A class of organic compounds based on phenoloxy-boron nitrogen structure and their applications

Abstract

This invention provides an organic compound with a phenol-oxygen-boron-nitrogen structure and relates to an organic electroluminescent device employing this organic compound. By constructing a rigid polycyclic aromatic boron-nitrogen skeleton, the compound of this invention exhibits high luminous efficiency, narrow spectral emission, and high stability. The organic compound of this invention is shown in general formula (1):

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and particularly to an organic compound with a phenol-oxygen-boron-nitrogen structure, as well as the application of this luminescent material and organic electroluminescent devices containing the compound. Background Technology

[0002] In the early stages of OLED development, traditional small-molecule organic fluorescent materials were mainly used, which exhibited good device stability. However, theoretically, only 25% of singlet excitons could be utilized, while the remaining 75% of triplet excitons underwent nonradiative inactivation. Second-generation phosphorescent materials, due to the spin-orbit coupling effect (SOC) of heavy metals, can effectively promote intersystem crossing of electrons from singlet to triplet states, fully utilizing all singlet and triplet excitons generated by electro-excitation, achieving a maximum theoretical quantum efficiency of 100%. However, phosphorescent materials typically require the introduction of extremely expensive rare heavy metals, resulting in high preparation costs and limited reserves of precious metals. Subsequently, Professor Adachi synthesized a series of thermally activated delayed fluorescence (TADF) materials with donor-acceptor frameworks. This donor-acceptor molecular design enables spatial separation of HOMO and LUMO, achieving minimal HOMO and LUMO overlap and a small singlet and triplet energy level difference ΔE. S1-T1 Under thermal excitation in the surrounding environment, it can achieve reverse intersystem crossing (RISC) from the lowest triplet excited state (T1) to the lowest singlet excited state (S1), thus effectively utilizing triplet excitons to generate delayed fluorescence, and its theoretical internal quantum efficiency can reach 100%. The biggest advantage of TADF materials is that they are made of pure organic materials, avoiding the use of metal-organic complexes containing precious metals, which has great application prospects in the field of OLEDs. However, according to the Franck-Condon principle, small HOMO and LUMO overlap will reduce the radiative transition rate, so traditional DA-type TADF materials are difficult to meet the requirements of simultaneously improving both the RISC rate and the radiative transition rate. In addition, this donor-acceptor structure TADF material has a large Stokes shift, resulting in a broad emission spectrum, a large device efficiency roll-off, and stability that does not yet meet the requirements of commercial applications.

[0003] Organoboron compounds possess unique optical and electronic properties, and have been extensively studied and used as organic optoelectronic materials, promising to achieve efficient and stable luminescence and solve the aforementioned problems. Rigid polycyclic aromatic boron-nitrogen structures can not only effectively suppress nonradiative energy loss caused by vibrational coupling and improve luminescence quantum efficiency, but also tune their electronic state structure to enhance electron transport capabilities and obtain excellent photophysical properties. Summary of the Invention

[0004] The purpose of this invention is to provide an organic compound based on a phenoxy-boron nitrogen structure, which can be used in the fields of OLED displays and lighting.

[0005] Its characteristic is that its chemical formula is as shown in general formula (1) or (2):

[0006]

[0007] In formula (1) or (2),

[0008] Y1 and Y2 independently represent single bonds, O, CO, SO2, S, and NR, respectively. a BR b CR c R d or SiR e R f ;

[0009] R a R b R c R d R e R f Each of them is independent and either not connected to its adjacent R1, R2, R3, and R4, or connected to form a loop;

[0010] The R a R b R c R d R e R f Each group is independently selected from one of the following groups, substituted or unsubstituted: hydrogen, deuterium, C1-C1. 36 Alkyl groups, C1-C 36 alkoxy groups, C3-C 36 cycloalkyl, C1-C 36 ethers, C5-C 60 heteroaryl, C4-C 60 aryl, C4-C 60 aryloxy groups, C4-C 30 arylamino groups or combinations thereof, wherein two adjacent substituents may fuse into a ring;

[0011] The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Each group is independently selected from one of the following groups: hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, silyl, cyano, amino, or substituted or unsubstituted: C1 to C2. 36 Alkyl groups, C1-C 36 alkoxy groups, C3-C 36 cycloalkyl, Cl ~C 20 Thioalkoxy groups, C1-C 36 ethers, C5-C 60 heteroaryl, C4-C 60 aryl, C4-C 60 aryloxy groups, C4-C 30 arylamino, C4-C 30 heteroarylamino groups or combinations thereof, wherein two adjacent substituents may fuse into a ring;

[0012] The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Each can be independently represented from a single substituent to the maximum permissible number of substituent groups;

[0013] The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Two adjacent elements are either not connected or connected by a single key;

[0014] Furthermore, in formula (1), R1, R2, R3, R4, and R5 are each independently selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, or substituted or unsubstituted groups from the following: C1 to C2. 36 Alkyl groups, C1-C 36 alkoxy groups, C3-C 36 cycloalkyl, C l ~C 20 Thioalkoxy groups, C1-C 36 ethers, C5-C 60 heteroaryl, C4-C 60 aryl, C4-C 60 aryloxy groups, C4-C 30 arylamino, C4-C 30 heteroarylamino groups or combinations thereof, wherein two adjacent substituents may fuse into a ring;

[0015] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10Each group is independently selected from hydrogen or from one or more combinations of the following groups: deuterium, cyano, trifluoromethyl, halogen, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, fluorene, spirodifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans ind[a]fluorene, trimenyl, isotriin , spirotri-indene, spiroisotri-indene, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, isoindoleyl, carbazoleyl, indoxarcarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthiazoleyl, phenanthreneazoleyl, pyridinazoleyl, pyrazinazoleyl, quinoxalo-imidazolyl, oxazolyl, benzooxazolyl, naphthiazoleyl, anthraquinazoleyl, phenanthrene Enoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazathanthyl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbazolinyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-enoxadiazolyl, 1,2, 5-Omnidiazolyl, 1,2,3-Thiadiazolyl, 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,3,5-Triazinyl, 1,2,4-Triazinyl, 1,2,3-Triazinyl, Tetrazolyl, 1,2,4,5-Tetrazolyl, 1,2,3,4-Tetrazolyl, 1,2,3,5-Tetrazolyl, Purinyl, Pteridyl, Indazinyl, Benzothiadiazolyl, Diphenylboryl, Dimethylboryl, Dipentafluorophenylboryl, Di(2,4,6-Triisopropylphenyl)boryl, 9,9-Dimethylacridyl, (poly)halobenzene, (poly)cyanobenzene or (poly)trifluoromethylbenzene;

[0016] Furthermore, the compounds of general formula (1) of the present invention can preferably be the following specific structural compounds BON1 to BON196, which are only representative examples:

[0017]

[0018]

[0019]

[0020]

[0021]

[0022]

[0023]

[0024] In the present invention, the "substituted or unsubstituted" group / ring may be substituted with one substituent or multiple substituents. When there are multiple substituents (at least two), they may be the same or different substituents; when the same expression is involved hereinafter, it shall have the same meaning. Unless otherwise specified, the selection range of the substituents is as shown above and will not be elaborated further.

[0025] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. When the same description is involved hereinafter, it shall have the same meaning.

[0026] In the present invention, for the description of chemical elements, unless otherwise specified, the concept of isotopes with the same chemical properties is included. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0027] In the present invention, unless otherwise specified, the heteroatoms of heteroaryl are selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0028] The term "heteroaryl" used in the present invention includes azetidinyl, dioxolanyl, furyl, imidazolyl, isothiazolyl, isoxazolyl, morpholinyl, oxazolyl (1,2,۳-oxadiazolyl, 1,2,5-oxadiazolyl and 1,3,4-oxadiazolyl), piperazinyl, piperidinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, pyrrolidinyl, tetrahydrofuryl, tetrahydropyranyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazolyl, 1,2,4,5-tetrazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thiazolyl, thienyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazolyl, 1,3,4-triazolyl, etc.

[0029] In this invention, the way the ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0030] In this invention, C a ~C b The expression indicates that the number of carbon atoms in the group is any number in the range from a to b. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms in the substituents.

[0031] In this invention, "each independently" means that when there are multiple subjects, they can be the same or different from each other.

[0032] The C1~C 36 Alkyl groups include C1 to C2. 36 Straight-chain alkyl groups, including C1 to C2. 36 Branched alkyl groups, preferably C1-C2 16 Straight-chain or branched alkyl groups, more preferably C1-C1. 10 Straight-chain or branched alkyl groups, exemplary including but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0033] The C1~C 36 Specific examples of alkoxy groups include monovalent groups obtained by attaching the aforementioned straight-chain or branched alkyl groups to O. The C1-C1... 20 Specific examples of thioalkoxy groups can be found in the monovalent groups obtained by attaching the above-mentioned straight-chain or branched alkyl groups to S.

[0034] The C3~C 36 Cycloalkyl, preferably C3-C 10 Cycloalkyl groups include monocyclic alkyl groups or polycyclic alkyl groups. Monocyclic alkyl groups refer to alkyl groups containing a single ring structure, while polycyclic alkyl groups refer to structures formed by two or more cycloalkyl groups sharing one or more carbon atoms on a ring. Examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0035] The C4~C 60 Aryl group, preferably C6-C 30 Aryl group, more preferably C6-C 20Aryl groups include monocyclic aryl and fused-ring aryl groups; a monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are linked by single bonds, including but not limited to: phenyl, biphenyl, terphenyl, etc.; a fused-ring aryl group means that the group contains at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms fused together, including but not limited to: naphthyl, anthraceneyl, phenanthryl, indene, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirodifluorenyl, benzo[a]fluorenyl, etc.), fluoranyl, triphenylene, pyrene, perylene, etc. Benzyl or tetraphenyl, etc.

[0036] The C5~C 60 heteroaryl, preferably C5-C 30 heteroaryl, more preferably C5-C 30 Heteroaryl groups include monocyclic heteroaryl groups and fused-ring heteroaryl groups. A monocyclic heteroaryl group refers to a molecule containing at least one heteroaryl group. When a molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and other groups are connected by a single bond, exemplarily including but not limited to: pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, etc. The term "fused-ring heteroaryl" refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two share two adjacent atoms fused together in a group. Examples include, but are not limited to: quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, isobenzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl and its derivatives (N-phenylcarbazoleyl, N-naphthylcarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, azacarbazoleyl, etc.), acridineyl, phenothiazinyl, phenotoxazinyl, hydrogenated acridineyl, etc.

[0037] In this invention, C4~C 60 The aryloxy group is a monovalent group formed by attaching the aforementioned aryl group to O, wherein the C4-C 30 The heteroaryl group is a monovalent group formed by attaching the aforementioned heteroaryl groups to O.

[0038] In this invention, C4~C 30 Specific examples of arylamino groups are monovalent groups formed by substituting at least one hydrogen atom in -NH2 with the aforementioned aryl group, including but not limited to: phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, biphenylamino, etc. The C4-C4 groups... 60Specific examples of heteroarylamino groups are monovalent groups formed by replacing at least one hydrogen atom in -NH2 with the aforementioned heteroaryl group, including but not limited to: pyridinylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0039] The compounds described in this invention may contain "optionally substituted" portions. Generally, the term "substituted" (regardless of whether the preceding term "optional") means that one or more hydrogen atoms of the indicated portion are replaced by suitable substituents. Unless otherwise stated, the "optionally substituted" group may have suitable substituents at each substituted position of the group, and when more than one position in any given structure is substituted with more than one substituent selected from the specified group, the substituents at each position may be the same or different. The combinations of substituents contemplated in this invention are preferably those that form stable or chemically viable compounds. In some aspects, unless clearly indicated to the contrary, it is also covered that individual substituents may be further optionally substituted (i.e., further substituted or unsubstituted).

[0040] In this invention, the organic compounds based on the phenol-oxygen-boron-nitrogen structure are electrically neutral to facilitate their purification by vacuum sublimation.

[0041] The organic compounds containing phenoloxy-boron nitrogen structures provided by this invention have a variety of uses. They can be used as luminescent materials in OLED devices, as host materials, guest materials, or other functional layer materials, and can be applied to full-color displays, lighting devices, etc. Furthermore, they can be used as luminescent materials in organic electroluminescent devices that emit ultraviolet to orange light.

[0042] The optical or electro-optical device involved in this invention comprises one or more of the above-mentioned organic compounds containing a phenolic oxide-boron nitrogen structure.

[0043] The present invention also aims to provide the application of the organic compound, wherein the organic compound is used as a light-emitting layer material in an organic electroluminescent device, specifically as a light-emitting material or a host material in the light-emitting layer.

[0044] A further objective of this invention is to provide an organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layers contain the organic compound of this invention described above.

[0045] Preferably, the light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region, with the light-emitting layer located between the hole transport region and the electron transport region; wherein the light-emitting layer contains the organic compound of the present invention described above.

[0046] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0047] This invention constructs a series of novel pure organoboron compounds with rigid polycyclic aromatic boron-nitrogen skeletons. Their radiative modes are primarily optically allowed π-π* locally excited state (LE) transitions, with only a portion of intramolecular charge-transfer (CT) states, thus exhibiting extremely high radiative rates (10⁻⁶). 8 S -1 The short radiation decay lifetime, small Stokes shift, and narrow half-maximum width at half-maximum effectively avoid problems such as large Stokes shift, broad emission spectrum, and impure color purity. Furthermore, this type of novel organic compound uses BO bonds (536 kJ / mol) with higher bond dissociation energy (536 kJ / mol) instead of traditional BC bonds (356 kJ / mol), resulting in higher chemical stability. Introducing BO covalent bonds can also utilize the heavy atom effect of heteroatoms to increase the reverse intersystem crossing rate of the material, further reducing the efficiency roll-off in devices and improving device stability.

[0048] Furthermore, the general formula compounds of this invention also exhibit easily adjustable structures, tunable luminescence efficiency, and controllable material energy levels. By designing changes in the peripheral substituents, the color of the light can be controlled in the range of violet to red light, while maintaining the characteristics of narrow half-peak width, and the lifespan of the device is greatly improved.

[0049] From a synthetic perspective, the synthetic route is simple. These compounds utilize the guiding effect of the O atom on the B atom of the phenol group to achieve the formation of the BO covalent bond, which further guides the effective occurrence of the BC electrophilic borylation reaction. The reaction yield is high, the reaction conditions are simple, it is easy to prepare in large quantities, and the preparation time cycle is short, with low time, manpower and material costs. Attached Figure Description

[0050] Figure 1 These are the emission spectra of compounds BON1, BON2, and BON97 in dichloromethane solution.

[0051] Figure 2 These are the thermogravimetric analysis and differential scanning calorimetry spectra of compound BON1.

[0052] Figure 3 These are the thermogravimetric analysis and differential scanning calorimetry spectra of compound BON2.

[0053] Figure 4 , Figure 5 , Figure 6 , Figure 7 , Figure 8 This is a theoretical calculation of the front-line track distribution diagram for some embodiments. Detailed Implementation

[0054] The following examples provide those skilled in the art with information on how to manufacture and evaluate the compounds described in this invention and their OLED devices. These examples are merely illustrative of the present disclosure and do not limit the scope of the invention. While every effort has been made to ensure accuracy regarding numerical values ​​(e.g., quantities, temperatures, etc.), some errors and deviations should be considered. Unless otherwise stated, temperatures are in °C or at ambient temperature, and pressures are at or near atmospheric pressure.

[0055] The method for preparing the disclosed compound described in this embodiment is one of many methods. Many other methods exist for preparing the compound disclosed in this application, and this application does not limit the scope. Therefore, those skilled in the art to which this disclosure pertains can easily modify the described method or use different methods to prepare one or more of the disclosed compounds. The following methods are merely exemplary; temperature, catalyst, concentration, reactant composition, and other process conditions can be varied, and those skilled in the art to which this disclosure pertains can easily select suitable reactants and conditions for preparation of the desired compound.

[0056] Performed on a Varian Liquid State NMR instrument 1 H and 13 C10 NMR spectroscopy was performed. The solvent was CDCl3 or DMSO-d6. If tetramethylsilane was present as an internal standard in the solvent, the chemical shift was referenced to tetramethylsilane (δ = 0.00 ppm); otherwise, if CDCl3 was used as the solvent, 1 The chemical shift of the 1H NMR spectrum is referenced to the residual solvent (δ = 7.26 ppm); if DMSO-d6 is used as the solvent, 1 The chemical shifts of the 1H NMR spectra were referenced to the residual solvent H2O (δ = 3.33 ppm). The NMR data in the examples are interpreted using the following abbreviations (or combinations thereof). 1 Multiplicity of H NMR: s = singlet, d = doublet, t = triplet, q = quadruplet, p = quintuplett, m = multiplyt, br = wide.

[0057] General synthetic route

[0058] The general synthetic routes for the compounds disclosed in this invention patent are as follows:

[0059]

[0060]

[0061] The reaction conditions and synthetic routes described herein are for reference only. Those skilled in the art can easily select suitable reactants and conditions for preparation.

[0062] Preparation Examples

[0063] Example 1: Compound BON1 can be synthesized via the following route:

[0064]

[0065] Synthesis of BON1-OMe: Br-OMe (2.60 g, 6.99 mmol, 1.0 equivalent), NH1 (2.96 g, 17.47 mmol, 2.5 equivalent), sodium tert-butoxide (3.36 g, 34.95 mmol, 5.0 equivalent), Pd2(dba)3 (192 mg, 0.21 mmol, 0.03 equivalent), and S-Phos (344 mg, 0.84 mmol, 0.12 equivalent) were added to a 100 mL three-necked flask. The mixture was purged with nitrogen three times, and toluene (40 mL) was added. The reaction was carried out at 110 °C for 40 hours. The reaction was cooled to room temperature, quenched with water, and extracted three times with ethyl acetate. The organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / ethyl acetate at a ratio of 100:1 to 10:1, yielding 3.02 g of a white solid (79% yield). 1 H NMR (500MHz, CDCl3) δ3.67 (s, 6H), 6.53 (d, J = 8.4Hz, 2H), 6.76 (d, J = 2.0Hz, 2H), 6.79 (t,J=2.0Hz,1H),6.93(tt,J=7.0,1.0Hz,4H),7.10–7.16(m,9H),7.17–7.22(m,8H).

[0066] Synthesis of BON1-OH: BON1-OMe (2.0 g, 3.65 mmol, 1.0 equivalent), pyridine hydrochloride (4.21 g, 36.45 mmol, 10.0 equivalent), and 1,3-dimethyl-2-imidazolinone (10 mL) were added to a 50 mL three-necked flask and reacted at 180 °C for 19 hours. After the reaction was completed, the mixture was quenched with sodium bicarbonate solution, extracted three times with ethyl acetate, the organic phases were combined, dried, and the solvent was removed. The mixture was then separated by silica gel column chromatography with petroleum ether / ethyl acetate at a ratio of 10:1 to 5:1, yielding 1.73 g of a yellow solid, with a yield of 91%. 1 H NMR(500MHz, CDCl3)δ5.10(s,2H),6.48(d,J=8.0Hz,2H),6.52(d,J=2.0Hz,2H), 6.85(t,J=2.0Hz,1H),6.99–7.04(m,5H),7.07–7.12(m,8H),7.21–7.25(m,8H).

[0067] Synthesis of BON1: BON1-OH (521 mg, 1.0 mmol, 1.0 equivalent), o-dichlorobenzene (16 mL), and boron tribromide (2.9 mL, 30 mmol, 30 equivalent) were added to a 50 mL three-necked flask and reacted at 170 °C for 21 hours. After the reaction was complete, the mixture was quenched with sodium carbonate solution, extracted three times with dichloromethane, and the organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 0:1, yielding 344 mg of a yellow solid, with a yield of 64%. 1 H NMR (500MHz, CDCl3) δ5.18 (s, 1H), 6.73 (d, J = 8.5Hz, 2H), 7.11–7.16 (m, 4H), 7.22 (td, J = 7. 0,1.0Hz,2H),7.38–7.47(m,10H),7.57(dd,J=8.5,7.5Hz,1H),8.38(dd,J=7.5,2.0Hz,2H).

[0068] Example 2: Compound BON2 can be synthesized via the following route:

[0069]

[0070] Synthesis of BON2-OMe: Cl-OMe (4.0 g, 14.13 mmol, 1.0 equivalent), NH2 (6.13 g, 31.08 mmol, 2.2 equivalent), sodium tert-butoxide (5.43 g, 56.51 mmol, 4.0 equivalent), Pd2(dba)3 (259 mg, 0.28 mmol, 0.02 equivalent), and S-Phos (464 mg, 1.13 mmol, 0.08 equivalent) were added to a 100 mL three-necked flask. The mixture was purged with nitrogen three times, and toluene (60 mL) was added. The reaction was carried out at 110 °C for 40 hours. The reaction was cooled to room temperature, quenched with water, and extracted three times with ethyl acetate. The organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 1:1, yielding 8.32 g of a white solid (97% yield).

[0071] Synthesis of BON2-OH: BON2-OMe (8.2 g, 13.56 mmol, 1.0 equivalent), pyridine hydrochloride (15.67 g, 135.58 mmol, 10.0 equivalent), and 1,3-dimethyl-2-imidazolinone (10 mL) were added to a 50 mL three-necked flask and reacted at 180 °C for 19 hours. After the reaction was completed, the mixture was quenched with sodium bicarbonate solution, extracted three times with ethyl acetate, the organic phases were combined, dried to remove the solvent, and then separated by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 1:1 to give 6.60 g of white solid, with a yield of 84%.

[0072] BON2 synthesis: BON2-OH (2.0 g, 3.47 mmol, 1.0 equivalent), o-dichlorobenzene (25 mL), and boron tribromide (9.8 mL, 104.03 mmol, 30 equivalent) were added to a 50 mL three-necked flask and reacted at 170 °C for 26 hours. After the reaction was completed, the mixture was quenched with sodium carbonate solution, extracted three times with dichloromethane, the organic phases were combined, dried, and the solvent was removed. The mixture was then separated by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 0:1, yielding 1.32 g of a yellow solid, with a yield of 64%. 1 H NMR(500MHz, CDCl3)δ2.46(d,J=3.0Hz,12H),5.18(s,1H),6.70(d,J=8.5Hz,2H),6.96–7.03(m ,4H),7.19–7.26(m,6H),7.37(d,J=8.0Hz,2H),7.55(dd,J=8.5,7.5Hz,1H),8.12–8.20(m,2H).

[0073] Example 3: Compound BON4 can be synthesized via the following route:

[0074]

[0075] Synthesis of BON4-OMe: Cl-OMe (300 mg, 1.06 mmol, 1.0 equivalent), NH3 (783 mg, 2.44 mmol, 2.3 equivalent), sodium tert-butoxide (407 mg, 4.23 mmol, 4.0 equivalent), Pd2(dba)3 (29 mg, 0.03 mmol, 0.03 equivalent), and S-Phos (35 mg, 0.085 mmol, 0.08 equivalent) were added to a 25 mL three-necked flask. The mixture was purged with nitrogen three times, and toluene (6 mL) was added. The reaction was carried out at 110 °C for 42 hours. The reaction was cooled to room temperature, quenched with water, and extracted three times with ethyl acetate. The organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 1:1, yielding a white solid that was directly used in the next step.

[0076] Synthesis of BON4-OH: BON4-OMe (904 mg, 1.06 mmol, 1.0 equivalent), pyridine hydrochloride (1.84 g, 15.90 mmol, 15.0 equivalent), and 1,3-dimethyl-2-imidazolinone (4 mL) were added to a 25 mL three-necked flask and reacted at 180 °C for 19 hours. After the reaction was completed, the solution was quenched with sodium bicarbonate solution, extracted three times with ethyl acetate, dried to remove the solvent, and then separated by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 1:1, yielding 595 mg of a white solid. The two-step yield was 68%.

[0077] BON4 synthesis: BON4-OH (500 mg, 0.61 mmol, 1.0 equivalent), o-dichlorobenzene (15 mL), and boron tribromide (1.76 mL, 18.30 mmol, 30 equivalent) were added to a 50 mL three-necked flask and reacted at 170 °C for 23 hours. After the reaction was complete, the mixture was quenched with sodium carbonate solution, extracted three times with dichloromethane, and the organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 0:1, yielding 210 mg of a yellow solid in 41% yield. MS: m / z 841.32 (M+H) +

[0078] Example 4: Compound BON97 can be synthesized via the following route:

[0079]

[0080] Synthesis of BON97-OMe: Br-OMe (1.0 g, 2.69 mmol, 1.0 equivalent), NH4 (1.41 g, 6.72 mmol, 2.5 equivalent), sodium tert-butoxide (1.16 g, 12.09 mmol, 4.5 equivalent), Pd2(dba)3 (74 mg, 0.081 mmol, 0.03 equivalent), and S-Phos (132 mg, 0.32 mmol, 0.12 equivalent) were added to a 25 mL three-necked flask. The mixture was purged with nitrogen three times, and toluene (25 mL) was added. The reaction was carried out at 110 °C for 44 hours. The reaction was cooled to room temperature, quenched with water, and extracted three times with ethyl acetate. The organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / ethyl acetate at a ratio of 100:1 to 5:1, yielding 1.62 g of a yellow solid, with a yield of 96%. 1 H NMR (400MHz, CDCl3) δ1.65 (s, 12H), 3.80 (s, 6H), 6.63–6.68 (m, 6H), 6.94 (td, J=7.6, 1.0Hz, 4H), 7.07 (ddd, J=8.4 ,7.6,1.6Hz,4H),7.21(t,J=2.0Hz,1H),7.29(t,J=8.4Hz,2H),7.45(dd,J=7.6,1.6Hz,4H),7.60(d,J=2.0Hz,2H).

[0081] Synthesis of BON97-OH: BON97-OMe (1.40 g, 2.23 mmol, 1.0 equivalent), pyridine hydrochloride (2.57 g, 22.26 mmol, 10.0 equivalent), and 1,3-dimethyl-2-imidazolinone (4 mL) were added to a 25 mL three-necked flask and reacted at 180 °C for 18 hours. After the reaction was completed, the solution was quenched with sodium bicarbonate solution, extracted three times with ethyl acetate, dried to remove the solvent, and then separated by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 1:1, yielding 1.07 g of a yellow solid, with a yield of 80%. 1 H NMR (400MHz, CDCl3) δ1.66 (s, 12H), 5.02 (s, 2H), 6.51–6.57 (m, 6H), 6.96 (td, J=7.6, 1.6Hz, 4H ),7.04–7.14(m,5H),7.41(t,J=2.0Hz,1H),7.46(dd,J=8.0,1.6Hz,4H),7.64(d,J=2.0Hz,2H).

[0082] Synthesis of BON97: BON97-OH (500 mg, 0.83 mmol, 1.0 equivalent), o-dichlorobenzene (15 mL), and boron tribromide (2.36 mL, 24.97 mmol, 30 equivalent) were added to a 50 mL three-necked flask and reacted at 170 °C for 21 hours. After the reaction was complete, the mixture was quenched with sodium carbonate solution, extracted three times with dichloromethane, and the organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 0:1, yielding 175 mg of a yellow solid, with a yield of 34%. 1 H NMR (400MHz, CDCl3) δ1.29(s,6H),1.99(s,6H),7.22–7.25(m,2H),7.34(ddd,J=8.5,7.5,1.5Hz,2H),7.38– 7.44(m,4H),7.55–7.63(m,3H),7.69(dd,J=7.5,1.5Hz,2H),7.87–7.95(m,3H),8.22(dd,J=7.5,1.5Hz,2H).

[0083] Example 5: Compound BON29 can be synthesized via the following route:

[0084]

[0085] Synthesis of BON29-OMe: Br-OMe (1.0 g, 2.69 mmol, 1.0 equivalent), NH5 (1.23 g, 6.72 mmol, 2.5 equivalent), sodium tert-butoxide (1.16 g, 12.09 mmol, 4.5 equivalent), Pd2(dba)3 (74 mg, 0.081 mmol, 0.03 equivalent), and S-Phos (132 mg, 0.32 mmol, 0.12 equivalent) were added to a 25 mL three-necked flask. The mixture was purged with nitrogen three times, and toluene (25 mL) was added. The reaction was carried out at 110 °C for 66 hours. The reaction was cooled to room temperature, quenched with water, and extracted three times with ethyl acetate. The organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / ethyl acetate at a ratio of 100:1 to 5:1, yielding 1.38 g of a white solid, with a yield of 89%. 1 H NMR (400MHz, CDCl3) δ3.77 (s, 6H), 6.18–6.27 (m, 4H), 6.60–6.76 (m, 14H), 7.27–7.31 (m, 2H), 7.52 (d, J = 2.0Hz, 2H).

[0086] Synthesis of BON29-OH: BON29-OMe (1.25 g, 2.17 mmol, 1.0 equivalent), pyridine hydrochloride (2.53 g, 21.70 mmol, 10.0 equivalent), and 1,3-dimethyl-2-imidazolinone (3 mL) were added to a 25 mL three-necked flask and reacted at 180 °C for 18 hours. After the reaction was completed, the solution was quenched with sodium bicarbonate solution, extracted three times with ethyl acetate, dried to remove the solvent, and then separated by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 1:1, yielding 1.1 g of a yellow solid, with a yield of 92%. 1 H NMR (400MHz, CDCl3) δ5.04 (s, 2H), 6.11–6.15 (m, 4H), 6.53 (d, J = 8.0Hz, 2H), 6.63– 6.72(m,12H),7.10(t,J=8.0Hz,1H),7.41(t,J=2.0Hz,1H),7.60(d,J=2.0Hz,2H).

[0087] Synthesis of BON29: BON29-OH (800 mg, 11.46 mmol, 1.0 equivalent), o-dichlorobenzene (20 mL), and boron tribromide (4.28 mL, 43.75 mmol, 30 equivalent) were added to a 50 mL three-necked flask and reacted at 170 °C for 19 hours. After the reaction was complete, the mixture was quenched with sodium carbonate solution, extracted three times with dichloromethane, and the organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 0:1, yielding 747 mg of a yellow solid in 91% yield. MS: m / z 565.15 (M+H) +

[0088] Example 6: Compound BON45 can be synthesized via the following route:

[0089]

[0090] Synthesis of BON45-OMe: Br-OMe (1.0 g, 2.69 mmol, 1.0 equivalent), NH6 (1.34 g, 6.72 mmol, 2.5 equivalent), sodium tert-butoxide (1.16 g, 12.09 mmol, 4.5 equivalent), Pd2(dba)3 (74 mg, 0.081 mmol, 0.03 equivalent), and S-Phos (132 mg, 0.32 mmol, 0.12 equivalent) were added to a 25 mL three-necked flask. The mixture was purged with nitrogen three times, and toluene (25 mL) was added. The reaction was carried out at 110 °C for 72 hours. The reaction mixture was cooled to room temperature, quenched with water, and extracted three times with ethyl acetate. The organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / ethyl acetate at a ratio of 100:1 to 5:1, yielding 1.28 g of a white solid in 78% yield. 1 H NMR (400MHz, CDCl3) δ3.80 (d, J=0.8Hz, 6H), 6.56 (dd, J=8.0, 1.2Hz, 4H), 6.67 (dd, J=8.4, 0.8Hz, 2H), 6.8 1–6.88(m,4H),6.90–6.98(m,4H),7.05(dt,J=7.6,1.2Hz,4H),7.28–7.35(m,2H),7.60(d,J=2.0Hz,2H).

[0091] Synthesis of BON45-OH: BON45-OMe (1.10 g, 1.81 mmol, 1.0 equivalent), pyridine hydrochloride (2.09 g, 18.07 mmol, 10.0 equivalent), and 1,3-dimethyl-2-imidazolinone (4 mL) were added to a 25 mL three-necked flask and reacted at 180 °C for 18 hours. After the reaction was completed, the solution was quenched with sodium bicarbonate solution, extracted three times with ethyl acetate, dried to remove the solvent, and then separated by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 1:1, yielding 1.01 g of a yellow solid, with a yield of 96%. 1 H NMR (400MHz, CDCl3) δ5.04 (s, 2H), 6.52 (d, J = 8.0 Hz, 2H), 6.80 (dd, J = 8.0, 1. 2Hz, 4H), 6.98 (td, J=7.6, 1.2Hz, 4H), 7.04–7.12 (m, 5H), 7.14–7.21 (m, 7H).

[0092] Synthesis of BON45: BON45-OH (500 mg, 0.86 mmol, 1.0 equivalent), o-dichlorobenzene (15 mL), and boron tribromide (2.44 mL, 25.83 mmol, 30 equivalent) were added to a 50 mL three-necked flask and reacted at 170 °C for 21 hours. After the reaction was complete, the mixture was quenched with sodium carbonate solution, extracted three times with dichloromethane, and the organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 0:1, yielding 277 mg of a yellow solid in 54% yield. MS: m / z 597.11 (M+H) +

[0093] Example 7: Compound BON141 can be synthesized via the following route:

[0094]

[0095] Synthesis of BON141-OMe: Br-Cz (1.5 g, 3.08 mmol, 1.0 equivalent), OMe (728 mg, 4.0 mmol, 1.3 equivalent), Pd(PPh3)4 (107 mg, 0.09 mmol, 0.03 equivalent), and potassium carbonate (851 mg, 6.16 mmol, 2.0 equivalent) were added to a 50 mL three-necked flask. Nitrogen gas was purged three times. Dioxane (15 mL) and water (3 mL) were added, and the reaction was carried out at 90 °C for 72 hours. The reaction was cooled to room temperature, quenched with water, and extracted three times with ethyl acetate. The organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / ethyl acetate at a ratio of 100:1 to 10:1, yielding 1.61 g of a white solid, with a yield of 96%. 1HNMR (400MHz, CDCl3) δ3.92 (s, 6H), 6.72 (d, J = 8.4Hz, 2H), 7.28–7.36 (m, 5H), 7.45 (ddd, J=8.4,7.2,1.2Hz,4H),7.73(d,J=8.4Hz,4H),7.76–7.81(m,3H),8.16(d,J=7.6Hz,4H).

[0096] Synthesis of BON141-OH: BON141-OMe (1.5 g, 2.75 mmol, 1.0 equivalent), pyridine hydrochloride (3.18 g, 27.54 mmol, 10.0 equivalent), and 1,3-dimethyl-2-imidazolinone (5 mL) were added to a 25 mL three-necked flask and reacted at 180 °C for 24 hours. After the reaction was completed, the solution was quenched with sodium bicarbonate solution, extracted three times with ethyl acetate, dried to remove the solvent, and then separated by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 1:1, yielding 1.20 g of a yellow solid, with a yield of 84%. 1 H NMR (400MHz, CDCl3) δ5.26(s,2H),6.60(d,J=8.0Hz,2H),7.16(t,J=8.0Hz,1H),7.32(td,J=7.4,1.2Hz,4H),7.45(ddd ,J=8.4,7.2,1.6Hz,4H),7.64–7.71(m,4H),7.83(d,J=2.0Hz,2H),7.91(t,J=2.0Hz,1H),8.16(dt,J=7.6,1.2Hz,4H).

[0097] Synthesis of BON141: BON141-OH (517 mg, 1.0 mmol, 1.0 equivalent), o-dichlorobenzene (13 mL), and boron tribromide (2.84 mL, 30 mmol, 30 equivalent) were added to a 50 mL three-necked flask and reacted at 170 °C for 26 hours. After the reaction was complete, the mixture was quenched with sodium carbonate solution, extracted three times with dichloromethane, and the organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 0:1, yielding 96 mg of a yellow solid in 18% yield. MS: m / z 533.16 (M+H) +

[0098] Example 8: Compound BON143 can be synthesized via the following route:

[0099]

[0100] Synthesis of BON143-OMe: Br-tBuCz (3.60 g, 5.06 mmol, 1.0 equivalent), OMe (1.20 g, 6.57 mmol, 1.3 equivalent), Pd(PPh3)4 (175 mg, 0.15 mmol, 0.03 equivalent), and potassium carbonate (1.40 g, 10.11 mmol, 2.0 equivalent) were added to a 50 mL three-necked flask. The mixture was purged with nitrogen three times. Dioxane (35 mL) and water (7 mL) were added, and the reaction was carried out at 90 °C for 72 hours. The reaction was cooled to room temperature, quenched with water, and washed with deionized water, anhydrous ethanol, ethyl acetate, and dichloromethane, respectively, to give 3.20 g of a white solid, with a yield of 82%.

[0101] Synthesis of BON143-OH: BON143-OMe (200 mg, 0.26 mmol, 1.0 equivalent), pyridine hydrochloride (300 mg, 2.6 mmol, 10.0 equivalent), and 1,3-dimethyl-2-imidazolinone (1 mL) were added to a 10 mL reaction flask and reacted at 180 °C for 24 hours. After the reaction was complete, the mixture was quenched with sodium bicarbonate solution, extracted three times with ethyl acetate, dried to remove the solvent, and then separated by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 1:1, yielding 175 mg of a yellow solid, with a yield of 91%.

[0102] Synthesis of BON143: BON143-OH (150 mg, 0.20 mmol, 1.0 equivalent), o-dichlorobenzene (6 mL), and boron tribromide (0.59 mL, 6.07 mmol, 30 equivalent) were added to a 25 mL three-necked flask and reacted at 170 °C for 26 hours. After the reaction was complete, the mixture was quenched with sodium carbonate solution, extracted three times with dichloromethane, and the organic phases were combined, dried, and the solvent was removed. Separation was then performed by silica gel column chromatography with petroleum ether / dichloromethane at a ratio of 10:1 to 0:1, yielding 30 mg of a yellow solid in 20% yield. MS: m / z 757.41 (M+H) +

[0103] The synthesis methods in the following examples are similar to those in Examples 1 and 7, except that the bromide and aromatic amine starting materials of the corresponding fragments in the examples are replaced.

[0104]

[0105] Example 9: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON169, a light yellow solid. MS: m / z 693.24 (M+H) +

[0106] Example 10: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON172, a grayish-white solid. MS: m / z 781.41 (M+H) +

[0107] Example 11: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON174, a yellow solid. MS: m / z 850.25 (M+H) +

[0108] Example 12: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON176, a white solid. MS: m / z 781.34 (M+H) +

[0109] Example 13: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON178, a yellow-green solid. MS: m / z 818.23 (M+H) +

[0110] Example 14: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON182, a white solid. MS: m / z 936.37 (M+H) +

[0111] Example 15: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON184, a light yellow solid. MS: m / z 903.40 (M+H) +

[0112] Example 16: The synthesis method is similar to that of Example 7, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 7 are replaced to synthesize the target compound BON194, an orange solid. MS: m / z 751.22 (M+H) +

[0113] Example 17: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON187, a white solid. MS: m / z 1039.56 (M+H) +

[0114] Example 18: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON188, a light yellow solid. MS: m / z 967.49 (M+H) +

[0115] Example 19: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON189, a yellow-green solid. MS: m / z 1175.28 (M+H) +

[0116] Example 20: The synthesis method is similar to that of Example 1, except that the bromide and aromatic amine starting materials of the corresponding fragments in Example 1 are replaced to synthesize the target compound BON192, a light yellow solid. MS: m / z 1109.43 (M+H) +

[0117] Performance Evaluation Examples

[0118] The following describes photophysical, thermogravimetric, and theoretical calculations performed on some of the compounds prepared in the above embodiments of the present invention:

[0119] Figure 1 These are the emission spectra of compounds BON1, BON2, and BON97 in dichloromethane solution.

[0120] Figure 2 These are the thermogravimetric analysis and differential scanning calorimetry spectra of compound BON1.

[0121] Figure 3 These are the thermogravimetric analysis and differential scanning calorimetry spectra of compound BON2.

[0122] Table 1. Photophysical properties of some luminescent materials

[0123]

[0124] Note: Peak refers to the strongest emission peak of the emission spectrum of the luminescent material in dichloromethane solution at room temperature; FWHM is the full width at half maximum (FWHM) of the emission spectrum; PLQY refers to the luminescence quantum efficiency.

[0125] From the appendix Figure 1 Appendix Figure 2 Appendix Figure 3As shown in Table 1, firstly, the material's emission color is easily adjustable: the emission color can be controlled simply by adjusting the aromatic amine donor structure while maintaining the parent core structure. Secondly, the material has high quantum efficiency: it exhibits a very high luminescent quantum efficiency (PLQY), reaching 99%. Thirdly, the material has excellent thermal stability: thermogravimetric analysis shows a 5% decomposition temperature as high as 460℃, and no significant glass transition was observed. These properties are all beneficial for its application as a doped emitting material or host material in OLED devices, and provide an effective way to solve the current shortage of blue emitting materials, thus greatly promoting the development of this field.

[0126] The following structures were calculated using density functional theory (DFT);

[0127]

[0128] Results calculated using density functional theory (DFT) (see attached) Figure 4 , 5 As shown in Tables 6, 7, 8 and 1, the electronic transitions of most compounds are mainly optically allowed π-π* localized excited state (LE) transitions, with some intramolecular charge-transfer (CT) states mixed in, thus exhibiting extremely high radiative rates (10). 8 S -1 The phenolic oxide-boron nitrogen structure developed in this invention exhibits characteristics such as short radiative decay lifetime, small Stokes shift, and narrow half-maximum width. By adjusting the substituents surrounding the parent core, the frontier orbital levels, singlet and triplet states, and oscillator strength of the compound can be effectively controlled, thereby achieving regulation of emission color and quantum efficiency. In summary, density functional theory (DFT) calculations demonstrate that the photophysical properties of luminescent materials can be efficiently controlled by adjusting the substituents surrounding the parent core. The above experimental data and theoretical calculations fully demonstrate that the phenolic oxide-boron nitrogen structure organic compound developed in this invention possesses easily tunable HOMO and LUMO orbital levels, narrow emission spectra, high quantum efficiency, and good thermal stability, indicating its great application potential in the OLED field.

[0129] Table 2. DFT theoretical calculation data

[0130]

[0131] Device Examples

[0132] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. This organic material layer can be further divided into multiple regions; for example, it may include a hole transport region, a light-emitting layer, and an electron transport region.

[0133] The anode material can be any combination of transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO). The cathode material can be any combination of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

[0134] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0135] The material for the hole transport region can be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene oxide, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0136] The emissive layer includes luminescent dyes (i.e., dopants) capable of emitting different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single-color emissive layer capable of emitting different colors such as red, green, and blue simultaneously. The electron transport region can be a single-layer electron transport layer (ETL), including single-layer electron transport layers containing only one compound and single-layer electron transport layers containing multiple compounds. The electron transport region can also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0137] All materials undergo high vacuum (10) testing before use. -5 -10 -6 The indium tin oxide (ITO) substrates used in the devices were purified by gradient heating sublimation under Torr conditions. All substrates were subjected to sequential ultrasonic treatment in deionized water, acetone, and isopropanol. The devices were then purified under a vacuum of less than 10... -7 The anode electrode was prepared by vacuum thermal evaporation under pressure from Torr. Indium tin oxide (ITO) cathode, with a thickness of [missing information]. Li2CO3 and The components are composed of Al. After all devices are fabricated, they are sealed in a nitrogen glove box with glass covers and epoxy resin, and a desiccant is added to the packaging.

[0138] The compounds from Examples 1 and 2 were used as luminescent guest materials in an OLED device, and the device structure is shown as follows:

[0139] Device 1: ITO / MoO3 (3nm) / mCP (40nm) / 8wt% BON1: BO-h (30nm) / PPT (30nm) / Liq (1nm) / Al;

[0140] Device 2: ITO / HATCN (5nm) / NPB (40nm) / TCTA (10nm) / CzSi (10nm) / BON2:TSPO1 (20nm) / TSPO1 (10nm) / TmPyPB (20nm) / LiF (0.8nm) / Al,

[0141] Device 3: ITO / HAT-CN (6nm) / HAT-CN (0.2wt%): TAPC (50nm) / TCTA: 10wt% BON1 (10nm) / CzSi: 10wt% BON1 (10nm) / Tm3PyP26PyB (50nm) / LiF (1nm) / Al (100nm)

[0142] Device 4: ITO / HATCN(10nm) / TAPC(65nm) / 8wt%BON2:mCBP(20nm) / Bepp2(10nm) / Li2CO3:Bepp2(5%, 30nm) / Li2CO3(1nm) / Al(100nm);

[0143] Device 5: Replace BON1 in Device 1 with BON2;

[0144] Device 6: Replace BON1 in Device 1 with BON3;

[0145] Device 7: Replace BON1 in Device 3 with BON4;

[0146] Device 8: Replace BON1 in Device 4 with BON29;

[0147] Device 9: Replace BON1 in Device 4 with BON45;

[0148] Device 10: Replace BON1 in Device 4 with BON97;

[0149] Device 11: Replace BON1 in device 4 with BON141;

[0150] Device 12: Replace BON1 in device 4 with BON169;

[0151] Comparison Device 1: ITO / HAT-CN (6nm) / HAT-CN (0.2wt%): TAPC (50nm) / TCTA: 10wt% CZ-MPS (10nm) / CzSi: 10wt% CZ-MPS (10nm) / Tm3PyP26PyB (50nm) / LiF (1nm) / Al (100nm)

[0152] The compound shown in Example 1 was used as the host material in an OLED device, and the device structure is shown as follows:

[0153] Device 13: ITO / HATCN(10nm) / BPBPA(70nm) / 26mCDTPy(5nm) / 8wt%PtON1:92wt%BON1(25nm) / DPEPO(10nm) / TmPyPB(30nm) / Li2CO3(1nm) / Al

[0154] Device 14: ITO / HATCN(10nm) / BPBPA(70nm) / 26mCDTPy(5nm) / 8wt%PtON1:46wt%BON1:46wt%26mCPy(25nm) / DPEPO(10nm) / TmPyPB(30nm) / Li2CO3(1nm) / Al

[0155] Device 15: ITO / HATCN (10nm) / BPBPA (70nm) / 26mCdTPy (5nm) / 8wt%PtON1:46wt%BON1:46wt%mCP (25nm) / DPEPO (10nm) / TmPyPB (30nm) / Li2CO3 (1nm) / Al

[0156] Device 16: ITO / HATCN(10nm) / BPBPA(70nm) / 26mCDTPy(5nm) / 8wt%PtON1:46wt%BON1:46wt%mCBP(25nm) / DPEPO(10nm) / TmPyPB(30nm) / Li2CO3(1nm) / Al

[0157] Device 17: Replace BON1 in device 13 with BON2;

[0158] Device 18: Replace BON1 in device 14 with BON3;

[0159] Device 19: Replace BON1 in device 15 with BON4;

[0160] Device 20: Replace BON1 in device 16 with BON169;

[0161] Device 21: Replace BON1 in device 16 with BON141;

[0162] Device 22: Replace BON1 in device 16 with BON2;

[0163] Comparison Device 2: ITO / HI (10nm) / HT (70nm) / 6wt% PtON1:94wt% 26mCy (25nm) / ET (30nm) / Li2CO3 (1nm) / Al

[0164] In this design, ITO is the transparent anode; MoO3 and HATCN are the hole injection layers; mCP and TCTA are the hole transport layers; BO-h and mCBP are the host materials; BON1 and BON2 are the guest materials; PPT and Bepp2 are the electron transport layers; Liq and Li2CO3 are the electron injection layers; and Al is the cathode. The numbers in parentheses, in nanometers (nm), represent the film thickness.

[0165]

[0166]

[0167] Table 3. Performance of the fabricated devices

[0168]

[0169] The above device data demonstrate that the novel phenoloxy-boron-nitrogen structure organic compounds provided by this invention exhibit excellent device performance when used as either guest or host materials in the fabrication of organic electroluminescent devices, exhibiting high color purity, high external quantum efficiency, and low start-up voltage. Therefore, these novel compounds of this invention are high-performance organic light-emitting functional materials and hold promise for widespread commercial application.

[0170] Although the invention has been described in conjunction with embodiments, the invention is not limited to the above embodiments. It should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the appended claims summarize the scope of the invention.

[0171] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic compound based on a phenoxy-boron nitrogen structure, characterized in that, Its chemical formula is shown in general formula (1) or (2): In formula (1) or (2), Y1 and Y2 independently represent single bonds, O, CO, SO2, S, and NR, respectively. a BR b CR c R d or SiR e R f ; R a R b R c R d R e R f Each of them can be independently disconnected from its adjacent R1, R2, R3, and R4, or connected to form a loop. The R a R b R c R d R e R f Each group is independently selected from one of the following groups, substituted or unsubstituted: hydrogen, deuterium, C1-C1. 36 Alkyl groups, C1-C 36 alkoxy groups, C3-C 36 cycloalkyl, C1-C 36 ethers, C5-C 60 heteroaryl, C4-C 60 aryl, C4-C 60 aryloxy groups, C4-C 30 arylamino groups or combinations thereof, wherein two adjacent substituents may fuse into a ring; The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Each group is independently selected from one of the following groups: hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, silyl, amino, or substituted or unsubstituted: C1 to C2. 36 Alkyl groups, C1-C 36 alkoxy groups, C3-C 36 cycloalkyl, C l ~C 20 Thioalkoxy groups, C1-C 36 ethers, C5-C 60 heteroaryl, C4-C 60 aryl, C4-C 60 aryloxy groups, C4-C 30 arylamino, C4-C 30 heteroarylamino groups or combinations thereof, wherein two adjacent substituents may fuse into a ring; The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Each substituent can be independently represented from a single substituent to the maximum permissible number of substituents; The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Two adjacent strings are either not connected or connected by a single key.

2. The organic compound according to claim 1, characterized in that, The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Each group is independently selected from hydrogen or from one or more combinations of the following groups: deuterium, cyano, trifluoromethyl, halogen, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azophenyl, terphenyl. Trimeric phenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimericininyl, spirotrimericininyl, spiroisotrimericininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5, 6-Quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoyl, benzimidazoleyl, naphthemidazoleyl, phenanthrenemidazoleyl, pyridinidazoleyl, pyrazinidazoleyl, quinoxalinidazoleyl, oxazolyl, benzooxazolyl, naphthemidazoleyl, anthraquinoxazolyl, phenanthrenemidazoleyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9, 10-Tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3, 5-Tetraazinyl, purinyl, pteridinyl, indazinyl, benzothiadiazolyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, 9,9-dimethylacridinyl, halobenzene, cyanobenzene, or trifluoromethylbenzene.

3. The organic compound with a phenoloxy-boron nitrogen structure as described in claim 1 or claim 2, characterized in that: The organic compound is one of the following: 。 4. The application of the organic compound according to any one of claims 1-3, wherein the organic compound is used as a light-emitting layer material in an organic electroluminescent device, specifically as a light-emitting material or a host material in the light-emitting layer.

5. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layers contain an organic compound as described in any one of claims 1-3.

6. The organic electroluminescent device according to claim 5, wherein the light-emitting functional layer comprises a hole transport region, a light-emitting layer, and an electron transport region, and the light-emitting layer is located between the hole transport region and the electron transport region; wherein, The light-emitting layer contains any one of the organic compounds described in claims 1-3.

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