Organic compound and application thereof, and organic electroluminescent device containing organic compound

Abstract

The invention relates to an organic compound containing boron and nitrogen, belongs to the technical field of organic light-emitting materials, and also relates to application of the compound in an organic light-emitting device. The organic compound has a structure shown in the following formula, and at least one of Ra, Rd, Re, Ar1 and Ar2 is selected from the structure shown in the formula (2). When the organic compound provided by the invention is applied to an organic electroluminescent device as a luminescent dye, the prepared device has higher efficiency and longer service life. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a boron-nitrogen-containing organic compound, belonging to the technical field of organic light-emitting materials. The present invention also relates to the application of the compound in an organic electroluminescent device. Background Art

[0002] With the continuous 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 current mainstream display devices due to their many advantages such as flexibility, bendability, self-luminescence, high contrast, large size, and low power consumption.

[0003] The light-emitting mechanism of OLEDs is that electrons and holes recombine to form excitons under electrical excitation. The excitons follow a probability statistical distribution, with singlet excitons accounting for approximately 25% and triplet excitons accounting for approximately 75%. The first-generation light-emitting technology is collectively referred to as fluorescence technology, which uses singlet excitons to emit light; the second-generation light-emitting technology is collectively referred to as phosphorescence technology, which uses triplet excitons to emit light. In theory, 100% internal quantum efficiency can be achieved, but the heavy metals required to construct phosphorescent dyes are not only expensive but also pollute the environment. Therefore, the currently widely used third-generation thermally activated delayed fluorescence technology constructed with organic small molecules is adopted. When the singlet-triplet energy level difference is very small, triplet excitons can undergo reverse intersystem crossing to the singlet state and then return to the ground state to emit light. Among them, the 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 lifespan of blue light materials do not meet the current commercial display requirements, and traditional fluorescent materials are still used in blue light devices to achieve high color purity and long device lifespan.

[0004] In recent years, research groups such as Takuji Hatakeyama and Junji Kido in Japan have reported a series of organic small molecule materials DABNA-1 based on boron-nitrogen resonance-type thermally activated delayed fluorescence (Adv. Mater. 2016, 28, 2777–2781; J. Mater. Chem. C, 2019, 7, 3082-3089). In these compounds, boron atoms, nitrogen atoms, and phenyl groups form a rigid polycyclic aromatic resonance skeleton, thus having a relatively high fluorescence quantum yield. Compared with traditional blue fluorescent dyes, these compounds have a narrower emission spectral bandgap and higher color purity. However, the rigid planar structure also leads to a relatively large energy level difference between the singlet and triplet states, slower reverse intersystem crossing from the triplet state to the singlet state, and serious efficiency roll-off after excitons recombine on the dye, resulting in a shorter device lifespan. In addition, the overly planar rigid structure often also causes adverse effects such as broadening and red-shifting of the emission spectrum due to too high doping concentration.

[0005]

[0006] Existing organic electroluminescent materials still have great room for improvement in terms of luminescence performance. The industry urgently needs to develop new luminescent material systems to meet commercial demands. Boron-nitrogen resonance materials have the advantages of high color purity and high luminescence efficiency, which have attracted extensive attention in the scientific research community and the industrial community. However, due to the small influence of peripheral substituents on their energy levels, that is, it is very difficult to regulate the luminescence color of the materials, and their light colors have been limited to the sky blue light region, which greatly restricts the further application of such materials in the fields of high-resolution display, full-color display, and white light illumination, etc.

[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 various problems of OLED products such as efficiency, lifespan, and cost. The researchers of the present invention, through careful thinking and continuous experiments, discovered a clever molecular design scheme and will elaborate it in detail below. Surprisingly, the compounds disclosed by the present invention are very suitable for application in OLEDs and can improve the device lifespan. Summary of the Invention

[0008] The present invention designs a class of resonance fluorescent dyes containing boron-nitrogen structures that can emit deep blue light and can effectively improve device efficiency and lifespan.

[0009] The present invention provides a boron-nitrogen-containing organic compound, which is characterized in that it has a structure shown in formula (1):

[0010]

[0011] Ring A, Ring D, and Ring E are each independently one of a C6-C50 aromatic ring and a C3-C50 heteroaromatic ring;

[0012] Ra, Rd, and Re represent substituents from single substitution to the maximum allowable number of substitutions, and Ra, Rd, and Re are each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 linear alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.

[0013] Ar1 and Ar2 are each independently one of an unsubstituted or R'-substituted C6-C50 aryl group or an unsubstituted or R'-substituted C3-C50 heteroaryl group;

[0014] R' groups adjacent to each other are not connected or are connected by a chemical bond to form a ring; the R' groups are not connected to adjacent ring structures or are connected by a chemical bond to form a ring;

[0015] Moreover, at least one of Ra, Rd, Re, Ar1, and Ar2 is selected from the structure of formula (2):

[0016]

[0017] In formula (2), L1 is selected from a single bond, an unsubstituted or R''-substituted C1-C20 linear alkyl group, or an unsubstituted or R''-substituted C6-C60 aryl group;

[0018] X1, X2, X3, X4, X5, X6, X7, X8, X9, X 10 , X 11 , X 12 are each independently N or CR 11 , R 11 are each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, an unsubstituted or R''-substituted C1-C20 linear alkyl group, an unsubstituted or R''-substituted C3-C20 cycloalkyl group, an unsubstituted or R''-substituted C1-C20 alkoxy group, an unsubstituted or R''-substituted C6-C30 arylamino group, an unsubstituted or R''-substituted C3-C30 heteroarylamino group, an unsubstituted or R''-substituted C6-C60 aryl group, an unsubstituted or R''-substituted C3-C60 heteroaryl group; R 11 are each independently not connected to adjacent ring structures or are connected by a chemical bond to form a ring;

[0019] And at least one of X1 - X 12 is selected from CR 11 , and this R 11 is selected from an unsubstituted or R''-substituted C6-C60 aryl group, an unsubstituted or R''-substituted C3-C60 heteroaryl group;

[0020] "*" represents the connection site; the expression of the ring structure with a "-" drawn through it indicates that the connection site is at any position on the ring structure capable of forming a bond;

[0021] Each of R' and R” is independently selected from any one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, C1-C20 linear alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0022] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expression is involved in the present invention, it has the same meaning, and the selection range of the substituents is as shown above and will not be elaborated one by one.

[0023] In this specification, the expression Ca~Cb means that the group has a carbon atom number of a~b. Generally, unless otherwise specified, the carbon atom number does not include the carbon atom number of the substituent.

[0024] In this specification, the expression of a ring structure with a "-" drawn across it indicates that the connection site is at any bond-forming position on the ring structure. "*" represents the connection site.

[0025] In this specification, "independently of each other" means that when there are multiple subjects, they can be the same or different from each other.

[0026] In the present invention, for the description of chemical elements, unless otherwise specified, the concept of its isotopes is usually included. For example, the description of "hydrogen (H)" includes the concepts of its isotopes 1H (protium or H) and 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., and will not be elaborated further.

[0027] The heteroatoms in the present invention usually refer to atoms or atomic groups selected from N, O, S, P, Si, and Se, preferably selected from N, O, and S.

[0028] In this specification, examples of halogens include fluorine, chlorine, bromine, iodine, etc.

[0029] In the present invention, unless otherwise specified, both aryl and heteroaryl include monocyclic and fused-ring cases.

[0030] 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.

[0031] Any of C3-C60 can 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.

[0032] Any of C1-C20 can be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0033] Any of C3-C20 can be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0034] Any of C6-C30 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0035] Any of C3-C30 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0036] Any of C2-C10 can be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0037] In the present invention, the substituted or unsubstituted C6-C60 aryl group (or C6-C50 aryl group) includes monocyclic aryl groups and polycyclic aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. 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 are connected by single bonds. Exemplarily, such as: phenyl group, biphenyl group, terphenyl group, etc. Specifically, the biphenyl group includes 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; 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. The polycyclic aryl group refers to a group containing at least two aromatic rings, and the aromatic rings are not independent of each other but share two adjacent carbon atoms and are fused together. Exemplarily, such as: naphthyl group, anthracenyl group, phenanthryl group, indenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, perylenyl group, Groups such as a base, a tetracenyl group, and their derivative groups. The naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracenyl group is selected from a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group; the fluorenyl group is selected from a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group; the pyrenyl group is selected from a 1-pyrenyl group, a 2-pyrenyl group, and a 4-pyrenyl group; the tetracenyl group is selected from a 1-tetracenyl group, a 2-tetracenyl group, and a 9-tetracenyl group. The derivative group of fluorene is selected from a 9,9-dimethylfluorenyl group, a 9,9-diethylfluorenyl group, a 9,9-dipropylfluorenyl group, a 9,9-dibutylfluorenyl group, a 9,9-dipentylfluorenyl group, a 9,9-dihexylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9,9-dinaphthylfluorenyl group, a 9,9'-spirobifluorenyl group, and a benzofluorenyl group.

[0038] The C3-C60 heteroaryl group (or C6-C50 heteroaryl group) mentioned in the present invention includes a monocyclic heteroaryl group and a fused-ring heteroaryl group, preferably a C3-C30 heteroaryl group, more preferably a C4-C20 heteroaryl group, and even more preferably a C5-C12 heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as an aryl group, a heteroaryl group, an alkyl group, etc.), the heteroaryl group and other groups are independent of each other and are connected by a single bond. Examples of the monocyclic heteroaryl group include a furyl group, a thienyl group, a pyrrolyl group, a pyridyl group, etc. The fused-ring heteroaryl group means that the molecule contains at least one heteroaromatic ring and an aromatic ring (heteroaromatic ring or aryl ring), and the two are not independent of each other but are fused to each other by sharing two adjacent atoms. Examples of the fused-ring heteroaryl group include a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an acridinyl group, an isobenzofuryl group, an isobenzothienyl group, a benzocarbazolyl group, an azacarbazolyl group, a phenothiazinyl group, a phenazinyl group, a 9-phenylcarbazolyl group, a 9-naphthylcarbazolyl group, a dibenzocarbazolyl group, an indolocarbazolyl group, etc.

[0039] Specific examples of the arylene group in the present invention can be a divalent group obtained by removing one hydrogen atom from the examples of the above aryl groups. The number of carbon atoms in the arylene group includes but is not limited to C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc. Specific examples of the heteroarylene group in the present invention can be a divalent group obtained by removing one hydrogen atom from the examples of the above heteroaryl groups.

[0040] The aryloxy group or heteroaryloxy group in the present invention can be a monovalent group formed by an oxygen atom and the above aryl group or heteroaryl group.

[0041] In the present invention, the arylamino group represents a group formed by substituting one or two hydrogen atoms on the amino group with an aryl group. The connection site of the arylamino group can be connected to the aryl group in the arylamino group or to the N in the arylamino group. The exemplary number of carbon atoms and specific groups of the aryl group in the arylamino group are the same as those above.

[0042] The C6-C60 arylamines (or C6-C30 arylamines) mentioned in the present invention include, for example: phenylamine, methylphenylamine, naphthylamine, anthrylamine, phenanthrylamine, biphenylamine, etc.

[0043] The C3-C60 heteroarylamines (or C3-C30 heteroarylamines) mentioned in the present invention include, for example: pyridylamine, pyrimidinylamine, dibenzofuranyl amine, etc.

[0044] In the present invention, the linear alkyl groups, unless otherwise specified, include straight-chain alkyl groups and branched-chain alkyl groups. Specifically, the substituted or unsubstituted C1-C30 linear alkyl groups are preferably substituted or unsubstituted C1-C16 linear alkyl groups, and more preferably substituted or unsubstituted C1-C10 linear alkyl groups. Examples of the substituted or unsubstituted C1-C10 linear alkyl groups 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, etc.

[0045] In the present invention, the cycloalkyl groups include monocyclic alkyl groups and polycyclic alkyl groups; among them, the monocyclic alkyl group refers to an alkyl group containing a single cyclic structure; the polycyclic alkyl group refers to a structure formed by two or more cycloalkyl groups sharing one or more ring carbon atoms; examples of the C3-C20 cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0046] In this specification, the substituted or unsubstituted C1-C20 alkoxy groups are preferably substituted or unsubstituted C1-C10 alkoxy groups. Examples of the C1-C20 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are preferred, and methoxy is more preferred.

[0047] In this specification, as the substituted or unsubstituted C1-C20 silyl groups, as the substituted or unsubstituted C1-C10 silyl groups, examples of the C1-C10 silyl groups may be silyl groups substituted by the groups exemplified in the above C1-C10 linear alkyl groups, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and other groups.

[0048] In this specification, the C2-C20 alkenyl group, preferably C2-C10 alkenyl group, is a hydrocarbon group containing at least 1 C═C double bond, and exemplarily includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0049] It should be noted that in this application, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. 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 each group, rather than the effect of a single group.

[0050] Furthermore, for this type of boron-nitrogen-containing organic compound of the present invention, the ring E has the structure shown in formula (c):

[0051]

[0052] Among them, the dotted line represents the fused bond of the group;

[0053] Z 1 、Z 2 、Z 3 are each independently CR 12 or N;

[0054] R 12 are each independently selected from at least one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C3-C60 heteroaryl; adjacent R 12 are not connected or are connected by a chemical bond to form a ring; R 12 are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring;

[0055] Preferably, at most one of the Z 1 、Z 2 、Z 3 is N.

[0056] Furthermore, for this type of boron-nitrogen-containing organic compound of the present invention, the boron-nitrogen-containing organic compound has the structure shown in formula (1-1):

[0057]

[0058] In formula (1-1), Z 1 、Z 2 、Z 3 have the same defined range as in formula (c);

[0059] Ring A, Ring D, Ar1, Ar2, Ra, and Rd have the same defined ranges as in formula (1);

[0060] In formula (1-1), the Z 1 , Z 2 , Z 3 At most one of them is N;

[0061] Preferably, in formula (1-1), the Z 1 , Z 2 , Z 3 Are each independently CR 12 .

[0062] Furthermore, for the boron-nitrogen organic compound containing such compounds in the present invention, Ring A and Ring D have the structures shown in formula (d) or formula (e):

[0063]

[0064] Among them, the dashed line represents the fused bond of the group;

[0065] X is selected from O or S;

[0066] U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 Are each independently CR 13 Or N;

[0067] R 13 Are each independently selected from at least one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl;

[0068] Adjacent R 13 Do not connect or are connected into a ring through a chemical bond; R 13 Are each independently not connected to the adjacent ring structure or are connected into a ring through a chemical bond;

[0069] Preferably, among the U 1 , U 2 , U 3 And U 4 , at most one is N; among the U 5 , U 6 , U 7 And U 8At most one of them is N;

[0070] Preferably, the U 1 , U 2 , U 3 and U 4 are each independently CR 13 ; the U 5 , U 6 , U 7 and U 8 are each independently CR 13 .

[0071] Furthermore, this kind of boron-nitrogen-containing organic compound of the present invention has a structure shown in formula (3-1) or formula (3-2):

[0072]

[0073] Among them, X has the same defined range as in formula (e);

[0074] U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 have the same defined range as in formula (d) and formula (e);

[0075] U 1 ', U 2 ', U 3 ', U 4 ' have the same defined range as U 1 , U 2 , U 3 , U 4 ;

[0076] Z 1 , Z 2 , Z 3 have the same defined range as in formula (c);

[0077] Ar1 and Ar2 have the same defined range as in formula (1).

[0078] Preferably, the boron-nitrogen-containing organic compound has a structure shown in formula (3-1).

[0079] Preferably, the boron-nitrogen-containing organic compound has a structure shown in formula (3-2).

[0080] Preferably, in the above formula (3-1) and formula (3-2), the Z 1 , Z2 , Z 3 are each independently CR 12 ;

[0081] At least one of the said R 12 , Ar1, and Ar2 is selected from the structure of formula (2);

[0082] Preferably, at least one of the said Ar1 and Ar2 is selected from the structure of formula (2). Preferably, at least one R 12 is selected from the structure of formula (2).

[0083] More preferably, at least one of the said Ar1 and Ar2 is selected from the structure of formula (2).

[0084] More preferably, one of the said Ar1 and Ar2 is selected from the structure of formula (2), and the other is selected from one of unsubstituted or R'-substituted C6-C30 aryl, unsubstituted or R'-substituted C3-C30 heteroaryl, where R' is selected from any one or a combination of at least two of halogen, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0085] For example, the other of Ar1 and Ar2 is selected from one of the following groups:

[0086]

[0087] etc. "*" represents the connection site; the expression of the ring structure with "—" drawn across indicates that the connection site is at any bond-forming position on the ring structure.

[0088] More preferably, in formula (2), the said X1-X 12 are each independently CR 11 , and R 11 are each independently selected from hydrogen, unsubstituted or R''-substituted C1-C20 linear alkyl, unsubstituted or R''-substituted C3-C20 cycloalkyl, unsubstituted or R''-substituted C1-C20 alkoxy, unsubstituted or R''-substituted C6-C30 arylamino, unsubstituted or R''-substituted C3-C30 heteroarylamino, unsubstituted or R''-substituted C6-C60 aryl, and unsubstituted or R''-substituted C3-C60 heteroaryl, and at least one R 11 is selected from one of unsubstituted or R''-substituted C6-C60 aryl and unsubstituted or R''-substituted C3-C60 heteroaryl;

[0089] Each R” is independently selected from any one or a combination of at least two of halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl;

[0090] Continuing preferably, in formula (2), the X1-X 12 are each independently CR 11 , R 11 are each independently selected from hydrogen, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C1-C20 alkoxy, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl, and at least one R 11 is selected from unsubstituted or R”-substituted C6-C60 aryl and unsubstituted or R”-substituted C3-C60 heteroaryl;

[0091] Each R” is independently selected from one or a combination of two of C1-C10 linear alkyl, C6-C30 arylamino, C6-C30 aryl, and C3-C30 heteroaryl;

[0092] Continuing further preferably, in formula (2), the X1-X 12 are each independently CR 11 , R 11 are each independently selected from hydrogen, unsubstituted or R”-substituted C1-C10 linear alkyl, unsubstituted or R”-substituted C3-C10 cycloalkyl, unsubstituted or R”-substituted C1-C10 alkoxy, unsubstituted or R”-substituted C6-C30 aryl, and unsubstituted or R”-substituted C3-C30 heteroaryl, and at least one R 11 is selected from unsubstituted or R”-substituted C6-C30 aryl and unsubstituted or R”-substituted C3-C30 heteroaryl;

[0093] Each R” is independently selected from one or a combination of two of C1-C6 linear alkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0094] Continuing further preferably, in formula (2), L1 is connected to X2, X3, X5, or X6; preferably, L1 is selected from a single bond, phenylene, and naphthylene;

[0095] Continuing preferably, in formula (2), at least one of X8, X9, X 11 , X 12 is CR11 , and the R 11 is selected from one of unsubstituted or R''-substituted C6-C60 aryl, unsubstituted or R''-substituted C3-C60 heteroaryl; each R'' is independently selected from one of C1-C10 linear alkyl, C6-C30 arylamino, C6-C30 aryl, C3-C30 heteroaryl;

[0096] More preferably, at least one of X8, X9, X 11 , X 12 is CR 11 , and the R 11 is selected from one of unsubstituted or R''-substituted C6-C30 aryl, unsubstituted or R''-substituted C3-C30 heteroaryl; each R'' is independently selected from one of C1-C6 linear alkyl, C6-C30 aryl, C3-C30 heteroaryl;

[0097] Even more preferably, at least one of X8, X9, X 11 , X 12 is CR 11 , and the R 11 is selected from one of C6-C30 aryl, C3-C30 heteroaryl, and more preferably R 11 is selected from one of C6-C20 aryl, C3-C20 heteroaryl.

[0098] For example, R 11 is phenyl, biphenyl, naphthyl, 4-tert-butylphenyl, 4-tert-butylnaphthyl, anthryl, phenanthryl, pyridyl, quinoline, fluorenyl, etc.

[0099] Furthermore, in the above general formula of the present invention, the R 12 , R 13 are each independently selected from one or a combination of two of hydrogen, C1-C20 linear alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, C3-C60 heteroaryl;

[0100] Preferably, the R 12 , R 13 are each independently selected from one or a combination of two of hydrogen, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C20 arylamino, C6-C20 aryl, C3-C20 heteroaryl.

[0101] For example, at least one R 12 , or at least one R 13 has the structure shown in formula (2), or R 12 , R 13 are each independently selected from hydrogen, methyl, or one of the following groups:

[0102] etc.

[0104] Furthermore, the organic compounds of the present invention may preferably be the specific structural compounds M1 to M82 shown below. These compounds are only representative and do not limit the scope of the present invention:

[0105]

[0106]

[0107]

[0108]

[0109] The preparation process of the compounds of the present invention is simple and easy to implement, the raw materials are easily available, suitable for mass production and scale-up, and very suitable for industrial applications.

[0110] The boron and nitrogen-containing organic compounds of the present invention, through the combination of the BN core and groups, reduce the triplet energy level of the material, improve the device lifetime, and at the same time increase the molecular rigidity and improve the device efficiency. At the same time the group is further substituted with an aryl or heteroaryl group, which can effectively inhibit the quenching of excitons, thereby improving the efficiency and lifetime of the device.

[0111] As another aspect of the present invention, there is also provided an application of the above-mentioned compound in an organic electroluminescent device. Specifically, the above-mentioned compound of the present invention has excellent luminescence performance, can give triplet excitons to achieve a high luminescence efficiency, and at the same time, based on its excellent carrier transport efficiency, is suitable for use as a luminescent dye.

[0112] Of course, since the compounds of the present invention can also be used as sensitizers to achieve a good light-emitting layer together with the host material and the dye. The devices to which it is applied include but are not limited to organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic papers, preferably organic electroluminescent devices.

[0113] The present invention also provides an organic electroluminescent device, which includes a first electrode, a second electrode, and at least one or more light-emitting functional layers inserted between the first electrode and the second electrode, and the light-emitting functional layer contains at least one of the compounds of the present invention.

[0114] The structure of the organic electroluminescent device of the present invention is the same as that of the existing devices, for example, it includes an anode layer, a plurality of light-emitting functional layers, and a cathode layer; the plurality of light-emitting functional layers at least include a light-emitting layer, and the above-mentioned organic compound of the present invention is contained in the light-emitting layer.

[0115] The OLED device prepared by using the compound of the present invention has a low turn-on voltage, a high luminous efficiency, and a better service life, and can meet the requirements of current panel and display manufacturing enterprises for high-performance materials. Detailed implementation manners

[0116] Synthesis example 1

[0117] Synthesis of compound M3

[0118]

[0119] Synthesis of intermediate M3-1:

[0120] Add 20 g of 6,12-dibromo 9.22 g of 4-tert-butylphenylboronic acid, 2.99 g of tetrakis(triphenylphosphine)palladium, and 14.32 g of potassium carbonate into a 1000 mL flask, add 400 mL of dioxane and 80 mL of water, heat to reflux under nitrogen protection for 5 hours, evaporate the solvent, mix with silica gel and perform column chromatography to obtain 11.7 g of a white solid. The molecular weight detected by mass spectrometry is 438.42 (theoretical value 438.10).

[0121] Synthesis of intermediate M3-2:

[0122] Add 10 g of intermediate M3-1, 3.4 g of 4-tert-butylaniline, 0.83 g of Pd(dppf)Cl2, and 4.37 g of sodium tert-butoxide into a 1000 mL flask, add 200 mL of toluene, heat to reflux under nitrogen protection for 12 hours, evaporate the solvent, mix with silica gel and perform column chromatography to obtain 10.54 g of a white solid. The molecular weight detected by mass spectrometry is 507.73 (theoretical value 507.29).

[0123] Synthesis of intermediate M3-3

[0124] Add 10 g of intermediate M3-2, 4.92 g of 3,5-dibromotoluene, 0.7 g of Pd132, and 3.79 g of sodium tert-butoxide into a 1000 mL flask, add 200 mL of toluene, heat to reflux under nitrogen protection for 2 hours, evaporate the solvent, mix with silica gel and perform column chromatography to obtain 11.14 g of a white solid. The molecular weight detected by mass spectrometry is 675.22 (theoretical value 675.25).

[0125] Synthesis of intermediate M3-4

[0126] Add 10 g of intermediate M3-3, 4.16 g of bis(4-tert-butylphenyl)amine, 0.5 g of Pd132, and 2.84 g of sodium tert-butoxide to a 1000 mL flask. Add 200 mL of toluene and heat to reflux under nitrogen protection for 2 hours. Rotavap the solvent and perform silica gel column chromatography with sample mixing to obtain 13.11 g of a white solid. The molecular weight detected by mass spectrometry is 876.25 (theoretical value 876.54).

[0127] Synthesis of Compound M3

[0128] Put 10 g of intermediate M3-4 into a 500 mL pressure-resistant bottle. Add 100 mL of o-dichlorobenzene and 28.56 g of boron tribromide, and heat to 180 °C for reaction for 12 hours. Extract with dichloromethane and water, combine the organic phases, rotavap the solvent, and perform silica gel column chromatography with sample mixing to obtain 1.32 g of a yellow solid. The molecular weight detected by mass spectrometry is 884.09 (theoretical value 884.52).

[0129] Synthesis Example 2

[0130] Synthesis of Compound M22

[0131]

[0132] The synthesis steps of Compound M22 are exactly the same as those of Compound M3, except that 4-tert-butylphenylboronic acid is replaced with α-naphthaleneboronic acid, 3,5-dibromotoluene is replaced with 3,5-dibromo-tert-butylbenzene, and bis(4-tert-butylphenyl)amine is replaced with 3,6-di-tert-butylcarbazole. The molecular weight detected by mass spectrometry is 918.50 (theoretical value 918.51).

[0133] Synthesis Example 3

[0134] Synthesis of Compound M45

[0135]

[0136] Synthesis of Intermediate M45-1:

[0137] The synthesis of M45-1 is exactly the same as that of M3-1, except that 4-tert-butylphenylboronic acid is replaced with phenylboronic acid. The molecular weight detected by mass spectrometry is 382.03 (theoretical value 382.04).

[0138] Synthesis of Intermediate M45-2

[0139] The synthesis of M45-2 is exactly the same as that of M45-1, except that 6,12-dibromo is replaced with M45-1, and phenylboronic acid is replaced with 3,5-dichlorophenylboronic acid. The molecular weight detected by mass spectrometry is 535.99 (theoretical value 535.98).

[0140] Synthesis of Intermediate M45-3

[0141] The synthesis of M45-3 is exactly the same as that of M3-4, except that M3-3 therein is replaced by M45-2. The molecular weight detected by mass spectrometry is 938.57 (theoretical value 938.55).

[0142] Synthesis of Compound M45

[0143] The synthesis of M45 is exactly the same as that of M3, except that the intermediate M3-4 therein is replaced by M45-3. The molecular weight detected by mass spectrometry is 946.56 (theoretical value 946.54).

[0144] The present invention exemplarily gives the specific synthesis methods of the above several compounds. For other compounds without specific synthesis methods given, they are also prepared by similar methods, and can be obtained only by replacing the raw materials, which will not be elaborated here, or those skilled in the art can also prepare them by other methods in the prior art.

[0145] Device Embodiment

[0146] Embodiment

[0147] The OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. The organic material can be further divided into multiple regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, and an electron transport region.

[0148] In a specific embodiment, a substrate can be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, waterproofness, and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate used as a display.

[0149] The first electrode can be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), etc. and any combination thereof can be used. When the first electrode is used as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. and any combination thereof can be used.

[0150] The organic material layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, printing, etc. The compounds used as the organic material layer can be organic small molecules, organic macromolecules, and polymers, as well as combinations thereof.

[0151] 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 multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); where the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0152] 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 poly(phenylene vinylene), 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 such as the compounds shown by HT-1 to HT-51 below; or any combination thereof.

[0153]

[0154]

[0155]

[0156] 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 adopt one or more of the above-mentioned compounds of HT-1 to HT-51, or adopt one or more of the following compounds of HI-1 to HI-3; it can also adopt one or more of the compounds of HT-1 to HT-51 doped with one or more of the compounds of HI-1 to HI-3.

[0157]

[0158] The light-emitting layer includes light-emitting dyes (i.e., dopants) that can emit spectra of different wavelengths, and can also include a host material at the same time. The light-emitting layer can be a single-color light-emitting layer that emits a single color such as red, green, or blue. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or stacked together to form a color light-emitting layer. When the 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.

[0159] According to different technologies, the light-emitting layer materials can be different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescence materials, etc. In an OLED device, a single light-emitting technology can be adopted, 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.

[0160] In one aspect of the present invention, the light-emitting layer adopts the technology of fluorescent electroluminescence. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or a combination of more than one of BFH-1 to BFH-17 listed below.

[0161]

[0162]

[0163] 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 a combination of more than one of PH-1 to PH-85.

[0164]

[0165]

[0166]

[0167]

[0168] The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or a combination of more than one of TDE1-TDE49 listed below.

[0169]

[0170]

[0171]

[0172]

[0173] In one aspect of the present invention, the electron blocking layer (EBL) is located between the hole transport layer and the light-emitting layer. The electron blocking layer can be made of, but not limited to, one or more compounds of HT-1 to HT-51 mentioned above, or can be made of, but not limited to, one or more compounds of PH-47 to PH-77 mentioned above; it can also be made of a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-47 to PH-77.

[0174] The OLED organic material layer may further include an electron transport region between the light-emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), 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 multi-layer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0175] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0176]

[0177]

[0178]

[0179]

[0180] In one aspect of the present invention, the hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer may be made of, but not limited to, one or more compounds of ET-1 to ET-73 mentioned above, or may be made of, but not limited to, one or more compounds of PH-1 to PH-46; it may also be made of, but not limited to, a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0181] The device may further include an electron injection layer between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, one or more combinations listed below.

[0182] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0183] Device Embodiment:

[0184] In this embodiment, the preparation process of the organic electroluminescent device is as follows:

[0185] Fabrication method of Device Example 1: The glass plate coated with the ITO transparent conductive layer is 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 all moisture is completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam on the surface;

[0186] Place the above-mentioned glass substrate with the anode in a vacuum chamber, evacuate to <1×10 -5Pa, a 10-nm-thick mixture of HT-4:HI-3 (97 / 3, w / w) was vacuum thermally evaporated in sequence on the above-mentioned anode layer film as a hole injection layer, a 60-nm-thick compound HT-4 as a hole transport layer, a 5-nm-thick compound HT-14 as an electron blocking layer, a 20-nm-thick binary mixture of BFH-4:M3 (100:3, w / w) as a light-emitting layer, a 5-nm-thick ET-23 as a hole blocking layer, a 25-nm-thick mixture of ET-69:ET-57 (50 / 50, w / w) as an electron transport layer, a 1-nm-thick LiF as an electron injection layer, and a 150-nm-thick metal aluminum as a cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm / second, and the evaporation rate of the metal electrode was controlled at 1 nm / second.

[0187] Device Examples 2 to 20 were fabricated using the same method as Device Example 1, except that the dopants in the light-emitting layer were different. The specific dopant material schemes are shown in Table 1 below.

[0188] Device Comparative Examples 1 to 4 were fabricated using the same method as Device Example 1, except that the dopants in the light-emitting layer were replaced with Compounds C1, C2, C3, and C4 in the prior art, respectively.

[0189]

[0190] Testing methods for the devices (including equipment and test conditions):

[0191] The following performance measurements were performed on the organic electroluminescent devices prepared by the above process:

[0192] The external quantum efficiency (EQE%) of the device was measured using the integrating sphere method;

[0193] At the same brightness, the lifetimes of the organic electroluminescent devices prepared in Examples 1 to 20 and Comparative Examples 1 to 4 were measured using a digital source meter and a PR650. Specifically,

[0194] The LT97 lifetime was tested as follows: Using a luminance meter, the initial luminance value of the device at a current density of 40 mA / cm 2 was measured. Keeping the current constant, the time when the luminance of the device dropped to 97% of the initial luminance was measured, with the unit of h; taking the LT97 lifetime test value of Device Comparative Example 1 as 1.0, the ratio of the LT97 lifetime test values of other devices to the LT97 lifetime test value of Device Comparative Example 1 was calculated;

[0195] The performance data of the organic electroluminescent devices prepared in each of the above device examples and comparative examples are shown in Table 1 below.

[0196] Table 1:

[0197]

[0198]

[0199] The compounds of the present invention exhibit higher efficiency and longer lifespan compared to compounds C1 and C2. This may be because the compounds of the present invention contain further aryl substitutions on the group, effectively suppressing the quenching of excitons, thereby enhancing the efficiency and lifespan of the device. In contrast, C1 and C2 have no further substituents or only alkyl substituents on the group, which cannot effectively protect the molecule, resulting in more severe quenching and affecting the device efficiency and lifespan.

[0200] The compounds of the present invention exhibit higher efficiency and longer lifespan compared to compound C3. This may be because the boron-oxygen group in the parent nucleus structure of C3 has lower luminescence efficiency and poorer stability than the boron-nitrogen group, so both the efficiency and lifespan are worse than those of the compounds of the present invention.

[0201] The compounds of the present invention exhibit higher efficiency compared to the comparative compound C4. This is mainly because the triplet energy level of the anthracene group in C4 is too low, which will severely quench the high-energy excitons in the system, resulting in a decrease in device efficiency.

[0202] The specific embodiments described above further elaborate on the objectives, technical solutions, and beneficial effects of the present invention. It should be understood that the above are only specific embodiments of the present invention and are not used to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention shall be included within the protection scope of the present invention.

Claims

1. A boron-nitrogen-containing organic compound, characterized in that, It has the structure shown in formula (1): In formula (1), ring A, ring D, and ring E are each independently one of a C6-C50 aromatic ring and a C3-C50 heteroaromatic ring; Ra, Rd, and Re represent a single-substituted group to the maximum allowable number of substituted groups, and Ra, Rd, and Re are each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 linear alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; Ar1 and Ar2 are each independently one of an unsubstituted or R'-substituted C6-C50 aryl and an unsubstituted or R'-substituted C3-C50 heteroaryl; Adjacent R's are not connected or are connected by a chemical bond to form a ring; the R' is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; Moreover, at least one of Ra, Rd, Re, Ar1, and Ar2 is selected from the structure of formula (2): In formula (2), L1 is selected from a single bond, unsubstituted or R''-substituted C1-C20 linear alkyl, and unsubstituted or R''-substituted C6-C60 aryl; X1, X2, X3, X4, X5, X6, X7, X8, X9, X 10 , X 11 , X 12 each independently represents N or CR 11 , R 11 each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C1-C20 alkoxy, unsubstituted or R”-substituted C6-C30 arylamino, unsubstituted or R”-substituted C3-C30 heteroarylamino, unsubstituted or R”-substituted C6-C60 aryl, unsubstituted or R”-substituted C3-C60 heteroaryl; R 11 Each is independently unconnected to an adjacent ring structure or is connected into a ring through a chemical bond; and X1-X 12 at least one of which is selected from CR 11 , and this R 11 is selected from an unsubstituted or R”-substituted C6-C60 aryl group, an unsubstituted or R”-substituted C3-C60 heteroaryl group; "*" represents a bonding site; the expression of a ring structure crossed by "—" indicates that the bonding site is at any position on the ring structure capable of forming a bond; R' and R'' are each independently selected from halogen, cyano, nitro, hydroxy, amino, C1-C20 linear alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of any one or at least two of them.

2. The boron and nitrogen-containing organic compound according to claim 1, wherein The ring E has the structure shown in formula (c): Among them, the dashed line represents the fused bond of the group; Z 1 、Z 2 、Z 3 Each independently is CR 12 or N; R 12 Each independently selected from at least one of hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C3-C60 heteroaryl; adjacent R 12 are not connected or are connected by a chemical bond to form a ring; R 12 each independently is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; Preferably, the Z 1 , Z 2 , Z 3 has at most one N.

3. The boron-nitrogen-containing organic compound according to claim 2, wherein The boron-nitrogen-containing organic compound has the structure shown in formula (1-1): In formula (1-1), Z 1 , Z 2 , Z 3 have the same defined range as in formula (c); Ring A, ring D, Ar1, Ar2, Ra, and Rd have the same defined ranges as in formula (1); In formula (1-1), the said Z 1 , Z 2 , Z 3 at most one of them is N; Preferably, in formula (1-1), the Z 1 , Z 2 , Z 3 are each independently CR 12 .

4. The boron-nitrogen-containing organic compound according to claim 1 or 3, characterized in that, The ring A and the ring D have the structures shown in formula (d) or formula (e): Among them, the dashed line represents the fused bond of the group; 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 13 or N; R 13 each independently selected from at least one of hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl; Adjacent R 13 are not connected or are connected by a chemical bond to form a ring; R 13 are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring; Preferably, the U 1 , U 2 , U 3 and U 4 has at most one N; the U 5 , U 6 , U 7 and U 8 has at most one N; Preferably, the U 1 , U 2 , U 3 and U 4 are each independently CR 13 ; the U 5 , U 6 , U 7 and U 8 are each independently CR 13 .

5. The boron-nitrogen-containing organic compound according to claim 4, wherein The boron-nitrogen-containing organic compound has the structure shown in formula (3-1) or formula (3-2): Among them, X has the same defined range as in formula (e); U 1 、U 2 、U 3 、U 4 、U 5 、U 6 、U 7 、U 8 has the same defined ranges as in formulas (d) and (e); U 1 ', U 2 ', U 3 ', U 4 ' have the same defined range as U 1 , U 2 , U 3 , U 4 ; Z 1 , Z 2 , Z 3 has the same defined range as in formula (c); Ar1 and Ar2 have the same defined ranges as in formula (1).

6. The boron and nitrogen-containing organic compound according to claim 5, characterized in that, Said Z 1 、Z 2 、Z 3 are each independently CR 12 ; The R 12 , Ar1, and Ar2 are each independently selected from the group consisting of the structure of formula (2); Preferably, at least one of the Ar1 and Ar2 is selected from the structure of formula (2).

7. The boron and nitrogen-containing organic compound according to any one of claims 1-6, characterized in that, In formula (2), the X1-X 12 are each independently CR 11 , and R 11 are each independently selected from one of hydrogen, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C1-C20 alkoxy, unsubstituted or R”-substituted C6-C30 arylamino, unsubstituted or R”-substituted C3-C30 heteroarylamino, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl, and at least one R 11 is selected from one of unsubstituted or R”-substituted C6-C60 aryl and unsubstituted or R”-substituted C3-C60 heteroaryl; Each of said R” is independently selected from any one or a combination of at least two of halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, in formula (2), the X1-X 12 are each independently CR 11 , R 11 are each independently selected from one of hydrogen, unsubstituted or R''-substituted C1-C20 linear alkyl, unsubstituted or R''-substituted C3-C20 cycloalkyl, unsubstituted or R''-substituted C1-C20 alkoxy, unsubstituted or R''-substituted C6-C60 aryl, and unsubstituted or R''-substituted C3-C60 heteroaryl, and at least one R 11 is selected from one of unsubstituted or R''-substituted C6-C60 aryl and unsubstituted or R''-substituted C3-C60 heteroaryl; Each of said R” is independently selected from a combination of one or two of C1-C10 linear alkyl, C6-C30 arylamino, C6-C30 aryl, and C3-C30 heteroaryl; More preferably, in formula (2), the X1-X 12 are each independently CR 11 , R 11 are each independently selected from one of hydrogen, unsubstituted or R”-substituted C1-C10 linear alkyl, unsubstituted or R”-substituted C3-C10 cycloalkyl, unsubstituted or R”-substituted C1-C10 alkoxy, unsubstituted or R”-substituted C6-C30 aryl, and unsubstituted or R”-substituted C3-C30 heteroaryl, and at least one R 11 is selected from one of unsubstituted or R”-substituted C6-C30 aryl and unsubstituted or R”-substituted C3-C30 heteroaryl; Each of said R” is independently selected from a combination of one or two of C1-C6 linear alkyl, C6-C30 aryl, and C3-C30 heteroaryl.

8. The boron-nitrogen-containing organic compound according to any one of claims 1-7, characterized in that, In formula (2), L1 is connected to X2, X3, X5, or X6; Preferably, in formula (2), at least one of X8, X9, X 11 , X 12 is CR 11 , and the R 11 is selected from one of unsubstituted or R''-substituted C6-C60 aryl, unsubstituted or R''-substituted C3-C60 heteroaryl; each of the R'' is independently selected from one or a combination of two of C1-C10 linear alkyl, C6-C30 arylamino, C6-C30 aryl, and C3-C30 heteroaryl; More preferably, at least one of X8, X9, X 11 , X 12 is CR 11 , and the R 11 is selected from one of C6-C20 aryl and C3-C20 heteroaryl.

9. The boron and nitrogen-containing organic compound according to any one of claims 4, 5 or 6, characterized in that, The R 12 , R 13 are each independently selected from one or a combination of two of hydrogen, C1-C20 linear alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, the R 12 , R 13 are each independently selected from one or a combination of two of hydrogen, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C20 arylamino, C6-C20 aryl, and C3-C20 heteroaryl.

10. The boron and nitrogen-containing organic compound according to claim 1, wherein The compound has the structure shown below:

11. Use of the boron-nitrogen-containing organic compound according to any one of claims 1 to 10, wherein the use is as a functional material in an organic electronic device, and the organic electronic device includes 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 use of the organic compound is as a light-emitting layer material in an organic electroluminescent device, and more preferably as a light-emitting dye in the light-emitting layer.

12. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the boron-nitrogen-containing organic compound according to any one of claims 1 to 10; Preferably, the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the light-emitting layer contains the boron-nitrogen-containing organic compound according to any one of claims 1 to 10.

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