in the present invention refers to a monovalent functional group represented by R'S - wherein the above R' is an aryl group having 6 to 50 carbon atoms. As non-limiting examples of such arylthio groups, there are phenylthio group, naphthylthio group, biphenylthio group, etc.

[0146] The alkylsilyl group used in the present invention refers to a silyl group substituted by an alkyl group having 1 to 30 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3. As non-limiting examples of the alkylsilyl group, there are trimethylsilyl group, triethylsilyl group, etc. The arylsilyl group refers to a silyl group substituted by an aryl group having 6 to 50 carbon atoms.

[0147] The arylphosphino group used in the present invention refers to a diarylphosphino group substituted by an aryl group having 6 to 50 carbon atoms. As non-limiting examples of the arylphosphino group, there are diphenylphosphino group, bis(4-trimethylsilylphenyl)phosphino group, etc. The aryloxyphosphino group is that the phosphorus atom of the diarylphosphino group is oxidized to the highest valence state.

[0148] The arylboron group used in the present invention refers to a diarylboron group substituted by an aryl group having 6 to 50 carbon atoms. As non-limiting examples of the arylboron group, there are diphenylboron group, bis(2,4,6-trimethylphenyl)boron group, etc. The alkylboron group refers to a dialkylboron group substituted by an alkyl group having 1 to 30 carbon atoms. As non-limiting examples of the alkylboron group, there are di-tert-butylboron group, diisobutylboron group, etc.

[0149] "Halogen", "halogen atom", "halo group", and "halogen radical" in the context of the present invention are used interchangeably and refer to fluorine, chlorine, bromine, or iodine.

[0150] As used herein, "a combination thereof" or "a group" means that one or more members of an applicable list are combined to form a known or chemically stable arrangement that can be envisioned by one of ordinary skill in the art from the applicable list. For example, an alkyl group and deuterium can be combined to form a partially or fully deuterated alkyl group; a halogen and an alkyl group can be combined to form a haloalkyl substituent, such as trifluoromethyl, etc.; and a halogen, an alkyl group, and an aryl group can be combined to form a haloarylalkyl.

[0151] As used herein, the term "substituted or unsubstituted" means being substituted or unsubstituted by one or more substituents selected from hydrogen, deuterium, halogen atoms, hydroxyl groups, nitrile groups, nitro groups, amino groups, amidino groups, hydrazino groups, hydrazono groups, carboxyl groups or their carboxylates, sulfonic acid groups or their sulfonates, phosphoric acid groups or their phosphates, C1-C 30 alkyl groups, C2-C 30 alkenyl groups, C2-C 30 alkynyl groups, C1-C 30 alkoxy groups, C3-C 30 cycloalkyl groups, C3-C 30 cycloalkenyl groups, C6-C 50 aryl groups, C6-C 50 aryloxy groups, C6-C 50 arylthioether groups, and C2-C 50 heteroaryl groups, or being substituted or unsubstituted by a substituent formed by linking two or more of the above-exemplified substituents.

[0152] In one example, the term substitution includes a combination of two to four of the listed groups.

[0153] In another example, the term substitution includes a combination of two to three groups. In yet another example, the term substitution includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms that are not hydrogen or deuterium, or combinations including up to forty atoms that are not hydrogen or deuterium, or combinations including up to thirty atoms that are not hydrogen or deuterium. In many cases, preferred combinations of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0154] In the substituted or unsubstituted rings formed by the binding or joining of adjacent groups described in the present invention, "ring" means a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. A fused ring means a fused aliphatic ring, a fused aromatic ring, a fused aliphatic heterocyclic ring, a fused aromatic heterocyclic ring, or a form composed of their combinations.

[0155] "EQE" in the present invention refers to the external quantum efficiency of a device, that is, the ratio of the number of photons emitted by the device to the number of electrons injected into the device.

[0156] Figure 1 FIG. shows a schematic diagram of an organic light-emitting device 100 according to a specific embodiment of the present invention. The illustration is not necessarily drawn to scale. The device 100 may include a substrate 101, an anode layer 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, an electron transport layer 107, an electron injection layer 108, a cathode layer 109, and a capping layer (CPL) 110. The device 100 can be fabricated by sequentially depositing the described layers.

[0157] Figure 2 FIG. shows a schematic diagram of an organic light-emitting device 200 with two light-emitting layers according to another specific embodiment of the present invention. The device includes a substrate 201, an anode layer 202, a hole injection 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode layer 213. The device 200 can be prepared by sequentially depositing the described layers. Since the most common OLED device has one light-emitting layer, while the device 200 has a first light-emitting layer and a second light-emitting layer, the emission peak shapes of the first light-emitting layer and the second light-emitting layer can be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of the device 200, materials similar to those described with respect to the device 100 can be used. Figure 2 An example of how to add some layers to the structure of the device 100 is provided.

[0158] Figure 1 and Figure 2The simple layered structure described is provided as a non-limiting example, and it should be understood that embodiments of the present invention can be used in combination with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be achieved by combining the described individual layers in different ways based on design, performance, and cost factors, or several layers can be completely omitted. Other layers not specifically described can also be included. Materials different from those specifically described can be used. Although many of the examples provided herein describe various layers as including a single material, it will be understood that combinations of materials can be used, such as a mixture of a matrix and a dopant, or more generally, mixtures. Also, the layers can have various sub-layers. The names given to the individual layers herein are not intended to be strictly restrictive. For example, in device 200, the hole transport layer 204 transports holes and injects holes into the light-emitting layer 205, and can be described as a hole transport layer or an electron blocking layer. In one embodiment, an OLED can be described as having an organic layer disposed between a cathode and an anode. This organic layer can include a single layer or can further include multiple layers of different organic materials as described, for example, Figure 1 and Figure 2 described.

[0159] Structures and materials not specifically described can also be used, such as PLEDs that include polymeric materials. As another example, an OLED having a single organic layer or multiple stacks can be used. The OLED structure can deviate from Figure 1 and Figure 2 the simple layered structure described. For example, the substrate can include angled reflective surfaces to improve light coupling.

[0160] Unless otherwise specified, any of the layers of the various embodiments can be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, organic vapor deposition methods, or the application of one or more layers by sublimation with a carrier gas, where the material is applied at a pressure between 10 -5 mbar and 1 bar. A particular example of this method is the organic vapor jet printing method, where the material is applied directly through a nozzle and is thus structured. Other suitable deposition methods include, for example, generating one or more layers by spin coating, or by any desired printing method such as screen printing, flexographic printing, lithographic printing, photo-thermal imaging, thermal transfer, inkjet printing, or nozzle printing. Soluble compounds, such as those obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers, and polymers. Also feasible are hybrid methods, where, for example, one or more layers are applied from a solution and one or more additional layers are applied by vapor deposition.

[0161] Devices manufactured according to embodiments of the present invention may further optionally include a barrier layer. One use of the barrier layer is to protect the electrodes and organic layers from damage due to exposure to harmful substances in the environment, including moisture, vapors, and / or gases, etc. The barrier layer may be deposited on the substrate, on the electrodes, under the substrate, under the electrodes, beside the substrate, beside the electrodes, or on any other part of the device, including on the edges. The barrier layer may include a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferably, the barrier layer includes a mixture of a polymeric material and a non-polymeric material. In order to be considered a mixture, the aforementioned polymeric and non-polymeric materials constituting the barrier layer should be deposited under the same conditions and / or simultaneously. The weight ratio of the polymeric material to the non-polymeric material may be in the range of 95 / 5 to 5 / 95. In one example, the mixture of the polymeric material and the non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

[0162] In any of the compounds mentioned above used in each layer of the above OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any specifically listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, etc. may be in their non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes (such as (but not limited to) alkyl, aryl, cycloalkyl, heteroaryl, etc.) may also be in their non-deuterated, partially deuterated, and fully deuterated forms.

[0163] The materials and structures described herein may be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may use the materials and structures.

[0164] Furthermore, organic devices such as organic transistors may use the materials and structures.

[0165] In the following embodiments of the present invention, unless otherwise specified, conventional preparation methods are used. The raw materials used can be obtained from public commercial sources unless otherwise specified, and the percentages are mass percentages unless otherwise specified.

[0166] To illustrate the present invention more clearly, the technical solutions of the present invention are described below in conjunction with some specific embodiments:

[0167] In the embodiments of the present invention, the performance detection conditions of the prepared electroluminescent device are as follows:

[0168] Chromaticity coordinates: Measured using a spectral scanner PhotoResearch PR-715;

[0169] Current-Voltage: Tested using a digital source meter Keithley 2420;

[0170] Power Efficiency: Tested using NEWPORT 1931-C;

[0171] Luminance: Tested using a luminance meter Minolta Cs-1000A.

[0172] Example 1

[0173] A method for preparing compound B005, comprising the following steps:

[0174] First step: Preparation of intermediate Int-1

[0175]

[0176] Under nitrogen protection, 10.0 mmol of 4-chloro-2,6-diiodobromobenzene (sub-1), 22.0 mmol of sub-2, 50.0 mmol of anhydrous sodium carbonate and 40 mL of toluene were mixed, then 0.1 mmol of Pd(PPh3)4, 20 mL of ethanol and 20 mL of water were added. The temperature was raised to 40 °C and stirred for 12 hours. 50 mL of water was added, and it was extracted with ethyl acetate. The organic phase was dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. It was purified by silica gel column or recrystallized with ethanol to obtain compound Int-1, yield: 70-80%.

[0177] Second step: Preparation of compound Int-2

[0178]

[0179] Under nitrogen protection, 20.0 mmol of Int-1 was dissolved in 80 mL of dry anisole, cooled to -78 °C, 24.0 mmol of 2.5 M n-butyllithium hexane solution was added dropwise, stirred for 30 minutes, 30.0 mmol of boron tribromide was added dropwise, the temperature was raised to room temperature and stirred for 1 hour, then 60.0 mmol of diisopropylethylamine was added, the temperature was raised to 150 °C and stirred for 24 hours, cooled to room temperature, 20 mL of saturated sodium acetate aqueous solution was added, the organic phase was separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined and dried, filtered, concentrated and dried under reduced pressure, and separated and purified by silica gel column to obtain compound Int-2, yield 45-55%.

[0180] Third step: Preparation of compound B005

[0181]

[0182] Under nitrogen protection, 20.0 mmol of Int-2, 22.0 mmol of carbazole or di-tert-butylcarbazole, 30.0 mmol of sodium tert-butoxide, 0.2 mmol of Pd2(dba)3, 0.4 mmol of 10% tri-tert-butylphosphine toluene solution and 80 mL of dry toluene were mixed, heated to 110°C, stirred for reaction for 15 hours, cooled to room temperature, added with 50 mL of saturated saline solution, extracted with ethyl acetate, dried the organic phase, concentrated under reduced pressure, and purified by silica gel column to obtain compound B005;

[0183] Y is O and O, Cz is 3,6-di-tert-butylcarbazole, white solid, yield: 56%, MS (TOF) m / z: 708.3947 [M+H]. 1 HNMR (δ, CDCl3): 8.02~8.00(2H,d); 7.86(2H,s); 7.52~7.46(4H,m); 7.38( 2H,s); 7.35~7.33(2H,d); 7.01~6.99(2H,d); 1.39(18H,s); 1.34(18H,s).

[0184] Y is S and S, Cz is 3,6-di-tert-butylcarbazole, white solid, yield: 58%, MS (TOF) m / z: 740.3502 [M+H]. 1 HNMR (δ, CDCl3): 8.08~8.06(2H,dd); 7.85(2H,s); 7.76~7.73(2H,dd); 7.41~7. 38(4H,m); 7.35~7.32(2H,dd); 6.97~6.95(2H,d); 1.39(18H,s); 1.36(18H,s).

[0185] Y is NAr and NAr, Cz is 3,6-di-tert-butylcarbazole, Ar is phenyl, light yellow solid, yield: 45%, MS (TOF) m / z: 858.4904 [M+H]. 1 HNMR (δ, CDCl3): 8.00~7.98(2H,d); 7.84(2H,s); 7.58~7.53(4H,m); 7.47(2H,s); 7.37~7.35( 4H,m); 7.33~7.28(6H,m); 7.11~7.09(2H,d); 6.97~6.95(2H,d); 1.39(18H,s); 1.33(18H,s).

[0186] Y is O and S, Cz is 3,6-di-tert-butylcarbazole, white solid, yield: 55%, MS (TOF) m / z: 724.3722 [M+H]. 1HNMR (δ, CDCl3): 8.08 - 8.06 (1H, dd); 8.02 - 8.00 (1H, dd); 7.85 - 7.84 (2H, d); 7.76 - 7.73 (1H, dd); 7.52 - 7.46 (3H, m); 7.41 - 7.38 (1H, t); 7.35 - 7.32 (2H, d); 7.29 (1H, s); 6.97 - 6.95 (2H, d); 1.39 (18H, s); 1.36 (9H, s); 1.34 (9H, s).

[0187] Y is O and NAr, Cz is 3,6 - di - tert - butylcarbazole, Ar is phenyl, white solid, yield: 42%, MS(TOF) m / z: 783.4421 [M + H]. 1 HNMR (δ, CDCl3): 8.02 - 7.98 (2H, t); 7.85 (2H, s); 7.54 - 7.49 (3H, m); 7.47 - 7.45 (2H, m); 7.39 (1H, s); 7.37 - 7.34 (3H, m); 7.32 - 7.28 (3H, m); 7.11 - 7.09 (1H, d); 6.97 - 6.95 (2H, d); 1.39 (18H, s); 1.36 (9H, s); 1.34 (9H, s).

[0188] Y is S and NAr, Cz is 3,6 - di - tert - butylcarbazole, Ar is phenyl, white solid, yield: 46%, MS(TOF) m / z: 799.4182 [M + H]. 1 HNMR (δ, CDCl3): 8.08 - 8.06 (1H, dd); 8.00 - 7.98 (2H, d); 7.84 (2H, s); 7.76 - 7.73 (1H, dd); 7.54 - 7.49 (2H, m); 7.41 - 7.38 (1H, m); 7.36 - 7.27 (7H, m); 7.11 - 7.09 (1H, d); 6.97 - 6.95 (2H, d); 1.39 (18H, s); 1.34 (9H, s); 1.26 (9H, s).

[0189] Example 2

[0190] Preparation method of compound B103, comprising the following steps:

[0191] The first step: Preparation of intermediate Int - 3

[0192]

[0193] Under nitrogen protection, 20.0 mmol of 4-fluoro-2,6-dibromochlorobenzene (sub-3), 48.0 mmol of sub-4, 80.0 mmol of potassium phosphate hydrate and 80 mL of toluene were mixed, then 0.2 mmol of Pd(PPh3)4, 40 mL of ethanol and 40 mL of water were added. The temperature was raised to reflux and stirred for 12 hours. 80 mL of water was added, and it was extracted with ethyl acetate. The organic phase was dried, filtered, and the filtrate was concentrated to dryness under reduced pressure and purified by silica gel column to obtain compound Int-3, yield: 70 - 80%.

[0194] Step 2: Preparation of intermediate Int-4

[0195]

[0196] Under nitrogen protection, 20.0 mmol of Int-3 and 2.0 mmol of p-toluenesulfonic acid were dissolved in 80 mL of dichloromethane. 42.0 mmol of NBS was added in batches, and the mixture was stirred for 15 hours. 50 mL of water was added for dilution, and it was extracted with dichloromethane. The organic phase was dried and concentrated to dryness under reduced pressure and separated and purified by silica gel column to obtain compound Int-4, yield 90 - 95%.

[0197] Step 3: Preparation of intermediate Int-5

[0198]

[0199] Under nitrogen protection, 20.0 mmol of Int-4, 20.0 mmol of p-tert-butylaniline, 60.0 mmol of sodium tert-butoxide, 0.2 mmol of Pd2(dba)3, 0.4 mmol of 10% tritert-butylphosphine toluene solution and 80 mL of toluene were mixed. The temperature was raised to 100 °C and stirred for 15 hours. It was cooled to room temperature, 50 mL of saturated ammonium chloride aqueous solution was added, and it was extracted with ethyl acetate. The organic phase was dried and concentrated to dryness under reduced pressure and separated and purified by silica gel column to obtain compound Int-5, yield 60 - 70%.

[0200] Step 4: Preparation of intermediate Int-6

[0201]

[0202] Under nitrogen protection, 20.0 mmol of Int-5, 20.0 mmol of carbazole or di-tert-butylcarbazole, 2.0 mmol of copper iodide, 30.0 mmol of anhydrous potassium carbonate and 80 mL of DMF were mixed. The temperature was raised to reflux and stirred for 20 hours. It was cooled to room temperature, and the reaction solution was poured into 150 mL of saturated brine solution, filtered, the filter cake was washed with water, dried and separated and purified by silica gel column to obtain compound Int-6, yield 80 - 90%.

[0203] Step 5: Preparation of Compound B103

[0204]

[0205] Under nitrogen protection, 20.0 mmol of Int-6 was dissolved in 80 mL of dry tert-butylbenzene. The temperature was lowered to -78 °C, and 24.0 mmol of 1 M tert-butyllithium pentane solution was added dropwise. The mixture was stirred for 30 minutes, then the temperature was raised to 0 °C and stirred for another 30 minutes. The temperature was then lowered to -78 °C, and 30.0 mmol of boron tribromide was added dropwise. The temperature was raised to 0 °C and stirred for 30 minutes. Then 0.1 mol of diisopropylethylamine was added, and the temperature was raised to 150 - 155 °C and stirred for 24 hours. It was cooled to room temperature, concentrated and dried under reduced pressure, and purified by silica gel column chromatography to obtain Compound B103;

[0206] Y is O and O, Cz is carbazole, yellow solid, yield: 38%, MS(TOF) m / z: 741.3588 [M+H]. 1 HNMR(δ, CDCl3): 8.12(2H, s); 7.66(2H, s); 7.36 - 7.26(6H, m); 7.19 - 7.15(2H, m); 7.12 - 7.10(2H, d); 7.08 - 7.06(2H, d); 7.00 - 6.98(2H, m); 1.36(9H, s); 1.34(18H, s).

[0207] Y is S and S, Cz is carbazole, yellow solid, yield: 44%, MS(TOF) m / z: 773.3122 [M+H]. 1 HNMR(δ, CDCl3): 8.12(2H, s); 7.72(2H, s); 7.36 - 7.26(6H, m); 7.19 - 7.15(2H, m); 7.12 - 7.09(2H, dd); 7.03 - 7.01(2H, d); 6.98 - 6.96(2H, m); 1.46(27H, s).

[0208] Y is NAr and NAr, Cz is carbazole, Ar is phenyl, yellow solid, yield: 46%, MS(TOF) m / z: 891.4533 [M+H]. 1 HNMR(δ, CDCl3): 8.13(2H, s); 7.74(2H, s); 7.62 - 7.58(4H, m); 7.49 - 7.43(6H, m); 7.41 - 7.36(6H, m); 7.29 - 7.25(2H, m); 7.19 - 7.17(2H, d); 6.95 - 6.92(2H, d); 6.55 - 6.53(2H, d); 1.32(9H, s); 1.26(18H, s).

[0209] Y is O and NAr, Cz is carbazole, Ar is phenyl, yellow solid, yield: 38%, MS(TOF) m / z: 816.4063 [M+H]. 1 HNMR (δ, CDCl3): 8.12 (2H, s); 7.74 (1H, s); 7.66 (1H, s); 7.63 - 7.58 (2H, m); 7.49 - 7.43 (4H, m); 7.41 - 7.36 (5H, m); 7.29 - 7.26 (2H, m); 7.22 - 7.20 (1H, d); 7.18 - 7.16 (1H, d); 6.95 - 6.93 (1H, d); 6.61 - 6.58 (1H, d); 6.55 - 6.51 (2H, m); 1.36 (9H, s); 1.26 (9H, s); 1.31 (9H, s).

[0210] Y is S and NAr, Cz is carbazole, Ar is phenyl, yellow solid, yield: 40%, MS(TOF) m / z: 832.3832 [M+H]. 1 HNMR (δ, CDCl3): 8.14 (2H, s); 7.77 (1H, s); 7.72 (1H, s); 7.63 - 7.58 (2H, m); 7.49 - 7.43 (6H, m); 7.41 - 7.36 (3H, m); 7.29 - 7.25 (2H, m); 7.22 - 7.20 (1H, d); 7.18 - 7.16 (1H, d); 6.95 - 6.93 (1H, d); 6.61 - 6.58 (1H, d); 6.55 - 6.51 (2H, m); 1.34 (9H, s); 1.26 (18H, s).

[0211] Y is O and S, Cz is carbazole, yellow solid, yield: 42%, MS(TOF) m / z: 757.3352 [M+H]. 1 HNMR (δ, CDCl3): 8.13 (2H, s); 7.75 (1H, s); 7.62 (1H, s); 7.46 - 7.43 (2H, m); 7.41 - 7.35 (4H, m); 7.29 - 7.26 (2H, m); 7.22 - 7.19 (2H, dd); 7.13 - 7.11 (1H, d); 7.08 - 7.06 (1H, d); 6.91 - 6.88 (2H, m); 1.34 (18H, s); 1.31 (9H, s).

[0212] Example 3

[0213] Preparation method of compound B127, comprising the following steps:

[0214] Step 1: Preparation of Intermediate Int-7

[0215]

[0216] Under nitrogen protection, 10.0 mmol of 4-chloro-2,6-diiodobromobenzene (sub-1), 12.0 mmol of sub-2, 20.0 mmol of anhydrous sodium carbonate and 40 mL of toluene were mixed. Then, 0.1 mmol of Pd(PPh3)4, 20 mL of ethanol and 20 mL of water were added. The mixture was stirred and reacted for 12 hours. 50 mL of water was added, and the mixture was extracted with ethyl acetate. The organic phase was dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. It was purified by silica gel column or recrystallized with ethanol to obtain compound Int-7, with a yield of 65 - 70%.

[0217] Step 2: Preparation of Intermediate Int-8

[0218]

[0219] Under nitrogen protection, 10.0 mmol of Int-7, 12.0 mmol of sub-4, 25.0 mmol of anhydrous sodium carbonate and 40 mL of toluene were mixed. Then, 0.1 mmol of Pd(PPh3)4, 20 mL of ethanol and 20 mL of water were added. The temperature was raised to 40 °C and the mixture was stirred and reacted for 12 hours. 50 mL of water was added, and the mixture was extracted with ethyl acetate. The organic phase was dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. It was purified by silica gel column or recrystallized with ethanol to obtain compound Int-8, with a yield of 75 - 80%.

[0220] Step 3: Preparation of Compound Int-9

[0221]

[0222] Under nitrogen protection, 20.0 mmol of Int-8 was dissolved in 60 mL of dry anisole. The temperature was cooled to -78 °C, and 24.0 mmol of 2.5 M n-butyllithium in hexane solution was added dropwise. The mixture was stirred and reacted for 30 minutes. Then, 30.0 mmol of boron tribromide was added dropwise and the mixture was stirred and reacted for 30 minutes. Then, 0.1 mol of diisopropylethylamine was added, and the temperature was raised to 150 °C and the mixture was stirred and reacted for 24 hours. It was cooled to room temperature, 40 mL of saturated sodium acetate aqueous solution was added, and the mixture was extracted with ethyl acetate. The organic phase was dried, filtered, and the filtrate was concentrated and dried under reduced pressure. It was separated and purified by silica gel column to obtain compound Int-9, with a yield of 40 - 55%.

[0223] Step 4: Preparation of Compound B127

[0224]

[0225] Under nitrogen protection, 20.0 mmol of Int-9, 21.0 mmol of sub-5, 30.0 mmol of sodium tert-butoxide and 0.2 mmol of Pd2(dba)3 were dissolved in 80 mL of dry toluene. Then, 0.4 mmol of 10% tri-tert-butylphosphine toluene solution was added. The temperature was raised to 110 °C and the mixture was stirred for 15 hours. After cooling to room temperature, 50 mL of saturated sodium acetate aqueous solution was added. The mixture was extracted with ethyl acetate. The organic phase was dried, filtered, and the filtrate was concentrated and dried under reduced pressure. It was separated and purified by silica gel column chromatography to obtain compound B127, a yellow solid.

[0226] Y1 is O, Y2 is O, yellow solid, yield: 85%, MS(TOF) m / z: 710.4117 [M+H]. 1 HNMR(δ, CDCl3): 7.99~7.97(1H, d); 7.65~7.61(2H, m); 7.53~7.51(1H, dd); 7.48~7.46(1H, d); 7.40~7.36(1H, t); 7.26(1H, s); 7.16~7.11(4H, m); 7.09~7.06(1H, dd); 7.02~6.98(4H, m); 1.48(18H, s); 1.36(9H, s); 1.32(9H, s).

[0227] Y1 is S, Y2 is S, yellow solid, yield: 82%, MS(TOF) m / z: 742.3648 [M+H]. 1 HNMR(δ, CDCl3): 8.05~8.03(1H, dd); 7.77~7.73(2H, m); 7.54~7.50(2H, m); 7.48~7.46(1H, dd); 7.40~7.37(1H, dd); 7.16~7.12(5H, m); 7.02~6.98(4H, m); 1.36(27H, s); 1.32(9H, s).

[0228] Y1 is C(CH3)2 and Y2 is C(CH3)2, yellow solid, yield: 86%, MS(TOF) m / z: 762.5156 [M+H]. 1 HNMR(δ, CDCl3): 8.25~8.23(1H, dd); 7.76(1H, s); 7.47~7.42(2H, m); 7.40~7.38(1H, m); 7.33~7.29(2H, m); 7.16~7.12(4H, m); 7.02~6.96(5H, m); 1.46(18H, s); 1.34(6H, s); 1.32(6H, s); 1.15(9H, s); 1.01(9H, s).

[0229] Y1 is NAr, Y2 is NAr, Ar is phenyl, yellow solid, yield: 84%, MS(TOF) m / z: 860.5053 [M+H]. 1 HNMR (δ, CDCl3): 8.26~8.24 (1H, d); 7.56~7.48 (6H, m); 7.39~7.35 (2H, m); 7.33~7.27 (5H, m); 7.19~7.12 (6H, m); 7.10~7.08 (1H, d); 7.01~6.99 (1H, d); 6.96~6.92 (4H, m); 1.36 (9H, s); 1.32 (18H, s); 1.26 (9H, s).

[0230] Y1 is O, Y2 is S, yellow solid, yield: 83%, MS(TOF) m / z: 726.3885 [M+H]. 1 HNMR (δ, CDCl3): 8.05~8.03 (1H, d); 7.76~7.73 (2H, m); 7.54~7.48 (3H, m); 7.16~7.09 (6H, m); 7.02~6.98 (4H, m); 1.36 (18H, s); 1.34 (9H, s); 1.32 (9H, s).

[0231] Y1 is S, Y2 is O, yellow solid, yield: 81%, MS(TOF) m / z: 726.3875 [M+H]. 1 HNMR (δ, CDCl3): 7.99~7.97 (1H, d); 7.66~7.62 (2H, m); 7.52~7.46 (2H, m); 7.43~7.37 (2H, m); 7.21 (1H, s); 7.16~7.12 (4H, m); 7.02~6.98 (4H, m); 1.34 (27H, s); 1.32 (9H, s).

[0232] Y1 is O, Y2 is NAr, Ar is phenyl, yellow solid, yield: 85%, MS(TOF) m / z: 785.4587 [M+H]. 1 HNMR (δ, CDCl3): 7.99~7.97 (1H, d); 7.64~7.61 (1H, t); 7.56~7.49 (3H, m); 7.46~7.42 (2H, m); 7.39~7.35 (2H, m); 7.32~7.25 (3H, m); 7.16~7.12 (4H, m); 7.09~7.07 (1H, d); 7.02~6.98 (4H, m); 1.36 (9H, s); 1.34 (18H, s); 1.31 (9H, s).

[0233] Y1 is NAr, Y2 is O, Ar is phenyl, yellow solid, yield: 85%, MS(TOF) m / z: 785.4577 [M+H]. 1 HNMR(δ, CDCl3): 7.97~7.95(1H, d); 7.74(1H, s); 7.54~7.48(3H, m); 7.46~7.43(2H, m); 7.34~7.30(2H, m); 7.27~7.25(2H, m); 7.16~7.08(6H, m); 7.02~6.98(4H, m); 1.34(18H, s); 1.32(9H, s); 1.26(9H, s).

[0234] Y1 is NAr, Y2 is S, Ar is phenyl, yellow solid, yield: 82%, MS(TOF) m / z: 801.4352 [M+H]. 1 HNMR(δ, CDCl3): 8.26~8.24(1H, d); 7.76(1H, s); 7.58~7.52(4H, m); 7.50~7.45(2H, m); 7.34~7.27(3H, m); 7.24(1H, s); 7.16~7.11(5H, m); 7.02~6.98(4H, m); 1.34(27H, s); 1.26(9H, s).

[0235] Y1 is S, Y2 is NAr, Ar is phenyl, yellow solid, yield: 84%, MS(TOF) m / z: 801.4348 [M+H]. 1 HNMR(δ, CDCl3): 8.05~8.03(1H, dd); 7.76~7.73(1H, dd); 7.55~7.48(5H, m); 7.39~7.35(2H, m); 7.32~7.27(1H, m); 7.23~7.21(2H, m); 7.16~7.12(4H, m); 7.09~7.06(1H, dd); 7.02~6.98(4H, m); 1.34(9H, s); 1.31(18H, s); 1.26(9H, s).

[0236] Example 4

[0237] Refer to the above similar synthesis method to prepare compounds B001~B174 (the specific structures are shown in Tables 1 and 2 of this application form).

[0238] Example 5

[0239] An organic electroluminescent device 100, such as Figure 1As shown, the organic electroluminescent device has a substrate 101, an anode layer 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, an electron transport layer 107, an electron injection layer 108, a cathode layer 109, and a capping layer (CPL) 110.

[0240] An OLED device 200, as Figure 2 shown, includes a substrate 201, an anode layer 202, a hole injection 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode layer 213. Materials similar to those described for element 100 can be used, and the manufacturing method is the same.

[0241] This embodiment Figure 1 The method for preparing the organic electroluminescent device shown in this embodiment includes the following steps:

[0242] (1) The glass substrate coated with the ITO conductive layer is ultrasonically treated in a cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in an acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with an ultraviolet light cleaning machine for 10 minutes, and bombarded with a low-energy cation beam on the surface. The treated ITO glass substrate is placed in a vacuum chamber, and the vacuum is pumped to less than 1×10 -5 Pa, and silver metal is evaporated on the above ITO film, and the film thickness is to obtain the anode layer.

[0243] (2) On the above anode layer film, the compound DNTPD is continuously evaporated as the hole injection layer, and the evaporation film thickness is On the above hole injection layer film, HTM is continuously evaporated as the hole transport layer, and the evaporation film thickness is

[0244] (3) On the hole transport layer, a layer of the compound HT100 is continuously evaporated as the electron blocking layer, and the evaporation film thickness is

[0245] (4) On the electron blocking layer, a layer of the compound shown in Formula IV-X, the organic boron compound of the present invention, HTH, and ETH are continuously evaporated as the organic light-emitting layer, wherein the mass ratio of Formula IV-X:organic boron compound:HTH:ETH is 10:1:59:30, and the evaporation film thickness is

[0246] (5) On the above light-emitting layer, a layer of the compounds LiQ and ET205 is continuously evaporated as the electron transport layer of the device, wherein the mass ratio of LiQ and ET205 is 1:1, and the evaporation film thickness is

[0247] (6) On the above-mentioned electron transport layer, deposit another layer of compound LiF as the electron injection layer of the device, and the deposited film thickness is

[0248] (7) Deposit metal magnesium and silver on the above-mentioned electron injection layer as the cathode layer of the device. Among them, the mass ratio of magnesium to silver is 10:1, and the deposited film thickness is

[0249] (8) Deposit compound HT038 on the above-mentioned cathode layer as the CPL layer, and the deposited film thickness is

[0250] The structural formula of the compound used in this embodiment is as follows:

[0251]

[0252] Comparative Example 1

[0253] Prepare an organic electroluminescent device according to the same steps as in Example 5, except that compound BD010 is used instead of the organoboron compound of the present invention.

[0254] The structure of compound BD010 is:

[0255]

[0256] Test Example 1

[0257] Perform performance detection on the organic electroluminescent devices prepared in Example 5 and Comparative Example 1. Specifically, increase the voltage at a rate of 0.1 V per second, and measure the voltage when the brightness of the organic electroluminescent element reaches 1000 cd / m 2 That is, the driving voltage, and at the same time measure the current density at this time; the ratio of brightness to current density is the current efficiency; the LT95% life test is as follows: use a luminance meter at 1000 cd / m 2 Brightness, keep a constant current, and measure the time when the brightness of the organic electroluminescent element decays to 950 cd / m 2 The unit is hours. The data listed in Table 2 are relative data compared with Comparative Example 1.

[0258] Table 2 Performance Detection Results

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268] Among them, Ph represents a phenyl group.

[0269] The above experimental data show that the hybrid unit and the large planar conjugated group of the organoboron compound of the present invention have a rigid backbone structure, which can reduce the degree of excited-state structural relaxation, thereby achieving a low driving voltage and a high luminous efficiency. A blue organic electroluminescent device is obtained as a blue light material and a sensitizer.

[0270] As described above, the above are only specific embodiments of the present invention, but the protection scope of the present invention is not limited thereto. Any person skilled in the art can easily think of changes or substitutions within the technical scope disclosed by the present invention, and all of them should be covered by the protection scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.

Claims

1. An organic boron compound having a structure shown in the following formula (0): in, Ring a, ring b, ring c and ring d are each independently selected from The condition is that one of ring a and ring b is And one of the rings c and d is Y is independently selected from O, S, Se, GeR'R", SiR'R", CR'R" or NAr 1 ; Optionally, ring a and ring c are connected by L to form a ring structure, and L is selected from a single bond, O, S, S=O, SO2, Se, GeR 10 R 11 、SiR 10 R 11 、C=O、CR 10 R 11 or NAr 2 ; R a , R b , R c and R d independently represents unsubstituted, monosubstituted or polysubstituted; R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 R' and R" are identical or different to each other at each occurrence and are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C6~C 50 Aryl, substituted or unsubstituted C3~C 30 Cycloalkyl, substituted or unsubstituted C2~C 50 Heteroaryl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C6~C 50 Aryloxy, substituted or unsubstituted C1~C 30 Alkylthio, substituted or unsubstituted C5~C 50 Arylthio, substituted or unsubstituted C1~C 30 Alkylamino, substituted or unsubstituted C5~C 50 Arylamine, substituted or unsubstituted C1~C 30 Alkylsilyl, substituted or unsubstituted C5~C 50 The group consisting of an arylsilyl group, a nitro group, a cyano group and a halogen atom; optionally, R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 In , R' and R", two or more adjacent groups are joined or fused to form a substituted or unsubstituted carbocyclic or heterocyclic ring, and the heteroatoms in the formed heterocyclic ring are selected from N, O, S, P, B, Si and Se; Ar 1 and Ar 2 Each independently selected from substituted or unsubstituted C6 to C 50 Aryl, substituted or unsubstituted C 12 ~C 50 Fused aromatic, substituted or unsubstituted C2~C 50 Heteroaryl, substituted or unsubstituted C6~C 50 A group consisting of arylamine groups; When R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 , R', R", Ar 1 and Ar 2 When the substituent is contained, the substituent is one or more and each is independently selected from the group consisting of the following groups: deuterium, halogen, C1~C 20 Alkyl, C1~C 20 Deuterated alkyl, C1~C 20 Halogenated alkyl, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C3~C 20 Cycloalkyl, C2~C 20 Heterocycloalkyl, C6~C 30 Aryl, C2~C 30 Heteroaryl.

2. The organoboron compound according to claim 1, characterized in that Ring a and ring c are each independently selected from Ring b and ring d are each independently selected from or Ring b and ring d are each independently selected from Ring a and ring c are each independently selected from or Ring a and ring d are each independently selected from Ring b and ring c are each independently selected from or Ring b and ring c are each independently selected from Ring a and ring d are each independently selected from Y has the same meaning as in claim 1; Preferably, Y is independently selected from O, S, Se, CR'R" or NAr 1 ; Preferably, R' and R" are identical or different to each other at each occurrence and are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C6~C 50 Aryl, substituted or unsubstituted C3~C 30 Cycloalkyl, substituted or unsubstituted C2~C 50 When R' and R" contain substituents, the substituents are one or more and each is independently selected from the group consisting of the following groups: deuterium, halogen, C1-C 20 Alkyl, C1~C 20 Deuterated alkyl, C1~C 20 Halogenated alkyl, C1~C 20 Alkoxy, C6~C 20 Aryloxy, C3~C 20 Cycloalkyl, C2~C 20 Heterocycloalkyl, C6~C 20 Aryl, C2~C 20 heteroaryl; Preferably, R' and R" are identical or different to each other at each occurrence and are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6~C 20 Aryl, substituted or unsubstituted C3~C 12 Cycloalkyl, substituted or unsubstituted C2~C 20 The group consisting of heteroaryl groups, when R' and R" contain substituents, the substituents are one or more and each is independently selected from the group consisting of the following groups: deuterium, halogen, C1-C 10 Alkyl, C1~C 10 Deuterated alkyl, C1~C 10 Halogenated alkyl, C1~C 10 Alkoxy, C6~C 15 Aryloxy, C3~C 12 Cycloalkyl, C2~C 15 Heterocycloalkyl, C6~C 15 Aryl, C2~C 15 heteroaryl; Preferably, R' and R" are identical or different to each other at each occurrence, and are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 deuterated alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, phenyl or deuterated phenyl; Preferably, R' and R" at each occurrence are identical or different from each other and are each independently selected from hydrogen, deuterium, methyl, ethyl or phenyl.

3. The organoboron compound according to claim 1 or 2, characterized in that R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 At each occurrence, they are the same or different from each other and are independently selected from hydrogen, deuterium, halogen atoms, cyano groups, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C1~C 20 Alkylsilyl, substituted or unsubstituted C5~C 30 Arylsilyl, substituted or unsubstituted C3~C 20 Cycloalkyl, substituted or unsubstituted C2~C 30 A group consisting of heteroaryl groups; when R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 When the substituent is contained, the substituent is one or more and each is independently selected from the group consisting of the following groups: deuterium, halogen, C1~C 10 Alkyl, C1~C 10 Deuterated alkyl, C1~C 10 Halogenated alkyl, C1~C 10 Alkoxy, C6~C 20 Aryloxy, C3~C 12 Cycloalkyl, C2~C 12 Heterocycloalkyl, C6~C 20 Aryl, C2~C 20 heteroaryl; Preferably, R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 At each occurrence, they are the same or different from each other and are independently selected from hydrogen, deuterium, cyano, halogen atoms, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6~C 20 Aryl, substituted or unsubstituted C2~C 20 The group consisting of heteroaryl groups; when R a , R b , R c , R d , R 4 , R 5 , R 6 When the substituent is contained, the substituent is one or more and each is independently selected from the group consisting of the following groups: deuterium, halogen, C1~C 10 Alkyl, C1~C 10 Deuterated alkyl, C1~C 10 Halogenated alkyl, C1~C 10 Alkoxy, C6~C 20 Aryloxy, C3~C 12 Cycloalkyl, C2~C 12 Heterocycloalkyl, C6~C 20 Aryl, C2~C 20 heteroaryl; Preferably, R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 At each occurrence, they are the same or different from each other and are independently selected from hydrogen, deuterium, cyano, halogen atoms, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C 15 Aryl, substituted or unsubstituted C5~C 15 The group consisting of heteroaryl groups; when R a , R b , R c , R d , R 4 , R 5 , R 6 When the substituent is contained, the substituent is one or more and each is independently selected from the group consisting of the following groups: deuterium, halogen, C1-C6 alkyl, C1-C6 deuterated alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C6-C 15 Aryloxy, C3-C8 cycloalkyl, C2-C8 heterocycloalkyl, C6-C 15 Aryl, C2~C 150 heteroaryl; Preferably, R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 At each occurrence, they are the same or different from each other and are independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, phenyl, biphenyl, naphthyl, carbazolyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, deuterated carbazolyl, phenyl substituted by C1-C6 alkyl, biphenyl substituted by C1-C6 alkyl, naphthyl substituted by C1-C6 alkyl, carbazolyl substituted by C1-C6 alkyl; Preferably, R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 At each occurrence, the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, methoxy, ethyl, ethoxy, propyl, propoxy, isopropyl, isopropoxy, butyl, butyloxy, isobutyl, isobutyloxy, tert-butyl, tert-butyloxy, trifluoromethyl, trifluoromethyloxy, pentafluoroethyl, pentafluoroethoxy, trimethylsilyl, substituted or unsubstituted phenyldimethylsilyl, cyclobutyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted a group consisting of substituted or unsubstituted peryl, substituted or unsubstituted fluoranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, and substituted or unsubstituted triazinyl; Preferably, R a , R b , R c , R d , R 4 , R 5 , R 6 , R 10 , R 11 At each occurrence, are the same or different from each other and are each independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl and the following groups:

4. The organoboron compound according to any one of claims 1 to 3, characterized in that The organic boron compound is selected from the compounds shown in the following structures: Among them, R a , R b , R c , R d , R 4 , R 5 , R 6 The definition of is the same as that in any one of claims 1 to 3; the definition of L is the same as that in claim 1; the definitions of Y1 and Y2 are the same as that of Y in claim 1 or 2; Preferably, Y1 and Y2 are the same or different and are independently selected from O, S, Se, CR 10 R 11 or NAr 1 ; Preferably, L is selected from O, S, Se, CR 10 R 11 or NAr 2 , more preferably NAr 2 ; Preferably, Ar 1 and Ar 2 Each independently selected from substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C 12 ~C 30 Fused aromatic, substituted or unsubstituted C5~C 30 Heteroaryl, substituted or unsubstituted C6~C 30 A group consisting of arylamine groups; when Ar 1 and Ar 2 When containing substituents, the substituents are one or more and each is independently selected from the group consisting of the following groups: deuterium, halogen, C1-C 10 Alkyl, C1~C 10 Deuterated alkyl, C1~C 10 Halogenated alkyl, C1~C 10 Alkoxy, C6~C 15 Aryloxy, C3~C 12 Cycloalkyl, C2~C 15 Heterocycloalkyl, C6~C 15 Aryl, C2~C 15 heteroaryl; Preferably, Ar 1 and Ar 2 Each independently substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C 12 ~C 30 Fused aromatic, substituted or unsubstituted C5~C 30 Heteroaryl, when Ar 1 and Ar 2 When containing substituents, the substituents are one or more and each is independently selected from the group consisting of the following groups: deuterium, halogen, C1-C6 alkyl, C1-C6 deuterated alkyl, C1-C6 haloalkyl, phenyl; Preferably, Ar 1 and Ar 2 Each of the following is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted a substituted or unsubstituted peryl group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group; when Ar 1 and Ar 2 When containing substituents, the substituents are one or more and are independently selected from the group consisting of the following groups: deuterium, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl; Preferably, Ar 1 and Ar 2 Each is independently selected from the group consisting of:

5. The organoboron compound according to any one of claims 1 to 4, characterized in that The organoboron compound is selected from any one of the following structures: Optionally, R 10 and R 11 Combined to form L, L is as defined in claim 1 or 4; R', R", R 4 ~R 6 , R 10 , R 11 ,Ar 1 ,Ar 2 The definition is the same as in any one of claims 1 to 4; R 1 ~R 3 , R 7 ~R 9 The same definition as R in any one of claims 1 to 4 a , R b , R c , R d Definition of; Preferably, L is selected from O, S, Se, CR 10 R 11 or NAr 2 ; Preferably, R', R" are each independently selected from methyl or phenyl; Preferably, R 1 ~R 11 and 4,6-diphenyl-2-yl, 4 ... a group consisting of substituted or unsubstituted peryl, substituted or unsubstituted fluoranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, and substituted or unsubstituted triazinyl; Preferably, Ar 1 ,Ar 2 Each of the following is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted The invention also comprises a group consisting of a substituted or unsubstituted perylenyl, a substituted or unsubstituted fluoranyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted dibenzofuranyl, and a substituted or unsubstituted dibenzothiophenyl.

6. The organoboron compound according to any one of claims 1 to 5, characterized in that The organoboron compound is selected from the compounds represented by formulas B001 to B174, or one of the compounds represented by formulas B001 to B174 substituted with one or more deuteriums: wherein Y, Y1 and Y2 are each independently selected from the group consisting of O, S, Se, C(CH3)2 or NAr; Ar is selected from the group consisting of: Cz is selected from the group consisting of:

7. An organic electroluminescent material, comprising the organic boron compound according to any one of claims 1 to 6; Preferably, the organic electroluminescent material comprises at least one host material and at least one dopant material, wherein the host material or the dopant material contains the organic boron compound; Preferably, the host material comprises the organic boron compound and / or a compound containing at least one of the following chemical groups: triphenylene, carbazolyl, dibenzothiophenyl, dibenzofuranyl, dibenzoselenophene, azatriphenylene, azacarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, azadibenzoselenophene, triazine, benzothiophenyl, benzofuranyl and indolyl; Preferably, in the organic electroluminescent material, the mass ratio of the doping material to the host material is 1:(1-99), preferably 1:(1-20).

8. Use of the organic boron compound according to any one of claims 1 to 6 or the organic electroluminescent material according to claim 7 in preparing an organic electroluminescent device; Preferably, the organic boron compound or the organic electroluminescent material is used as the light-emitting material of the organic light-emitting layer of the organic electroluminescent device; Preferably, the organic boron compound is used as a host material or a doping material of an organic light-emitting layer of the organic electroluminescent device; Preferably, the organic light-emitting layer comprises a host material and a doping material, and the mass ratio of the doping material to the host material is 1:(1-99), more preferably 1:(1-20).

9. An organic electroluminescent element, comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, wherein: The organic layer comprises the organic boron compound according to any one of claims 1 to 6 or the organic electroluminescent material according to claim 7; Preferably, the organic layer comprises one or more light-emitting layers, wherein at least one light-emitting layer comprises the organic boron compound according to any one of claims 1 to 6 or the organic electroluminescent material according to claim 7; Preferably, the light-emitting layer comprises a host material and a dopant material, the host material comprises the organic boron compound and / or a compound containing at least one of the following chemical groups: triphenylene, carbazole, dibenzothiophenyl, dibenzofuranyl, dibenzoselenophene, azatriphenylene, azacarbazole, azadibenzothiophenyl, azadibenzofuranyl, azadibenzoselenophene, triazine, benzothiophenyl, benzofuranyl and indolyl; or the dopant material comprises the organic boron compound according to any one of claims 1 to 6; preferably, the mass ratio of the dopant material to the host material is 1:(1 to 99); Preferably, the organic layer further comprises at least one layer of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, a hole blocking layer, and an electron blocking layer.

10. A consumer product comprising the organic boron compound according to any one of claims 1 to 6, the organic electroluminescent material according to claim 7 or the organic electroluminescent element according to claim 9.

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