A boron-nitrogen organic compound and application thereof, and an organic electroluminescent device

Abstract

The application provides a boron-nitrogen organic compound and application and an organic electroluminescent device, the boron-nitrogen organic compound has a structure as shown in formula I, through the design and cooperation of a boron-nitrogen multiple resonance structure and specific groups connected thereto, the boron-nitrogen organic compound has a narrow spectrum and high luminous efficiency, meanwhile, the triplet energy level is reduced, the efficiency roll-off and life decay caused by the slow reverse intersystem crossing of the boron-nitrogen multiple resonance material are eliminated, and excellent photoelectric performance is achieved. The boron-nitrogen organic compound is used in the organic electroluminescent device, and is especially suitable for being used as a doping material to provide excellent light emitting effect, improve the light emitting efficiency of the device, prolong the service life of the device, and comprehensively improve the performance of the device.

Description

Technical Field

[0001] This invention belongs to the field of organic light-emitting materials technology, specifically relating to a boron-nitrogen organic compound and its applications, and organic electroluminescent devices. Background Technology

[0002] With the continuous progress and development of science, 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-illumination, high contrast, large size, and low power consumption.

[0003] The light-emitting mechanism of OLEDs involves the recombination of electrons and holes under electrical excitation to form excitons. These excitons follow a probability statistical distribution, with singlet excitons accounting for approximately 25% and triplet excitons for approximately 75%. First-generation light-emitting technologies are collectively known as fluorescence technology, which utilizes singlet excitons for light emission. Second-generation light-emitting technologies are collectively known as phosphorescence technology, which utilizes triplet excitons for light emission. Theoretically, it can achieve 100% internal quantum efficiency. However, the heavy metals required to construct phosphorescent dyes are not only expensive but also cause environmental pollution. Therefore, the third-generation thermally excited delayed fluorescence technology, constructed using small organic molecules, is currently widely used. When the energy difference between the singlet and triplet states is small, triplet excitons can undergo reverse intersystem crossing to the singlet state and then return to the ground state to emit light. Currently, red and green dyes, as the three primary colors, have become the mainstream in commercial display devices due to their high electroluminescence efficiency and low power consumption. However, the color saturation and lifespan of blue light materials do not meet current commercial display requirements. Blue light devices still use traditional fluorescent materials to achieve high color purity and long device lifespan.

[0004] In recent years, research groups led by 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 excited delayed fluorescence. (Adv. Mater. 2016, 28, 2777-2781; J. Mater. Chem. C, 2019, 7, 3082-3089) The compounds, with boron, nitrogen, and phenyl atoms forming a rigid polycyclic aromatic resonance framework, exhibit high fluorescence quantum yield. Compared to traditional blue fluorescent dyes, these compounds have narrower emission band gaps and higher color purity. However, the rigid planar structure of the compounds also leads to a large energy difference between singlet and triplet states, slow anti-intersystem crossing from triplet to singlet states, and severe efficiency roll-off after exciton recombination on the dye, resulting in short device lifetime. Furthermore, the overly planar rigid structure often leads to excessively high doping concentrations, resulting in adverse effects such as emission spectrum broadening and redshift.

[0005] Existing organic electroluminescent materials still have significant room for improvement in luminescent performance, and the industry urgently needs to develop new luminescent material systems to meet commercialization demands. Boron-nitrogen resonant materials, with their advantages of high color purity and high luminous efficiency, have attracted widespread attention from the scientific and industrial communities. However, the higher excited-state energy levels of blue light-emitting materials result in a significantly shorter device lifetime compared to red and green OLEDs, greatly limiting their further application in high-resolution displays, full-color displays, and white light illumination.

[0006] As OLED products gradually enter the market, people have increasingly higher demands for their performance. Current OLED materials and device structures cannot fully address various aspects of OLED products, including color emission, efficiency, lifespan, and cost. Therefore, providing new organic electroluminescent materials is key to achieving these expectations and is a problem urgently needing to be solved in this field. Summary of the Invention

[0007] To address the shortcomings of existing technologies, the present invention aims to provide a boron-nitrogen organic compound and its applications, as well as an organic electroluminescent device. Through molecular structure design, the boron-nitrogen organic compound possesses excellent photoelectric properties. When used in organic electroluminescent devices, it is particularly suitable for luminescent materials, effectively improving the luminous efficiency of the device and extending its lifespan.

[0008] To achieve this objective, the present invention adopts the following technical solution:

[0009] In a first aspect, the present invention provides a boron-nitrogen organic compound having the structure shown in Formula I:

[0010]

[0011] In Formula I, M1 and M2 are each independently selected from O, S or NAr, and at least one of M1 and M2 is NAr.

[0012] In Formula I, ring A is selected from unsubstituted or R A Substituted C6-C30 aromatic rings, unsubstituted or R A Any of the substituted C3-C30 heteroaryl rings.

[0013] Ar is selected from R P Unreplaced or R B Substituted C6-C30 aryl, unsubstituted or R B Any of the substituted C3-C30 heteroaryl groups.

[0014] In this invention, the "unsubstituted or R" B The "substituent" group can replace a substituent R. B It can also replace R with multiple substituents.B When substituent R B When there are multiple (at least two) substituents, they can be the same or different substituents; the same expression used below has the same meaning. "Unsubstituted or R" A The same applies to "replacement," and for the sake of simplicity, it will not be elaborated further.

[0015] R A R B Each independently selected from R P The following are all of the following: halogen, cyano, substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0016] In Formula I, X1, X2, X3, X4, X5, X6, X7, X8, X1', X2', X3', X4', X5', X6', X7', and X8' are each independently selected from N or CR1; R1 in multiple (≥2, 2-16) CR1s are the same or different groups.

[0017] R1 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups.

[0018] The Ar, R1, R A R B At least one of them is a group R P .

[0019] It should be noted that in the boron-nitrogen organic compounds provided by this invention, the structure shown in Formula I has at least one R group attached to it. P The R P It can be Ar (i.e., bonded to a N atom), R P It can be attached to C atoms in X1-X8 and X1'-X8', to C atoms in ring A, or as a substituent for Ar and attached to C atoms in Ar.

[0020] The R P It has the structure shown in equation a:

[0021]

[0022] In formula a, -* represents the linking site of a group.

[0023] In equation a, Y1, Y2, Y3, Y4, Y 10 Each is independently selected from C, N, or CR2, with one of them being C, where C is R. P The linkage sites; Y5, Y6, Y7, Y8, and Y9 are each independently selected from N or CR2. The R2 in multiple (≥2, e.g., 2, 3, 4, 5, 6, 7, 8, 9) CR2 groups may be the same or different groups.

[0024] R2 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0025] R A R B The substituents described in R1 and R2 are each independently selected from any one or a combination of at least two of the following: halogen, cyano, amino, C1-C30 straight-chain or branched alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0026] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents (at least two), they can be the same or different substituents; the same expression used below has the same meaning. Unless otherwise specified, the selection range of substituents is as shown above and will not be repeated.

[0027] The boron-nitrogen organic compound provided by this invention has a molecular structure as shown in Formula I, which includes a boron-nitrogen multiple resonance structure. Two carbazole groups are introduced into a specific ring structure of the boron-nitrogen multiple resonance structure, which can lower the energy level of the molecule. At the same time, a group R, represented by Formula a, with a low triplet energy level, is introduced. P (Preferably pyrene-derived groups); through the design of the groups and structure, and the combined effect of the structures of each group, the boron-nitrogen organic compound exhibits a narrow spectrum and high luminous efficiency. Simultaneously, it lowers the triplet energy level, eliminating the efficiency roll-off and lifetime decay caused by the slow reverse intersystem crossing in boron-nitrogen multiple resonance materials, resulting in excellent photoelectric performance. The boron-nitrogen organic compound is used in organic electroluminescent devices, and is particularly suitable as a luminescent material (also known as a "dopant," "dopant," or "guest") to provide excellent luminescence, enabling devices to have higher luminous efficiency and longer lifetime.

[0028] It should be noted that in the present invention, 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 essential reason for obtaining good performance is the optimized combination of the entire molecular structure, which is the result of the synergistic effect between each group, rather than the effect of a single group / feature.

[0029] The following are the preferred technical solutions of the present invention, but they do not limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved.

[0030] In the present invention, the halogen can be fluorine, chlorine, bromine or iodine. The same description involved below has the same meaning.

[0031] In the present invention, for the expression of chemical elements, unless otherwise specified, the concept of isotopes with the same chemical properties is included. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0032] In the present invention, the hydrogen at any site on the boron-nitrogen organic compound with the structure shown in Formula I can be optionally replaced by deuterium.

[0033] In the present invention, unless otherwise specified, the heteroatoms of heteroaryl are selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0034] In the present invention, the expression of the ring structure with a "-" drawn across it indicates that the connection site is at any position on the ring structure where bonding can occur.

[0035] In the present invention, both "-*" and "*" represent the connection sites of groups.

[0036] In the present invention, the expression Ca-Cb represents that the group has a carbon atom number of a-b. Unless otherwise specified, the carbon atom number does not include the carbon atom number of substituents.

[0037] In the present invention, "independently of each other" means that when its subject has multiple ones, they can be the same or different from each other.

[0038] In the present invention, the C6-C30 can be C6, C9, C10, C11, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.

[0039] C3-C30 can all be C4, C5, C6, C8, C9, C10, C11, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.

[0040] C1-C30 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26 or C28, etc.

[0041] C6-C60 can all 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.

[0042] 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.

[0043] C2-C30 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26 or C28, etc.

[0044] In this invention, the C6-C30 aryl (C6-C30 aromatic ring), preferably C6-C20 aryl (C6-C20 aromatic ring), includes monocyclic aryl and fused-ring aryl groups; the monocyclic aryl means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are linked by single bonds, exemplarily including but not limited to: phenyl, biphenyl, terphenyl, tetraphenyl, etc.; the fused-ring aryl means that the group contains at least two rings (and at least one ring is an aromatic ring). Furthermore, the rings share two adjacent carbon atoms bonded together by a group, exemplarily including but not limited to: naphthyl, anthraceneyl, phenanthryl, indene, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirodifluorenyl, benzo[a]fluorenyl, etc.), fluoranthyl, triphenylene, pyrene, perylene, Aryl, tetraphenyl, acenaphthyl, benzo[a]acenaphthyl, etc. It should be noted that monocyclic aryl and fused-ring aryl groups linked by single bonds also fall under the aryl group category, such as phenylnaphthyl, naphthylphenyl, binaphthyl, phenylnaphthylphenyl, etc.

[0045] The C3-C30 heteroaryl group (C3-C30 heteroaryl ring), preferably a C3-C20 heteroaryl group (C3-C20 heteroaryl ring), includes monocyclic heteroaryl groups or fused-ring heteroaryl groups. A monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and other groups are connected by a single bond, exemplarily including but not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, bipyridyl, phenylpyridinyl, pyridylphenyl, etc. The term "fused-ring heteroaryl" refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), with the two sharing two adjacent atoms fused together in a group. Exemplary examples include, but are not limited to: quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, isobenzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl and its derivatives (N-phenylcarbazoleyl, N-naphthylcarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, azacarbazoleyl, etc.), acridineyl, phenothiazinyl, phenothiazinyl, hydrogenated acridineyl, etc. It should be noted that heteroaryl groups linked by single bonds, and aryl groups linked by single bonds, also fall within the scope of heteroaryl groups, such as phenylpyridinyl, phenylpyrimidinyl, diphenylpyridinyl, diphenylpyrimidinyl, etc.

[0046] In this invention, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl group with O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl group with O.

[0047] In this invention, specific examples of the C6-C60 arylamino group are monovalent groups obtained by substituting at least one hydrogen atom in the -NH2 group with the aforementioned aryl group, including but not limited to: phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, biphenylamino, etc. Specific examples of the C3-C60 heteroarylamino group are monovalent groups obtained by substituting at least one hydrogen atom in the -NH2 group with the aforementioned heteroaryl group, including but not limited to: pyridinylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0048] In this invention, the C1-C30 straight-chain or branched alkyl group is preferably a C1-C20 straight-chain or branched alkyl group, more preferably a C1-C16 straight-chain or branched alkyl group, and even more preferably a C1-C10 straight-chain or branched alkyl group. Exemplarily, it includes, but is not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0049] Specific examples of the C1-C30 alkoxy groups can be exemplified by the monovalent groups obtained by connecting the aforementioned straight-chain or branched alkyl groups to O.

[0050] The C3-C30 cycloalkyl group, preferably C3-C20 cycloalkyl group, and more preferably C3-C10 cycloalkyl group, includes monocyclic alkyl groups or polycyclic alkyl groups. Monocyclic alkyl groups refer to alkyl groups containing a single ring structure, while polycyclic alkyl groups refer to structures composed of two or more cycloalkyl groups sharing one or more carbon atoms on a ring; exemplary examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0051] The C2-C30 alkenyl group, preferably C2-C20 alkenyl group, more preferably C2-C10 alkenyl group, contains at least one C=C group, and includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0052] Preferably, the boron-nitrogen organic compound has the structure shown in Formula II:

[0053]

[0054] In Equation II, M1, M2, X1, X2, X3, X4, X5, X6, X7, X8, X1', X2', X3', X4', X5', X6', X7' and X8' have the same range of limitation as in Equation I.

[0055] In Formula II, Z1, Z2, and Z3 are each independently selected from N or CR3; R3 in multiple (2 or 3) CR3 groups are the same or different groups.

[0056] R3 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups;

[0057] The substituents described in R3 are each independently selected from any one or a combination of at least two of the following: halogen, cyano, amino, C1-C30 straight-chain or branched alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0058] Preferably, the boron-nitrogen organic compound has the structure shown in Formula III:

[0059]

[0060] In Equation III, M1, M2, X1, X2, X3, X4, X5, X6, X7, X8, X1', X2', X3', X4', X5', X6', X7', X8', Z1, Z2, and Z3 have the same defined range as in Equation II.

[0061] In this invention, at least one of M1 and M2 is NAr; preferably, M1 and M2 are each independently NAr, and the Ar in the two NArs are the same or different groups.

[0062] Preferably, the Ar is selected from R P Unreplaced or R B Substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, unsubstituted, or R B Any one of the substituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl groups, further preferably R P Unreplaced or R B The substitution may be made by any one of the following groups: phenyl, naphthyl, biphenyl, terphenyl, pyridyl, phenylpyridyl, pyridylphenyl, bipyridyl.

[0063] Preferably, the R B Each independently selected from R P The following are preferred: substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups; substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups; R is further preferred. P Any one of C1-C6 straight-chain or branched alkyl groups and phenyl groups.

[0064] Preferably, the Ar is selected from R P Or any one of the following groups;

[0065] Here, -* represents the linking site of a group.

[0066] U1, U2, U3, U4, U5, U6, U7, U8, and U9 are each independently selected from N or CR4; the R4 in multiple (≥2, 2-9) CR4 groups are the same or different groups.

[0067] R4 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups;

[0068] The substituents described in R4 are each independently selected from any one or a combination of at least two of the following: halogen, cyano, amino, C1-C30 straight-chain or branched alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, the substituents described in R4 are each independently selected from any one or a combination of at least two of the following: C1-C10 straight-chain or branched alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0069] Preferably, U1, U2, U3, U4, U5, U6, U7, U8 and U9 are each independently selected from CR4.

[0070] Preferably, each of the R4s is independently selected from hydrogen, R... P The following are possible selections: substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups; substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups; further preferably hydrogen or R. P Any one of C1-C6 straight-chain or branched alkyl groups and phenyl groups.

[0071] Preferably, at most one of X1, X2, X3, and X4 (0 or 1) is N; and / or, at most one of X5, X6, X7, and X8 (0 or 1) is N; and / or, at most one of X1', X2', X3', and X4' (0 or 1) is N; and / or, at most one of X5', X6', X7', and X8' (0 or 1) is N.

[0072] Preferably, X1, X2, X3, X4, X5, X6, X7, X8, X1', X2', X3', X4', X5', X6', X7', and X8' are each independently selected from CR1.

[0073] Preferably, X1, X2, X7, X8, X1', X2', X7' and X8' are CH, and X3, X4, X5, X6, X3', X4', X5' and X6' are each independently selected from CR1.

[0074] Preferably, the number of CHs in X1, X2, X3, and X4 is 3-4; and / or, the number of CHs in X5, X6, X7, and X8 is 3-4; and / or, the number of CHs in X1', X2', X3', and X4' is 3-4; and / or, the number of CHs in X5', X6', X7', and X8' is 3-4.

[0075] Preferably, each of R1 is independently selected from hydrogen, R P The following are possible selections: substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups; substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups; further preferably hydrogen or R. P Any one of C1-C6 straight-chain or branched alkyl groups and phenyl groups.

[0076] Preferably, at most one of Z1, Z2, and Z3 (0 or 1) is N.

[0077] Preferably, Z1, Z2, and Z3 are each independently selected from CR3.

[0078] Preferably, Z1 and Z3 are CH, and Z2 is CR3.

[0079] Preferably, each of the R3s is independently selected from hydrogen, R... PThe following are possible selections: substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups; substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups; further preferably hydrogen or R. P Any one of C1-C6 straight-chain or branched alkyl groups and phenyl groups.

[0080] Preferably, the substituents in R1 and R3 are each independently selected from any one or a combination of at least two of the following: C1-C10 straight-chain or branched alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0081] Preferably, the boron-nitrogen organic compound has the structure shown in Formula IV:

[0082]

[0083] In equation IV, R 11 R 12 R 13 R 14 R1 and R2 independently represent unsubstituted, monosubstituted, and the maximum permissible substitution; specifically, R2... 11 Indicates no substitution (R) 11 (e.g., hydrogen), monosubstituted, disubstituted, or trisubstituted; when R 11 When indicating di- or tri-substituted, multiple Rs 11 For the same or different groups; R 12 R 13 R 14 The same applies to R3; for the sake of brevity, it will not be repeated.

[0084] R 11 R 12 R 13 R 14 R3 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups.

[0085] Ar1 and Ar2 are each independently selected from R P Unreplaced or R B Substituted C6-C30 aryl, unsubstituted or R BAny one of the substituted C3-C30 heteroaryl groups;

[0086] R B Each independently selected from R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups.

[0087] R 11 R 12 R 13 R 14 R3, R B The substituents described herein are each independently selected from any one or a combination of at least two of the following: halogen, cyano, amino, C1-C30 straight-chain or branched alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0088] The R 11 R 12 R 13 R 14 R3, Ar1, Ar2, R B At least one of them is a group R P .

[0089] Preferably, Ar1 and Ar2 are each independently selected from R P Unreplaced or R B Substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, unsubstituted, or R B Any one of the substituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl groups, further preferably R P Unreplaced or R B The substitution may be made by any one of the following groups: phenyl, naphthyl, biphenyl, terphenyl, pyridyl, phenylpyridyl, pyridylphenyl, bipyridyl.

[0090] Preferably, the R B Each independently selected from R PThe following are preferred: substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups; substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups; R is further preferred. P Any one of C1-C6 straight-chain or branched alkyl groups and phenyl groups, more preferably R P C1-C3 straight-chain alkyl groups

[0091] Preferably, Ar1 and Ar2 are each independently selected from R P Or any one of the following groups;

[0092] Here, -* represents the linking site of a group.

[0093] U1, U2, U3, U4, U5, U6, U7, U8, and U9 are each independently selected from N or CR4; the R4 in multiple (≥2, 2-9) CR4 groups are the same or different groups.

[0094] R4 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups;

[0095] Preferably, the substituents in R4 are each independently selected from any one or a combination of at least two of the following: C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0096] Preferably, at least one R4 is selected from R P .

[0097] Preferably, U1, U2, U3, U4, U5, U6, U7, U8 and U9 are each independently selected from CR4.

[0098] Preferably, each of the R4s is independently selected from hydrogen, R... P The following are possible selections: substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups; substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups; further preferably hydrogen or R. PAny one of C1-C6 straight-chain or branched alkyl groups, or phenyl groups, more preferably hydrogen or R... P C1-C3 straight-chain alkyl groups

[0099] Preferably, Ar1 and Ar2 are each independently selected from R P Or any one of the following groups;

[0100]

[0101]

[0102] More preferably, Ar1 and Ar2 are each independently selected from R P Or any one of the following groups;

[0103]

[0104] Preferably, the R 11 R 12 R 13 R 14 R3 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups; substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups.

[0105] Preferably, R 11 R 12 R 13 R 14 The substituents described in R3 are each independently selected from any one or a combination of at least two of the following: C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0106] More preferably, the R 11 R 12 R 13 R 14 R3 is independently selected from hydrogen, R P Any one of C1-C6 straight-chain or branched alkyl groups, or phenyl groups, more preferably hydrogen or R... P C1-C3 straight-chain alkyl groups

[0107] Preferably, the R 11It is a monosubstituted substance located at the para position of the carbon atom to which N (carbazole N) is attached; and / or, the R 12 It is a monosubstituted substance located at the para position of the carbon atom to which N (carbazole N) is attached; and / or, the R 13 It is a monosubstituted substance located at the para position of the carbon atom to which N (carbazole N) is attached; and / or, the R 14 It is a monosubstituted substance located at the para position of the carbon atom to which N (carbazole N) is attached; and / or, the R3 is a monosubstituted substance located at the para position of the carbon atom to which B is attached.

[0108] In this invention, the R P It has a structure as shown in any one of equations a-1, a-2, and a-3:

[0109]

[0110] Preferably, Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y 10 Each is independently selected from CR2, wherein R P It is a pyrene group.

[0111] Preferably, each of the R2s is independently selected from hydrogen, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, and substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups.

[0112] Preferably, the substituents in R2 are each independently selected from any one or a combination of at least two of C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0113] More preferably, each of the R2s is independently selected from hydrogen, C1-C6 straight-chain or branched alkyl groups, and phenyl groups.

[0114] Preferably, the R P Selected from R2' is independently selected from any one of the following: substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups, and more preferably any one of C1-C6 straight-chain or branched alkyl groups or phenyl groups.

[0115] Preferably, the R PSelected from Any one of them.

[0116] Preferably, the boron-nitrogen organic compound has any one of the following structures:

[0117]

[0118]

[0119]

[0120]

[0121] In a second aspect, the present invention provides an application of the boron-nitrogen organic compound as described in the first aspect, wherein the boron-nitrogen organic compound is used in organic electronic devices.

[0122] Preferably, 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 organic thin-film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper, and more preferably an organic electroluminescent device.

[0123] Preferably, the organic electronic device includes an organic electroluminescent device.

[0124] Preferably, the boron-nitrogen organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0125] Preferably, the boron-nitrogen organic compound is used as a dopant material (also known as "dye", "dopant", "guest material" or "luminescent material") in the light-emitting layer of an organic electroluminescent device.

[0126] Thirdly, the present invention provides an organic electroluminescent device, the 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 comprising at least one boron-nitrogen organic compound as described in the first aspect.

[0127] Preferably, the organic layer includes a light-emitting layer, which includes at least one boron-nitrogen organic compound as described in the first aspect.

[0128] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material (also known as a "dopant", "dye", "guest material", or "light-emitting material") comprises at least one boron-nitrogen organic compound as described in the first aspect.

[0129] Preferably, the boron-nitrogen organic compound provided by the present invention is used as the fluorescent dopant material of the light-emitting layer.

[0130] Preferably, the mass percentage of the doped material in the light-emitting layer is 0.1-10%, for example, it can be 0.2%, 0.5%, 0.8%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8% or 9%, and more preferably 0.3-5%.

[0131] Preferably, the light-emitting layer further includes a sensitizer.

[0132] Preferably, the sensitizer includes any one or a combination of at least two of thermally activated delayed fluorescence materials and phosphorescent materials.

[0133] Preferably, the mass percentage of the sensitizer in the luminescent layer is 0-40%, for example, it can be 0, 0.1%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30% or 35%, etc.

[0134] Preferably, the sensitizer comprises a phosphorescent material (phosphorescent sensitizer), and the mass percentage of the phosphorescent material in the luminescent layer is 0.1-12%.

[0135] Preferably, the sensitizer is a thermally activated delayed fluorescence material (thermally activated delayed fluorescence sensitizer), and the mass percentage of the thermally activated delayed fluorescence material in the luminescent layer is 1-40%.

[0136] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0137] Preferably, the hole transport region includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, and an electron blocking layer.

[0138] Preferably, the electron transport region includes any one or a combination of at least two of the electron injection layer, electron transport layer, and hole blocking layer.

[0139] In a preferred embodiment, the organic light-emitting device (OLED device) includes a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer can be further divided into multiple regions, such as a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer contains at least one boron-nitrogen organic compound as described in the first aspect.

[0140] In a preferred embodiment, the organic electroluminescent device includes a first electrode, a plurality of light-emitting functional layers (organic layers), and a second electrode arranged sequentially. The organic layers include 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 arranged sequentially, with the hole injection layer in contact with the first electrode (anode). The organic layer (preferably the light-emitting layer) contains at least one boron-nitrogen organic compound as described in the first aspect.

[0141] In a preferred embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material possessing excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, the substrate used for a display may also incorporate thin-film transistors (TFTs).

[0142] The first electrode can be formed by sputtering or depositing the material to be used as the first electrode on a substrate. When the first electrode is used as the anode, it can be a transparent conductive oxide material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode is used as the cathode, it can be 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), or any combination thereof.

[0143] Organic layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used as organic layers can be small organic molecules, large organic molecules, or polymers, as well as combinations thereof.

[0144] The hole transport region is located between the anode and the emissive layer. The hole transport region can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. Alternatively, the hole transport region can be a multilayer structure including at least one 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 emissive layer.

[0145] The material for the hole transport region may be selected from, but is 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 compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0146]

[0147]

[0148]

[0149] 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 be one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1 to HI-3 described below; it can also be one or more compounds of HT-1 to HT-51 doped with one or more compounds of HI-1 to HI-3 described below.

[0150]

[0151] The emissive layer consists of a luminescent dye (i.e., a dopant) that emits different wavelengths of light and a host material. The emissive layer can be a monochromatic layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that simultaneously emits different colors such as red, green, and blue.

[0152] Depending on the technology used, the light-emitting layer material can be various, including fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescence materials. An OLED device can employ a single light-emitting technology or a combination of different technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0153] In one aspect of the invention, the light-emitting layer employs fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0154]

[0155] In one aspect of the invention, the blocking layer surrounding the light-emitting layer may be selected from, but is not limited to, one or more combinations of PH-1 to PH-87.

[0156]

[0157]

[0158]

[0159]

[0160] In one aspect of the invention, the light-emitting layer employs phosphorus-sensitized electroluminescence technology. The phosphorus sensitizer of the light-emitting layer may be selected from, but is not limited to, one or more combinations of BPD-1-BPD-16 listed below.

[0161]

[0162] In one aspect of the invention, the luminescent layer employs thermally activated sensitized fluorescence luminescence technology. The sensitizer of the luminescent layer, i.e., the thermally activated delayed fluorescence material, can be selected from, but is not limited to, one or more combinations of TDE1-TDE49 listed below.

[0163]

[0164]

[0165]

[0166]

[0167] In one aspect of the present invention, the light-emitting layer employs thermally activated sensitized fluorescence luminescence technology, and the main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-87 mentioned above.

[0168] 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 employ, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-86 described above; or a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-47 to PH-86 may be employed.

[0169] The organic layer of an OLED may also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including single-layer electron transport layers containing only one compound and single-layer electron transport layers containing multiple compounds. Alternatively, the electron transport region can be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0170] 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.

[0171]

[0172]

[0173]

[0174]

[0175] 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 employ, but is not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46 and PH-87; or it may employ, but is 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 and PH-87.

[0176] 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, Yb.

[0177] The present invention also provides a display device comprising an organic electroluminescent device as described in the third aspect.

[0178] Preferably, the display device includes a display screen or a display panel.

[0179] The present invention also provides an electronic device having a display screen or display panel, wherein the display screen or display panel employs the aforementioned organic electroluminescent device.

[0180] Compared with the prior art, the present invention has the following beneficial effects:

[0181] The boron-nitrogen organic compound provided by this invention has the structure shown in Formula I. Through the design and synergistic effect of the boron-nitrogen multiple resonance structure and the specific groups attached to it, the boron-nitrogen organic compound exhibits a narrow spectrum and high luminous efficiency. Simultaneously, it lowers the triplet energy level, eliminating the efficiency roll-off and lifetime decay caused by the slow reverse intersystem crossing in boron-nitrogen multiple resonance materials, thus demonstrating excellent photoelectric performance. This boron-nitrogen organic compound is particularly suitable as a dopant material in organic electroluminescent devices, providing high color purity luminescence, improving device luminous efficiency, extending device lifetime, and comprehensively improving device performance. Detailed Implementation

[0182] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention.

[0183] The boron-nitrogen organic compounds represented by Formula I of this invention can be synthesized using organic synthesis methods known in the art. Exemplary synthetic routes are given below, but those skilled in the art can also obtain them using other known methods.

[0184] In one specific embodiment, the boron-nitrogen organic compound has the structure shown in Formula II, where M1 and M2 are each independently NAr, and can be prepared via the synthetic route shown below:

[0185]

[0186] Among them, X1, X2, X3, X4, X5, X6, X7, X8, X1', X2', X3', X4', X5', X6', X7', X8', Z1, Z2, and Z3 have the same limiting range as in Equation II; the two Ars may be the same or different, and are each independently selected from R. P Unreplaced or R B Substituted C6-C30 aryl, unsubstituted or R B The substituted C3-C30 heteroaryl group can be any one of the following; Hal1 and Hal2 are each independently selected from halogens, for example, any one of F, I, Br or Cl. The order of reaction I and reaction II can be adjusted according to the synthesis situation, that is, reaction I can be carried out first and then reaction II, or reaction II can be carried out first and then reaction I, or they can be carried out simultaneously (the starting materials S1 and S2 are the same).

[0187] In one specific embodiment, raw material S1 can be prepared by the following synthetic route:

[0188]

[0189] Hal3 is selected from halogens, such as any one of F, I, Br or Cl.

[0190] In one specific embodiment, raw material S2 can be prepared by a route similar to that used for synthesizing S1, which will not be described in detail for the sake of brevity.

[0191] It should be noted that obtaining the organic compounds is not limited to the synthetic methods and raw materials used in this invention. Those skilled in the art can also select other methods or routes to obtain the boron-nitrogen organic compounds proposed in this invention. The compounds and solvents used in the synthetic methods not mentioned in this invention are all commercially available raw material products, or are prepared in-house using these raw material products according to known methods.

[0192] The mass spectrometry (MS, m / z) characterization data of the intermediates and target products in the following specific embodiments of the present invention were obtained by liquid chromatography-mass spectrometry (LC-MS / Q-TOF instrument model 6530LC / Q-TOF, Agilent, ion source: ESI+APCI), specifically M+1. For the identification of compounds with the same molecular weight but different substitution sites, the correctness of the structure can be confirmed by referring to the HPLC peak time and the different raw materials used.

[0193] The specific preparation methods of the boron-nitrogen organic compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0194] Synthesis Example 1: Synthesis of Boron-Nitrogen Organic Compound M2

[0195]

[0196] (1) Synthesis of intermediate M2-1

[0197] 3-Carbazole bromobenzene (20 g), 4-tert-butylaniline (9.26 g), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride Pd(dppf)Cl2 (2.27 g), and sodium tert-butoxide NaOtBu (11.93 g) were added to a 1000 mL flask, followed by 400 mL of toluene. The mixture was heated to reflux under nitrogen protection and reacted for 4 h. The solvent was evaporated, and the mixture was subjected to silica gel column chromatography to obtain intermediate M2-1 (white solid, 20.3 g).

[0198] The mass spectrometry data of intermediate M2-1 were characterized, and the measured mass spectrometry value was 391.54 (theoretical value 390.53).

[0199] (2) Synthesis of intermediate M2-2

[0200] The synthesis of intermediate M2-2 was carried out using the same method as that used for intermediate M2-1, except that 4-tert-butylaniline was replaced with 2-pyrene-4-tert-butylaniline. Other raw materials, steps and process parameters were the same as in step (1) to obtain intermediate M2-2.

[0201] The mass spectrometry data of intermediate M2-2 were characterized, and the measured mass spectrometry value was 591.85 (theoretical value 590.77).

[0202] (3) Synthesis of compound M2-3

[0203] Intermediate M2-1 (20 g), M2-2 (20 g), 5-tert-butyl-1,3-dibromobenzene (14.95 g), tris(dibenzylideneacetone)dipalladiumPd2(dba)3 (2.34 g), and sodium tert-butoxide (19.69 g) were added to a 2000 mL flask, followed by 800 mL of toluene. The mixture was heated to reflux under nitrogen protection and reacted for 4 h. The solvent was evaporated, and the mixture was subjected to silica gel column chromatography to obtain intermediate M2-3 (white solid, 41.7 g).

[0204] The mass spectrometry data of intermediate M2-3 were characterized, and the measured mass spectrometry value was 1111.53 (theoretical value 1110.56).

[0205] (4) Synthesis of boron-nitrogen organic compound M2

[0206] Intermediate M2-3 (20 g) was added to a 1000 mL pressure-resistant reaction flask, followed by 1,2,4-trichlorobenzene (400 mL) and boron tribromide (45 g). The reaction was carried out at 180 °C for 24 h under nitrogen protection. Heating was then stopped, and the mixture was extracted with dichloromethane and water. The organic phases were combined and subjected to column chromatography to obtain the target compound M2 (yellow solid, 4.2 g).

[0207] The mass spectrometry data of compound M2 were characterized, and the measured mass spectrometry value was 1119.32 (theoretical value 1118.55).

[0208] Synthesis Example 2: Synthesis of Boron-Nitrogen Organic Compound M61

[0209]

[0210] (1) Synthesis of intermediate M61-1

[0211] The synthesis of intermediate M61-1 was carried out using the same method as that used for intermediate M2-1, except that 3-carbazole bromobenzene was replaced with 3-(3,6-di-tert-butylcarbazole)bromobenzene and 4-tert-butylbenzene was replaced with 4-tert-pentylaniline; the other raw materials, steps and process parameters were the same as those in step (1) of synthesis example 1, and intermediate M61-1 was obtained.

[0212] The mass spectrometry data of intermediate M61-1 were characterized, and the measured mass spectrometry value was 517.24 (theoretical value 516.35).

[0213] (2) Synthesis of intermediate M61-2

[0214] The synthesis of intermediate M61-2 was carried out using the same method as that used for intermediate M2-1, except that 4-tert-butylbenzene was replaced with 1-pyreneamine. Other raw materials, steps and process parameters were the same as in step (1) of synthesis example 1, and intermediate M61-2 was obtained.

[0215] The mass spectrometry data of intermediate M61-2 were characterized, and the measured mass spectrometry value was 571.20 (theoretical value 570.30).

[0216] (3) Synthesis of intermediate M61-3

[0217] The synthesis of intermediate M61-3 was carried out using the same method as that used for intermediate M2-3, except that M2-1 was replaced with M61-1, M2-2 was replaced with M61-2, and 5-tert-butyl-1,3-dibromobenzene was replaced with 1,3-dibromobenzene. Other raw materials, steps and process parameters were the same as those in step (3) of synthesis example 1, and intermediate M61-3 was obtained.

[0218] The mass spectrometry data of intermediate M61-3 were characterized, and the measured mass spectrometry value was 1161.42 (theoretical value 1160.67).

[0219] (4) Synthesis of boron-nitrogen organic compound M61

[0220] The synthesis of compound M61 was carried out using the same method as that used for the synthesis of M2, except that M2-3 was replaced with M61-3. Other raw materials, steps and process parameters were the same as step (4) of the synthesis example 1, and the target compound M61 was obtained.

[0221] The mass spectrometry data of compound M61 were characterized, and the measured mass spectrometry value was 1169.50 (theoretical value 1168.66).

[0222] Synthesis Example 3: Synthesis of Boron-Nitrogen Organic Compound M67

[0223]

[0224] (1) Synthesis of intermediate M67-1

[0225] The synthesis of intermediate M67-1 was carried out using the same method as that used for intermediate M2-3, except that M2-2 was replaced with M2-1 and 5-tert-butyl-1,3-dibromobenzene was replaced with 5-pyrene-1,3-dibromobenzene. Other raw materials, steps and process parameters were the same as those in step (3) of synthesis example 1, and intermediate M67-1 was obtained.

[0226] The mass spectrometry data of intermediate M67-1 were characterized, and the measured mass spectrometry value was 1055.52 (theoretical value 1054.50).

[0227] (2) Synthesis of boron-nitrogen organic compound M67

[0228] The synthesis of compound M67 was carried out using the same method as that used for the synthesis of M2, except that M2-3 was replaced with M67-1; the other raw materials, steps and process parameters were the same as step (4) of the synthesis example 1, and the target compound M67 was obtained.

[0229] The mass spectrometry data of compound M67 were characterized, and the measured mass spectrometry value was 1063.50 (theoretical value 1062.48).

[0230] This invention provides exemplary methods for synthesizing representative intermediates and some compounds. Other compounds for which no specific synthesis method is provided can also be prepared using similar methods, requiring only the replacement of raw materials. These methods will not be elaborated here. Alternatively, those skilled in the art can prepare these compounds using other methods in the prior art.

[0231] Theoretical calculations:

[0232] In this invention, theoretical calculations for boron-nitrogen organic compounds were performed using the Gaussian 16 program, and the structure of the lowest triplet excited state of the molecule was optimized using the B3LYP / 6-31G* method. Specific results are shown in Table 1.

[0233] Table 1

[0234] compound <![CDATA[Theoretical calculation of the triplet energy level T1 (eV)]]> M2 2.35 M6 2.30 M20 2.34 M54 2.29 C3 2.45

[0235] As shown in the table above, based on theoretical calculations, the boron-nitrogen organic compounds provided by this invention can effectively reduce the triplet energy level, thereby improving device lifetime.

[0236] Device Example 1

[0237] An organic electroluminescent device includes 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) stacked sequentially. The fabrication method of this organic electroluminescent device is as follows:

[0238] (1) The glass plate coated with ITO transparent conductive layer was ultrasonically treated in commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone / ethanol mixed solvent, baked in a clean environment until the moisture was completely removed, cleaned with ultraviolet light and ozone, and bombarded with low-energy cation beam.

[0239] (2) Place the glass plate with the ITO anode into the vacuum chamber and evacuate to <1×10⁻⁶. -5 Pa, on the above-mentioned anode layer, a mixture of compound HT-4:HI-3 (97 / 3, w / w) was vacuum thermally evaporated as a hole injection layer, with a evaporation rate of 0.1 nm / s and a film thickness of 10 nm;

[0240] (3) A compound HT-4 with a thickness of 60 nm was vacuum-deposited on the hole injection layer as a hole transport layer at a deposition rate of 0.1 nm / s.

[0241] (4) A compound HT-14 with a thickness of 5 nm was vacuum-deposited on the hole transport layer as an electron blocking layer at a deposition rate of 0.1 nm / s.

[0242] (5) A light-emitting layer is vacuum-deposited on the electron blocking layer. The light-emitting layer includes a host material (BFH-4) and a dopant material (boron-nitrogen organic compound M2 provided by the present invention). The mass ratio (w / w) of the host material and the dopant material is 100:3, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 20 nm.

[0243] (6) A 5 nm thick compound ET-23 was vacuum-deposited on the light-emitting layer as a hole blocking layer at a deposition rate of 0.1 nm / s.

[0244] (7) A mixture of compound ET-69:ET-57 (50 / 50, w / w) was vacuum-deposited on the hole blocking layer as an electron transport layer. The deposition rate was 0.1 nm / s and the total film thickness was 25 nm.

[0245] (8) A 1 nm layer of compound LiF was vacuum-deposited on the electron transport layer as an electron injection layer at a deposition rate of 0.1 nm / s.

[0246] (9) A 150 nm thick layer of metallic aluminum is vacuum-deposited on the electron injection layer as a cathode at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0247] Device Examples 2-9, Device Comparative Examples 1-4

[0248] An organic electroluminescent device is disclosed, which differs from device example 1 only in that the doping materials of the light-emitting layer are the compounds shown in Table 2; the other layers, thicknesses, materials and preparation methods are the same as those in device example 1.

[0249] Device Example 10

[0250] An organic electroluminescent device differs from Example 1 only in that the electron blocking layer material is replaced with PH-86, and the light-emitting layer is replaced with a mixture of host material, phosphorescent photosensitizer, and dopant material in a ratio of 89:10:1 (w / w / w). The host material is a PH-86:PH-87 (60 / 40, w / w) mixture, the phosphorescent photosensitizer is BPD-1, and the dopant material is the boron-nitrogen organic compound M2 provided by this invention. The hole blocking layer is replaced with PH-87. Other layers, thicknesses, materials, and preparation methods are the same as in Example 1.

[0251] Device Examples 11-18, Device Comparative Examples 5-8

[0252] An organic electroluminescent device is disclosed, which differs from device example 10 only in that the doping materials of the light-emitting layer are the compounds shown in Table 3; the other layers, thicknesses, materials and preparation methods are the same as those of device example 10.

[0253] The structures of the doped materials in Comparative Examples 1-8 are as follows:

[0254]

[0255] The following performance measurements were performed on the above-mentioned organic electroluminescent devices:

[0256] (1) The external quantum efficiency (EQE, %) of the device was measured using the integrating sphere method;

[0257] (2) At the same brightness, the lifetime of the organic electroluminescent devices prepared in Device Examples 1-18 and Device Comparative Examples 1-8 was measured using a digital source meter and a PR650. Specifically, the lifetime of LT97 was tested as follows: using a luminance meter at 40 mA / cm²... 2 The initial brightness value of the device under current density, and the time it takes for the device brightness to drop to 97% of the initial brightness while maintaining a constant current, is measured in hours.

[0258] In Table 2, the LT97 lifetime test value of device comparison example 1 is recorded as 1.0. Calculate the ratio of the LT97 lifetime test value of other devices to the test value of device comparison example 1.

[0259] In Table 3, the LT97 lifetime test value of device comparison example 5 is recorded as 1.0. The ratio of the LT97 lifetime test value of other devices to the test value of device comparison example 5 is calculated.

[0260] Table 2

[0261]

[0262]

[0263] Table 3

[0264] Device Number Doped materials Light color EQE (%) Lifespan LT97 Device Example 10 M2 Deep Blue 15.2 5.8 Device Example 11 M6 Deep Blue 15.9 6.0 Device Example 12 M20 Deep Blue 15.3 5.7 Device Example 13 M54 Deep Blue 14.8 5.7 Device Example 14 M57 Deep Blue 14.9 5.2 Device Example 15 M61 Deep Blue 14.5 5.4 Device Example 16 M68 Deep Blue 14.3 5.5 Device Example 17 M69 Deep Blue 14.0 4.8 Device Example 18 M70 Deep Blue 14.8 5.1 Device Comparison Example 5 C1 Sky blue 11.1 1.0 Device Comparison Example 6 C2 Sky blue 11.2 1.1 Device Comparison Example 7 C3 Deep Blue 12.4 0.1 Device Comparison Example 8 C4 Sky blue 10.3 1.3

[0265] As shown in Tables 2 and 3, the boron-nitrogen organic compounds provided by this invention are suitable as doping materials for organic electroluminescent devices. They can be matched with fluorescent electroluminescence technology and sensitized fluorescent luminescence technology to achieve excellent deep blue luminescence effect, effectively improve the luminous efficiency of the device, and extend its service life.

[0266] Compared to comparative compounds C1 and C2, the boron-nitrogen organic compounds of the present invention exhibit higher efficiency and longer lifetime. This may be because the diphenylamine structure in compounds C1 and C2, compared to the carbazole structure in the compounds of the present invention, cannot effectively reduce the HOMO energy level of the molecule, resulting in more charge carriers being captured by the dye, thus causing the device efficiency and lifetime to be worse than that of the device using the compounds of the present invention as doping materials.

[0267] Compared to the comparative compound C3, the boron-nitrogen organic compound of the present invention exhibits higher efficiency and longer lifetime, which may be due to the pyrene group in the compound effectively reducing the triplet energy level of the compound, thereby improving the stability and efficiency of the device.

[0268] Compared to the comparative compound C4, the boron-nitrogen organic compound of the present invention exhibits higher efficiency and longer lifetime. This may be because compound C4 does not contain a carbazole structure, resulting in a shallower HOMO energy level, which leads to more charge carriers being captured by the dye, thus causing the device to have lower efficiency and lifetime than the device using the compound of the present invention as the doping material.

[0269] The applicant declares that this invention illustrates the boron-nitrogen organic compound and its application, as well as organic electroluminescent devices, through the above embodiments. However, this invention is not limited to the above embodiments, meaning that this invention does not necessarily rely on the above embodiments for implementation. Those skilled in the art should understand that any improvements to this invention, equivalent substitutions of raw materials for the products of this invention, additions of auxiliary components, and selection of specific methods all fall within the protection and disclosure scope of this invention.

Claims

1. A boron-nitrogen organic compound, characterized in that, The boron-nitrogen organic compound has the structure shown in Formula I: Among them, M1 and M2 are each independently selected from O, S or NAr, and at least one of them is NAr; Ring A is selected from unsubstituted or R A Substituted C6-C30 aromatic rings, unsubstituted or R A Any one of the substituted C3-C30 heteroaryl rings; Ar is selected from R P Unreplaced or R B Substituted C6-C30 aryl, unsubstituted or R B Any one of the substituted C3-C30 heteroaryl groups; R A R B Each independently selected from R P Halogen, cyano, substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; X1, X2, X3, X4, X5, X6, X7, X8, X1', X2', X3', X4', X5', X6', X7', and X8' are each independently selected from N or CR1; R1 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups; The Ar, R1, R A R B At least one of them is a group R P The R P It has the structure shown in equation a: Where -* represents the linking site of the group; Y1, Y2, Y3, Y4, Y 10 Each is independently selected from C, N, or CR2, with one of them being C, where C is R. P Connection sites; Y5, Y6, Y7, Y8, and Y9 are each independently selected from N or CR2; R2 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl. R A R B The substituents described in R1 and R2 are each independently selected from any one or a combination of at least two of the following: halogen, cyano, amino, C1-C30 straight-chain or branched alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

2. The boron-nitrogen organic compound according to claim 1, characterized in that, The boron-nitrogen organic compound has the structure shown in Formula II: Among them, M1, M2, X1, X2, X3, X4, X5, X6, X7, X8, X1', X2', X3', X4', X5', X6', X7' and X8' have the same limited range as in Formula I; Z1, Z2, and Z3 are each independently selected from N or CR3; R3 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups; The substituents described in R3 are each independently selected from any one or a combination of at least two of the following: halogen, cyano, amino, C1-C30 straight-chain or branched alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, the boron-nitrogen organic compound has the structure shown in Formula III: Among them, M1, M2, X1, X2, X3, X4, X5, X6, X7, X8, X1', X2', X3', X4', X5', X6', X7', X8', Z1, Z2 and Z3 have the same range of limitation as in Formula II.

3. The boron-nitrogen organic compound according to claim 1 or 2, characterized in that, At least one of M1 and M2 is NAr; Ar is selected from R P Or any one of the following groups; Where -* represents the linking site of the group; U1, U2, U3, U4, U5, U6, U7, U8, and U9 are each independently selected from N or CR4; R4 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups; Preferably, U1, U2, U3, U4, U5, U6, U7, U8 and U9 are each independently selected from CR4; Preferably, each of the R4s is independently selected from hydrogen, R... P Any one of substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, or substituted or unsubstituted C6-C20 aryl groups, further preferably hydrogen or R. P Any one of C1-C6 straight-chain or branched alkyl groups and phenyl groups; The substituents described in R4 are each independently selected from any one or a combination of at least two of the following: C1-C10 straight-chain or branched alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

4. The boron-nitrogen organic compound according to claim 1 or 2, characterized in that, X1, X2, X3, X4, X5, X6, X7, X8, X1', X2', X3', X4', X5', X6', X7', and X8' are each independently selected from CR1; Preferably, each of R1 is independently selected from hydrogen, R P Any one of substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, or substituted or unsubstituted C6-C20 aryl groups, further preferably hydrogen or R. P Any one of C1-C6 straight-chain or branched alkyl groups and phenyl groups; Preferably, Z1, Z2, and Z3 are each independently selected from CR3; Preferably, each of the R3s is independently selected from hydrogen, R... P Any one of substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, or substituted or unsubstituted C6-C20 aryl groups, further preferably hydrogen or R. P Any one of C1-C6 straight-chain or branched alkyl groups and phenyl groups; The substituents described in R1 and R3 are each independently selected from any one or a combination of at least two of the following: C1-C10 straight-chain or branched alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

5. The boron-nitrogen organic compound according to claim 1, characterized in that, The boron-nitrogen organic compound has the structure shown in Formula IV: Among them, R 11 R 12 R 13 R 14 R3 and R3 independently represent no substitution, single substitution, and the maximum permissible substitution. R 11 R 12 R 13 R 14 R3 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups; Ar1 and Ar2 are each independently selected from R P Unreplaced or R B Substituted C6-C30 aryl, unsubstituted or R B Any one of the substituted C3-C30 heteroaryl groups; R B Each independently selected from R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups; R 11 R 12 R 13 R 14 R3, R B The substituents described herein are each independently selected from any one or a combination of at least two of the following: halogen, cyano, amino, C1-C30 straight-chain or branched alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl. The R 11 R 12 R 13 R 14 R3, Ar1, Ar2, R B At least one of them is a group R P .

6. The boron-nitrogen organic compound according to claim 5, characterized in that, Ar1 and Ar2 are each independently selected from R P Or any one of the following groups; Where -* represents the linking site of the group; U1, U2, U3, U4, U5, U6, U7, U8, and U9 are each independently selected from N or CR4; R4 is independently selected from hydrogen, R P Any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups; The substituents described in R4 are each independently selected from any one or a combination of at least two of the following: C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, at least one R4 is selected from R P ; Preferably, Ar1 and Ar2 are each independently selected from R P Or any one of the following groups; 7. The boron-nitrogen organic compound according to claim 5, characterized in that, The R 11 R 12 R 13 R 14 R3 is independently selected from hydrogen, R P Any one of substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, or substituted or unsubstituted C6-C20 aryl groups, preferably hydrogen or R. P Any one of C1-C6 straight-chain or branched alkyl groups and phenyl groups; R 11 R 12 R 13 R 14 The substituents described in R3 are each independently selected from any one or a combination of at least two of the following: C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl.

8. The boron-nitrogen organic compound according to any one of claims 1-7, characterized in that, The R P It has a structure as shown in any one of equations a-1, a-2, and a-3: Preferably, Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y 10 Each was independently selected from CR2; Preferably, each of the R2s is independently selected from hydrogen, substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C6-C20 aryl groups, and more preferably from hydrogen, C1-C6 straight-chain or branched alkyl groups, or phenyl groups. The substituents described in R2 are each independently selected from any one or a combination of at least two of the following: C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl.

9. The boron-nitrogen organic compound according to claim 1, characterized in that, The boron-nitrogen organic compound has any one of the following structures:

10. The use of a boron-nitrogen organic compound as described in any one of claims 1-9, characterized in that, The boron-nitrogen organic compounds are used in organic electronic devices; Preferably, the organic electronic device includes an organic electroluminescent device; Preferably, the boron-nitrogen organic compound is used as a light-emitting layer material in an organic electroluminescent device.

11. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; the organic layer includes at least one boron-nitrogen organic compound as described in any one of claims 1-9; Preferably, the organic layer includes a light-emitting layer, wherein the light-emitting layer includes at least one boron-nitrogen organic compound as described in any one of claims 1-9; Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material comprises at least one boron-nitrogen organic compound as described in any one of claims 1-9.

12. A display device, characterized in that, The display device includes the organic electroluminescent device as described in claim 11.

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