Boron-nitrogen-containing organic compound, application thereof and organic electroluminescent device

Abstract

The invention provides a boron-nitrogen-containing organic compound, application thereof and an organic electroluminescent device. The organic compound containing boron and nitrogen has a structure as shown in the following formula, a ring A, a ring D and a ring E are independently selected from one of unsubstituted or R '-substituted C6-C60 aryl and unsubstituted or R'-substituted C3-C60 heteroaryl, and at least one of the ring A and the ring D is selected from a group as shown in the formula (2). The compound containing boron and nitrogen has excellent luminescence performance and excellent carrier transport efficiency, effectively avoids molecular aggregation, can be used as a resonance type fluorescent dye to realize narrow-spectrum emission and high color purity, and can adjust light color. When the compound is applied to the organic electroluminescent device, the service life of the organic electroluminescent device can be prolonged, and the efficiency of the organic electroluminescent device can be improved. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a boron-nitrogen-containing organic compound and application thereof, and an organic electroluminescent device. Background Art

[0002] With the progress and development of social sciences, display technology has become crucial in people's lives. Organic light-emitting diodes (OLEDs) have become one of the mainstream display devices due to their many advantages such as flexibility, bendability, self-luminescence, high contrast, large size, and low power consumption.

[0003] The luminescence mechanism of OLED is that electrons and holes recombine to form excitons under electrical excitation. Excitons obey probability statistical distribution, with singlet excitons accounting for about 25% and triplet excitons accounting for about 75%. The first generation of luminescence technology is collectively referred to as fluorescence technology, which uses singlet excitons to emit light and has low efficiency; the second generation of luminescence technology is collectively referred to as phosphorescence technology, which uses triplet excitons to emit light and can theoretically achieve 100% internal quantum efficiency, but the heavy metals required to construct phosphorescent dyes are not only expensive but also pollute the environment. Therefore, the third generation of thermally excited delayed fluorescence technology constructed using organic small molecules is currently widely used. When the energy level difference between singlet and triplet states is very small, triplet excitons can reverse intersystem crossing to singlet states, and then return to the ground state to emit light. Among them, red and green dyes as the three primary colors have become the mainstream of current commercial display devices due to their high electroluminescence efficiency and low power consumption. However, the chromaticity and life of blue light materials do not meet the current commercial display requirements. Blue light devices still use the first generation of traditional fluorescent materials to achieve high color purity and long device life.

[0004] In recent years, the research groups of Takuji Hatakeyama and Junji Kido in Japan have reported a series of organic small molecule materials DABNA-1 based on the thermally excited delayed fluorescence of boron nitrogen resonance (Adv. Mater., 2016, 28, pp. 2777-2781; J. Mater. Chem. C, 2019, 7, pp. 3082-3089), whose structure is

[0005] The boron atoms, nitrogen atoms and phenyl groups in this type of compound form a rigid polycyclic aromatic resonance skeleton, which has a high fluorescence quantum yield. Compared with traditional blue fluorescent dyes, this type of compound has a narrower emission spectrum band gap and higher color purity. However, the rigid planar structure also leads to a large difference in energy levels between its singlet and triplet states, and the reverse intersystem crossing from triplet to singlet state is slow. After the excitons recombine on the dye, it will cause a serious efficiency roll-off and a short device life. In addition, an overly planar rigid structure will also lead to adverse effects such as widening of the emission spectrum and red shift due to excessive doping concentration.

[0006] Existing organic electroluminescent materials still have a lot of room for improvement in terms of luminescence performance, and the industry urgently needs to develop new luminescent material systems to meet commercial needs. Boron nitrogen resonance materials have the advantages of high color purity and high luminescence efficiency, which has attracted widespread attention from the scientific research and industry. However, the luminescence color of this type of material is difficult to control, and its light color has always been limited to the sky blue light area, which greatly limits the further application of this type of material in high-resolution display, full-color display and white light lighting.

[0007] As OLED products gradually enter the market, people have higher and higher requirements for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED products in terms of light color, efficiency, life span, cost, etc. Therefore, the development of more types of organic electroluminescent materials with better performance is still an urgent problem to be solved in this field. Summary of the invention

[0008] In view of the deficiencies in the prior art, the purpose of the present invention is to provide a boron-nitrogen-containing organic compound and its application, and an organic electroluminescent device. The boron-nitrogen-containing organic compound has excellent electroluminescent properties, is suitable for organic electroluminescent devices, can effectively adjust the light color, improve the device life, and optimize the luminescent performance.

[0009] To achieve this object, the present invention adopts the following technical solutions:

[0010] In a first aspect, the present invention provides a boron-nitrogen-containing organic compound, wherein the boron-nitrogen-containing organic compound has a structure as shown in formula (1):

[0011]

[0012] In formula (1), ring A, ring D, and ring E are independently selected from unsubstituted or R'-substituted C6-C60 aryl groups and unsubstituted or R'-substituted C3-C60 heteroaryl groups, and at least one of ring A and ring D is selected from the group represented by formula (2);

[0013]

[0014] In formula (2), X is selected from O, S, NR 1 or CR 2 R 3 ;

[0015] R 1 , R 2 , R 3are independently selected from a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; 2 With R 3 Not connected or connected into rings by chemical bonds;

[0016] R 1 , R 2 , R 3 The substituents are each independently selected from at least one of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl;

[0017] Ring F is selected from unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl;

[0018] Ar 1 ,Ar 2 are independently selected from unsubstituted or R"-substituted C6-C60 aryl groups, unsubstituted or R"-substituted C3-C60 heteroaryl groups, and Ar 1 ,Ar 2 At least one of the groups is selected from the group represented by formula (3):

[0019]

[0020] In formula (3), Z1, Z2, Z3, and Z4 each independently represent N or CR 4 , X1, X2, X3, X4, and X5 each independently represent N or CR 8 ;

[0021] The R 4 , R 8 Each independently represents one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;

[0022] At least one of X1 to X5 represents CR 8 , and the R 8 represents a substituted or unsubstituted C1-C10 chain alkyl group;

[0023] R 4 , R 8The substituents are each independently selected from at least one of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl;

[0024] Furthermore, the R 1 , R 2 , R 3 , R 4 , R 8 At least one of R', R" is selected from the group shown in formula (4);

[0025]

[0026] In formula (4), R 5 , R 6 , R 7 Each independently represents a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; and R 5 , R 6 , R 7 At least one of the following is selected from substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, and at least one of the following is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0027] R 5 , R 6 , R 7 The substituents are each independently selected from one or a combination of at least two of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl;

[0028] The R' and R" are each independently selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, C1-C20 chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0029] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expressions are involved in the present invention, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0030] In the present specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent.

[0031] In the present specification, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0032] In the present specification, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0033] In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of isotopes thereof. For example, the expression "hydrogen (H)" includes its isotopes. 1 H (hydrogen or H), 2 The concept of H (deuterium or D); carbon (C) includes 12 C. 13 C, etc., no further details.

[0034] The heteroatom in the present invention generally refers to an atom or an atom group selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0035] In the present specification, examples of halogen include fluorine, chlorine, bromine, and iodine.

[0036] In the present invention, unless otherwise specified, aryl and heteroaryl include both monocyclic and condensed ring forms.

[0037] In the present invention, the C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0038] The C3~C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0039] The C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0040] The C3~C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0041] The C6 to C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0042] The C3~C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0043] The C2 to C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0044] In the present invention, the substituted or unsubstituted C6-C60 aryl group includes a monocyclic aryl group and a condensed aryl group, preferably a C6-C30 aryl group, and more preferably a C6-C20 aryl group. The so-called monocyclic aryl group refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as: phenyl, biphenyl, terphenyl, etc. Specifically, the biphenyl group includes 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. A condensed aryl group refers to a molecule containing at least two aromatic rings, and the aromatic rings are not independent of each other but share two adjacent carbon atoms to condense each other. For example, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl, fluoranthenyl, triphenylene, pyrenyl, peryl, The naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthacenyl group is selected from 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl. The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirobifluorene and benzofluorenyl.

[0045] The C3-C60 heteroaryl mentioned in the present invention includes monocyclic heteroaryl and condensed ring heteroaryl, preferably C3-C30 heteroaryl, more preferably C4-C20 heteroaryl, and more preferably C5-C12 heteroaryl. A monocyclic heteroaryl refers to a molecule containing at least one heteroaryl. When the molecule contains one heteroaryl and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl include furanyl, thienyl, pyrrolyl, pyridyl, etc. A condensed ring heteroaryl refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share two adjacent atoms and are fused to each other. Examples of fused ring heteroaryl groups include benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl and the like.

[0046] The chain alkyl mentioned in the present invention, unless otherwise specified, includes straight-chain alkyl and branched alkyl. Specifically, the substituted or unsubstituted C1-C30 chain alkyl is preferably a substituted or unsubstituted C1-C16 chain alkyl, and more preferably a substituted or unsubstituted C1-C10 chain alkyl. Examples of the substituted or unsubstituted C1-C10 chain alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, and the like.

[0047] In the present invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein the monocycloalkyl group refers to an alkyl group containing a single cyclic structure; the polycycloalkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; the C3-C20 cycloalkyl group can be exemplified by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0048] In the present specification, the substituted or unsubstituted C1~C20 alkoxy group is preferably a substituted or unsubstituted C1~C10 alkoxy group. Examples of C1~C10 alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like. Among them, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy and isopentyloxy are preferred, and methoxy is more preferred.

[0049] In the present specification, as the substituted or unsubstituted C1~C20 alkylsilyl group, as the substituted or unsubstituted C1~C10 alkylsilyl group, examples of the C1~C10 alkylsilyl group can be a silyl group substituted by the groups listed in the above-mentioned C1~C10 alkyl groups, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like groups.

[0050] In the present specification, the C2~C10 alkenyl group is a hydrocarbon group containing at least one C=C double bond, and illustratively includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl and the like.

[0051] It should be noted that, for the sake of convenience, the possible effects of each group / feature are described separately in this application, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between the various groups, rather than the effect of a single group.

[0052] Furthermore, in the general formula of the present invention, the ring E has a structure as shown in formula (5):

[0053]

[0054] Among them, the dotted lines represent the fused bonds of the groups;

[0055] Y 1 , Y 2 , Y 3 Each independently is CR 11 or N, R 11 Each is independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino or one of the following substituted or unsubstituted groups: C1-C20 chain alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;

[0056] R 11 The substituted substituents are each independently selected from one of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of at least two thereof.

[0057] Furthermore, the boron-nitrogen-containing organic compound of the present invention has a structure as shown in formula (6):

[0058]

[0059] Among them, ring A, ring D, Ar 1 ,Ar 2 has the same limited range as formula (1), wherein Y 1 , Y 2 , Y 3 has the same limited range as in formula (5), and the Y 1 , Y 2 , Y 3 At most one of them is N;

[0060] Preferably, the Y 2 CR 11 , R 11 is selected from the following substituted or unsubstituted groups: C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl, R 11 The substituents are each independently selected from one or a combination of two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C6-C30 aryloxy group, a C6-C60 aryl group, and a C3-C60 heteroaryl group;

[0061] More preferably, the Y 2 CR 11 , R 11 is selected from the group represented by formula (4), R 5 , R 6 , R 7 The substituents in the substitution are each independently selected from one of C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl and C3-C60 heteroaryl.

[0062] Furthermore, in the general formula of the present invention, the ring A and the ring D have a structure as shown in formula (7) or formula (8), and at least one has a structure as shown in formula (8):

[0063]

[0064] Among them, the dotted lines represent the fused bonds of the groups;

[0065] X is selected from O, S, NR 1 or CR 2 R 3 , R 1 , R 2 , R 3 It has the same definition as formula (1); preferably, X is selected from O or S;

[0066] U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 Each independently is CR 9 or N, R 9Each is independently selected from one or a combination of two of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl;

[0067] Preferably, the U 1 , U 2 , U 3 and U 4 At most one of them is N;

[0068] Preferably, the U 5 , U 6 , U 7 and U 8 At most one of them is N.

[0069] Furthermore, the boron-nitrogen-containing organic compound of the present invention has a structure as shown in any one of formulas (9) to (13):

[0070]

[0071] Among them, Ar 1 ,Ar 2 has the same limited range as formula (1), Y 1 , Y 2 , Y 3 has the same limited range as in formula (5), and the Y 1 , Y 2 , Y 3 At most one of them is N;

[0072] X, X' are each independently O or S;

[0073] U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 , U 5 '、U 6 '、U 7 '、U 8 'Each independently CR 9 or N, R 9Each is independently selected from one or a combination of hydrogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;

[0074] Preferably, the Y 2 CR 11 , R 11 is selected from the following substituted or unsubstituted groups: C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl, R 11 The substituents are each independently selected from one or a combination of two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C6-C30 aryloxy group, a C6-C60 aryl group, and a C3-C60 heteroaryl group;

[0075] More preferably, the Y 2 CR 11 , R 11 is selected from the group represented by formula (4), R 5 , R 6 , R 7 The substituents in the substitution are each independently selected from one of C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl and C3-C60 heteroaryl.

[0076] Furthermore, in formula (9) to formula (13) of the present invention, the U 5 or U 6 At least one of them is CR 9 , and the R 9 Any one selected from hydrogen, C1-C20 chain alkyl, C6-C60 aryl, C3-C60 heteroaryl, and / or the U 5’ or U 6’ At least one of them is CR 9 , and the R 9 Any one selected from hydrogen, C1-C20 chain alkyl, C6-C60 aryl, C3-C60 heteroaryl;

[0077] In formula (9) and formula (10), U 1 , U 2 , U 3 , U 4 At least one of them is CR 9 , the R 9 Any one selected from hydrogen, C1-C20 chain alkyl, C6-C60 aryl, C3-C60 heteroaryl;

[0078] Preferably, the U 7 or U 8 CR 9 , and the R 9 is hydrogen; and / or said U 7’ or U 8’ CR 9 , and the R 9 is hydrogen;

[0079] Preferably, the U 1 or U 2 CR 9 , the R 9 is hydrogen; or, said U 3 or U 4 CR 9 , the R 9 For hydrogen.

[0080] Furthermore, in the general formula of the present invention, the Ar 1 ,Ar 2 At least one of the groups is selected from the group represented by formula (3), wherein at least one of X1 to X5 represents CR 8 , and the R 8 Represents a C1-C6 chain alkyl group;

[0081] Preferably, any two of X1 to X5 represent CR 8 , and the R 8 It represents a C1-C6 chain alkyl group.

[0082] Furthermore, the Ar 1 ,Ar 2 At least one of the groups is selected from the group represented by formula (3), wherein Z1, Z2, Z3, and Z4 are independently CR 4 , and R 4 represents hydrogen, a C1-C6 chain alkyl group, or a group selected from the group represented by formula (4).

[0083] Furthermore, in formula (4) of the present invention, R 5 , R 6 , R 7 At least one of them is selected from C6-C60 aryl;

[0084] Preferably, R 5 , R 6 , R 7 One or two of them are C6-C60 aryl groups;

[0085] More preferably, R 5 , R 6 , R 7 One or two of them are phenyl.

[0086] Preferably, the boron-nitrogen-containing organic compound has a structure shown in any one of the following M1 to M96:

[0087]

[0088]

[0089]

[0090]

[0091] In a second aspect, the present invention provides an application of the boron-nitrogen-containing organic compound as described in the first aspect, wherein the boron-nitrogen-containing organic compound is applied to an organic electronic device.

[0092] Preferably, the organic electronic device is selected from an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper, and an organic electroluminescent device is further preferred.

[0093] Preferably, the boron-nitrogen-containing organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0094] Preferably, the boron-nitrogen-containing organic compound is used as a luminescent dye of a luminescent layer in an organic electroluminescent device, and more preferably is a blue light-emitting dye.

[0095] In a third aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one boron-nitrogen-containing organic compound as described in the first aspect.

[0096] Preferably, the organic layer comprises at least one boron-nitrogen-containing organic compound having a structure shown by M1 to M96.

[0097] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one boron-nitrogen-containing organic compound as described in the first aspect, and further preferably comprises at least one boron-nitrogen-containing organic compound having a structure shown by M1 to M96.

[0098] Preferably, the light-emitting layer includes a host material and a dye, and the dye includes at least one boron-nitrogen-containing organic compound as described in the first aspect. Further preferably, the dye includes at least one boron-nitrogen-containing organic compound having a structure shown by M1 to M96.

[0099] The boron-nitrogen-containing organic compound provided by the present invention has excellent luminescent properties. When used in an organic electroluminescent device, it can provide triplet excitons to achieve higher luminescent efficiency. At the same time, based on its excellent carrier transport efficiency, it is suitable for use as a dye for a light-emitting layer.

[0100] In another preferred technical solution, the boron-nitrogen-containing organic compound is used as a sensitizer of the light-emitting layer, and together with the host material and the dye, achieves a good light-emitting effect.

[0101] Preferably, the organic layer further comprises any one of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, or a combination of at least two thereof.

[0102] In a preferred technical solution, an organic electroluminescent device (OLED device) includes a first electrode, a second electrode, and an organic layer between the electrodes. The organic layer can be divided into multiple regions, such as a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer includes at least one boron-nitrogen-containing organic compound as described in the first aspect, and further preferably includes at least one boron-nitrogen-containing organic compound having a structure shown in M1 to M96.

[0103] In a preferred technical solution, the organic electroluminescent device includes a substrate, and a first electrode, a plurality of light-emitting functional layers (organic layers) and a second electrode sequentially arranged on the substrate; the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer sequentially arranged, and the hole injection layer is in contact with the first electrode. The organic layer (preferably the light-emitting layer) contains at least one boron-nitrogen-containing organic compound as described in the first aspect, and further preferably contains at least one boron-nitrogen-containing organic compound having a structure shown in M1 to M96.

[0104] In a preferred technical solution, a substrate can be used below the first electrode or above the second electrode. The substrate is glass or polymer material with excellent mechanical strength, thermal stability, water resistance and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate used as a display.

[0105] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0106] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule or a polymer, and a combination thereof.

[0107] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0108] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0109]

[0110]

[0111]

[0112] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0113]

[0114] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a host material (Host). The light-emitting layer can be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors can be arranged in a plane according to a pixel pattern, or they can be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0115] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0116] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0117]

[0118] In one aspect of the present invention, the barrier layer around the light-emitting layer can be selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of TDE1-TDE49 listed below.

[0125]

[0126]

[0127]

[0128] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0129] The organic layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an electron transport layer (ETL) of a single-layer structure, including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0130] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0131]

[0132]

[0133]

[0134]

[0135] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0136] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes but is not limited to one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg or Yb.

[0137] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0138] Compared with the prior art, the present invention has the following beneficial effects:

[0139] In the boron-nitrogen organic compound provided by the present invention, the boron-nitrogen organic compound has excellent luminescent properties through the special design of the molecular structure, can be used as a resonant fluorescent dye, achieve narrow spectrum emission and high color purity, and adjust the light color. The boron-nitrogen organic compound has good stability and spatial configuration, can give triplet excitons to achieve higher luminous efficiency, has excellent carrier transfer efficiency, and effectively avoids molecular aggregation, improves the life and efficiency of organic electroluminescent devices. The preparation process of the boron-nitrogen organic compound is simple and easy, the raw materials are easy to obtain, and it is suitable for mass production and amplification. It is used as a material for the light-emitting layer in an organic electroluminescent device, so that the device achieves high-quality luminous effect, and effectively prolongs the life of the device and optimizes the luminous efficiency. DETAILED DESCRIPTION

[0140] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0141] In a specific embodiment, the boron-nitrogen-containing organic compound can be prepared by the following synthetic route:

[0142]

[0143] Among them, ring A, ring D, ring E, Ar 1 ,Ar 2 It has the same limited range as formula (1).

[0144] The specific preparation method of the boron-nitrogen-containing organic compound of the present invention will be described in detail below using a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0145] It should be noted that obtaining the boron-nitrogen-containing organic compound is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art may also select other methods or routes to obtain the boron-nitrogen-containing organic compound proposed in the present invention. The compounds for which the synthesis method is not mentioned in the present invention are raw materials obtained from commercial channels, or are prepared by these raw materials according to known methods.

[0146] The solvents and reagents used in the present invention can all be purchased from the chemical product market.

[0147] The analysis and detection of the intermediates and target products in the following synthetic examples of the present invention were performed using an ABSCIEX mass spectrometer (4000QTRAP).

[0148] Synthesis Example 1: Boron-nitrogen containing organic compound M2

[0149]

[0150] (1) Synthesis of intermediate M2-1

[0151] To a 1000mL flask, add 3-bromo-5-phenylisopropyliodobenzene (20g), N-(2-(3,5-di-tert-butyl)-4-tert-butylphenyl)-4-tert-butylaniline (23.42g), cuprous iodide (1g), 1,10-phenanthroline (1g), potassium carbonate (13.78g), and DMF 400mL. Under nitrogen protection, heat to 140°C and react for 24h. After stopping heating, add dichloromethane and water for extraction. The organic phase is spin-dried and column chromatography is performed to obtain 31.7g of white solid M2-1.

[0152] (2) Synthesis of intermediate M2-2

[0153] To a 1000mL flask, add intermediate M2-1 (30g), raw material A (13.68g), palladium acetate (0.45g), tri-tert-butylphosphine tetrafluoroborate (1.69g), sodium tert-butoxide (7.76g), and 600mL of toluene. Heat to reflux under nitrogen protection for 2h. Filter on silica gel and dry the solvent. Recrystallize from toluene and ethanol to obtain 35.1g of white solid M2-2.

[0154] (3) Synthesis of target product M2

[0155] Add intermediate M2-2 (20 g), boron tribromide (40.10 g), and o-dichlorobenzene 200 mL to a 500 mL reactor, and heat to 180 ° C for 24 h under nitrogen protection. After silica gel column chromatography, recrystallization with ethyl acetate was performed to obtain a yellow-green solid, which was the target product M2, with a total of 4.7 g. Mass spectrometry detected molecular weight: 1007.33 (theoretical value: 1007.33).

[0156] Synthesis Example 2: Boron-nitrogen containing organic compound M8

[0157]

[0158] The synthetic route of M8 is exactly the same as that of M2, except that 3-bromo-5-phenylisopropyliodobenzene is replaced by 3-bromo-5-(1,1-diphenylethyl)iodobenzene, and raw material A is replaced by raw material B. The molecular weight detected by mass spectrometry is 1124.72 (theoretical value: 1124.72).

[0159] Synthesis Example 3: Boron-nitrogen containing organic compound M28

[0160]

[0161] The synthetic route of M28 is exactly the same as that of M2, except that the raw material 3-bromo-5-phenylisopropyliodobenzene is replaced by 3-bromoiodobenzene, and the raw material A is replaced by raw material C. The molecular weight detected by mass spectrometry is 950.56 (theoretical value: 950.57).

[0162] Device Example 1

[0163] An organic electroluminescent device comprises an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode (Al) arranged in sequence. The preparation method of the organic electroluminescent device is as follows:

[0164] (1) a glass substrate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0165] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, vacuum evaporating a mixture of HT-4:HI-3 (97 / 3, w / w) on the above anode layer as a hole injection layer, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm;

[0166] (3) vacuum evaporating compound HT-4 on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 60 nm;

[0167] (4) vacuum evaporating compound HT-14 on the hole transport layer as an electron blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0168] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer includes a binary mixture of a main material BFH-4 and a dye (the boron-nitrogen-containing organic compound M2), BFH-4:M2 (100:3, w / w), with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 20 nm;

[0169] (6) vacuum evaporating compound ET-23 on the light-emitting layer as a hole blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0170] (7) vacuum evaporating a mixture of compounds ET-69:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 25 nm;

[0171] (8) Vacuum evaporation of LiF as an electron injection layer on the electron transport layer at a rate of 0.1 nm / s and a thickness of 1 nm;

[0172] (9) Vacuum-evaporating an Al layer with a thickness of 150 nm on the electron injection layer as the cathode of the device at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0173] Device Examples 2-15, Device Comparative Examples 1-4

[0174] An organic electroluminescent device, which differs from device embodiment 1 only in that the dyes of the light-emitting layer are the compounds shown in Table 1; other layers, thicknesses, materials and preparation methods are the same as those of device embodiment 1.

[0175] The dye structures in device comparison examples 1-4 are as follows:

[0176]

[0177] Device performance test:

[0178] (1) The LT97 life test is as follows: Use a brightness meter at 40mA / cm 2 The initial brightness value of the device under the current density is measured by maintaining a constant current and measuring the time for the device brightness to drop to 97% of the initial brightness, in hours; the LT97 life test value of device comparison example 1 is recorded as 1.0, and the ratio of the LT97 life test value of other devices to the LT97 life test value of device comparison example 1 is calculated;

[0179] (2) The test method for external quantum efficiency is as follows: The external quantum efficiency (EQE, %) of the device is measured using the integrating sphere method.

[0180] The test results are shown in Table 1:

[0181] Table 1

[0182]

[0183]

[0184] According to the performance data of Table 1, the boron-nitrogen-containing organic compound provided by the present invention can significantly improve the efficiency of the device and significantly extend the life span as the light-emitting layer dye of the organic electroluminescent device. Specifically, relative to the comparison compounds C1 and C4, the device comprising the compound of the present invention has higher efficiency and longer life span, which may be due to the alkyl substituted by the aryl group contained in the compound of the present invention having a larger steric hindrance, which is conducive to suppressing exciton quenching, thereby improving the efficiency and life span of the device, compared to the comparison compound C2, the device comprising the compound of the present invention has higher efficiency and longer life span, which may be due to the group of the formula (3) structure contained in the ortho position of the N atom of the compound of the present invention can suppress exciton quenching, and increase the bond dissociation energy, thereby due to the improvement of efficiency and life span, compared to compound C3, the device comprising the compound of the present invention has higher efficiency and longer life span, which may be due to the benzothiophene structure contained in the compound of the present invention can significantly reduce the triplet energy level, which is conducive to life span improvement, while the alkyl substitution on the aryl group can suppress exciton quenching, which is conducive to efficiency improvement.

[0185] The aryl-substituted alkyl contained in the compound of the present invention has a large steric hindrance, which is beneficial to inhibiting exciton quenching, thereby improving the efficiency and life of the device. At the same time, since the aryl-substituted alkyl has a large mass, it is beneficial to inhibit molecular vibration under the action of the aryl group substituted by the alkyl adjacent to the N atom, thereby improving the efficiency.

[0186] In summary, the present invention uses the boron-nitrogen-containing organic compound as a dye for the light-emitting layer through the special design of the molecular structure, which can significantly prolong the device life and optimize the light-emitting performance of the device.

[0187] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the boron-nitrogen organic compounds and their applications and organic electroluminescent devices of the present invention, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A boron-nitrogen-containing organic compound, characterized in that: The boron-nitrogen-containing organic compound has a structure as shown in formula (1): In formula (1), ring A, ring D, and ring E are independently selected from unsubstituted or R'-substituted C6-C60 aryl groups and unsubstituted or R'-substituted C3-C60 heteroaryl groups, and at least one of ring A and ring D is selected from the group represented by formula (2); In formula (2), X is selected from O, S, NR 1 or CR 2 R 3 ; R 1 , R 2 , R 3 are independently selected from a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; 2 With R 3 Not connected or connected into rings by chemical bonds; R 1 , R 2 , R 3 The substituents are each independently selected from at least one of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Ring F is selected from unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; Ar 1 ,Ar 2 are independently selected from unsubstituted or R"-substituted C6-C60 aryl groups, unsubstituted or R"-substituted C3-C60 heteroaryl groups, and Ar 1 ,Ar 2 At least one of the groups is selected from the group represented by formula (3): In formula (3), Z1, Z2, Z3, and Z4 each independently represent N or CR 4 , X1, X2, X3, X4, and X5 independently represent N or CR 8 ; The R 4 , R 8 Each independently represents one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; At least one of X1 to X5 represents CR 8 , and the R 8 represents a substituted or unsubstituted C1-C10 chain alkyl group; R 4 , R 8 The substituents are each independently selected from at least one of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Furthermore, the R 1 , R 2 , R 3 , R 4 , R 8 At least one of R', R" is selected from the group shown in formula (4); In formula (4), R 5 , R 6 , R 7 Each independently represents a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; and R 5 , R 6 , R 7 At least one of the following is selected from substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, and at least one of the following is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; R 5 , R 6 , R 7 The substituents are each independently selected from one or a combination of at least two of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; The R' and R" are each independently selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, C1-C20 chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

2. The boron-nitrogen-containing organic compound according to claim 1, characterized in that: The ring E has a structure as shown in formula (5): Among them, the dotted lines represent the fused bonds of the groups; Y 1 , Y 2 , Y 3 Each independently is CR 11 or N, R 11 Each is independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino or one of the following substituted or unsubstituted groups: C1-C20 chain alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; R 11 The substituted substituents are each independently selected from one of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of at least two thereof.

3. The boron-nitrogen-containing organic compound according to claim 2, characterized in that: The boron-nitrogen-containing organic compound has a structure as shown in formula (6): Among them, ring A, ring D, Ar 1 ,Ar 2 has the same limited range as formula (1), wherein Y 1 , Y 2 , Y 3 has the same limited range as in formula (5), and the Y 1 , Y 2 , Y 3 At most one of them is N; Preferably, the Y 2 CR 11 , R 11 is selected from the following substituted or unsubstituted groups: C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl, R 11 The substituents are each independently selected from one or a combination of two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C6-C30 aryloxy group, a C6-C60 aryl group, and a C3-C60 heteroaryl group; More preferably, the Y 2 CR 11 , R 11 is selected from the group represented by formula (4), R 5 , R 6 , R 7 The substituents in the substitution are each independently selected from one of C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl and C3-C60 heteroaryl.

4. The boron-nitrogen-containing organic compound according to claim 1 or 3, characterized in that: The ring A and the ring D have a structure as shown in formula (7) or formula (8), and at least one has a structure as shown in formula (8): Among them, the dotted lines represent the fused bonds of the groups; X is selected from O, S, NR 1 or CR 2 R 3 , R 1 , R 2 , R 3 It has the same definition as formula (1); preferably, X is selected from O or S; U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 Each independently is CR 9 or N, R 9 Each is independently selected from one or a combination of two of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, the U 1 , U 2 , U 3 and U 4 At most one of them is N; Preferably, the U 5 , U 6 , U 7 and U 8 At most one of them is N.

5. The boron-nitrogen-containing organic compound according to claim 4, characterized in that: The boron-nitrogen-containing organic compound has a structure as shown in any one of formulas (9) to (13): Among them, Ar 1 ,Ar 2 has the same limited range as formula (1), Y 1 , Y 2 , Y 3 has the same limited range as in formula (5), and the Y 1 , Y 2 , Y 3 At most one of them is N; X, X' are each independently O or S; U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 , U 5 '、U 6 '、U 7 '、U 8 'Each independently CR 9 or N, R 9 Each is independently selected from one or a combination of hydrogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; Preferably, the Y 2 CR 11 , R 11 is selected from the following substituted or unsubstituted groups: C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl, R 11 The substituents are each independently selected from one or a combination of two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C6-C30 aryloxy group, a C6-C60 aryl group, and a C3-C60 heteroaryl group; More preferably, the Y 2 CR 11 , R 11 is selected from the group represented by formula (4), R 5 , R 6 , R 7 The substituents in the substitution are each independently selected from one of C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl and C3-C60 heteroaryl.

6. The boron-nitrogen-containing organic compound according to claim 5, characterized in that: In formula (9) to formula (13), U 5 or U 6 At least one of them is CR 9 , and the R 9 Any one selected from hydrogen, C1-C20 chain alkyl, C6-C60 aryl, C3-C60 heteroaryl, and / or the U 5’ or U 6’ At least one of them is CR 9 , and the R 9 Any one selected from hydrogen, C1-C20 chain alkyl, C6-C60 aryl, C3-C60 heteroaryl; In formula (9) and formula (10), U 1 , U 2 , U 3 , U 4 At least one of them is CR 9 , the R 9 Any one selected from hydrogen, C1-C20 chain alkyl, C6-C60 aryl, C3-C60 heteroaryl; Preferably, the U 7 or U 8 CR 9 , and the R 9 is hydrogen; and / or said U 7’ or U 8’ CR 9 , and the R 9 is hydrogen; Preferably, the U 1 or U 2 CR 9 , the R 9 is hydrogen; or, said U 3 or U 4 CR 9 , the R 9 For hydrogen.

7. The boron-nitrogen-containing organic compound according to any one of claims 1, 3 or 5, characterized in that: The Ar 1 ,Ar 2 At least one of the groups is selected from the group represented by formula (3), wherein at least one of X1 to X5 represents CR 8 , and the R 8 Represents a C1-C6 chain alkyl group; Preferably, any two of X1 to X5 represent CR 8 , and the R 8 It represents a C1-C6 chain alkyl group.

8. The boron-nitrogen-containing organic compound according to any one of claims 1, 3, 5 or 7, characterized in that: The Ar 1 ,Ar 2 At least one of the groups is selected from the group represented by formula (3), wherein Z1, Z2, Z3, and Z4 are independently CR 4 , and R 4 represents hydrogen, a C1-C6 chain alkyl group, or a group selected from the group represented by formula (4).

9. The boron-nitrogen-containing organic compound according to any one of claims 1, 3, 5, 7 or 8, characterized in that: In formula (4), R 5 , R 6 , R 7 At least one of them is selected from C6-C60 aryl; Preferably, R 5 , R 6 , R 7 One or two of them are C6-C60 aryl groups; More preferably, R 5 , R 6 , R 7 One or two of them are phenyl.

10. The boron-nitrogen-containing organic compound according to claim 1, characterized in that: The boron-nitrogen-containing organic compound has a structure shown in any one of the following M1 to M96:

11. Use of the boron-nitrogen-containing organic compound according to any one of claims 1 to 10, characterized in that: The boron-nitrogen-containing organic compound is applied to an organic electronic device, wherein the organic electronic device is selected from an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the boron-nitrogen-containing organic compound is used as a light-emitting layer material in an organic electroluminescent device.

12. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one boron-nitrogen-containing organic compound according to any one of claims 1 to 10; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one boron-nitrogen-containing organic compound according to any one of claims 1 to 10; Preferably, the light-emitting layer comprises a host material and a dye, and the dye comprises at least one boron-nitrogen-containing organic compound as claimed in any one of claims 1 to 10.

13. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 12.

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