Boron-containing nitrogen heterocyclic resonance organic light-emitting compounds, organic electroluminescent devices comprising the same, and applications thereof

Abstract

This invention provides a boron-nitrogen heterocyclic resonant organic light-emitting compound, an organic electroluminescent device comprising the same, and its applications, belonging to the field of organic semiconductor technology. The boron-nitrogen heterocyclic resonant organic light-emitting compound has a structure as shown in formula (1), wherein each group is as defined in the specification. Formula (1)

Description

Technical Field

[0001] This invention belongs to the field of organic semiconductor technology, and particularly relates to a boron-nitrogen heterocyclic resonant organic light-emitting compound and organic electroluminescent devices and applications containing the same. Background Technology

[0002] Organic light-emitting diodes (OLEDs), as a new generation of display technology, have been widely used in smartphones, automotive displays and wearable devices due to their significant advantages such as self-illumination, high contrast, wide viewing angle and fast response.

[0003] OLEDs generally consist of an anode, a metal cathode, and an organic functional layer located between them. The organic functional layer mainly includes a hole injection layer, a hole transport layer, an electron blocking layer, and an emissive layer. The emissive layer is a key factor determining the luminous efficiency, color purity, and lifetime of an OLED. Typically, the emissive layer comprises a host material and a luminescent material; the selection and combination of these materials can improve color purity, luminous efficiency, and stability. Furthermore, to enhance the performance of OLED devices, sensitized OLEDs, where the host material, sensitizer, and luminescent material form the emissive layer, have been proposed in recent years.

[0004] With the evolution of technology, luminescent materials have undergone three generations of transformation: (1) The first generation of fluorescent materials has a stable structure and low cost, but due to the spin statistical law, its theoretical internal quantum efficiency (IQE) is only 25%. Even the TTA fluorescence quantum efficiency using triplet upconversion cannot break through the limit of 62.5%, and the efficiency bottleneck is obvious; (2) The second generation of phosphorescent materials promotes intersystem crossing by introducing heavy metals such as iridium (Ir) and platinum (Pt), achieving a theoretical IQE of nearly 100%. However, precious metals are expensive, and the stability and lifespan of blue phosphorescent materials are still problems in the industry; (3) The third generation of thermally activated delayed fluorescence (TADF) materials reduces the energy difference between singlet and triplet states through molecular design, so that triplet excitons are converted into singlet states for emission, and the theoretical IQE can reach 100%. However, traditional TADF molecules are prone to significant structural relaxation in the excited state, resulting in a wide emission spectrum (half-width is often greater than 70 nm) and insufficient color purity.

[0005] In recent years, boron-nitrogen resonance structures have been developed, resulting in more rigid fused-ring frameworks that achieve highly localized non-bonded molecular orbitals at the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO). This weakens vibrational coupling and the vibrational relaxation of the S1 state, significantly suppressing the broadening of the full width at half maximum (FWHM) of the luminescent material. See, for example, the following literature:

[0006] (1)Hatakeyama T, et al. ,Ultrapure Blue Thermally Activated DelayedFluorescence Molecules: Efficient HOMO-LUMO Separation by the MultipleResonance Effect. Advanced Materials. 2016, 28, 2777-2781;

[0007] (2)Liu J, et al., Toward a BT.2020 green emitter through a combined multiple resonance effect and multi-lock strategy, Nature Communications.2022, 13, 4876;

[0008] (3) Zhang Zehua et al., Design strategy for multiple resonance TADF molecules, Acta Physico-Chimica Sinica, 2025, 41(1):100006;

[0009] (4) CN114621272A;

[0010] (5) CN107851724A; and

[0011] (6)CN116925113A.

[0012] Boron-nitrogen resonant structures, with their unique rigid framework and localized electron cloud distribution, exhibit excellent color purity and luminous efficiency, and have become the mainstream technology trend in OLED development. However, there is still a need to develop organic electroluminescent compounds and organic electroluminescent materials with superior color purity, luminous efficiency, stability, and lifespan for use as dopants in the emissive layer. Summary of the Invention

[0013] In view of the above, the present invention provides a boron-nitrogen heterocyclic resonant organic light-emitting compound, an organic electroluminescent device containing the same, and its applications, in order to at least partially solve the above-mentioned technical problems. The technical solution provided by the present invention is as follows.

[0014] (1) By introducing the macrocyclic donor 4H-azaporphyrin [2,3,4,5-DEF:6,7,1-J'K']biscarbazole (hereinafter referred to as "azaporphyrin biscarbazole"), which has extremely strong planar rigidity, into the system, compared with flexible diphenylamine or semi-rigid biscarbazole (such as 9H-4,9'-biscarbazole or 9H-3,9'-biscarbazole, etc.), it can more effectively lock the molecular configuration and greatly suppress the low-frequency vibrations in the excited state, thereby further narrowing the emission spectrum. At the same time, this invention innovatively uses a spirocyclic structure as a steric hindrance adjustment unit. By utilizing its vertically staggered spatial arrangement, it not only effectively blocks the close packing between molecules and reduces the exciton quenching probability, but also significantly increases the thermal decomposition temperature (T) of the material. d ) and glass transition temperature (T g This helps to improve the thermal stability and film quality of the light-emitting layer film.

[0015] (2) More importantly, this invention achieves highly rigid interlocking between the central benzene ring and the macrocyclic donor unit through single-bond linkage or atomic anchoring. This "cooperative rigidification" effect not only enhances the radiative transition rate but also strengthens the molecular skeleton's resilience in electrochemical and photochemical processes. Experiments show that organic electroluminescent devices containing such compounds achieve narrowband emission and improved color purity while significantly reducing efficiency loss at high current densities and exhibiting excellent operating life. Furthermore, the compounds described in this invention have a mature synthesis process, stable yield, and industrial application value.

[0016] According to an embodiment of the first aspect of the present invention, a boron-nitrogen heterocyclic resonant organic light-emitting compound is provided, having a structure as shown in formula (1):

[0017] Equation (1);

[0018] Among them, R1-R 18Each element is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 heteroalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted C2-C20 alkoboro, substituted or unsubstituted C3-C20 alksilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or Unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C8-C20 arylsilalkyl, substituted or unsubstituted C9-C20 silylaryl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, sulfinyl, sulfonyl, phosphine, and combinations thereof;

[0019] R1-R 18 The substituents in the middle are connected by single bonds or circumferential rings;

[0020] R1-R 17 Any two adjacent substituents can connect to form a ring;

[0021] Z is either N or C, where Z is N, the adjacent Z is C, and R1-R connected to N are... 17 It does not exist;

[0022] X1 and X2 are each independently selected from -C(R a )2-、-N(R a )2-、-Si(R a )2-、-P(R a )3-、-P(R a )-、-P(R a )=O-、-Ge(R a -2-, -S(=O)2-, -S-, -O-, -Se-, -Te-, single bond or not present;

[0023] R a Selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, C6-C30 aryl, and C5-C30 heteroaryl;

[0024] R a It can be monosubstituted, disubstituted, polysubstituted, or unsubstituted;

[0025] The substituents used for the above-mentioned substituents are selected from any one of deuterium, tritium, halogen, cyano, C1-C20 alkyl, deuterium or tritium-substituted C1-C20 alkyl, C5-C30 heteroaryl, deuterium or tritium-substituted C5-C30 heteroaryl.

[0026] The heteroatom in the heteroalkyl or heterocyclic alkyl group is selected from at least one of O, S, N, Se, Si, and B;

[0027] The heteroatom in the heteroaryl group is selected from at least one of O, S, N, Se, Si, and B.

[0028] In embodiments of the present invention, a rigid boron-nitrogen resonance framework composed of boron atoms and surrounding nitrogen atoms is used as the core, and multiple aromatic rings (or heterocyclic aromatic rings) are fused together to form an extended conjugated system. Polycyclic aromatic amines are introduced into the structure as donor units, with aziridine biscarbazole being a representative fused polycyclic aromatic amine. Its large planar rigid framework effectively suppresses vibrational relaxation of the donor portion in the resonance core, which is beneficial for achieving narrow-spectrum emission. Simultaneously, the biscarbazole unit imparts higher rigidity and steric hindrance to the compound, suppressing excessively dense molecular packing in the solid state, improving processability, and reducing concentration quenching caused by π-π packing. Furthermore, spirocyclic or bridged ring structures (e.g., connected by boron, oxygen, silicon, etc.) are further constructed on the boron-nitrogen resonance framework, forming multi-dimensional bonds with the aziridine biscarbazole unit, constituting a fused-ring system with higher conformational rigidity and stereo shielding effect. This synergistic structure, while maintaining higher color purity and narrow half-peak emission, can significantly suppress luminescence quenching caused by molecular aggregation, thereby improving the luminescence efficiency, thermal stability, and operating life of organic light-emitting compounds in organic electroluminescent devices.

[0029] In this invention, the expression Ca~Cb represents the number of carbon atoms in the group as a~b. Unless otherwise specified, this number of carbon atoms generally does not include the number of carbon atoms in the substituents. In this invention, the description of chemical elements includes the concept of isotopes with the same chemical properties, such as the expression for "hydrogen," as well as the concepts of "deuterium" and "tritium" with the same chemical properties. It should be noted that in this invention, "D" can also be used to represent "deuterium."

[0030] In this invention, * indicates the bonding location.

[0031] In this invention, the term "heteroalkyl" refers to a group formed by replacing one or more carbon atoms in a carbon chain (-CH3-CH2-CH2-) with heteroatoms, such as methylthiomethyl (e.g., CH3-S-CH2-), methoxymethyl (CH3-O-CH2-), and ethylaminoethyl.

[0032] In this invention, the term "alkoxy" refers to a group formed by the connection of an oxygen atom and an alkyl group through a single bond, with the general formula -O-alkyl, such as methoxy (-OCH3), ethoxy (-OCH2CH3), and propoxy (-OCH2CH2CH3).

[0033] In this invention, the term "alkylthio" refers to a group formed by a sulfur atom and an alkyl group connected by a single bond, with the general formula -S-alkyl, such as methylthio (-S-CH3), ethylthio, and isopropylthio.

[0034] In this invention, the term "alkylsilyl" refers to a group formed by replacing hydrogen atoms in a silane molecule with alkyl groups, such as trimethylsilyl (TMS) and tert-butyldimethylsilyl (TBS).

[0035] In this invention, the term "halogen" refers to fluorine, chlorine, bromine, or iodine.

[0036] In this invention, the C1-C20 alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, and n-eicosyl.

[0037] In this invention, the substituted or unsubstituted C2-C20 heteroalkyl groups include substituted or unsubstituted methoxymethyl, substituted or unsubstituted 2-methoxyethyl, substituted or unsubstituted 2-ethoxyethyl, substituted or unsubstituted 2-dimethylaminoethyl, substituted or unsubstituted 2-diethylaminoethyl, substituted or unsubstituted 3-methoxypropyl, substituted or unsubstituted 3-ethoxypropyl, substituted or unsubstituted 2-cyanoethyl, substituted or unsubstituted 3-cyanopropyl, substituted or unsubstituted 2-chloroethyl, substituted or unsubstituted 3-chloropropyl, substituted or unsubstituted 2-fluoroethyl, and substituted... Or unsubstituted 3-fluoropropyl, substituted or unsubstituted 2,2-difluoroethyl, substituted or unsubstituted 3,3,3-trifluoropropyl, substituted or unsubstituted methoxyethoxy, substituted or unsubstituted 2-(2-methoxyethoxy)ethyl, substituted or unsubstituted 2-(2-ethoxyethoxy)ethyl, substituted or unsubstituted tetrahydrofuran-2-ylmethyl, substituted or unsubstituted tetrahydrofuran-3-ylmethyl, substituted or unsubstituted tetrahydropyran-2-ylmethyl, substituted or unsubstituted tetrahydropyran-3-ylmethyl, substituted or unsubstituted tetrahydropyran-4-ylmethyl, but not limited thereto.

[0038] In this invention, substituted or unsubstituted C1-C20 alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy, neopentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-dodecyloxy, n-tetradecyloxy, n-hexadecyloxy, n-octadecyloxy, n-eicosyloxy, and their substituted derivatives.

[0039] In this invention, the substituted or unsubstituted C1-C20 alkylthio groups include, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, isobutylthio, tert-butylthio, n-pentylthio, isopentylthio, neopentylthio, n-hexylthio, n-heptylthio, n-octylthio, n-nonylthio, n-decylthio, n-dodecylthio, n-tetradecylthio, n-hexadecylthio, n-octadecylthio, n-eicosylthio, and their substituted derivatives.

[0040] In this invention, the substituted or unsubstituted C2-C20 alkylboryl groups include, but are not limited to, diethylboryl, propargyl, isopropargyl, n-butargyl, sec-butargyl, tert-butargyl, n-pentylboryl, isopentylboryl, neopentylboryl, n-hexylboryl, n-octylboryl, n-decylboryl, n-dodecylboryl, n-tetradecylboryl, n-hexadecylboryl, n-octadecylboryl, n-eicosylboryl and their substituted derivatives.

[0041] In this invention, the substituted or unsubstituted C3-C20 alkylsilyl groups include trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-tert-butylsilyl, tri-n-pentylsilyl, tri-n-hexylsilyl, tri-n-octylsilyl, tri-n-decylsilyl, tri-dodecanylsilyl, tri-tetradecylsilyl, tri-hexadecylsilyl, tri-octadecylsilyl, tri-eicosylsilyl and their substituted derivatives, but are not limited thereto.

[0042] In this invention, the substituted or unsubstituted C3-C20 cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclododecyl, adamantyl, norbornyl, isobornyl, and their substituted derivatives.

[0043] In this invention, substituted or unsubstituted C2-C20 heterocyclic alkyl groups include, but are not limited to, azeotropic, oxecyclobutyl, thiocyclobutyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, tetrahydropyranyl, piperazinyl, morpholinyl, thiomorpholinyl, azeotropic heptyl, oxecycloheptyl, 1,4-dioxacyclohexyl, 1,3-dioxacyclopentyl, quininecycloyl, 1,2,3,4-tetrahydroisoquinolinyl, decahydroisoquinolinyl, decahydroquinolinyl, and their substituted derivatives.

[0044] In this invention, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C7-C30 aralkyl groups, substituted or unsubstituted C6-C30 aryloxy groups, substituted or unsubstituted C6-C30 arylthio groups, and substituted or unsubstituted C6-C30 arylamine groups include pyrroleyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrazinyl, triazinyl, indolyl, isoyindolyl, benzofuranyl, benzothiopheneyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, and quinazolinyl. The following groups are included in the list of carboxyl, quinoxalinyl, carbazolyl, phenothiazinyl, phenotoxazinyl, dibenzofuranyl, dibenzothiopheneyl, azacarbazolyl, diazacarbazolyl, phenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, biphenyl, terphenyl, fluorenyl, triphenylene, tetraphenyl, benzyl, phenethyl, phenylpropyl, naphthylmethyl, naphthylethyl, anthracenemethyl, fluorenylmethyl, biphenylmethyl, phenoxy, naphthoxy, anthraceneoxy, phenanthreneoxy, biphenyloxy, fluorenyloxy, terphenyloxy, phenylthio, naphthio, anthracenethio, phenanthrenethio, biphenylthio, fluorenylthio, terphenylthio, aniline, naphthylamine, anthraceneamine, diphenylamine, N-phenylnaphthylamine, carbazo-9-yl and their derivatives, but not limited thereto.

[0045] In this invention, the substituted or unsubstituted C0-C20 amino groups include, but are not limited to, amino, methylamino, dimethylamino, ethylamino, diethylamino, propylamino, isopropylamino, aniline, benzylamino, diphenylamino, pyrrolyl, piperidinyl, morpholinyl, N-methylaniline, N-acetamido and their substituted derivatives.

[0046] In this invention, the acyl group includes, but is not limited to, formyl, acetyl, propionyl, butyryl, benzoyl, naphthoyl, nicotinyl, furanoyl, and their substituted derivatives.

[0047] In some implementations, R1-R 18 Each is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 heteroalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkoboryl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C8-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof;

[0048] R1-R 18 The replacement method is either a single key or a parallel loop connection;

[0049] R1-R 17 Any adjacent substituents can be optionally linked to form a ring;

[0050] X1 and X2 are each independently selected from -C(R a )2-、-N(R a )2-、-Si(R a )2-、-P(R a )3-、-P(R a )-、-P(R a )=O-、-Ge(R a )2-, -S(=O)2-, -S-, -O-, -Se-, -Te-;

[0051] When X1 and X2 are -C(R) a )2-、-N(R a )2-、-Si(R a )2-、-P(R a )3-、-P(R a )-、-P(R a )=O-、-Ge(R a In the case of )2-, R a Adjacent substituents can be optionally linked to form a ring;

[0052] Given that X1 and X2 exist, R1-R 18 It is not simultaneously hydrogen, and can optionally connect with adjacent substituents to form a ring;

[0053] R a Selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C3-C 20 cycloalkyl, substituted or unsubstituted C7-C 30 Aryl groups, C6-C 30 aryl, C5-C 30 heteroaryl groups;

[0054] R a It can be monosubstituted, disubstituted, polysubstituted, or unsubstituted;

[0055] The substituents used for the above-mentioned substituent groups are selected from deuterium, tritium, halogens, cyano groups, and C1-C groups. 20 Alkyl, deuterium or tritium-substituted C1-C 20 Alkyl, C5-C 30 C5-C substituted with heteroaryl, deuterium or tritium 30 Any one of the heteroaryl groups;

[0056] The heteroatom in the heteroalkyl group is selected from at least one of O, S, N, Se, Si, and B;

[0057] The heteroatom in the heteroaryl group is selected from at least one of O, S, N, Se, Si, and B.

[0058] In some implementations, R1-R 18 Each is independently selected from one or more of the following: hydrogen, deuterium, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, methoxyethyl, 2-dimethylaminoethyl, methoxy, ethoxy, isopropoxy, trimethylsilyl, tert-butyldimethylsilyl, cyclopropyl, cyclohexyl, adamantyl, pyridyl, thiophene, pyrrole, carbazole, dibenzofuranyl, phenyl, naphthyl, anthracene, biphenyl, methoxyphenyl, terphenyl, tolyl, benzyl, phenoxy, naphthoxy, diphenylamino, carbazole-9-yl, phenylnaphthylamino, triphenylsilyl, methyldiphenylsilyl, amino, dimethylamino, acetamino, aniline, acetyl, aldehyde, carboxyl, methyl ester, ethyl ester, cyano, isocyano, mercapto, methylthio, and diphenylphosphino.

[0059] In some embodiments, the structure of the boron-nitrogen heterocyclic resonant organic light-emitting compound is shown in any one of formulas (1-1) to (1-3):

[0060] Equation (1-1);

[0061] Equation (1-2);

[0062] Equation (1-3);

[0063] R1-R 17 Each is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 heteroalkyl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7 -C30 aralkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C8-C20 arylsilalkyl, substituted or unsubstituted C9-C20 silylaryl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof;

[0064] R 18The group is selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 heteroalkyl, substituted or unsubstituted C3-C15 alkylsilyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C18 heteroaryl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C7-C18 aralkyl, substituted or unsubstituted C6-C18 aryloxy, substituted or unsubstituted C6-C18 arylthio, substituted or unsubstituted C6-C18 arylamine, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof;

[0065] R 35 -R 38 Each is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 heteroalkyl, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof;

[0066] R1-R 18 R 35 -R 38 The substituents in the middle are connected by single bonds or circumferential rings;

[0067] R 35 and R 36 R 37 and R 38 They can be connected to form a loop, R1-R 17 R 35 -R 38 Any two adjacent substituents can connect to form a ring;

[0068] X1 and X2 are each independently selected from -C(R a )2-、-N(R a )2-、-Si(R a )2-、-P(R a )3-、-P(R a )-、-P(R a )=O-、-Ge(R a )2-, -S(=O)2-, -S-, -O-, -Se-, -Te-;

[0069] When X1 and X2 are -C(R) a )2-、-N(R a)2-、-Si(R a )2-、-P(R a )3-、-P(R a )-、-P(R a )=O-、-Ge(R a In the case of )2-, R a Adjacent substituents can be optionally linked to form a ring;

[0070] R a Selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, C6-C30 aryl, and C5-C30 heteroaryl;

[0071] R a It can be monosubstituted, disubstituted, polysubstituted, or unsubstituted;

[0072] The substituents used for the above-mentioned substituents may be selected from any one of deuterium, tritium, halogen atom, cyano, C1-C20 alkyl, deuterium or tritium-substituted C1-C20 alkyl, C5-C30 heteroaryl, deuterium or tritium-substituted C5-C30 heteroaryl.

[0073] In embodiments of the present invention, the organic light-emitting compound skeleton is a highly delocalized skeleton composed of a benzene ring, a six-membered ring, and a seven-membered ring fused together. Compared to skeletons containing heteroatoms, this structure can more effectively regulate the molecular orbital energy levels. For example, the energy of the highest occupied molecular orbital (HOMO) increases, while the energy of the lowest unoccupied molecular orbital (LUMO) may also change accordingly, thereby achieving control over the light color (which can be adjusted towards red or blue light). Since the light emission process of the fused-ring skeleton is based on a more rigid molecular skeleton, vibrational relaxation and recombination energies are reduced, which is beneficial for obtaining purer emission colors and narrower spectral peak widths.

[0074] In some implementations, preferably, R a The C6-C30 aralkyl group is selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-dimethylenefluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, and substituted or unsubstituted phenanthryl.

[0075] Among them, R aThe heteroaryl groups in C5-C30 are selected from substituted or unsubstituted xanthanes, thioxanthanes, tin-oxanthanes, germanium-oxanthanes, azirmonyl, substituted or unsubstituted thiofluorenyl, spirodifluorenyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted tetraphenylsilyl, substituted or unsubstituted silylspirol, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted aniline, substituted or unsubstituted diphenylamine, and substituted or unsubstituted N-phenylcarbazoyl.

[0076] In some embodiments, the structure of the boron-nitrogen heterocyclic resonant organic light-emitting compound is shown in formula (2-1):

[0077] Equation (2-1);

[0078] Among them, X1 and X2 are each independently selected from Si or C;

[0079] R1-R 17 R 20 -R 25 R 28 -R 33 Each is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 heteroalkyl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C8-C20 arylsilyl, substituted or unsubstituted C9-C20 silylaryl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof;

[0080] R 18The group is selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 heteroalkyl, substituted or unsubstituted C3-C15 alkylsilyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C18 heteroaryl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C7-C18 aralkyl, substituted or unsubstituted C6-C18 aryloxy, substituted or unsubstituted C6-C18 arylthio, substituted or unsubstituted C6-C18 arylamine, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof;

[0081] R 19 R 26 R 27 R 34 Each is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 heteroalkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof;

[0082] R1-R 34 The substituents in the middle are connected by single bonds or circumferential rings;

[0083] R1-R 17 Any two adjacent substituents can connect to form a ring;

[0084] The substituents used for the above-mentioned substituents may be selected from any one of deuterium, tritium, halogen, cyano, C1-C20 alkyl, deuterium or tritium-substituted C1-C20 alkyl, C5-C30 heteroaryl, deuterium or tritium-substituted C5-C30 heteroaryl.

[0085] In embodiments of the present invention, the introduction of two spirocycles into the organic light-emitting compound structure not only enhances the overall structural rigidity of the molecule, but also, through the "spatial bridging" effect of the spirocycles themselves, connects R1 and R2. 17 R 18 By fixing the substituents in specific spatial positions, the torsion and vibration of these substituents in the excited state are significantly suppressed, thereby improving the stability of the organic light-emitting compound. At the same time, this extended conjugation effect reduces the HOMO-LUMO energy level difference of the molecule, driving a systematic redshift in the emission spectrum.

[0086] In some embodiments, more preferably, R1-R 17 R20 -R 25 R 28 -R 33 Each is independently selected from one or more of the following: hydrogen, deuterium, fluorine, chlorine, methyl, ethyl, isopropyl, n-hexyl, n-octyl, tert-butyl, methoxymethyl, dimethylaminoethyl, trimethylsilyl, cyclohexyl, tetrahydrofuran-2-yl, carbazole-9-yl, phenyl, benzyl, phenethyl, phenoxy, naphthoxy, diphenylamine-4-yl, triphenylsilyl, dimethylamino, aniline, acetyl, ethyl acetate, cyano, isonitrile, thio, and diphenylphosphine.

[0087] In some implementations, R 18 It is selected from one or more of the following: hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, tert-butyl, n-hexyl, n-decyl, methoxyethyl, dimethylaminopropyl, methylthiomethyl, trimethylsilyl, triethylsilyl, cyclohexyl, cyclopentyl, adamantane-1-yl, tetrahydrofuran-2-yl, morpholino-4-yl, piperidin-1-yl, pyridin-2-yl, thiophene-2-yl, carbazole-9-yl, benzofuran-2-yl, phenyl, naphthyl-1-yl, biphenyl-4-yl, anthracene-9-yl, benzyl, phenethyl, naphthylmethyl, phenoxy, naphthoxy, phenylthio, diphenylamine-4-yl, carbazole-3-yl, amino, methylamino, diethylamino, aniline, acyl, acetyl, carbonyl, carboxylic acid, ethyl acetate, methyl benzoate, cyano, isonitrile, thio, and triphenylphosphine.

[0088] In some implementations, R 19 R 26 R 27 R 34 Each is independently selected from one or more of the following: hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, tert-butyl, n-hexyl, methoxymethyl, methylthioethyl, dimethylaminopropyl, cyclohexyl, cyclopentyl, tetrahydrofuran-2-yl, morpholino-4-yl, piperidin-1-yl, trimethylsilyl, triethylsilyl, phenyl, naphth-1-yl, biphenyl-4-yl, amino, dimethylamino, aniline, acetyl, carbonyl, carboxylic acid, methyl acetate, ethyl benzoate, cyano, isonitrile, thio, and diphenylphosphine.

[0089] In some embodiments, the structures of boron-nitrogen heterocyclic resonant organic light-emitting compounds are shown in formulas (2-2) to (2-3):

[0090] Equation (2-2);

[0091] Equation (2-3);

[0092] Among them, X1 and X2 are each independently selected from Si or C;

[0093] R1-R 17 R 20 -R 25 R 28 -R 33 Each element is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 heteroalkyl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7- Aryl groups of C30, substituted or unsubstituted aryloxy groups of C6-C30, substituted or unsubstituted arylthio groups of C6-C30, substituted or unsubstituted arylamine groups of C6-C30, substituted or unsubstituted arylsilyl groups of C8-C20, substituted or unsubstituted silylaryl groups of C9-C20, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isonitrile groups, thio groups, phosphin groups, and combinations thereof;

[0094] R 18 Each is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 heteroalkyl, substituted or unsubstituted C3-C15 alkylsilyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C18 heteroaryl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C7-C18 aralkyl, substituted or unsubstituted C6-C18 aryloxy, substituted or unsubstituted C6-C18 arylthio, substituted or unsubstituted C6-C18 arylamine, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof;

[0095] R 19 R 26 R 27 R 34 R 35 R 36 R 37 R 38 Each is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 heteroalkyl, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof;

[0096] R1-R 34 The substituents in the middle are connected by single bonds or circumferential rings;

[0097] R1-R 17 R 35 R 38 Any two adjacent substituents can connect to form a ring;

[0098] The substituents used for the above-mentioned substituents may be selected from any one of deuterium, tritium, halogen, cyano, C1-C20 alkyl, deuterium or tritium-substituted C1-C20 alkyl, C5-C30 heteroaryl, deuterium or tritium-substituted C5-C30 heteroaryl.

[0099] In embodiments of the present invention, a single spirocyclic structure is introduced into the molecular structure of the organic light-emitting compound through the X1 or X2 site. This spirocyclic structure enhances the overall planar rigidity of the organic light-emitting compound molecule while effectively locking in nearby substituents (e.g., R1, R2). 17 or R 18 The spatial positioning of the spirocyclic rings inhibits the torsion of these groups under photoexcitation or thermal perturbation. Simultaneously, the stereoorthogonal structure of the spirocyclic ring effectively suppresses intermolecular packing quenching, thereby enhancing the conformational and photothermal stability of the molecules. In terms of photoelectric properties, this spirocyclic structure, through its unique electronic effects, moderately extends the delocalized system, promoting a suitable redshift in the emission spectrum of organic light-emitting compounds.

[0100] In some implementations, R1-R 34Each of the following is independently represented as hydrogen, deuterium, tritium, fluorine, bromine, cyano, substituted or unsubstituted boronyl, substituted or unsubstituted methoxy, substituted or unsubstituted tert-butoxy, substituted or unsubstituted phenoxy, substituted or unsubstituted phenylthio, substituted or unsubstituted phenylselenoyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenselenoyl, substituted or unsubstituted adamantyl, substituted or unsubstituted methyl, trifluoromethyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted diphenyletheryl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted Or unsubstituted phenanthrene, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted aniline, substituted or unsubstituted diphenylamine, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted thiofluorenyl, spirodifluorenyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted tetraphenylsilyl, substituted or unsubstituted silylspiroyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted trimethylsilyl;

[0101] The substituents replacing the above-mentioned substituents are selected from deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, deuterated adamantyl, cyano, methyl, deuterated methyl, benzyl, ethyl, deuterated ethyl, phenethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, tert-pentyl, deuterated tert-pentyl, tert-butyl, deuterated tert-butyl, phenyl tert-butyl, n-butyl, phenyl n-butyl, methoxy, tert-butyloxy, phenyl, tert-butylphenyl, tolyl, ethylphenyl, isopropylphenyl, m-xylyl group, trimethylyl, m-diisopropylphenyl, di One or more of the following: biphenyl, methyl diphenyl, tert-butyl diphenyl, naphthyl, anthraceneyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalyl, quinolinyl, isoquinoxalyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, aziphenanthyl, tert-butoxy, phenoxy, phenylthio, phenylselenoyl, phenoxazinyl, phenthiazolyl, and phenselenozinyl.

[0102] In some implementations, R1-R 17 R 19 -R 34R 35 -R 38 Each can be independently classified into any of the following structures:

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] .

[0114] In some implementations, R 36 R 18 R 37 Each is independently selected from the following structure:

[0115] Hydrogen, deuterium, fluorine, bromine, cyano, methyl, tert-butyl, ethyl, isopropyl, deuterated methyl, cyclopentane, cyclohexane, dimethylcyclohexane;

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] .

[0122] In some embodiments, the boron-nitrogen heterocyclic resonant organic light-emitting compound has any one of the following structures:

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252] 。

[0253] According to an embodiment of a second aspect of the present invention, a material for an organic electroluminescent device is provided, comprising a boron-nitrogen heterocyclic resonant organic light-emitting compound.

[0254] According to an embodiment of a third aspect of the present invention, an application of a boron-nitrogen heterocyclic resonant organic light-emitting compound is provided, including at least one of: organic electroluminescent devices, organic solar cells, organic field-effect transistors, organic thin-film transistors, organic lasers, organic spintronic devices, electronic component modules, and lighting panels.

[0255] In some embodiments, an organic electroluminescent device is also provided, including an emissive layer comprising a boron-nitrogen heterocyclic resonant organic light-emitting compound.

[0256] In some embodiments, the luminescent layer includes a host material and a dopant material, wherein the dopant material is the aforementioned boron-nitrogen heterocyclic resonance organic light-emitting compound. By incorporating the organic light-emitting compound as a guest luminescent agent into a host material with suitable energy levels, its narrow-band luminescence characteristics and efficient reverse intersystem crossing ability brought about by multiple resonance effects can be fully utilized.

[0257] In some embodiments, the light-emitting layer further includes an exciton-sensitizing material; wherein the exciton-sensitizing material is a metal-containing complex. Due to its strong spin-orbit coupling, the metal-containing complex can efficiently convert injected triplet excitons into singlet excitons that can be utilized by the light-emitting guest, thereby significantly improving the overall utilization rate of excitons.

[0258] In some embodiments, the host material includes a first host material and a second host material, at least one of which is a thermally activated delayed fluorescence (TEF) material. By using a TEF material as the host material, the efficient conversion of triplet excitons to singlet excitons can be achieved, thereby significantly improving the exciton utilization rate of the host system.

[0259] In some embodiments, the organic electroluminescent device further includes: a substrate, a first electrode, and a second electrode, wherein the light-emitting layer is located between the first electrode and the second electrode; the first electrode and the second electrode are each independently and differently a cathode or an anode.

[0260] In some embodiments, the substrate includes, but is not limited to, a glass substrate, such as soda-lime glass, borosilicate glass, or quartz glass; a polymer substrate, such as polyethylene terephthalate, polyethylene naphthalate, or polyimide; a metal foil substrate, such as stainless steel foil, aluminum foil, or titanium foil; or a reinforced substrate with a planarization layer coated on the glass surface. Preferably, the substrate is an indium tin oxide (ITO) conductive glass substrate.

[0261] In some embodiments, an application of an organic electroluminescent device is provided, including at least one of the following: a display element; a lighting device; and an electronic device. The display element includes displays for smartphones, tablets, televisions, and wearable devices; the lighting device includes indoor and outdoor functional lighting, surface light sources, and automotive lighting systems; and the electronic device includes end products with integrated display or lighting functions.

[0262] Based on the above technical solution, the boron-nitrogen heterocyclic resonant organic light-emitting compound and the organic electroluminescent device and application containing it of the present invention have at least one of the following beneficial effects:

[0263] (1) In the technical solution of this invention, the donor (azapyridine biscarbazole) and the acceptor fragment (boron atom) are interconnected through rigid structural fragments. Compared with the traditional boron-nitrogen resonance structure, the luminescent layer material of this invention, by introducing a rigid spirocyclic structure and a rigid azapyridine biscarbazole donor fragment, anchors both the donor and acceptor on the rigid boron-nitrogen framework, thereby achieving synergistic regulation of HOMO and LUMO molecular orbitals and enhancing the tunability of the emission color. The rigid framework of the polycyclic aromatic amine can enhance the overall rigidity of the molecule, which can effectively suppress the structural relaxation of the entire molecule and facilitate narrowband emission. The biscarbazole unit imparts rigidity while increasing the steric hindrance of the molecule, suppressing quenching caused by molecular stacking, thus resulting in higher color purity and higher external quantum efficiency (EQE). max Excellent overall performance with a maximum external quantum efficiency (>30%) and low efficiency roll-off. Organic electroluminescent devices prepared based on the compounds of this invention generally have a maximum external quantum efficiency greater than 30%.

[0264] (2) In the technical solution of this invention, the molecular design that introduces a spiro-ring structure as an inert rigid unit effectively improves the stability and lifespan of organic electroluminescent devices. This structure, without affecting the advantages of the original resonant structure, effectively enhances the chemical stability of the molecules and increases the distance between molecules or between molecules and the host material, thereby reducing unnecessary intermolecular interactions. This effectively avoids problems such as decreased solution processing performance and fluorescence quenching caused by excessive molecular stacking, thus significantly improving the stability and lifespan of organic electroluminescent devices.

[0265] (3) In the technical solution of the present invention, the light-emitting layer material includes a host material, a guest light-emitting material, and an exciton-sensitizing material. The boron-nitrogen heterocyclic multi-resonance material of the present invention has excellent thermal stability and can effectively suppress the destruction of molecular structure caused by long-term high-temperature heating during device fabrication. OLED devices fabricated using the boron-nitrogen heterocyclic resonance material of the present invention exhibit excellent performance in suppressing efficiency roll-off, and can also maintain stable and high brightness emission at high voltages (10 V and above), thereby significantly improving the device's performance at high brightness (1000 cd / m²).2 The efficiency, stability, and overall reliability of the OLED devices fabricated using the boron-nitrogen heterocyclic resonant material of this invention are improved. Furthermore, the OLED devices fabricated using this invention exhibit outstanding operational stability while maintaining high color purity. Attached Figure Description

[0266] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device based on the boron-nitrogen heterocyclic resonant organic light-emitting compound of the present invention. Detailed Implementation

[0267] Hereinafter, embodiments of the present invention will be described with reference to the accompanying drawings. However, it should be understood that these descriptions are exemplary only and are not intended to limit the scope of the invention. In the following detailed description, numerous specific details are set forth to provide a thorough understanding of the embodiments of the invention for ease of explanation. However, it will be apparent that one or more embodiments may be practiced without these specific details. Furthermore, descriptions of well-known structures and techniques are omitted in the following description to avoid unnecessarily obscuring the concept of the invention.

[0268] All raw materials involved in the synthesis examples of this invention can be purchased from the market or obtained by conventional preparation methods in the art.

[0269] Example 1

[0270] Synthetic compound 1

[0271]

[0272] Synthesis of intermediate C1

[0273] Under nitrogen protection, starting material a1 (5 g, 18.39 mmol), intermediate B1 (5.52 g, 16.72 mmol), cesium carbonate (10.89 g, 33.44 mmol), and 50 mL of N,N-dimethylformamide were added to a two-necked flask, and the reaction was carried out at 130 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to give intermediate c1 (7.98 g, yield 82%).

[0274] Synthesis of intermediate e1

[0275] Under nitrogen protection, intermediate c1 (5 g, 8.59 mmol), starting material Z3 (1.72 g, 10.30 mmol), cesium carbonate (5.56 g, 17.17 mmol), and 50 mL of N,N-dimethylformamide were added to a two-necked flask, and the reaction was carried out at 130 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to give intermediate e1 (4.89 g, yield 78%).

[0276] Synthesis of intermediate g1

[0277] Under nitrogen protection, intermediate e1 (5 g, 6.85 mmol) was added to a two-necked flask, dissolved in 50 mL of tetrahydrofuran, cooled to -78 °C, and stirred for 5 minutes. A solution of n-butyllithium in n-hexane (3.14 mL, 7.54 mmol) was added dropwise. After reacting for 1 hour, intermediate C1 of the C-series was dissolved in tetrahydrofuran and injected into the reaction mixture. The mixture was stirred at room temperature for 2 hours. The organic phase was then removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was dissolved in 40 mL of glacial acetic acid, and 2 mL of concentrated hydrochloric acid was added. The mixture was refluxed and stirred for 8 hours. After cooling, the reaction mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to give intermediate g1 (3.62 g, 4.04 mmol).

[0278] Synthesis of intermediate h1

[0279] In a single-necked flask, intermediate g1 (5 g, 5.58 mmol) was dissolved in 50 mL of chloroform, protected from light, and stirred in an ice bath at 0 °C. N-bromosuccinimide (993.15 mg, 5.58 mmol) was added in portions, and the mixture was stirred for 3 hours. After the reaction was complete, the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether:ethyl acetate = 15:1) to give intermediate h1 (3.54 g, yield 62%).

[0280] Synthesis of Compound 1

[0281] Under nitrogen protection, intermediate h1 (5 g, 5.13 mmol) was added to a two-necked flask, dissolved in 50 mL of xylene, cooled to -40 °C, and stirred for 5 min. A solution of n-butyllithium in n-hexane (2.35 mL, 5.64 mmol) was slowly added dropwise, stirred for 5 min, and then heated to 60 °C and stirred for 1 h. The mixture was cooled again to -40 °C, and boron tribromide (2.57 g, 10.26 mmol) was added, stirred for 5 min, and then heated to 60 °C and stirred for 2 h. The reaction mixture was cooled to 0 °C, and diisopropylethylamine (1.99 g, 15.39 mmol) was added. The reaction was carried out at 150 °C for 12 h. After the reaction was completed, the organic phase was removed by vacuum distillation, the resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether / ethyl acetate = 15:1) to give compound 1 (1.72 g, yield 37%).

[0282] Example 2

[0283] Synthetic compound 69

[0284]

[0285] Intermediate c1 and intermediate e1 were prepared using the preparation method of Example 1.

[0286] Synthesis of intermediate f1

[0287] Under nitrogen protection, intermediate e1 (5 g, 6.85 mmol), isopropyl boron ester (903.89 mg, 10.23 mmol), tetrakis(triphenylphosphine) palladium (293 mg, 0.245 mmol), tri-tert-butylphosphine (100 mg, 0.473 mmol), potassium carbonate (2.83 g, 20.05 mmol), 50 mL tetrahydrofuran, and 12.5 mL water were added to a two-necked flask, and the mixture was reacted at 70 °C for 24 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to give intermediate f1 (4.18 g, yield 88%).

[0288] Synthesis of intermediate g2

[0289] Under nitrogen protection, intermediate f1 (5 g, 6.85 mmol) was added to a two-necked flask, dissolved in 50 mL of tetrahydrofuran, cooled to -78 °C, and stirred for 5 minutes. A hexane solution of n-butyllithium (3.14 mL, 7.54 mmol) was added dropwise, and after reacting for 1 hour, intermediate C1 (1.43 g, 7.54 mmol) was dissolved in tetrahydrofuran and injected into the reaction mixture. The mixture was stirred at room temperature for 2 hours. The organic phase was then removed by vacuum distillation, and the resulting mixture was extracted with dichloromethane. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was dissolved in 40 mL of glacial acetic acid, and 2 mL of concentrated hydrochloric acid was added. The mixture was refluxed and stirred for 8 hours. After the reaction solution was cooled, it was extracted with dichloromethane, the organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to give intermediate g2 (3.62 g, yield 64.6%).

[0290] Synthesis of intermediate h2

[0291] In a single-necked flask, intermediate g2 (5 g, 5.58 mmol) was dissolved in 50 mL of chloroform, protected from light, and stirred in an ice bath at 0 °C. N-bromosuccinimide (993.15 mg, 5.58 mmol) was added in portions, and the mixture was stirred for 3 hours. After the reaction was complete, the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether:ethyl acetate = 15:1) to give intermediate h2 (3.54 g, yield 62%).

[0292] Synthesis of Compound 69

[0293] Under nitrogen protection, intermediate h2 (5 g, 5.13 mmol) was added to a two-necked flask, dissolved in 50 mL of xylene, cooled to -40 °C, and stirred for 5 min. A hexane solution of n-butyllithium (2.35 mL, 5.64 mmol) was slowly added dropwise, stirred for 5 min, and then heated to 60 °C and stirred for 1 h. The mixture was cooled again to -40 °C, boron tribromide (2.57 g, 10.26 mmol) was added, stirred for 5 min, and then heated to 60 °C and stirred for 2 h. The reaction mixture was cooled to 0 °C, diisopropylethylamine (1.99 g, 15.39 mmol) was added, and the reaction was carried out at 150 °C for 12 h. After the reaction was completed, the organic phase was removed by vacuum distillation, the resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether / ethyl acetate = 15:1) to give compound 69 (1.72 g, yield 37%).

[0294] Example 3

[0295] Synthetic compound 34

[0296]

[0297] Synthesis of intermediate C2

[0298] Under nitrogen protection, starting material a2 (5 g, 18.39 mmol), intermediate B1 (5.52 g, 16.72 mmol), cesium carbonate (10.89 g, 33.44 mmol), and 50 mL of N,N-dimethylformamide were added to a two-necked flask, and the reaction was carried out at 130 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to give intermediate c2 (7.98 g, yield 82%).

[0299] Synthesis of intermediate e2

[0300] Under nitrogen protection, intermediate C2 (5 g, 8.59 mmol), starting material Z3 (1.72 g, 10.30 mmol), cesium carbonate (5.56 g, 17.17 mmol), and 50 mL of N,N-dimethylformamide were added to a two-necked flask, and the reaction was carried out at 130 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to give intermediate E2 (4.89 g, yield 78%).

[0301] Synthesis of intermediate f2

[0302] Under nitrogen protection, intermediate e2 (5 g, 7.69 mmol) was added to a two-necked flask and dissolved in 50 mL of xylene. The reaction mixture was cooled to -40 °C and stirred for 5 min. A hexane solution of n-butyllithium (3.52 mL, 8.45 mmol) was slowly added dropwise, and stirring was continued for 5 min after the addition was complete. The temperature was then raised to 60 °C and the reaction was carried out for 1 h. The system was cooled to -40 °C again, and boron tribromide (3.85 g, 15.37 mmol) was added. After stirring for 5 min, the temperature was raised to 60 °C and the reaction was carried out for 2 h. After the reaction mixture was cooled to 0 °C, diisopropylethylamine (2.98 g, 23.06 mmol) was added, and the reaction was carried out at 150 °C for 12 h. After the reaction was completed, the organic phase was concentrated under reduced pressure, the resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. Finally, it was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to give intermediate f2 (1.56 g, yield 35%).

[0303] Synthesis of Compound 34

[0304] Under nitrogen protection, intermediate f2 (5 g, 8.63 mmol), sulfur (13.85 g, 431 mmol), iodine (547.5 mg, 4.37 mmol), and 50 mL of o-dichlorobenzene were added to a two-necked flask, and the mixture was refluxed for 48 hours. After the reaction was completed, the organic phase was removed by vacuum distillation, the resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to give compound 34 (1.77 g, yield 32%).

[0305] Example 4

[0306] Synthetic compound 337

[0307]

[0308] Synthesis of intermediate C3

[0309] Under nitrogen protection, starting material a2 (5 g, 18.39 mmol), intermediate B7 (5.52 g, 16.72 mmol), cesium carbonate (10.89 g, 33.44 mmol), and 50 mL of N,N-dimethylformamide were added to a two-necked flask, and the reaction was carried out at 130 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to give intermediate c3 (7.98 g, yield 82%).

[0310] Synthesis of intermediate e3

[0311] Under nitrogen protection, intermediate C3 (5 g, 8.59 mmol), starting material Z3 (1.72 g, 10.30 mmol), cesium carbonate (5.56 g, 17.17 mmol), and 50 mL of N,N-dimethylformamide were added to a two-necked flask, and the reaction was carried out at 130 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to give intermediate E3 (4.89 g, yield 78%).

[0312] Synthesis of intermediate f3

[0313] Under nitrogen protection, intermediate E3 (5 g, 7.69 mmol) was added to a two-necked flask and dissolved in 50 mL of xylene. The reaction mixture was cooled to -40 °C and stirred for 5 minutes. A hexane solution of n-butyllithium (3.52 mL, 8.45 mmol) was slowly added dropwise, and stirring was continued for 5 minutes after the addition was complete. The temperature was then raised to 60 °C and the reaction was carried out for 1 hour. The system was cooled to -40 °C again, and boron tribromide (3.85 g, 15.37 mmol) was added. After stirring for 5 minutes, the temperature was raised to 60 °C and the reaction was carried out for 2 hours. After the reaction mixture was cooled to 0 °C, diisopropylethylamine (2.98 g, 23.06 mmol) was added, and the reaction was carried out at 150 °C for 12 hours. After the reaction was completed, the organic phase was concentrated under reduced pressure, the resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Finally, it was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to obtain intermediate f3 (1.56 g, yield 35%).

[0314] Synthesis of Compound 337

[0315] Under nitrogen protection, intermediate f3 (5 g, 8.63 mmol), sulfur (6.83 g, 216 mmol), iodine (547.5 mg, 4.37 mmol), and 50 mL of o-dichlorobenzene were added to a two-necked flask, and the mixture was refluxed for 48 hours. After the reaction was completed, the organic phase was removed by vacuum distillation, the resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 20:1) to give compound 337 (1.93 g, yield 36%).

[0316] Example 5

[0317] Synthetic compound 381

[0318]

[0319] Synthesis of intermediate C4

[0320] Under nitrogen protection, starting material a3 (5 g, 21.98 mmol), Z-series starting material Z4 (5.30 g, 19.99 mmol), cesium carbonate (2 g, 39.97 mmol), and 50 mL of N,N-dimethylformamide were added to a two-necked flask, and the reaction was carried out at 130 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to give intermediate c4 (6.71 g, yield 69%).

[0321] Synthesis of intermediate e4

[0322] Under nitrogen protection, intermediate C4 (5 g, 10.27 mmol) was added to a two-necked flask, dissolved in 50 mL of tetrahydrofuran, cooled to -78 °C, and stirred for 5 minutes. A solution of n-butyllithium in n-hexane (4.28 mL, 10.27 mmol) was added dropwise. After reacting for 1 hour, intermediate C1 (5.55 g, 30.81 mmol) was dissolved in tetrahydrofuran and injected into the reaction mixture. The mixture was stirred at room temperature for 2 hours. The organic phase was then removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was dissolved in 40 mL of glacial acetic acid, and 2 mL of concentrated hydrochloric acid was added. The mixture was refluxed and stirred for 8 hours. After the reaction solution was cooled, it was extracted with dichloromethane, the organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to give intermediate e4 (3.40 g, yield 58%).

[0323] Synthesis of intermediate f4

[0324] Under nitrogen protection, intermediates e4 (5 g, 8.77 mmol), B1 (5.79 g, 17.54 mmol), cesium carbonate (2 g, 17.54 mmol), and 50 mL of N,N-dimethylformamide were added to a two-necked flask, and the reaction was carried out at 130 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to give intermediate f4 (4.71 g, yield 61%).

[0325] Synthesis of Compound 381

[0326] Under nitrogen protection, intermediate f4 (5 g, 5.13 mmol) was added to a two-necked flask, dissolved in 50 mL of xylene, cooled to -40 °C, and stirred for 5 min. A solution of n-butyllithium in n-hexane (472 mmL, 7.38 mmol) was slowly added dropwise, stirred for 5 min, and then heated to 60 °C and stirred for 1 h. The mixture was cooled again to -40 °C, and boron tribromide (2.85 g, 11.36 mmol) was added, stirred for 5 min, and then heated to 60 °C and stirred for 2 h. The reaction mixture was cooled to 0 °C, and diisopropylethylamine (2.20 g, 17.04 mmol) was added. The reaction was carried out at 150 °C for 12 h. After the reaction was completed, the organic phase was removed by vacuum distillation, the resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, filtered, concentrated under vacuum, and then purified by silica gel column chromatography (petroleum ether / ethyl acetate = 15:1) to give compound 381 (1.26 g, yield 26%).

[0327] The following target compounds were synthesized using the same preparation process as in Examples 1-5, with the only difference being the use of intermediates A, B, C, Y, Y, and Z listed in Table 1 below.

[0328] Table 1

[0329]

[0330]

[0331]

[0332] Synthesis of intermediate A1

[0333]

[0334] Synthesis of intermediate A1: Under nitrogen protection, starting material Z1 (5 g, 15.38 mmol), starting material Y1 (2.98 g, 33.85 mmol), tetratetraphenylphosphine palladium (Pd(PPH3)4, 887 mg, 0.76 mmol), tri-tert-butylphosphine (t-Bu3P, 311 mg, 1.54 mmol), potassium carbonate (K2CO3, 8.5 g, 61.54 mmol), 50 mL tetrahydrofuran (THF), and 12.5 mL water (H2O) were added to a two-necked flask. The mixture was stirred at 70 °C for 24 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and the organic solvent was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to give intermediate A1 (2.75 g, yield 71%).

[0335] Synthesis of intermediate A12

[0336]

[0337] Synthesis of intermediate A12: Under nitrogen protection, starting materials Z1 (5 g, 20.32 mmol), Y2 (5.45 g, 44.71 mmol), tetratetraphenylphosphine palladium (1.16 g, 1 mmol), tri-tert-butylphosphine (411.5 mg, 2.03 mmol), potassium carbonate (11.23 g, 81.29 mmol), 50 mL tetrahydrofuran, and 12.5 mL water were added to a two-necked flask. The reaction was carried out at 70 °C for 24 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to give intermediate A12 (3.17 g, yield 67%).

[0338] Synthesis of intermediate A23

[0339]

[0340] Synthesis of intermediate A23: Under nitrogen protection, starting material Z2 (2.5 g, 10.16 mmol), starting material Y3 (4.79 g, 22.35 mmol), tetraphenylphosphine palladium (912 mg, 0.865 mmol), potassium carbonate (4.22 g, 30.64 mmol), 50 mL tetrahydrofuran, and 12.5 mL water were added to a two-necked flask, and the reaction was carried out at 70 °C for 24 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain intermediate A23 (4.94 g, yield 73%).

[0341] Synthesis of intermediate M1

[0342]

[0343] Synthesis of intermediate M1: Under nitrogen protection, starting material Z3 (5 g, 20.24 mmol), starting material Y5 (4.05 g, 24.35 mmol), tetraphenylphosphine palladium (912 mg, 0.865 mmol), potassium carbonate (5.59 g, 40.47 mmol), 50 mL tetrahydrofuran, and 12.5 mL water were added to a two-necked flask, and the reaction was carried out at 70 °C for 8 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to give intermediate M1 (4.33 g, yield 75%).

[0344] Synthesis of intermediate A5

[0345]

[0346] Synthesis of intermediate A5: Under nitrogen protection, intermediate M1 (4 g, 13.83 mmol), cesium carbonate (Cs₂CO₃, 22.53 g, 69.13 mmol), triphenylphosphine (PPh₃, 18.13 g, 69.13 mmol), and 50 mL of o-dichlorobenzene (ODCB) were added to a two-necked flask, and the reaction was carried out at 180 °C for 12 h. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to give intermediate A5 (2.77 g, yield 78%).

[0347] It should be noted that the synthesis methods of the above intermediates A13 and A7 are similar to some of the synthesis steps of the above intermediate A5, and the synthesis steps of the above intermediates A17 and A19 are similar to some of the synthesis steps of intermediate A11.

[0348] Synthesis of intermediate N1

[0349]

[0350] Synthesis of intermediate N1: Under nitrogen protection, starting material Z6 (5 g, 21.15 mmol), starting material Y6 (7.6 g, 19.035 mmol), tetraphenylphosphine palladium (1.2 g, 1.06 mmol), potassium carbonate (5.85 g, 42.29 mmol), 50 mL tetrahydrofuran, and 12.5 mL water were added to a two-necked flask, and the reaction was carried out at 70 °C for 8 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain intermediate N1 (8.75 g, yield 81%).

[0351] Synthesis of intermediate M2

[0352]

[0353] Synthesis of intermediate M2: Under nitrogen protection, intermediate N1 (5 g, 9.78 mmol), cesium carbonate (9.56 g, 29.35 mmol), palladium acetate (Pd(OAc)2, 109.8 mg, 0.489 mmol), 10 mL of N,N-dimethylacetamide (DMA), and 40 mL of xylene were added to a two-necked flask, and the reaction was carried out at 75 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to give intermediate M2 (2.69 g, yield 58%).

[0354] Synthesis of intermediate B2:

[0355]

[0356] Synthesis of intermediate B2: Under nitrogen protection, intermediate M1 (5 g, 10.54 mmol), cesium carbonate (13.73 g, 42.12 mmol), triphenylphosphine (11.05 g, 42.12 mmol), and 50 mL of o-dichlorobenzene were added to a two-necked flask, and the reaction was carried out at 160 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to give intermediate B2 (2.77 g, yield 78%).

[0357] Synthesis of intermediate Y10

[0358]

[0359] Synthesis of intermediate Y10: Under nitrogen protection, intermediate A5 (5 g, 19.43 mmol), starting material Y8 (3.90 g, 19.43 mmol), sodium tert-butoxide (3.73 g, 38.80 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-Phos, 968.54 mg, 2.03 mmol), dibenzylacetone palladium (Pd2(dba)3, 889 mg, 0.97 mmol), and 50 mL of xylene were added to a two-necked flask, and the reaction was carried out at 140 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to give intermediate Y10 (5.4 g, yield 79%).

[0360] Synthesis of intermediate N5

[0361]

[0362] Synthesis of intermediate N5: Under nitrogen protection, starting material Z6 (5 g, 21.15 mmol), intermediate Y10 (7.18 g, 19.035 mmol), tetraphenylphosphine palladium (1.2 g, 1.06 mmol), potassium carbonate (5.85 g, 42.29 mmol), 50 mL tetrahydrofuran, and 12.5 mL water were added to a two-necked flask, and the reaction was carried out at 70 °C for 8 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain intermediate N5 (7.55 g, yield 73%).

[0363] Synthesis of intermediate M5

[0364]

[0365] Synthesis of intermediate M5: Under nitrogen protection, intermediate N5 (5 g, 10.23 mmol), cesium carbonate (10 g, 30.68 mmol), palladium acetate (Pd(OAc)2, 229 mg, 1.02 mmol), 10 mL N,N-dimethylacetamide (DMA), and 40 mL xylene were added to a two-necked flask, and the reaction was carried out at 75 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether:ethyl acetate = 10:1) to give intermediate M5 (2.78 g, yield 60%).

[0366] Synthesis of intermediate B5

[0367]

[0368] Synthesis of intermediate B5: Under nitrogen protection, intermediate M5 (5 g, 11.54 mmol), cesium carbonate (14.4 g, 44.12 mmol), triphenylphosphine (11.59 g, 44.12 mmol), and 50 mL of o-dichlorobenzene were added to a two-necked flask, and the reaction was carried out at 160 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to give intermediate B5 (3.53 g, yield 76%).

[0369] It should be noted that the synthesis methods of the above intermediates B12, B3, and B18 are similar to the synthesis method of the above intermediate B5.

[0370] Synthesis of intermediate C3

[0371]

[0372] Synthesis of intermediate C3: Under nitrogen protection, starting material W1 (5 g, 14.79 mmol), starting material Y1 (2.86 g, 32.54 mmol), tetratetraphenylphosphine palladium (855 mg, 0.74 mmol), tri-tert-butylphosphine (300 mg, 1.48 mmol), potassium carbonate (8.5 g, 61.54 mmol), 50 mL tetrahydrofuran, and 12.5 mL water were added to a two-necked flask, and the reaction was carried out at 70 °C for 24 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to give intermediate C3 (2.93 g, yield 75%).

[0373] Synthesis of intermediate C9

[0374]

[0375] Synthesis of intermediate C9: Under nitrogen protection, starting material W4 (5 g, 23.56 mmol), starting material H1 (10.03 g, 70.69 mmol), potassium carbonate (13.03 g, 94.25 mmol), and 50 mL of acetone were added to a two-necked flask, and the reaction was carried out at 60 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the organic phase was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain intermediate C9 (4.53 g, yield 80%).

[0376] Synthesis of intermediate H1

[0377]

[0378] Synthesis of intermediate H1: Under nitrogen protection, starting material K1 (5 g, 19.08 mmol), starting material E1 (5.96 g, 19.08 mmol), potassium carbonate (K2CO3, 7.91 g, 57.24 mmol), cuprous iodide (CuI, 726 mg, 3.82 mmol), reduced iron powder (Fe, 1.07 g, 19.08 mmol), and 50 mL of dimethyl sulfoxide (DMSO) were added to a two-necked flask, and the reaction was carried out at 120 °C for 12 hours. After the reaction was completed, the mixture was cooled, and the solvent was removed by vacuum distillation. The resulting mixture was extracted with dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography to obtain the crude product (such as intermediate G1). The crude product was dissolved in 80 mL of deionized water, potassium hydroxide (KOH, 2.14 g, 38.16 mmol) was added, and the mixture was heated under reflux for 12 hours. After the reaction solution was cooled, excess hydrochloric acid (HCl) was added dropwise, and a solid was precipitated. The solid was filtered and washed with ethanol to obtain intermediate H1 (4.39 g, yield 83%).

[0379] Synthesis of intermediate C16

[0380]

[0381] Synthesis of intermediate C16: Intermediate H1 (5 g, 18.04 mmol) was dissolved in trifluoromethanesulfonic acid (TfOH), and the mixture was stirred at 100 °C for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the reaction was quenched with deionized water, and a solid precipitated. The solid was filtered and washed with ethanol to give intermediate C16 (4.83 g, yield 92%).

[0382] It should be noted that the synthesis methods of the above intermediates C1, C2, C8, and C15 are similar to the synthesis method of the above intermediate C3, and the synthesis method of intermediate C15 is similar to the synthesis method of the above intermediate C16.

[0383] To compare material properties, the following six molecules were selected as comparative examples.

[0384]

[0385] Table 2 below compares the thermal stability and thin film stability of the polycyclic luminescent molecules of the compounds in the examples and the comparative compounds. The thermogravimetric temperature represents the temperature at which the mass loss of the compound in the luminescent layer reaches 5% of the total mass, and the glass transition temperature refers to the critical temperature at which the material changes from an amorphous state to a crystalline state.

[0386] Table 2

[0387]

[0388]

[0389] Thermodynamic testing results show that the introduction of seven-membered rings and spiro rings significantly improves the thermal stability of organic electroluminescent devices. Further comparison of the performance of organic electroluminescent devices prepared from organic light-emitting compounds containing different numbers of spiro rings confirms that the overall rigid structure design of this invention not only helps improve color purity and luminous efficiency but also contributes to improving the thermal stability of organic electroluminescent devices.

[0390] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device based on the boron-nitrogen heterocyclic resonant organic light-emitting compound of the present invention.

[0391] Organic electroluminescent devices were prepared using the compounds of the examples and comparative compounds described above. The devices included an ITO anode layer 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and an Al cathode layer 10, which were sequentially laminated on a transparent glass substrate 1.

[0392] Organic electroluminescent device Example 1.1

[0393] The process is as follows: an indium tin oxide (ITO) glass substrate 1 is placed in a vacuum chamber, and a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially deposited on the anode (ITO) 2. Finally, the organic electroluminescent device prepared above is encapsulated with ultraviolet light-curing adhesive to isolate it from the influence of water, oxygen, and dust.

[0394] The organic electroluminescent device in Example 1.1 was fabricated using a vacuum evaporation method. The transparent substrate layer 1 was a glass substrate. The ITO anode layer 2 (135 nm thick) was cleaned sequentially using commercial cleaning agents, deionized water, ethanol, and acetone via ultrasonic cleaning, three times with each solvent, each time for 10 minutes. After cleaning, the substrate was baked and dried in a clean environment for 6 hours, followed by ultraviolet ozone treatment to remove organic residues from the transparent ITO surface. The cleaned ITO glass substrate was placed in a vacuum chamber, and the vacuum was evacuated to below 1 × 10⁻⁶. -5Pa. Using a vacuum evaporation apparatus, HI-1 and HT-1 with a thickness of 10 nm were deposited as hole injection layer 3, with a mass ratio of HI-1 to HT-1 of 10:90. Next, HT-1 with a thickness of 50 nm was deposited as hole transport layer 4. Subsequently, Tri-PCz with a thickness of 10 nm was deposited as electron blocking layer 5. After the electron blocking materials were deposited, the emitting layer 6 of the OLED light-emitting device was fabricated, using mCBP as the host material, compound 1 as the dopant material, and S1 (5CzTRZ) as the exciton sensitizer material. The emitting layer was prepared by three-source co-evaporation of mCBP, S1 (5CzTRZ), and the compound at a mass ratio of 85:10:5, with a film thickness of 20 nm. After the emitting layer 6, CF3-TRZ was vacuum-deposited with a thickness of 5 nm; this layer served as hole blocking layer 7. Following the hole-blocking layer 7, BPPB and Liq are co-evaporated at a mass ratio of 75:25, resulting in a 35 nm thick film, which serves as the electron transport layer 8. On top of the electron transport layer 8, a 1.5 nm thick Liq layer is fabricated using a vacuum evaporation apparatus; this serves as the electron injection layer 9. On top of the electron injection layer 9, a 100 nm thick Al electrode layer is fabricated using a vacuum evaporation apparatus; this serves as the cathode layer 10. Finally, UV-curable adhesive is used to bond the OLED glass to a glass cover or metal cover, achieving a seal between the organic layers and electrodes on the substrate. This isolates the OLED from external water, oxygen, and dust, ensuring stable operation of the organic light-emitting device.

[0395] Examples of organic electroluminescent devices: 1.2-1.32

[0396] Except for replacing the final luminescent material in the luminescent layer of Organic Electroluminescent Device Example 1.1 with the boron-nitrogen resonance organic compounds mentioned in Table 3 below, Organic Electroluminescent Device Examples 1.2-1.32 were fabricated under the same conditions as Organic Electroluminescent Device Example 1.1.

[0397] Organic electroluminescent devices: Comparative examples 1.1-1.6

[0398] Except for replacing the final luminescent material in the luminescent layer of Organic Electroluminescent Device Example 1.1 with the comparative compounds listed in Table 3 below, comparative organic electroluminescent devices 1.1-1.6 were fabricated under the same conditions as Organic Electroluminescent Device Example 1.1.

[0399] The molecular structural formulas of the relevant materials used in the examples and comparative examples of organic electroluminescent devices are shown below.

[0400]

[0401] Table 3

[0402]

[0403]

[0404]

[0405]

[0406]

[0407] Under ambient temperature and pressure, the luminescence performance of the devices prepared in Device Examples 1.1-1.32 and Comparative Examples 1.1-1.6 of this invention was tested, and the test results are shown in Table 3. It should be noted that the electroluminescence spectra were measured using a Photo Research PR655 spectrometer; the external quantum efficiency of the devices was calculated according to the method described in the literature "Adv. Mater., 2003, 15, 1043-1048". Among them, EQE... max EQE represents the maximum external quantum efficiency of the device. 1000 This indicates that the device has a brightness of 1000 cd / m². 2 External quantum efficiency at time; device lifetime expressed at initial luminance of 1000 cd / m². 2 Under the given conditions, the time it takes for the device brightness to decay to 95% of its initial value is measured. The test results are shown in Table 4.

[0408] Table 4

[0409]

[0410]

[0411] Organic electroluminescent device Example 2.1

[0412] The process is as follows: an indium tin oxide (ITO) glass substrate 1 is placed in a vacuum chamber, and a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially deposited on the anode (ITO) 2. Finally, the organic electroluminescent device prepared above is encapsulated with ultraviolet light-curing adhesive to isolate it from the influence of water, oxygen, and dust.

[0413] The organic electroluminescent device in Example 2.1 was fabricated using a vacuum evaporation method. The transparent substrate layer 1 was a glass substrate. The ITO anode layer 2 (135 nm thick) was cleaned sequentially using commercial cleaning agents, deionized water, ethanol, and acetone via ultrasonic cleaning, three times with each solvent, each time for 10 minutes. After cleaning, the substrate was baked and dried in a clean environment for 6 hours, followed by ultraviolet ozone treatment to remove organic residues from the transparent ITO surface. The cleaned ITO glass substrate was placed in a vacuum chamber, and the vacuum was evacuated to less than 1 × 10⁻⁶. -5 Pa. Using a vacuum evaporation apparatus, HI-1 and HT-1 with a thickness of 10 nm were deposited as hole injection layer 3, with a mass ratio of HI-1 to HT-1 of 10:90. Next, HT-1 with a thickness of 50 nm was deposited as hole transport layer 4. Subsequently, Tri-PCz with a thickness of 10 nm was deposited as electron blocking layer 5. After the electron blocking materials were deposited, the emitting layer 6 of the OLED light-emitting device was fabricated, using mCBP as the host material, compound 1 as the dopant, and S2 as the exciton sensitizer. The emitting layer was prepared by three-source co-evaporation of mCBP, S2, and the compound at a mass ratio of 80:15:5, with a film thickness of 20 nm. After the emitting layer 6, CF3-TRZ was vacuum-deposited with a film thickness of 5 nm; this layer served as hole blocking layer 7. After the hole blocking layer 7, BPPB and Liq were co-evaporated at a mass ratio of 75:25, with a film thickness of 35 nm; this layer served as electron transport layer 8. On the electron transport layer 8, a 1.5 nm thick Liq layer is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, a 100 nm thick Al electrode layer is fabricated using a vacuum evaporation apparatus; this layer serves as the cathode layer 10. Finally, the OLED glass is bonded to a glass cover plate or a metal cover plate using UV-curable adhesive, achieving a seal between the organic layer and the electrode on the substrate. This isolates the OLED from external water, oxygen, and dust corrosion, ensuring stable operation of the organic light-emitting device.

[0414] Examples of organic electroluminescent devices 2.2-2.18

[0415] Except for replacing the final luminescent material in the luminescent layer of Organic Electroluminescent Device Example 2.1 with the boron-nitrogen resonance organic compound mentioned in Table 5 below, Organic Electroluminescent Device Examples 2.2-2.32 were fabricated under the same conditions as Organic Electroluminescent Device Example 2.1.

[0416] Organic electroluminescent devices: Comparative Examples 2.1-2.6

[0417] Except for replacing the final luminescent material in the luminescent layer of Organic Electroluminescent Device Example 2.1 with the comparative compounds listed in Table 5 below, comparative organic electroluminescent devices 2.1-2.6 were fabricated under the same conditions as Organic Electroluminescent Device Example 2.1.

[0418] The specific materials and thicknesses used in Examples 2.1-2.18 and Comparative Examples 2.1-2.6 are shown in Table 5.

[0419] The molecular structural formulas of the relevant materials used in the examples and comparative examples of organic electroluminescent devices are shown below.

[0420]

[0421] Table 5

[0422]

[0423]

[0424]

[0425] Under normal temperature and pressure conditions, the light-emitting performance of the devices prepared in Device Examples 2.1-2.18 and Device Comparative Examples 2.1-2.6 of the present invention was tested, and the test results are shown in Table 6.

[0426] Table 6

[0427]

[0428]

[0429] As shown in Tables 4 and 6, the organic electroluminescent device prepared using the boron-nitrogen heterocyclic resonance organic light-emitting compound provided by this invention significantly outperforms the comparative device in terms of device lifetime, external quantum efficiency, and full width at half maximum (FWHM). This invention effectively reduces the FWHM while retaining the color modulation effect of the spirocyclic and heteroatom bridging structures (oxygen, sulfur, etc.), and significantly improves the efficiency roll-off problem of organic electroluminescent devices. Simultaneously, the introduction of the polycyclic aromatic amine structure further enhances the molecular planar rigidity of the boron-nitrogen resonance system, further extending the device lifetime and mitigating efficiency roll-off. The combined effect of the polycyclic aromatic amine and spirocyclic structures enhances the overall rigidity of the organic light-emitting compound, effectively suppressing excited-state structural relaxation, thus enabling the organic light-emitting compound to simultaneously possess the advantages of high luminous efficiency, narrow spectral emission, and long operating lifetime.

[0430] In summary, the boron-nitrogen heterocyclic resonant organic light-emitting compound of the present invention can be used as a light-emitting guest or dopant in organic electroluminescent devices. It is a high-performance organic light-emitting functional material with good prospects for commercial application.

[0431] The specific embodiments described above further illustrate the purpose, technical solution, and beneficial effects of the present invention. It should be understood that the above descriptions are merely specific embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A boron-nitrogen heterocyclic resonance organic light-emitting compound, characterized in that, It has the structure shown in equation (1): Equation (1); Among them, R1-R 18 Each element is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 heteroalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted C2-C20 alkoboro, substituted or unsubstituted C3-C20 alksilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or Unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C8-C20 arylsilalkyl, substituted or unsubstituted C9-C20 silylaryl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, sulfinyl, sulfonyl, phosphine, and combinations thereof; R1-R 18 The substituents in the middle are connected by single bonds or circumferential rings; R1-R 17 Any two adjacent substituents can connect to form a ring; Z is either N or C, where Z is N, the adjacent Z is C, and R1-R connected to N are... 17 It does not exist; X1 and X2 are each independently selected from -C(R a )2-、-N(R a )2-、-Si(R a )2-、-P(R a )3-、-P(R a )-、-P(R a )=O-、-Ge(R a -2-, -S(=O)2-, -S-, -O-, -Se-, -Te-, single bond or not present; R a Selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, C6-C30 aryl, and C5-C30 heteroaryl; R a It can be monosubstituted, disubstituted, polysubstituted, or unsubstituted; The substituents used for the above-mentioned substituents are selected from any one of deuterium, tritium, halogen, cyano, C1-C20 alkyl, deuterium or tritium-substituted C1-C20 alkyl, C5-C30 heteroaryl, deuterium or tritium-substituted C5-C30 heteroaryl. The heteroalkyl group or heterocyclic alkyl group contains heteroatoms selected from at least one of O, S, N, Se, Si, and B. The heteroatom in the heteroaryl group is selected from at least one of O, S, N, Se, Si, and B.

2. The boron-nitrogen heterocyclic resonance organic light-emitting compound according to claim 1, characterized in that, In the structure shown in equation (1): R1-R 18 Each is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 heteroalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkoboryl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C8-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof; R1-R 18 The replacement method is either a single key or a parallel loop connection; R1-R 17 Any adjacent substituents can be optionally linked to form a ring; X1 and X2 are each independently selected from -C(R a )2-、-N(R a )2-、-Si(R a )2-、-P(R a )3-、-P(R a )-、-P(R a )=O-、-Ge(R a )2-, -S(=O)2-, -S-, -O-, -Se-, -Te-; When X1 and X2 are -C(R) a )2-、-N(R a )2-、-Si(R a )2-、-P(R a )3-、-P(R a )-、-P(R a )=O-、-Ge(R a In the case of )2-, R a Adjacent substituents can be optionally linked to form a ring; Given that X1 and X2 exist, R1-R 18 It is not simultaneously hydrogen, and can optionally connect with adjacent substituents to form a ring; R a Selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, C6-C30 aryl, and C5-C30 heteroaryl; R a It can be monosubstituted, disubstituted, polysubstituted, or unsubstituted; The substituents used for the above-mentioned substituents are selected from any one of deuterium, tritium, halogen, cyano, C1-C20 alkyl, deuterium or tritium-substituted C1-C20 alkyl, C5-C30 heteroaryl, deuterium or tritium-substituted C5-C30 heteroaryl. The heteroatom in the heteroalkyl group is selected from at least one of O, S, N, Se, Si, and B; The heteroatom in the heteroaryl group is selected from at least one of O, S, N, Se, Si, and B.

3. The boron-nitrogen heterocyclic resonance organic light-emitting compound according to claim 1, characterized in that, The structure of the boron-nitrogen heterocyclic resonance organic light-emitting compound is shown in any one of formulas (1-1) to (1-3): Equation (1-1); Equation (1-2); Equation (1-3); R1-R 17 Each is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 heteroalkyl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7 -C30 aralkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C8-C20 arylsilalkyl, substituted or unsubstituted C9-C20 silylaryl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof; R 18 The group is selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 heteroalkyl, substituted or unsubstituted C3-C15 alkylsilyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C18 heteroaryl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C7-C18 aralkyl, substituted or unsubstituted C6-C18 aryloxy, substituted or unsubstituted C6-C18 arylthio, substituted or unsubstituted C6-C18 arylamine, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof; R 35 -R 38 Each is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 heteroalkyl, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof; R1-R 18 R 35 -R 38 The substituents in the middle are connected by single bonds or circumferential rings; R 35 and R 36 R 37 and R 38 They can be connected to form a loop, R1-R 17 R 35 -R 38 Any two adjacent substituents can connect to form a ring; X1 and X2 are each independently selected from -C(R a )2-、-N(R a )2-、-Si(R a )2-、-P(R a )3-、-P(R a )-、-P(R a )=O-、-Ge(R a )2-, -S(=O)2-, -S-, -O-, -Se-, -Te-; When X1 and X2 are -C(R) a )2-、-N(R a )2-、-Si(R a )2-、-P(R a )3-、-P(R a )-、-P(R a )=O-、-Ge(R a In the case of )2-, R a Adjacent substituents can be optionally linked to form a ring; R a Selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, C6-C30 aryl, and C5-C30 heteroaryl; R a It can be monosubstituted, disubstituted, polysubstituted, or unsubstituted; The substituents used for the above-mentioned substituents may be selected from any one of deuterium, tritium, halogen atom, cyano, C1-C20 alkyl, deuterium or tritium-substituted C1-C20 alkyl, C5-C30 heteroaryl, deuterium or tritium-substituted C5-C30 heteroaryl.

4. The boron-nitrogen heterocyclic resonance organic light-emitting compound according to any one of claims 1-3, characterized in that, The R a The C6-C30 aralkyl group is selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-dimethylenefluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, and substituted or unsubstituted phenanthryl. The R a The heteroaryl groups of C5-C30 are selected from substituted or unsubstituted xanthanes, thioxanthanes, tin-oxanthanes, germanium-oxanthanes, azirmonyl, substituted or unsubstituted thiofluorenyl, spirodifluorenyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted tetraphenylsilyl, substituted or unsubstituted silylspiroyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted aniline, substituted or unsubstituted diphenylamine, and substituted or unsubstituted N-phenylcarbazoyl.

5. The boron-nitrogen heterocyclic resonance organic light-emitting compound according to claim 3, characterized in that, The structure of the boron-nitrogen heterocyclic resonance organic light-emitting compound is shown in formula (2-1): Equation (2-1); Among them, X1 and X2 are each independently selected from Si or C; R1-R 17 R 20 -R 25 R 28 -R 33 Each is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 heteroalkyl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C8-C20 arylsilyl, substituted or unsubstituted C9-C20 silylaryl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof; R 18 The group is selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 heteroalkyl, substituted or unsubstituted C3-C15 alkylsilyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C18 heteroaryl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C7-C18 aralkyl, substituted or unsubstituted C6-C18 aryloxy, substituted or unsubstituted C6-C18 arylthio, substituted or unsubstituted C6-C18 arylamine, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof; R 19 R 26 R 27 R 34 Each is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 heteroalkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof; R1-R 34 The substituents in the middle are connected by single bonds or circumferential rings; R1-R 17 Any two adjacent substituents can connect to form a ring; The substituents used for the above-mentioned substituents may be selected from any one of deuterium, tritium, halogen, cyano, C1-C20 alkyl, deuterium or tritium-substituted C1-C20 alkyl, C5-C30 heteroaryl, deuterium or tritium-substituted C5-C30 heteroaryl.

6. The boron-nitrogen heterocyclic resonance organic light-emitting compound according to claim 3, characterized in that, The structures of the boron-nitrogen heterocyclic resonance organic light-emitting compounds are shown in formulas (2-2) to (2-3): Equation (2-2); Equation (2-3); Among them, X1 and X2 are each independently selected from Si or C; R1-R 17 R 20 -R 25 R 28 -R 33 Each element is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 heteroalkyl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7- Aryl groups of C30, substituted or unsubstituted aryloxy groups of C6-C30, substituted or unsubstituted arylthio groups of C6-C30, substituted or unsubstituted arylamine groups of C6-C30, substituted or unsubstituted arylsilyl groups of C8-C20, substituted or unsubstituted silylaryl groups of C9-C20, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isonitrile groups, thio groups, phosphin groups, and combinations thereof; R 18 Each is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 heteroalkyl, substituted or unsubstituted C3-C15 alkylsilyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C18 heteroaryl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C7-C18 aralkyl, substituted or unsubstituted C6-C18 aryloxy, substituted or unsubstituted C6-C18 arylthio, substituted or unsubstituted C6-C18 arylamine, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof; R 19 R 26 R 27 R 34 R 35 R 36 R 37 R 38 Each is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 heteroalkyl, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C0-C8 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isonitrile, thio, phosphine, and combinations thereof; R1-R 34 The substituents in the middle are connected by single bonds or circumferential rings; R1-R 17 R 35 R 38 Any two adjacent substituents can connect to form a ring; The substituents used for the above-mentioned substituents may be selected from any one of deuterium, tritium, halogen, cyano, C1-C20 alkyl, deuterium or tritium-substituted C1-C20 alkyl, C5-C30 heteroaryl, deuterium or tritium-substituted C5-C30 heteroaryl.

7. The boron-nitrogen heterocyclic resonance organic light-emitting compound according to claim 5 or 6, characterized in that, The R1-R 34 Each of the following is independently represented as hydrogen, deuterium, tritium, fluorine, bromine, cyano, substituted or unsubstituted boronyl, substituted or unsubstituted methoxy, substituted or unsubstituted tert-butoxy, substituted or unsubstituted phenoxy, substituted or unsubstituted phenylthio, substituted or unsubstituted phenylselenoyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenselenoyl, substituted or unsubstituted adamantyl, substituted or unsubstituted methyl, trifluoromethyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted diphenyletheryl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted Or unsubstituted phenanthrene, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted aniline, substituted or unsubstituted diphenylamine, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted thiofluorenyl, spirodifluorenyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted tetraphenylsilyl, substituted or unsubstituted silylspiroyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted trimethylsilyl; The substituents replacing the above-mentioned substituents are selected from deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, deuterated adamantyl, cyano, methyl, deuterated methyl, benzyl, ethyl, deuterated ethyl, phenethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, tert-pentyl, deuterated tert-pentyl, tert-butyl, deuterated tert-butyl, phenyl tert-butyl, n-butyl, phenyl n-butyl, methoxy, tert-butyloxy, phenyl, tert-butylphenyl, tolyl, ethylphenyl, isopropylphenyl, m-xylyl group, trimethylyl, m-diisopropylphenyl, di One or more of the following: biphenyl, methyl diphenyl, tert-butyl diphenyl, naphthyl, anthraceneyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalyl, quinolinyl, isoquinoxalyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, aziphenanthyl, tert-butoxy, phenoxy, phenylthio, phenylselenoyl, phenoxazinyl, phenthiazolyl, and phenselenozinyl.

8. The boron-nitrogen heterocyclic resonance organic light-emitting compound according to claim 7, characterized in that, The R1-R 17 R 19 -R 34 R 35 -R 38 Each can be independently classified into any of the following structures: 。 9. The boron-nitrogen heterocyclic resonance organic light-emitting compound according to claim 6, characterized in that, The R 36 R 18 R 37 Each is independently selected from the following structure: Hydrogen, deuterium, fluorine, bromine, cyano, methyl, tert-butyl, ethyl, isopropyl, deuterated methyl, cyclopentane, cyclohexane, dimethylcyclohexane; 。 10. The boron-nitrogen heterocyclic resonance organic light-emitting compound according to claim 1, characterized in that, It has any of the following structures: 。 11. A material for use in organic electroluminescent devices, characterized in that, Including boron-nitrogen heterocyclic resonant organic light-emitting compounds as described in any one of claims 1-10.

12. An application of the boron-nitrogen heterocyclic resonance organic light-emitting compound according to any one of claims 1-10, characterized in that, The applications include at least one of the following: organic electroluminescent devices, organic solar cells, organic field-effect transistors, organic thin-film transistors, organic lasers, organic spintronic devices, electronic component modules, and lighting panels.

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