Boron-nitrogen organic compound and application thereof

Abstract

The invention provides a boron-nitrogen organic compound and application thereof.The boron-nitrogen organic compound has a structure shown in the formula I. Through molecular structure design and structural compounding, the boron-nitrogen organic compound has the properties of multiple resonance molecules and conjugated molecules, namely, the boron-nitrogen organic compound has narrow fluorescence emission spectrum and high quantum efficiency and is applied to organic electroluminescent devices, and the application range of the boron-nitrogen organic compound is widened. The material can be used as a fluorescent doping material of a light-emitting layer, can effectively improve the light-emitting efficiency and prolong the service life of an organic light-emitting device, enables the device to have higher color purity, and fully meets the requirements of the current panel and display manufacturing industry for high-performance materials.

Description

Technical Field

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

[0002] OLED (Organic Light-Emitting Diode) refers to an organic semiconductor made of an extremely thin coating of organic material and a substrate, which emits light when an electric current passes through it. As a next-generation display technology, OLED offers superior display performance compared to LCD, boasting advantages such as self-illumination, excellent display quality, low power consumption, high flexibility, and ultra-thinness. It is widely used in screens of smartphones, automotive electronics, smart wearable devices, VR devices, and other products.

[0003] The main light-emitting materials of OLEDs are divided into three types: blue, red, and green, which together determine the self-emissive performance and lifespan of OLEDs. Among them, blue light-emitting materials emit brighter light, but compared with red and green light-emitting materials, their luminous efficiency is lower and their lifespan is shorter. Currently, red and green OLED phosphors have been mass-produced and applied in OLED screens, but blue OLED phosphors have always had defects in terms of color purity and lifespan. Therefore, blue phosphors are still commonly used in commercial OLED products.

[0004] As OLED products gradually enter the market, people have increasingly higher requirements for their performance. To improve OLED performance, existing technologies CN112645968A and CN112174992A disclose a class of multiple resonance fluorescent compounds based on the BN resonance structure TADF (Thermally Activated Delayed Fluorescence). These compounds consist of a rigid polycyclic aromatic skeleton composed of B, N, and benzene rings. The nitrogen atom exhibits a resonance effect opposite to that of the boron atom, and this opposite resonance effect is enhanced at its para position. Therefore, this effect can significantly separate HOMO and LUMO orbitals, thus exhibiting certain TADF characteristics. Although this series of materials has broad application prospects, the severe intramolecular rotation causes energy loss due to vibrational-rotational energy levels, resulting in low external quantum efficiency. Even with the use of dimethylfluorene structures to suppress intramolecular rotational energy levels in some compound structures, the device lifetime is still poor due to charge transport imbalance. Therefore, there is still considerable room for improvement in the luminescence performance of this type of organic electroluminescent material, making it difficult to meet commercialization demands.

[0005] Because existing organic electroluminescent materials still have significant shortcomings in terms of efficiency, stability, and lifespan, there is considerable room for improvement in the luminescent performance of OLED devices. Therefore, the industry urgently needs to develop higher-performance luminescent material systems to meet the demands for improved device performance. Summary of the Invention

[0006] To address the shortcomings of existing technologies, the present invention aims to provide a boron-nitrogen organic compound and its applications. Through molecular structure design, the boron-nitrogen organic compound possesses excellent luminescent properties and stability. When used in organic electroluminescent devices, it can effectively improve the luminescent efficiency of the devices, extend their lifespan, reduce voltage and energy consumption, and improve color purity.

[0007] To achieve this objective, the present invention adopts the following technical solution:

[0008] In a first aspect, the present invention provides a boron-nitrogen organic compound having the structure shown in Formula I:

[0009]

[0010] In Formula I, rings A, B, C, D, and E are each independently selected from unsubstituted or R. A Substituted C6-C60 aromatic rings, unsubstituted or R A Any of the substituted C3-C60 heteroaryl rings.

[0011] In formula I, ring F is selected from unsubstituted or R B Substituted C4-C20 alicyclic, unsubstituted or R B Any of the substituted C3-C20 aliphatic heterocycles.

[0012] R A R B Each is independently selected from any one of the following: substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 heterocycloalkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C1-C20 alkylsilyl groups, halogens, cyano groups, nitro groups, hydroxyl groups, ester groups, amino groups, substituted or unsubstituted C6-C60 arylamino groups, substituted or unsubstituted C3-C60 heteroarylamino groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups; The R A Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds.

[0013] In this invention, "R" A "Not connected to adjacent ring structures" means R A Only connected to C atoms via a single bond; "R A"To form a ring with adjacent ring structures through chemical bonds" means that R A In addition to being chemically bonded to carbon atoms, it is also chemically bonded to adjacent rings, thus forming a fused ring structure. The same descriptions used below have the same meaning and will not be repeated hereafter.

[0014] In Formula I, Z1 and Z2 are each independently selected from N or CR0; R0 in multiple (2) CR0 groups are the same or different groups.

[0015] R0 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0016] In Formula I, dashed lines represent single bonds or no connection. Specifically, when a dashed line represents a single bond, it indicates that ring A and ring E are connected via Y1 (i.e., m1 is 1), and / or ring B and ring C are connected via Y2 (i.e., m2 is 1). When a dashed line represents no connection, it means that the chemical bond shown by the dashed line does not exist, and ring A and ring E are not connected (i.e., m1 is 0), and / or ring B and ring C are not connected (i.e., m2 is 0). The same descriptions will have the same meaning in the following text and will not be repeated here.

[0017] In Equation I, m1 and m2 are each independently 0 or 1.

[0018] In Equation I, Y1 and Y2 are each independently selected from single bonds and CR 11 R 12 NR 13 Any one of S or O.

[0019] It should be noted that when Y1 is a single bond (m1 is 1), it indicates that ring A and ring E are connected by a single bond to form a five-membered ring (pyrrole ring); when Y1 is selected from CR... 11 R 12 NR 13 When Y1 is S or O (m1 is 1), it indicates that ring A and ring E are connected by Y1 to form a six-membered ring; when Y2 is a single bond (m2 is 1), it indicates that ring B and ring C are connected by a single bond to form a five-membered ring (pyrrole ring); when Y2 is selected from CR 11 R 12 NR 13 When S or O (m2 is 1), it indicates that ring B and ring C are connected by Y2 to form a six-membered ring. The same descriptions used below have the same meaning and will not be repeated hereafter.

[0020] R 11 R 12 R 13 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

[0021] R0, R A R B R 11 R 12 R 13 The substituents described herein are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl; each substituent is independently not connected to the adjacent ring structure or is connected to the ring structure by a chemical bond to form a ring.

[0022] 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.

[0023] The boron-nitrogen organic compound provided by this invention has the molecular structure shown in Formula I. Its core contains multiple BN structures, and the B atom resonates with the N atom within the same ring, giving the boron-nitrogen organic compound multiple resonance properties, suitable conjugation properties, and planar structural characteristics. This allows for the regulation and improvement of molecular-level dipole orientation or molecular vibrational-rotational energy levels, exhibiting excellent photoelectric performance and TADF properties, a narrow fluorescence emission spectrum, high quantum efficiency, and higher stability. Simultaneously, the closed-ring structure of the F ring effectively reduces the vibrational-rotational energy of the molecular structure, improving the stability of the material molecules. When used in organic electroluminescent devices, the boron-nitrogen organic compound can serve as a dye (guest material, dopant, or dopant) in the luminescent layer to achieve excellent blue light emission, effectively improving the device's luminous efficiency, extending device lifespan, reducing voltage and energy consumption, and giving the device higher color purity.

[0024] 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.

[0025] The following are the preferred technical solutions of the present invention, but do not limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the purpose and beneficial effects of the present invention can be better achieved and realized.

[0026] In the present invention, the halogen can be fluorine, chlorine, bromine or iodine. The same description involved below has the same meaning.

[0027] In the present invention, for the expression of chemical elements, if there is no special explanation, it includes the concept of isotopes with the same chemical properties. 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.

[0028] In the present invention, if there is no special explanation, the heteroatoms of heteroaryl are selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatoms in heterocycloalkyl are selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatoms in aliphatic heterocycles are selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0029] In the present invention, the expression of the ring structure with a "-" crossed means that the connection site is at any position on the ring structure where bonding can occur.

[0030] In the present invention, both "-*" and "*" represent the connection sites of groups.

[0031] In the present invention, "independently of each other" means that when the subject has multiple ones, they can be the same or different from each other.

[0032] In the present invention, the expression of Ca-Cb represents that the group has a carbon atom number of a-b. Without special explanation, the carbon atom number does not include the carbon atom number of substituents.

[0033] The C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C46, C48, C50, C52, C54, C56 or C58, etc.

[0034] 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.

[0035] C4-C20 can all be C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0036] C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0037] C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0038] C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

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

[0040] C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0041] C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0042] In this invention, unless otherwise specified, the C6-C60 aryl (C6-C60 aromatic ring) and C6-C30 aryl (C6-C30 aromatic ring) include monocyclic aryl and fused-ring aryl groups; the monocyclic aryl group 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, including but not limited to: phenyl, biphenyl, terphenyl, tetraphenyl, etc.; the fused-ring aryl group means that the group contains at least two rings (and at least one ring is aromatic). The rings (often referred to as rings) share two adjacent carbon atoms bonded together, including but not limited to: naphthyl, anthraceneyl, phenanthryl, indene, fluorenyl and their 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, etc. Aryl, tetraphenyl, acenaphthenyl, benzo[a]acenaphthenyl, etc. It should be noted that monocyclic aryl and fused-ring aryl groups linked by single bonds also fall under the category of aryl groups, such as phenylnaphthyl, naphthylphenyl, and binaphthyl.

[0043] The C3-C60 heteroaryl (C3-C60 heteroaryl ring) and C6-C30 heteroaryl (C3-C30 heteroaryl ring) include monocyclic heteroaryl or fused-ring heteroaryl. A monocyclic heteroaryl 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, thiopheneyl, 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, phenotoxazinyl, 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, pyridylphenyl, phenylpyrimidinyl, diphenylpyridinyl, etc.

[0044] In this invention, specific examples of the C6-C60 arylamino and C6-C30 arylamino groups are monovalent groups obtained by substituting at least one hydrogen atom in -NH2 with the aforementioned aryl group, including but not limited to: phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, biphenylamino, etc. Specific examples of the C3-C60 heteroarylamino and C3-C30 heteroarylamino groups are monovalent groups obtained by substituting at least one hydrogen atom in -NH2 with the aforementioned heteroaryl group, including but not limited to: pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0045] 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.

[0046] The C4-C20 alicyclic ring, preferably C5-C10, includes saturated or unsaturated alicyclic rings. The C3-C20 heterocyclic ring, preferably C3-C10, includes saturated or unsaturated heterocyclic rings, which can be understood as a ring structure formed by replacing at least one ring carbon atom in the alicyclic ring with a heteroatom (e.g., N, S, O, etc.). The unsaturated alicyclic ring and unsaturated heterocyclic ring contain at most one unsaturated bond.

[0047] The C1-C20 straight-chain or branched alkyl group, preferably C1-C16 straight-chain or branched alkyl group, and more preferably C1-C10 straight-chain or branched alkyl group, 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.

[0048] Specific examples of the C1-C20 alkoxy groups can be exemplified by the monovalent groups obtained by connecting the above-mentioned straight-chain or branched alkyl groups to O.

[0049] Specific examples of the C1-C20 alkylsilyl group are monovalent groups formed by replacing at least one hydrogen in -SiH3 with the aforementioned straight-chain or branched alkyl groups, including but not limited to: trimethylsilyl, dimethylsilyl, di(methyl)ethylsilyl, di(methyl)propylsilyl, triethylsilyl, tripropylsilyl, etc.

[0050] The C3-C20 cycloalkyl group, preferably C3-C10 cycloalkyl group, includes monocycloalkyl or polycycloalkyl groups. Monocycloalkyl refers to an alkyl group containing a single ring structure, while polycycloalkyl refers to a structure formed by 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] Specific examples of the C2-C20 heterocyclic alkyl group include groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (e.g., N, O, S, etc.), including but not limited to: epoxy group, oxetane, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyrroleyl, tetrahydropyranyl, piperidinyl, piperazineyl, dioxaneyl, morpholinyl, etc.

[0052] The C2-C20 alkenyl group, preferably C2-C10 alkenyl group, contains at least one C=C, and includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0053] Preferably, the boron-nitrogen organic compound has the structure shown in Formula II:

[0054]

[0055] In Equation II, rings D, F, Z1, Z2, Y1, Y2, m1, and m2 have the same defined range as in Equation I.

[0056] In Equation II, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z 10 Z 11 Each is independently selected from N or CR1; the R1 in multiple (e.g., 2, 3, 4, 5, 6, 7, 8, 9) CR1 groups are the same or different groups.

[0057] In Formula II, X1, X2, X3, and X4 are each independently selected from N, C, or CR2, and two of them are adjacent C. The chemical bond formed by the two adjacent Cs is a fused bond with ring F. R2 in multiple (two) CR2 groups can be the same or different groups.

[0058] R1 and R2 are each independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, halogen, cyano, nitro, hydroxy, ester, amino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; R1 and R2 are each independently not connected to adjacent ring structures or connected to form a ring by chemical bonds; at least two adjacent groups in R1 and R2 are not connected to each other or connected to form a ring by chemical bonds.

[0059] Preferably, the boron-nitrogen organic compound has a structure as shown in any one of formula II-1, II-2, or II-3:

[0060]

[0061] Among them, rings D, F, Z1, Z2, Y1, Y2, m1, and m2 have the same limited range as Equation I.

[0062] Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z 10 Z 11 Each is independently selected from N or CR1; the R1 in multiple (e.g., 2, 3, 4, 5, 6, 7, 8, 9) CR1 groups are the same or different groups.

[0063] X1 and X2 are each independently selected from N or CR2; R2 in multiple (2) CR2 groups are the same or different groups.

[0064] R1 and R2 are each independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, halogen, cyano, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; each R1 is independently not connected to an adjacent ring structure or is connected to form a ring by a chemical bond; at least two adjacent groups in R1 and R2 are not connected to each other or are connected to form a ring by a chemical bond.

[0065] Preferably, the boron-nitrogen organic compound has a structure as shown in any one of formula III-1, III-2, or III-3:

[0066]

[0067] Among them, rings F, Z1, Z2, Y1, Y2, X1, X2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, and Z 10 Z 11 m1 and m2 have the same limited range as Equation II.

[0068] Ring D is selected from any one of C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aromatic rings or C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaromatic rings, and is further preferably a benzene ring, a benzofuran ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzofuran ring, or a pyridine ring.

[0069] R 33 Indicates no substitution, monosubstituted, or the maximum permissible substitution; specifically, R 33 Indicates no substitution (R) 33 (e.g., hydrogen), monosubstituted, polysubstituted (e.g., disubstituted, trisubstituted, etc.); when R 33 When indicating multiple substitution, multiple (≥2) R 33 These can be the same or different groups.

[0070] R 31 R 32 R 33 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; the R 31 R 32 R 33 Each is independently unconnected to adjacent ring structures or connected to form a ring by chemical bonds; the R 31 R 32 R 33 At least two adjacent groups in the group are not connected or are linked by chemical bonds to form a ring.

[0071] Preferably, the R 31 and R 32 They are not both hydrogen.

[0072] Preferably, the R 31 R 32 R 33Each 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, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocyclic alkyl groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy groups, halogens, cyano groups, and substituted or unsubstituted C6-C20 (e.g., C6, C9, C2 ... The following groups are preferred: aryl (C10, C12, C14, C15, C16 or C18, etc.), substituted or unsubstituted C3-C20 (e.g. C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl groups, further preferably hydrogen, halogen (e.g. F, Cl, Br, I), substituted or unsubstituted groups, any one of the following: C1-C6 straight-chain or branched alkyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrolyl, phenyl, naphthyl, biphenyl, terphenyl, C1-C6 alkoxy.

[0073] Preferably, the R 31 R 32 R 33 At least two adjacent groups in the group are not connected or are linked by chemical bonds to form a ring (e.g., forming a ring). (The dashed lines represent fusion sites).

[0074] Preferably, the ring F is selected from unsubstituted or R. B Substituted C5-C10 (e.g., C6, C7, C8, C9, etc.) alicyclic, unsubstituted or R B Any one of the substituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) aliphatic heterocycles, and more preferably any one of the following groups: In this context, the dashed lines represent the fused bonds of functional groups.

[0075] R 41 R 42 R 43 R 44 R 45 R 46 R 47 R 48Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, preferably hydrogen, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl.

[0076] Preferably, Z1 and Z2 are each independently selected from CR0.

[0077] Preferably, each of the R0s 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, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocyclic alkyl groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl groups, substituted or Any one of unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, further preferably hydrogen, substituted or unsubstituted any one of the following groups: C1-C6 straight-chain or branched alkyl, C1-C6 alkoxy, C1-C6 alkylsilyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrole, tetrahydropyranyl, methyltetrahydropyranyl, phenyl, naphthyl, biphenyl, terphenyl, pyridyl.

[0078] Preferably, Z1 and Z2 are CH.

[0079] Preferably, at most one (0 or 1) of Z3, Z4, and Z5 is N; and / or, at most one (0 or 1) of Z6, Z7, and Z8 is N; and / or, at most one (0 or 1) of Z9, Z 10 and Z 11 At most one (0 or 1) is N.

[0080] Preferably, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z 10 Z 11Each was selected independently from CR1.

[0081] Preferably, Z3, Z5, Z6, Z8 and Z 11 CH, referring to Z4, Z7, Z9, Z 10 Each was selected independently from CR1.

[0082] Preferably, each of the R1s 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, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocyclic alkyl groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl groups, halogens, cyano groups, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C9, C9, C9, C9, etc.) alkylsilyl groups, halogens, cyano groups, and substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C9 ... 12. Any one of the following groups: aryl (C14, C15, C16 or C18, etc.), substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.), further preferably hydrogen, any one of the following groups: C1-C6 straight-chain or branched alkyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrole, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, diphenylamino, C1-C6 alkylsilyl.

[0083] Preferably, each R1 is independently unconnected to an adjacent ring structure or connected to form a ring by chemical bonds (e.g., forming a ring). (The dashed line represents a fused bond).

[0084] Preferably, X1 and X2 are each independently selected from N or CR2, and at most one (0 or 1) is N.

[0085] 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, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocyclic alkyl groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl groups, halogens, cyano groups, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C9, C9, C9, C9, etc.) alkylsilyl groups, halogens, cyano groups, and substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C9 ... 12. Any one of the following groups: aryl (C14, C15, C16 or C18, etc.), substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.), further preferably hydrogen, any one of the following groups: C1-C6 straight-chain or branched alkyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrole, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, diphenylamino, C1-C6 alkylsilyl.

[0086] As a preferred embodiment of the present invention, in the "substituted or unsubstituted" groups, each of the substituents is independently selected from deuterium, halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C1-C10 (e.g., C2, C3 ... Any one or a combination of at least two of the following: alkoxy groups (C6, C7, C8, C9, etc.), aryl groups (C6-C20, e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.), and heteroaryl groups (C3-C20, e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.). Further preferred are deuterium, halogens (F, Cl, Br, I), and C1-C6 straight-chain or branched alkyl groups; more preferably, deuterium, F, C1-C3 straight-chain alkyl groups, and isopropyl groups. tert-butyl Isobutyl tert-amyl

[0087] Preferably, Y1 and Y2 are each independently selected from single bonds and CR bonds. 11 R 12 NR 13 Any one of S or O, preferably at least one of which is a single bond, CR 11 R 12 S or O.

[0088] Preferably, m1+m2≥1.

[0089] Preferably, the R 11 R 12 R 13 Each is independently selected from any one or a combination of at least two of the following: C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, and C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.). More preferably, each is selected from any one of the following: C1-C6 straight-chain or branched alkyl groups, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, and naphthylphenyl.

[0090] As a preferred embodiment of the present invention, Y1 and Y2 are each independently a single bond and a CR bond. 11 R 12 S or O, m1+m2=2; thus, the boron-nitrogen organic compound can have better planar properties, while ensuring that the material molecules maintain a conjugated structure within the maximum range, which is more conducive to improving the efficiency and lifespan of the device while ensuring accurate light color.

[0091] Preferably, the boron-nitrogen organic compound has a structure as shown in any one of formulas IV-1, IV-2, IV-3, IV-4, and IV-5:

[0092]

[0093]

[0094] In this context, dashed lines represent single bonds or no connection, with single bonds being the preferred representation.

[0095] m2 can be 0 or 1, preferably 1.

[0096] Y1 is selected from CR 11 R 12 NR 13 Any one of S or O.

[0097] Y2 is selected from single bond, CR 11 R 12 NR 13It can be any one of S or O, preferably a single bond.

[0098] R 11 R 12 R 13 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

[0099] R0, R 21 R 22 R 23 R 24 and R 33 Each can be independently represented from unsubstituted, monosubstituted to the most permissible substitution; specifically, R0 represents unsubstituted (R0 is hydrogen), monosubstituted, or disubstituted; R 21 Indicates no substitution (R) 21 (Hydrogen), monosubstituted, disubstituted, or trisubstituted; R 22 R 23 and R 33 Similarly, I will not elaborate further. R 24 Indicates no substitution (R) 24 (containing hydrogen), monosubstituted or disubstituted. When R0, R... 21 R 22 R 23 R 24 R 33 When multiple substitutions are indicated, the multiple substituents are either the same or different groups.

[0100] R0 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0101] R 21 R 22 R 23 R 24 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, halogen, cyano, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0102] R 31 R 32 R 33 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0103] The R 21 R 22 R 23 R 31 R 32 R 33 Each is independently unconnected to adjacent ring structures or connected to form a ring by chemical bonds; the R 21 R 22 R 23 R 31 R 32 R 33 At least two adjacent groups in the group are not connected or are linked by chemical bonds to form a ring.

[0104] In Formula IV-5, U1 and U2 are each independently selected from O or CR. 45 R 46 Furthermore, at least one of U1 and U2 is 0.

[0105] R 41 R 42 R 43 R 44 R 45 R 46 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0106] n is 1 or 2; when n is 1, it indicates that the alicyclic ring is a pentagonal ring; when n is 2, it indicates that the alicyclic ring is a hexacyclic ring with 2 R's. 43 For the same or different groups, 2 R 44 These can be the same or different groups.

[0107] Alternatively, the boron-nitrogen organic compound has a structure as shown in Formula IV-6: Dashed lines represent single bonds or no connection; m2, Y2, R0, R 21 R22 R 23 R 24 R 41 R 42 R 43 R 44 R 45 R 46 And n has the same limiting range as described above; Ar is selected from any one of substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl groups, further preferably substituted or unsubstituted C3-C20 heteroaryl groups, more preferably any one of the following substituted or unsubstituted groups: pyridinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl.

[0108] Preferably, the R 11 R 12 R 13 Each is independently selected from any one of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, or C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl groups, further preferably any one of C1-C6 straight-chain or branched alkyl groups, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, or naphthylphenyl, and even more preferably methyl or phenyl.

[0109] Preferably, each of the R0s 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, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl groups, and substituted or unsubstituted C6-C2... 0 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, further preferably hydrogen, substituted or unsubstituted any of the following groups: C1-C6 straight-chain or branched alkyl, C1-C6 alkoxy, C1-C6 alkylsilyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrole, tetrahydropyranyl, methyltetrahydropyranyl, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, even more preferably hydrogen, C1-C3 straight-chain alkyl, C1-C3 straight-chain alkoxy groups, Trimethylsilyl.

[0110] Preferably, the R 21 R 22 R 23 and R 24Each 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, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C1... 2. Any one of the following groups: C14, C15, C16, or C18 heteroaryl groups; substituted or unsubstituted C6-C30 arylamino groups (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.); further preferably hydrogen; or any one of the following substituted or unsubstituted groups: C1-C6 straight-chain or branched alkyl groups, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrolyl, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, diphenylamino, C1-C6 alkylsilyl; even more preferably hydrogen, C1-C3 straight-chain alkyl groups,

[0111] Trimethylsilyl.

[0112] Preferably, the R 21 R 22 R 23 R 24 Each is independently unconnected to adjacent ring structures or connected to form a ring by chemical bonds; the R 21 R 22 R 23 At least two adjacent groups in the group are not connected or are linked by chemical bonds to form a ring (e.g., forming a ring). Dashed lines represent fusion bonds; specifically, the R... 23 (At least two adjacent groups in the group are not connected or are linked by chemical bonds to form a ring).

[0113] Preferably, the R 31 R 32 R 33Each 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, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocyclic alkyl groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy groups, halogens, cyano groups, and substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, etc.) groups. The following groups are preferred: aryl (C1-C15, C16, or C18, etc.), substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl groups; hydrogen, halogen (e.g., F, Cl, Br, I), substituted or unsubstituted groups; and any one of the following groups: C1-C6 straight-chain or branched alkyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrolyl, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, C1-C6 alkoxy, and even more preferably hydrogen, F, C1-C3 straight-chain alkyl, ...

[0114] Methoxy, deuterated methyl.

[0115] Preferably, the R 31 and R 32 Not both are hydrogen. More preferably, R 31 and R 32 At least one is selected from any one of the following: substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, and substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl.

[0116] Preferably, the R 31 R 32 R 33 At least two adjacent groups in the group are not connected or are linked by chemical bonds to form a ring (e.g., forming a ring). (The dashed lines represent fusion sites).

[0117] Preferably, the R 41 R42 R 43 R 44 R 45 R 46 Each is independently selected from hydrogen, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, with hydrogen or methyl being more preferred.

[0118] Preferably, the R 41 R 42 R 45 R 46 Each is independently selected from any one of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, with methyl groups being more preferred; the R 43 and R 44 It is hydrogen.

[0119] Preferably, the boron-nitrogen organic compound has the structure shown in any one of the following:

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128] In a second aspect, the present invention provides an application of the organic compound as described in the first aspect, wherein the organic compound is applied to an organic electronic device.

[0129] 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.

[0130] Preferably, the organic electronic device includes an organic electroluminescent device.

[0131] Preferably, the organic compound is used in an organic electroluminescent device.

[0132] Preferably, the organic compound serves as the light-emitting layer material in the organic electroluminescent device.

[0133] Preferably, the organic compound is used as a dopant material (also known as "dye", "dopant", or "guest material") in the light-emitting layer of an organic electroluminescent device.

[0134] 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 organic compound as described in the first aspect.

[0135] Preferably, the organic layer includes at least one organic compound with the structure shown in M1-M159.

[0136] Preferably, the organic layer includes a light-emitting layer, which includes at least one organic compound as described in the first aspect; more preferably, it includes at least one organic compound with the structure shown in M1-M159.

[0137] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material comprises at least one organic compound as described in the first aspect.

[0138] 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 0.3-3%.

[0139] Preferably, the host material includes any one or a combination of at least two of the following: a P-type host material, an N-type host material, or a monomolecular excitosome host material.

[0140] Preferably, the light-emitting layer further includes a sensitizer.

[0141] Preferably, the sensitizer includes any one or a combination of at least two of thermally activated delayed fluorescence materials and phosphorescent materials.

[0142] Preferably, the energy of the lowest triplet state (T1) of the sensitizer is greater than or equal to the energy of the lowest singlet state (S1) of the organic compound of the present invention.

[0143] Preferably, the maximum emission wavelength of the sensitizer is less than the maximum emission wavelength of the organic compound of the present invention.

[0144] Preferably, the mass percentage of the sensitizer in the luminescent layer is 0.1-40%, for example, it can be 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30% or 35%, etc.

[0145] Preferably, the sensitizer includes a phosphorescent material, and the mass percentage of the phosphorescent material (phosphorescent sensitizer) in the luminescent 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%, etc.

[0146] Preferably, the sensitizer is a thermally activated delayed fluorescence material, and the mass percentage of the thermally activated delayed fluorescence material (thermally activated delayed fluorescence sensitizer) in the luminescent layer is 0.1-40%, for example, it can be 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30% or 35%, etc.

[0147] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0148] 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.

[0149] 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.

[0150] 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 organic compound as described in the first aspect, and more preferably contains at least one organic compound with the structure shown in M1-M159.

[0151] 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 organic compound as described in the first aspect, and more preferably contains at least one organic compound with the structure shown in M1-M159.

[0152] An OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. This organic material layer can be further divided into multiple regions. For example, the organic material layer may include a hole transport region, a light-emitting layer, and an electron transport region.

[0153] 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).

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 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.

[0158]

[0159]

[0160]

[0161] 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 mentioned above, or one or more compounds of HI-1 to HI-3 mentioned 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 mentioned below.

[0162]

[0163] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive 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 can simultaneously emit different colors such as red, green, and blue.

[0164] 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.

[0165] In one aspect of the invention, the light-emitting layer employs phosphorus-sensitized electroluminescence technology. The host material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-117.

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] 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.

[0173]

[0174]

[0175] In one aspect of the invention, the light-emitting layer employs thermally activated sensitized fluorescence luminescence technology. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-117 described above.

[0176] In one aspect of the invention, the luminescent layer employs a thermally activated sensitized fluorescence luminescence technique. Its thermally activated delayed fluorescence sensitizer may be selected from, but is not limited to, one or more combinations of TDE1-TDE49 listed below.

[0177]

[0178]

[0179]

[0180]

[0181] 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-51 to PH-77, PH-86 to PH-88, PH-92, PH-94 to PH-105 described above; or it may employ, but is not limited to, one or more compounds of HT-1 to HT-51 and one or more compounds of PH-51 to PH-77, PH-86 to PH-88, PH-92, PH-94 to PH-105.

[0182] The OLED organic material layer 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).

[0183] 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.

[0184]

[0185]

[0186]

[0187]

[0188] 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-50, PH-78 to PH-85, PH-89 to PH-91, PH-93, PH-106 to PH-117; or it may employ, but is not limited to, one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-50, PH-78 to PH-85, PH-89 to PH-91, PH-93, PH-106 to PH-117.

[0189] 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.

[0190] Fourthly, the present invention provides a display device comprising the organic electroluminescent device as described in the third aspect.

[0191] Preferably, the display device includes a display screen or a display panel.

[0192] The present invention also provides an electronic device, which includes the aforementioned display device.

[0193] Compared with the prior art, the present invention has the following beneficial effects:

[0194] The organic compound provided by this invention has the structure shown in Formula I. Through the design of the molecular structure and the mutual complexation between the structures, it has the properties of both multiple resonance molecules and conjugated molecules, that is, it has a narrow fluorescence emission spectrum and high quantum efficiency. When applied to organic electroluminescent devices, it can be used as a fluorescent dopant material for the light-emitting layer, which can effectively improve the luminous efficiency and lifespan of organic electroluminescent devices, make the devices have higher color purity, and reduce voltage and energy consumption, fully meeting the requirements of the current panel and display manufacturing industry for high-performance materials. Detailed Implementation

[0195] 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 in any way.

[0196] 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.

[0197] In one specific embodiment, the boron-nitrogen organic compound can be prepared via the following synthetic route:

[0198] In this formula, rings A, B, C, D, E, F, Z1, Z2, Y1, Y2, m1, and m2 have the same definitions as in Formula I; Hal1, Hal2, Hal3, Hal4, and Hal5 are each independently selected from halogens, for example, any one of F, I, Br, or Cl. The order of reactions I and II can be adjusted according to the synthesis situation; that is, reaction I can be carried out first, followed by reaction II, or reaction II can be carried out first, followed by reaction I.

[0199] In one specific embodiment, reaction I and reaction II are carried out in the presence of cesium carbonate (Cs₂CO₃).

[0200] In one specific embodiment, reactions III and IV are carried out in the presence of organolithium (e.g., n-butyllithium).

[0201] 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.

[0202] It should be noted that obtaining the boron-nitrogen 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. Compounds synthesized using 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.

[0203] The intermediates and target products in the preparation and synthesis examples of this invention were analyzed and detected using an ABSCIEX mass spectrometer (4000QTRAP). The structural analysis of the intermediates and compounds in this invention was performed using a gas chromatography-mass spectrometry (GC-MS, Shimadzu QP2010 SE) ion source, with an APCI source. The test results were calculated as target molecular weight + 1 (M + H).

[0204] Preparation Example 1: Preparation of Intermediate A1

[0205]

[0206] 1-Methylcyclohexanol (20 g) and 2-chloroaniline (22.34 g) were added to a 500 mL single-necked flask, and about 250 mL of tetrahydrofuran (THF) was added. Under nitrogen protection at -60 °C, boron trifluoride diethyl ether solution (40 g) was slowly added to the reaction system. The mixture was then brought to room temperature and heated to 50 °C for 3 h. Heating was stopped, and 300 mL of dichloromethane and 300 mL of water were added. The mixture was washed, separated, dried, concentrated, and purified by vacuum distillation to obtain the target intermediate A1 (34.67 g, MS: 223.74 / 224.56, theoretical / test value).

[0207] Preparation Example 2: Preparation of Intermediate A2

[0208]

[0209] Intermediate A1 (30 g), 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (35.83 g), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride Pd(dppf)Cl2 (2.94 g), and sodium tert-butoxide (19.33 g) were added to a 1 L single-necked flask. 400 mL of toluene was added, and the mixture was reacted at 100 °C for 10 h under nitrogen protection. Heating was then stopped, and the mixture was washed with water, separated, dried, and concentrated. The mixture was purified by column chromatography to obtain the target intermediate A2 (48.67 g, MS: 409.25 / 410.04, theoretical / test value).

[0210] Preparation Example 3: Preparation of Intermediate A3

[0211]

[0212] Intermediate A2 (45 g), tris(dibenzylacetone)dipalladium Pd2(dba)3 (3.75 g), 2-biscyclohexylphosphine-2',6'-dimethoxybiphenyl S-Phos (4.51 g), and sodium tert-butoxide (15.82 g) were added to a 1 L single-necked flask. 500 mL of toluene was added, and the mixture was reacted at 100 °C for 10 h under nitrogen protection. Heating was then stopped, and the mixture was washed with water, separated, dried, concentrated, and purified by column chromatography to obtain the target intermediate A3 (38.41 g, MS: 373.58 / 374.69, theoretical / test value).

[0213] Preparation Example 4: Preparation of Intermediate A4

[0214]

[0215] Intermediate A1 in Preparation Example 2 was replaced with an equivalent amount of 4-tert-butyl-2-chloroaniline, and the target intermediate A4 (29.56 g, MS: 333.25 / 334.12, theoretical / tested value) was prepared according to the methods in Preparation Examples 2 and 3.

[0216] Preparation Example 5: Preparation of Intermediate A5

[0217]

[0218] Intermediate A1 in Preparation Example 2 was replaced with an equivalent amount of 4-phenyl-2-chloroaniline, and the target intermediate A5 (33.08 g, MS: 353.21 / 354.51, theoretical / tested value) was prepared according to the methods in Preparation Examples 2 and 3.

[0219] Preparation Example 6: Preparation of Intermediate A6

[0220]

[0221] 1-Methylcyclohexanol (26.18 g), bromobenzene (30 g), and aluminum trichloride (38.21 g) were added to a 1 L single-necked flask, along with 300 mL of toluene. The mixture was reacted at 100 °C under nitrogen protection for 5 h. Heating was then stopped, and the reaction system was filtered. The filtrate was washed with water, separated, dried, concentrated, and purified by vacuum distillation to obtain the target intermediate A6 (25.53 g, MS: 252.05 / 253.18, theoretical / tested value).

[0222] Preparation Example 7: Preparation of Intermediate A7

[0223]

[0224] 2,4-Di-tert-butyl-1,6-dibromobenzene (30 g), phenylboronic acid (10.51 g), tetrakis(triphenylphosphine)palladium Pd(PPh3)4 (2.99 g), and potassium carbonate (17.87 g) were added to a 1 L single-necked flask. 300 mL of a mixed solution of 1,4-dioxane:water = 5:1 (volume ratio) was added. The mixture was reacted at 100 °C for 5 h under nitrogen protection. Heating was stopped, and the mixture was washed with water, separated, dried, concentrated, and purified by vacuum distillation to obtain the target intermediate A7 (24.48 g, MS: 344.11 / 345.32, theoretical value / test value).

[0225] Preparation Example 8: Preparation of Intermediate A8

[0226]

[0227] The target intermediate A8 (36.3 g, MS: 289.05 / 290.20, theoretical value / test value) was prepared by replacing 2,4-di-tert-butyl-1,6-dibromobenzene with an equivalent amount of 2-tert-butyl-1,6-dibromobenzene and phenylboronic acid with an equivalent amount of 4-pyridineboronic acid in Preparation Example 7.

[0228] Preparation Example 9: Preparation of Intermediate B1

[0229]

[0230] 1,3-Dibromo-2,6-difluorobenzene (30 g), 3,6-di-tert-butylcarbazole (32.37 g), and cesium carbonate (54 g) were added to a 1 L single-necked flask. 300 mL of N,N-dimethylformamide (DMF) was added, and the mixture was reacted overnight at 80 °C. After heating was stopped and the mixture was allowed to return to room temperature, 500 mL of water was added. A large amount of solid precipitated out. After drying, the solid was purified by column chromatography to obtain the target intermediate B1 (41.03 g, MS: 529.04 / 530.34, theoretical / tested value).

[0231] Preparation Example 10: Preparation of Intermediate B2

[0232]

[0233] The target intermediate B2 (33.84 g, MS: 571.09 / 572.30, theoretical value / test value) was prepared by replacing 3,6-di-tert-butylcarbazole in Preparation Example 9 with an equivalent amount of 2,7-di-tert-butyl-9,9-dimethyl-9,10-dihydroacridine.

[0234] Preparation Example 11: Preparation of Intermediate B3

[0235]

[0236] The target intermediate B3 (35.49 g, MS: 568.98 / 569.67, theoretical / tested value) was prepared by replacing the 3,6-di-tert-butylcarbazole in Preparation Example 9 with an equivalent amount of 3,6-diphenylcarbazole and following the method in Preparation Example 9.

[0237] Preparation Example 12: Preparation of Intermediate B4

[0238]

[0239] Intermediate B1 (30 g), A4 (19 g), and cesium carbonate (27.60 g) were added to a 1 L single-necked flask. Approximately 300 mL of DMF was added, and the mixture was reacted at 140 °C for 10 h under nitrogen protection. Heating was then stopped, and the mixture was allowed to return to room temperature. 500 mL of water was added, and a large amount of solid precipitated out. After filtration, the solid was recrystallized twice using toluene and ethanol to obtain the target intermediate B4 (40.06 g, MS: 842.28 / 843.54, theoretical / tested values).

[0240] Preparation Example 13: Preparation of Intermediate B5

[0241]

[0242] In Preparation Example 12, A4 was replaced with an equivalent amount of A5, and the target intermediate B5 (30.16 g, MS: 862.25 / 863.17, theoretical / tested value) was prepared according to the method in Preparation Example 12.

[0243] Preparation Example 14: Preparation of Intermediate B6

[0244]

[0245] In Preparation Example 12, A4 was replaced with an equivalent amount of A3, and intermediate B1 was replaced with an equivalent amount of B3. The target intermediate B6 (28.89 g, MS: 922.25 / 923.42, theoretical value / test value) was prepared according to the method in Preparation Example 12.

[0246] Preparation Example 15: Preparation of Intermediate B7

[0247]

[0248] In Preparation Example 12, A4 was replaced with an equivalent amount of A5, and intermediate B1 was replaced with an equivalent amount of B2. The target intermediate B7 (31.20 g, MS: 904.30 / 905.45, theoretical / test value) was prepared according to the method in Preparation Example 12.

[0249] Synthesis Example 1: Synthesis of Boron-Nitrogen Organic Compound M-8

[0250]

[0251] Intermediate B4 (10 g) was added to a 500 mL three-necked flask, followed by 100 mL of xylene. Under nitrogen protection at -60 °C, 20 mL of n-butyllithium (2.4 M) was slowly added. The mixture was then allowed to return to room temperature and activated at 70 °C for 1 h. Heating was then stopped, and the mixture was cooled to -60 °C. Boron tribromide (17.79 g) was added, and the mixture was allowed to return to room temperature. The mixture was then reacted at 90 °C for 3 h. The boron tribromide and xylene were then evaporated under reduced pressure and the reaction mixture was set aside for later use.

[0252] Intermediate A6 (6g) was added to a 100mL three-necked flask, and about 50mL of THF was added. Then, n-butyllithium (10mL, 2.4M) was added at -60℃. After a few minutes, the lithiation system was added to the original reaction system. The reaction was heated to 70℃ for 3h, and then the heating was stopped. The reaction system was diluted with 100mL of dichloromethane, washed with water, separated, dried and concentrated, and purified by column chromatography to obtain the target product M-8 (1.5g, MS: 876.57 / 877.89, theoretical value / test value).

[0253] Synthesis Example 2: Synthesis of Boron-Nitrogen Organic Compound M-16

[0254]

[0255] The raw materials in Synthesis Example 1 were replaced with the materials described above, and the target product M-16 (1.1 g, MS: 926.59 / 927.25, theoretical value / test value) was prepared according to the method in Synthesis Example 1.

[0256] Synthesis Example 3: Synthesis of Boron-Nitrogen Organic Compound M-43

[0257]

[0258] The raw materials in Synthesis Example 1 were replaced with the materials described above, and the target product M-43 (1.2 g, MS: 952.51 / 953.20, theoretical value / test value) was prepared according to the method in Synthesis Example 1.

[0259] Synthesis Example 4: Synthesis of Boron-Nitrogen Organic Compound M-58

[0260]

[0261] The raw materials in Synthesis Example 1 were replaced with the materials described above, and the target product M-58 (2.1 g, MS: 1012.51 / 1013.31, theoretical value / test value) was prepared according to the method in Synthesis Example 1.

[0262] Synthesis Example 5: Synthesis of Boron-Nitrogen Organic Compound M-74

[0263]

[0264] The raw materials in Synthesis Example 1 were replaced with the materials described above, and the target product M-74 (1.6 g, MS: 1048.60 / 1049.09, theoretical value / test value) was prepared according to the method in Synthesis Example 1.

[0265] Synthesis Example 6: Synthesis of Boron-Nitrogen Organic Compound M-78

[0266]

[0267] The raw materials in Synthesis Example 1 were replaced with the materials described above, and the target product M-78 (0.8 g, MS: 993.54 / 994.54, theoretical value / test value) was prepared according to the method in Synthesis Example 1.

[0268] Synthesis Example 7: Synthesis of Boron-Nitrogen Organic Compound M-87

[0269]

[0270] The raw materials in Synthesis Example 1 were replaced with the materials described above, and the target product M-87 (1.3 g, MS: 994.98 / 995.43, theoretical value / test value) was prepared according to the method in Synthesis Example 1.

[0271] Synthesis Example 8: Synthesis of Boron-Nitrogen Organic Compound M-139

[0272]

[0273] The raw materials in Synthesis Example 1 were replaced with the materials described above, and the target product M-139 (1.7 g, MS: 865.51 / 866.46, theoretical value / test value) was prepared according to the method in Synthesis Example 1.

[0274] Synthesis Example 9: Synthesis of Boron-Nitrogen Organic Compound M-141

[0275]

[0276] The raw materials in Synthesis Example 1 were replaced with the materials described above, and the target product M-141 (2.0 g, MS: 890.46 / 891.34, theoretical value / test value) was prepared according to the method in Synthesis Example 1.

[0277] Device Example 1

[0278] 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 the organic electroluminescent device is as follows:

[0279] (1) The glass substrate 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.

[0280] (2) Place the glass substrate with the anode into a vacuum chamber and evacuate it to 1×10⁻⁶. -5Pa, a mixture of HT-4:HI-3 (97 / 3, w / w) was vacuum-deposited on the above-mentioned anodic layer as a hole injection layer, and the thickness of the deposited film was 10 nm.

[0281] (3) The compound HT-4 was vacuum-deposited on the hole injection layer as a hole transport layer, and the total film thickness was 60 nm.

[0282] (4) The compound PH-86 was vacuum-deposited on the hole transport layer as an electron blocking layer, and the total film thickness was 5 nm.

[0283] (5) A light-emitting layer is vacuum-deposited on the electron blocking layer. The light-emitting layer includes a host material, a sensitizer, and a dopant material (fluorescent dye). The doping ratio is adjusted by adjusting the evaporation rate of various materials using a multi-source co-evaporation method. The total film thickness is 35 nm.

[0284] The light-emitting layer adopts phosphorus photosensitization luminescence technology. The ratio of the main material, phosphorus photosensitizer, and dopant is 89:10:1 (w / w / w). The main material is a PH-86:PH-89 (60 / 40, w / w) mixed main material. The phosphorus photosensitizer is BPD-1, and the dopant is the organic compound M-8 provided by this invention.

[0285] (6) The compound PH-89 was vacuum-deposited on the light-emitting layer as a hole blocking layer, and the total film thickness was 5nm.

[0286] (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, with a total film thickness of 25 nm.

[0287] (8) Vacuum evaporation of LiF as an electron injection layer on the electron transport layer with a thickness of 1 nm;

[0288] (9) An Al layer with a thickness of 150 nm is vacuum-deposited on the electron injection layer as the cathode of the device to obtain the organic electroluminescent device; the total deposition rate of all organic layers and LiF is controlled at 0.1 nm / s, and the deposition rate of the metal electrode is controlled at 1 nm / s.

[0289] Device Examples 2-21, Device Comparative Examples 1-4

[0290] An organic electroluminescent device is disclosed, which differs from device example 1 only in that the fluorescent dyes of the light-emitting layer are the compounds shown in Table 1; the other layers, thicknesses, materials and preparation methods are the same as those in device example 1.

[0291] The structures of the fluorescent dyes in Comparative Examples 1-4 are as follows:

[0292]

[0293] Device performance testing:

[0294] External quantum efficiency: The external quantum efficiency (EQE, %) of organic electroluminescent devices was determined using an integrating sphere;

[0295] LT97 lifespan: 40mA / cm using a luminance meter 2 The initial brightness value of the device was obtained by testing at a current density. While maintaining a constant current, the time it took for the device brightness to drop to 97% of the initial brightness was measured, in hours.

[0296] Voltage: The voltage was increased at a rate of 0.1V per second, and the current density of the organic electroluminescent device was measured when it reached 10mA / cm². 2 The voltage at that time, i.e., the driving voltage;

[0297] The color and color purity of a material can be characterized by the maximum emission peak wavelength (Peak, nm) and full width at half maximum (FWHM, nm) of the fluorescence emission spectrum: using a fluorescence spectrometer F7000 with an excitation wavelength of 365 nm, the room temperature fluorescence spectrum of a 0.01 g / mL toluene solution was tested, and the relevant data can be directly read from the spectrum;

[0298] The test values ​​of EQE and LT97 lifetime of device Comparative Example 1 are recorded as 1.00. The EQE and LT97 lifetime of other devices are the ratios of their respective test values ​​to the test values ​​of device Comparative Example 1 (relative EQE, relative lifetime).

[0299] The test results are shown in Table 1:

[0300] Table 1

[0301]

[0302]

[0303] Based on the performance data in Table 1, compared with Comparative Examples 1-4, the boron-nitrogen organic compound provided by this invention, as a fluorescent dye for organic electroluminescent devices, exhibits a significant improvement in device performance due to its specific molecular structure. While maintaining or even reducing the operating voltage of the device, the external quantum efficiency is improved, with an increase of up to 10% or more. Simultaneously, the device's lifetime is significantly extended. This may be because the molecular-level dipole orientation or molecular vibrational-rotational energy level of the boron-nitrogen organic compound of this invention is improved, thereby increasing efficiency. Furthermore, the introduction of a fused alicyclic structure (ring F) into the BN structure enhances molecular stability, resulting in a significant extension of the device lifetime in the examples.

[0304] Furthermore, through the design and optimization of molecular structure, this invention can further improve the luminous efficiency and lifetime of the device; for example, in M-139, since there are no substituents at the adjacent positions of ring D and B atom, there is no structure to protect the exposed B atom, so the device lifetime is relatively low.

[0305] In Comparative Examples 1-4, N1's carbazole structure lacks a fused alicyclic structure, and the simple tert-butyl group results in a large molecular vibrational rotation energy level, leading to a broadened emission spectrum and affecting the device's color purity and efficiency. N2's parent nucleus does not contain a carbazole structure or a fused alicyclic structure, and the entire molecule lacks planarity, affecting efficiency and lifetime. N3's conjugated structure is too large, resulting in a reddish light color and low efficiency. N4 also has an excessively large conjugated structure and exhibits severe intramolecular charge transport, leading to poor color purity and further affecting device efficiency.

[0306] The applicant declares that the boron-nitrogen organic compounds and their applications are illustrated through the above embodiments, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A boron-nitrogen organic compound, characterized in that, The boron-nitrogen organic compound has the structure shown in Formula I: Among them, rings A, B, C, D, and E are each independently selected from unsubstituted or R. A Substituted C6-C60 aromatic rings, unsubstituted or R A Any one of the substituted C3-C60 heteroaryl rings; Ring F is selected from unsubstituted or R B Substituted C4-C20 alicyclic, unsubstituted or R B Any one of the substituted C3-C20 aliphatic heterocycles; R A R B Each is independently selected from any one of the following: substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 heterocycloalkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C1-C20 alkylsilyl groups, halogens, cyano groups, nitro groups, hydroxyl groups, ester groups, amino groups, substituted or unsubstituted C6-C60 arylamino groups, substituted or unsubstituted C3-C60 heteroarylamino groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups; The R A Each ring is independent and not connected to adjacent ring structures or is linked to form a ring by chemical bonds; Z1 and Z2 are each independently selected from N or CR0; R0 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; Dashed lines represent single bonds or no connection; m1 and m2 are each independently 0 or 1; Y1 and Y2 are each independently selected from single bonds and CR 11 R 12 NR 13 Any one of S or O; R 11 R 12 R 13 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; R0, R A R B R 11 R 12 R 13 The substituents described herein are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl; each substituent is independently not connected to the adjacent ring structure or is connected to the ring structure by a chemical bond to form a ring.

2. The boron-nitrogen organic compound according to claim 1, characterized in that, The boron-nitrogen organic compound has a structure as shown in any one of formula II-1, II-2, or II-3: Among them, rings D, F, Z1, Z2, Y1, Y2, m1, and m2 have the same limited range as Equation I; Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z 10 Z 11 Each is independently selected from N or CR1; X1 and X2 are each independently selected from N or CR2; R1 and R2 are each independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, halogen, cyano, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; each R1 is independently not connected to an adjacent ring structure or is connected to form a ring by a chemical bond; at least two adjacent groups in R1 and R2 are not connected to each other or are connected to form a ring by a chemical bond.

3. The boron-nitrogen organic compound according to claim 2, characterized in that, The boron-nitrogen organic compound has a structure as shown in any one of formula III-1, III-2, or III-3: Among them, rings F, Z1, Z2, Y1, Y2, X1, X2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, and Z 10 Z 11 m1 and m2 have the same defined range as in Equation II; Ring D is selected from any one of C6-C30 aromatic rings or C3-C30 heteroaromatic rings, and is further preferably a benzene ring, a benzofuran ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzofuran ring, or a pyridine ring; R 33 Indicates no substitution, single substitution, and the maximum permissible substitution; R 31 R 32 R 33 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; the R 31 R 32 R 33 Each is independently unconnected to adjacent ring structures or connected to form a ring by chemical bonds; the R 31 R 32 R 33 At least two adjacent groups in the group are not connected or are linked by chemical bonds to form a ring; Preferably, the R 31 and R 32 They are not both hydrogen.

4. The boron-nitrogen organic compound according to any one of claims 1-3, characterized in that, The ring F is selected from unsubstituted or R. B Substituted C5-C10 alicyclic, unsubstituted or R B Any of the substituted C3-C10 aliphatic heterocycles, preferably any of the following groups: In this context, the dashed lines represent the fused bonds of functional groups; R 41 R 42 R 43 R 44 R 45 R 46 R 47 R 48 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, preferably hydrogen or any one of substituted or unsubstituted C1-C10 straight-chain or branched alkyl.

5. The boron-nitrogen organic compound according to claim 2 or 3, characterized in that, Z1 and Z2 are each independently selected from CR0; Preferably, each of the R0s is independently selected from any one of hydrogen, substituted or unsubstituted C1-C10 straight-chain or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl. Preferably, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z 10 Z 11 Each was independently selected from CR1; Preferably, each of the R1s is independently selected from any one of hydrogen, substituted or unsubstituted C1-C10 straight-chain or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, halogen, cyano, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, and substituted or unsubstituted C6-C30 arylamino. Preferably, X1 and X2 are each independently selected from N or CR2, and at most one of them is N; Preferably, each of the R2s is independently selected from any one of hydrogen, substituted or unsubstituted C1-C10 straight-chain or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, halogen, cyano, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, and substituted or unsubstituted C6-C30 arylamino. Preferably, Y1 and Y2 are each independently selected from single bonds and CR bonds. 11 R 12 NR 13 Any one of S or O; Preferably, m1+m2≥1.

6. The boron-nitrogen organic compound according to claim 1, characterized in that, The boron-nitrogen organic compound has a structure as shown in any one of formulas IV-1, IV-2, IV-3, IV-4, and IV-5: In this context, dashed lines represent single bonds or no connection; m2 is 0 or 1; Y1 is selected from CR. 11 R 12 NR 13 Any one of S or O; Y2 is selected from single bond, CR 11 R 12 NR 13 Any one of S or O; R 11 R 12 R 13 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; R0, R 21 R 22 R 23 R 24 and R 33 Each can be used independently to represent no substitution, single substitution, or the maximum permissible substitution. R0 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; R 21 R 22 R 23 R 24 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, halogen, cyano, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; R 31 R 32 R 33 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; The R 21 R 22 R 23 R 24 R 31 R 32 R 33 Each is independently unconnected to adjacent ring structures or connected to form a ring by chemical bonds; the R 21 R 22 R 23 R 24 R 31 R 32 R 33 At least two adjacent groups in the group are not connected or are linked by chemical bonds to form a ring; U1 and U2 are each independently selected from O or CR. 45 R 46 And at least one of them is 0; R 41 R 42 R 43 R 44 R 45 R 46 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; n is 1 or 2.

7. The boron-nitrogen organic compound according to claim 6, characterized in that, The R 11 R 12 R 13 Each is independently selected from any one of C1-C10 straight-chain or branched alkyl groups and C6-C20 aryl groups; Preferably, each of the R0 groups is independently selected from hydrogen, substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C2-C10 heterocycloalkyl groups, substituted or unsubstituted C1-C10 alkoxy groups, substituted or unsubstituted C1-C10 alkylsilyl groups, substituted or unsubstituted C6-C20 aryl groups, and substituted or unsubstituted C3-C20 heteroaryl groups. More preferably, hydrogen or substituted or unsubstituted groups are selected from the following groups: C1-C6 straight-chain or branched alkyl groups, C1-C6 alkoxy groups, C1-C6 alkylsilyl groups, cyclopentyl groups, methylcyclopentyl groups, cyclohexyl groups, methylcyclohexyl groups, 1,4,4-trimethylcyclohexyl groups, tetrahydropyrrole groups, tetrahydropyranyl groups, methyltetrahydropyranyl groups, phenyl groups, naphthyl groups, biphenyl groups, and pyridyl groups. Preferably, the R 21 R 22 R 23 and R 24 Each group is independently selected from hydrogen, substituted or unsubstituted C1-C10 straight-chain or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, and substituted or unsubstituted C6-C30 arylamino. More preferably, hydrogen or substituted or unsubstituted groups are selected from the following groups: C1-C6 straight-chain or branched alkyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrole, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, diphenylamino, and C1-C6 alkylsilyl. Preferably, the R 31 R 32 R 33 Each group is independently selected from any one of hydrogen, substituted or unsubstituted C1-C10 straight-chain or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, and more preferably any one of hydrogen, halogen, substituted or unsubstituted groups from the following: C1-C6 straight-chain or branched alkyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrole, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, C1-C6 alkoxy; Preferably, the R 31 and R 32 They are not both hydrogen; Preferably, the R 41 R 42 R 43 R 44 R 45 R 46 Each is independently selected from any one of hydrogen, C1-C10 straight-chain or branched alkyl groups, with hydrogen or methyl being more preferred.

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

9. The application of a boron-nitrogen organic compound as described in any one of claims 1-8, 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.

10. 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 1-8; 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 1-8; Preferably, the light-emitting layer comprises a host material and a dye, wherein the dye comprises at least one boron-nitrogen organic compound as described in any one of claims 1-8.

11. A display device, characterized in that, The display device includes the organic electroluminescent device as described in claim 10.

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