Organic light-emitting material with chirality and narrow-band emission performance as well as preparation method and application of organic light-emitting material

Abstract

The invention discloses an organic light-emitting material with both chirality and narrow-band emission performance and a preparation method and application thereof, the core of the organic light-emitting material is that vibration coupling between S1-S0 transition and excited state structure relaxation can be effectively inhibited by utilizing a multi-resonance structure to form remarkable narrow-band emission, and meanwhile, by utilizing the axial chirality characteristic of BINOL and utilizing a chirality disturbance strategy, the organic light-emitting material with both chirality and narrow-band emission performance is obtained. Circularly polarized light is formed. The invention also provides a preparation method of the material, which comprises the following steps: reacting a compound C with a compound D to obtain a compound B, and reacting a compound A with the compound B to obtain the organic light-emitting material. The material has a multi-resonance effect induced thermal activation delayed fluorescence characteristic and a circular polarization luminescence characteristic, can be applied to the fields of 3D display, molecular probes, spin information and optical data storage and processing, photoelectric devices and the like, and is simple in synthesis process, wide in raw material source, low in cost and suitable for wide application.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic photoelectric materials, and in particular relates to an organic light-emitting material having both chirality and narrow-band emission performance, and a preparation method and application thereof. Background Art

[0002] Organic light-emitting materials have attracted wide attention due to their multifunctional responsiveness and broad prospects for optoelectronic applications. Organic Light-Emitting Diode (OLED), also known as organic electric laser display and organic light-emitting display, is an emerging display and lighting technology. In the OLED family, circularly polarized organic light-emitting diode (CP-OLED) has broad application prospects in future display and optoelectronic technologies, especially in display screens.

[0003] Due to the "forbidden principle", the internal quantum efficiency (IQE) of traditional organic fluorescent materials for OLED fluorescent materials is only 25%, which limits the development of fluorescent materials. (Zhang Wenwen, Chen Zhuo, Li Ge, Yan Xuewen, Jiao Bo, Wu Chaoxin. Acta Photonica Sinica, 2020, 49, 0123001.) Organic phosphorescent materials can use singlet and triplet excitons to emit light, so that their IQE can reach 100%; but because the emission of triplet states depends on transition metal complexes, it is not suitable for large-scale production of OLEDs. (JM Teng, YF Wang and CF Chen, J. Mater. Chem. C, 2020, 8, 11340.) Thermally activated delayed fluorescence (TADF) materials are pure organic molecules. They use the reverse intersystem crossing (RISC) process to convert triplet excitons into singlet excitons, so that their IQE reaches 100%. TADF materials maintain the high internal quantum efficiency of organic phosphorescent materials and the stability of traditional organic fluorescent materials. At the same time, TADF materials eliminate the cost and resource limitations of organic phosphorescent materials and the low internal quantum efficiency of traditional organic fluorescent materials, making it one of the most promising candidate materials for the next generation of OLEDs and a research hotspot in recent years.

[0004] OLEDs with TADF molecules have been widely used in display and lighting technologies. However, OLEDs need to use polarizers to obtain high image contrast, and usually suffer at least 50% brightness loss and energy loss. CP-OLEDs can emit circularly polarized light, which will not have brightness loss when passing through polarizers, and can achieve more energy-efficient OLED displays. By introducing chiral structures (chiral center, axial chirality, planar chirality and helical chirality, etc.) into the luminescent group, not only can organic small molecules be induced to produce molecular circularly polarized luminescence (CPL) signals, but also the corresponding chiral aggregates can maintain CPL signals. (F.Song, Z. Xu, Q. Zhang, Z. Zhao, H. Zhang, W. Zhao, Z. Qiu, C. Qi, H. Zhang,HHY Sung, ID Williams, JWY Lam, Z. Zhao, A. Qin, D. Ma and BZTang, Adv. Funct. Mater., 2018, 28, 1800051.) The obtained chiral aggregates can achieve synergistic amplification of chiral signals, which is an effective method to construct high-performance organic luminescent materials.

[0005] However, chiral materials used to construct circularly polarized luminescence usually face the problems of complex preparation and high cost; and how to achieve narrow-band emission with high efficiency and high color purity while maintaining excellent circular polarization performance remains a difficulty in current technical research. Summary of the invention

[0006] The first purpose of the present invention is to provide an organic light-emitting material with both chiral and narrow-band emission properties in view of the shortcomings of the prior art. The synthesis of the organic light-emitting material is simple and efficient, the fluorescence quantum yield is high, and it is easy to mass produce. The luminous efficiency of the corresponding device is better than that of traditional fluorescent material devices, and the narrow-band emission and chiral luminescence phenomena are significant. The organic light-emitting material can be widely used in the fields of organic optoelectronic materials and 3D displays.

[0007] The specific technical solutions adopted are as follows: An organic light-emitting material having both chirality and narrow-band emission performance, having one of the structures shown in the following formulas Ⅰ, Ⅱ, Ⅲ, Ⅳ, V, Ⅵ, Ⅶ, and Ⅷ: Among them, R1 is selected from one of H, methyl, cyano, and methoxy; R2 is selected from one of H, methyl, ethyl, and tert-butyl; X1, X2, X3, and X4 are independently selected from one of O, S, and Se atoms, and X1, X2, X3, and X4 may be the same or different.

[0008] The organic light-emitting material having both chirality and narrow-band emission performance utilizes the chiral synergistic amplification effect of BINOL, introduces a narrow-band emission luminophore into its skeleton, and obtains a new type of circularly polarized light-emitting material having narrow-band emission. The TADF properties of circularly polarized luminescence and narrow-band emission are simultaneously exhibited on the same molecule. The molecule can introduce circularly polarized light on the basis of high color purity caused by small FHWM, thereby reducing the brightness loss caused by polarizers and filters.

[0009] The second object of the present invention is to provide a method for preparing an organic light-emitting material having both chirality and narrow-band emission properties, wherein the organic light-emitting material having both chirality and narrow-band emission properties is obtained by reacting compound A with compound B, wherein compound B is obtained by reacting compound C with compound D; The compound A is selected from one of the following structural formulas: , , or , wherein R1 is selected from one of H, methyl, cyano and methoxy.

[0010] The compound B is selected from one of the following structural formulas: , , , , , , , or , wherein X5 is one of Br, Cl, and I; and R2 is one of H, methyl, ethyl, and tert-butyl.

[0011] The compound C is selected from one of the following structural formulas: , , , , wherein R2 is one of methyl, ethyl and tert-butyl.

[0012] The compound D is , wherein X5 is one of Br, Cl and I.

[0013] Specifically, the preparation method comprises the following steps: (1) Compound C and compound D are added together with a base in an organic solvent at a molar ratio of 1:1.1-3.0, reacted at 60-140° C. for 36-72 hours, and the product obtained after separation and purification is dissolved in o-dichlorobenzene, and n-butyl lithium, boron tribromide and N,N-diethylpropylethylamine are added respectively at 0° C., reacted at 160-200° C. for 12-24 hours, and compound B is obtained after separation and purification.

[0014] (2) Compound A and compound B are added to a mixed solvent of toluene, ethanol and water at a molar ratio of 1:1.5-4.0 together with a base and a palladium catalyst, and reacted at 80-120° C. for 36-72 hours. After separation, an organic light-emitting material having structures shown in I-VIII and having both chirality and narrow-band emission properties is obtained.

[0015] Preferably, the base is an alkali metal hydride, an alkali metal hydroxide or a metal carbonate; more preferably, the base is one of NaH, NaOH, KOH, Na2CO3, K2CO3, and Cs2CO3.

[0016] Preferably, the palladium catalyst is tetrakis(triphenylphosphine)palladium, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride or palladium acetate; and the organic solvent is toluene or N,N-dimethylformamide (DMF) or N-methylpyrrolidone (NMP).

[0017] The third object of the present invention is to provide an organic light-emitting material having both chirality and narrow-band emission properties as an organic light-emitting layer for use in the optoelectronic field.

[0018] The fourth object of the present invention is to provide an organic electroluminescent device, comprising glass, a conductive glass substrate layer, a hole injection layer, a hole transport layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, and a cathode layer, wherein the organic light-emitting layer contains the organic light-emitting material having both chirality and narrow-band emission properties.

[0019] Compared with the prior art, the advantages of the present invention are: (1) The present invention provides a new type of organic light-emitting material with both chirality and narrow-band emission performance. The multiple resonance structure can effectively suppress the vibration coupling between the S1-S0 transition and the excited state structural relaxation, forming a significant narrow-band emission. At the same time, the chiral synergistic amplification effect of BINOL is used to enable the entire molecule to emit circularly polarized light through a chiral perturbation strategy, and a narrow-band emission luminophore is introduced into its skeleton to obtain a new type of circularly polarized light-emitting material with narrow-band emission. The TADF properties of circularly polarized luminescence and narrow-band emission are simultaneously exhibited on the same molecule.

[0020] (2) The organic light-emitting material with both chirality and narrow-band emission properties prepared by the present invention has readily available raw materials, simple synthesis, high quantum efficiency, and can be used for large-scale production in the field of organic electroluminescence.

[0021] (3) The efficiency of the organic electroluminescent device made by using the organic light-emitting material with both chirality and narrow-band emission performance is generally better than that of the device using traditional fluorescent materials, among which the highest device efficiency can reach 14.6%. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 1 in toluene solution.

[0023] Figure 2 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 2 in toluene solution.

[0024] Figure 3 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 3 in toluene solution.

[0025] Figure 4 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 4 in toluene solution.

[0026] Figure 5 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 5 in toluene solution.

[0027] Figure 6 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 6 in toluene solution.

[0028] Figure 7 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 7 in toluene solution.

[0029] Figure 8 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 8 in toluene solution.

[0030] Fig. 9 This is a transient photoinduced spectrum decay curve of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 4 in a toluene solution.

[0031] Fig.10 This is a transient photoinduced spectrum decay curve of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 7 in a toluene solution.

[0032] Fig.11 Schematic diagram of the structure of an organic electroluminescent device. DETAILED DESCRIPTION

[0033] The present invention will be further described below in conjunction with the accompanying drawings and embodiments. It should be understood that these embodiments are only used to illustrate the present invention and are not intended to limit the scope of the present invention.

[0034] Unless otherwise specified, the raw materials involved in the following examples can be purchased from domestic and foreign commercial channels, for example, compounds A, C, and D can all be purchased. Compound B was prepared by the following method:

[0035] , , , , , , , , .

[0036] (1) Synthesis of Compound B1 D1 (0.27 g, 1 mmol), compound C1 (0.45 g, 3 mmol) and potassium carbonate (0.42 g, 3 mmol) were dissolved in 30 mL NMP solvent in Ar atmosphere, heated and stirred at 140 °C for 36 hours, the solvent was distilled off under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain an intermediate compound. The intermediate compound was then dissolved in anhydrous o-dichlorobenzene solvent in Ar atmosphere, stirred at 0 °C for 30 minutes, and then 2.5 M n-butyl lithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop. After 30 minutes, it was stirred at room temperature for 1 hour; then 2 M boron tribromide (1 mL, 2 mmol) was added at a rate of 2 s / drop at -17 °C, and after 30 minutes, it was stirred at room temperature for 30 minutes, and then stirred at 50 °C for 1 hour; then N,N-diisopropylethylamine (0.26 g, 2 mmol), stirred at room temperature for 30 minutes after 30 minutes, then stirred at 180 ° C for 12 hours, the solvent was distilled off under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain compound B1 as a white solid (yield 40%).

[0037] (2) Synthesis of Compound B2 D2 (0.27 g, 1 mmol) was dissolved in 30 mL of anhydrous DMF solvent in Ar atmosphere and added to a bottle containing sodium hydride (0.06 g, 2.5 mmol). Compound D1 (0.27 g, 1 mmol) and compound C1 (0.15 g, 1 mmol) were then added to the above mixed solvent, heated and stirred at 60 °C for 8 hours, the solvent was distilled off under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain an intermediate compound. The intermediate compound was then dissolved in anhydrous o-dichlorobenzene solvent in Ar atmosphere, stirred at 0 °C for 30 minutes, and then 2.5M n-butyl lithium (0.44 mL, 1.1 mmol) was added at a rate of 2s / drop, and stirred at room temperature for 1 hour after 30 minutes; then 2M boron tribromide (1 mL, 2 mmol) was added at a rate of 2s / drop at -17 °C, and stirred at room temperature for 30 minutes after 30 minutes, and then heated at 50 °C for 2 hours. The mixture was stirred at 0 °C for 1 hour; then N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at a rate of 2 s / drop at 0 °C, and after 30 minutes, the mixture was stirred at room temperature for 30 minutes, and then stirred at 170 °C for 16 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain compound B2 as a yellow solid (yield 25%).

[0038] (3) Synthesis of Compound B3 D1 (0.27 g, 1 mmol), compound C1 (0.15 g, 1 mmol), compound C3 (0.21 g, 1mmol) and potassium carbonate (0.42 g, 3 mmol) were dissolved in 30 mL of anhydrous DMF solvent in Ar atmosphere, heated and stirred at 140 °C for 72 hours, the solvent was distilled off under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain an intermediate compound, which was then dissolved in anhydrous o-dichlorobenzene solvent in Ar atmosphere, stirred at 0 °C for 30 minutes, and then 2.5 M n-butyl lithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop, and stirred at room temperature for 1 hour after 30 minutes; then 2 M boron tribromide (1 mL, 2 mmol) was added at a rate of 2 s / drop at -17 °C, and stirred at room temperature for 30 minutes after 30 minutes, and then stirred at 50 °C for 1 hour; then heated at 0 °C for 2 hours. N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at a rate of 2s / drop at 190 °C. After 30 minutes, the mixture was stirred at room temperature for 30 minutes and then stirred at 190 °C for 12 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain compound B3 as a yellow solid (yield 20%).

[0039] (4) Synthesis of Compound B4 D1 (0.27 g, 1 mmol) was dissolved in 30 mL of anhydrous DMF solvent in an Ar atmosphere and added to a bottle containing sodium hydride (0.06 g, 2.5 mmol). Compound C2 (0.42 g, 2.5 mmol) was then added to the above mixed solvent, heated and stirred at 60 °C for 4 hours, the solvent was distilled off under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain an intermediate compound. The intermediate compound was then dissolved in anhydrous o-dichlorobenzene solvent in an Ar atmosphere, stirred at 0 °C for 30 minutes, and then 2.5 M n-butyl lithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop. After 30 minutes, it was stirred at room temperature for 1 hour; then 2 M boron tribromide (1 mL, 2 mmol) was added at a rate of 2 s / drop at -17 °C, and after 30 minutes, it was stirred at room temperature for 30 minutes, and then stirred at 50 °C for 1 hour; then the mixture was heated at 0 °C for 30 minutes. N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at a rate of 2s / drop at 400 °C. After 30 minutes, the mixture was stirred at room temperature for 30 minutes and then stirred at 170 °C for 16 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain compound B4 as a yellow solid (yield 50%).

[0040] (5) Synthesis of Compound B5 D2 (0.27 g, 1 mmol) was dissolved in 30 mL of anhydrous DMF solvent in Ar atmosphere and added to a bottle containing sodium hydride (0.06 g, 2.5 mmol). Compound C2 (0.18 g, 1.1 mmol) and compound C3 (0.24 g, 1.1 mmol) were then added to the above mixed solvent, heated and stirred at 100 °C for 12 hours, the solvent was removed by distillation under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain an intermediate compound. The intermediate compound was then dissolved in anhydrous o-dichlorobenzene solvent in Ar atmosphere, stirred at 0 °C for 30 minutes, and then 2.5 M n-butyl lithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop, and stirred at room temperature for 1 hour after 30 minutes; then 2 M boron tribromide (1 mL, 2 mmol) was added at a rate of 2 s / drop at -17 °C, and stirred at room temperature for 30 minutes after 30 minutes, and then heated at 50 °C for 2 hours. The mixture was stirred at 0 °C for 1 hour; then N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at a rate of 2 s / drop at 0 °C, and after 30 minutes, the mixture was stirred at room temperature for 30 minutes, and then stirred at 170 °C for 16 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain compound B5 as a yellow solid (yield 24%).

[0041] (6) Synthesis of Compound B6 D2 (0.27 g, 1 mmol), compound C1 (0.15 g, 1 mmol), compound C4 (0.31 g, 1.1 mmol) and cesium carbonate (0.98 g, 3 mmol) were dissolved in 30 mL of DMF solvent in Ar atmosphere, heated and stirred at 100 °C for 40 hours, the solvent was distilled off under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain an intermediate compound, which was then dissolved in anhydrous o-dichlorobenzene solvent in Ar atmosphere, stirred at 0 °C for 30 minutes, and then 2.5 M n-butyl lithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop, and stirred at room temperature for 1 hour after 30 minutes; then 2 M boron tribromide (1 mL, 2 mmol) was added at a rate of 2 s / drop at -17 °C, and stirred at room temperature for 30 minutes after 30 minutes, and then stirred at 50 °C for 1 hour; then heated at 0 N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at a rate of 2s / drop at 400 °C. After 30 minutes, the mixture was stirred at room temperature for 30 minutes and then stirred at 160 °C for 24 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain compound B6 as a white solid (yield 35%).

[0042] (7) Synthesis of Compound B7 D2 (0.27 g, 1 mmol) was dissolved in 30 mL of anhydrous DMF solvent in Ar atmosphere and added to a bottle containing sodium hydride (0.06 g, 2.5 mmol). Compound C2 (0.18 g, 1.1 mmol) and compound C4 (0.31 g, 1.1 mmol) were then added to the above mixed solvent, heated and stirred at 90 °C for 6 hours, the solvent was removed by distillation under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain an intermediate compound. The intermediate compound was then dissolved in anhydrous o-dichlorobenzene solvent in Ar atmosphere, stirred at 0 °C for 30 minutes, and then 2.5M n-butyl lithium (0.44mL, 1.1 mmol) was added at a rate of 2s / drop, and stirred at room temperature for 1 hour after 30 minutes; then 2M boron tribromide (1 mL, 2 mmol) was added at a rate of 2s / drop at -17 °C, and stirred at room temperature for 30 minutes after 30 minutes, and then heated at 50 °C for 2 hours. The mixture was stirred at 0 °C for 1 hour; then N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at a rate of 2 s / drop at 0 °C, and after 30 minutes, the mixture was stirred at room temperature for 30 minutes, and then stirred at 160 °C for 24 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain compound B5 as a yellow solid (yield 34%).

[0043] (8) Synthesis of Compound B8 D2 (0.27 g, 1 mmol), compound C3 (0.24 g, 1.1 mmol), compound C4 (0.31 g, 1.1 mmol) and cesium carbonate (0.98 g, 3 mmol) were dissolved in 30 mL of anhydrous DMF solvent in Ar atmosphere, heated and stirred at 80 °C for 60 hours, the solvent was distilled off under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain an intermediate compound, which was then dissolved in anhydrous o-dichlorobenzene solvent in Ar atmosphere, stirred at 0 °C for 30 minutes, and then 2.5 M n-butyl lithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop, and stirred at room temperature for 1 hour after 30 minutes; then 2 M boron tribromide (1 mL, 2 mmol) was added at a rate of 2 s / drop at -17 °C, and stirred at room temperature for 30 minutes after 30 minutes, and then stirred at 50 °C for 1 hour; then heated at 0 °C for 1 hour. N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at a rate of 2 s / drop at 40 °C. After 30 minutes, the mixture was stirred at room temperature for 30 minutes and then stirred at 190 °C for 16 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain compound B8 as a yellow solid (yield 30%).

[0044] (9) Synthesis of Compound B9 D1 (0.27 g, 1 mmol), compound C3 (0.64 g, 3 mmol) and potassium carbonate (0.42 g, 3 mmol) were dissolved in 30 mL DMF solvent in Ar atmosphere, heated and stirred at 120 °C for 72 hours, the solvent was distilled off under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain an intermediate compound. The intermediate compound was then dissolved in anhydrous o-dichlorobenzene solvent in Ar atmosphere, stirred at 0 °C for 30 minutes, and then 2.5 M n-butyl lithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop, and stirred at room temperature for 1 hour after 30 minutes; then 2 M boron tribromide (1 mL, 2 mmol) was added at a rate of 2 s / drop at -17 °C, and stirred at room temperature for 30 minutes after 30 minutes, and then stirred at 50 °C for 1 hour; then N,N-diisopropylethylamine (0.26 g, 2 mmol), after 30 minutes, the mixture was stirred at room temperature for 30 minutes, and then stirred at 200 ° C for 18 hours, the solvent was distilled off under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain compound B9 as a white solid (yield 36%).

[0045] The present invention is further described below in conjunction with specific embodiments.

[0046] (1) Example 1: Preparation of Z1 Intermediate A1 (0.49 g, 1 mmol), compound B1 (0.51 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 36 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 80%). Figure 1 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 1 in toluene solution.

[0047] Elemental analysis theoretical value C52H41BO4 (%): C 84.32; H 5.58; B 1.46; O 8.64; found value: C 84.34; H 5.57; B 1.45; O 8.63.

[0048] (2) Example 2: Preparation of Z2 Intermediate A2 (0.49 g, 1 mmol), compound B1 (0.51 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, and the mixture was heated under reflux for 36 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material having both chiral and narrow-band emission properties (yield 82%).

[0049] Elemental analysis theoretical value C52H41BO4 (%): C 84.32; H 5.58; B 1.46; O 8.64; found value: C 84.33; H 5.55; B 1.44; O 8.65.

[0050] Figure 2 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 2 in toluene solution.

[0051] (3) Example 3: Preparation of Z3 Intermediate A1 (0.49 g, 1 mmol), compound B2 (0.52 g, 1.1 mmol), palladium acetate (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 75%).

[0052] Elemental analysis theoretical value C52H41BO3S (%): C 82.53; H 5.46; B 1.43; O 6.34; S 4.24; found value: C 82.54; H 5.45; B 1.41; O 6.34; S 4.26.

[0053] Figure 3 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 3 in toluene solution.

[0054] (4) Example 4: Preparation of Z4 Intermediate A2 (0.49 g, 1 mmol), compound B2 (0.52 g, 1.1 mmol), palladium acetate (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 70%).

[0055] Elemental analysis theoretical value C52H41BO3S (%): C 82.53; H 5.46; B 1.43; O 6.34; S 4.24; found value: C 82.51; H 5.44; B 1.43; O 6.35; S 4.25.

[0056] Figure 4 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 4 in toluene solution. Fig. 9 This is a transient photoinduced spectrum decay curve of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 4 in a toluene solution.

[0057] (5) Example 5: Preparation of Z5 Intermediate A1 (0.49 g, 1 mmol), compound B3 (0.58 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 72 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 65%).

[0058] Elemental analysis theoretical value C52H41BO3Se (%): C 77.71; H 5.14; B 1.35; O 5.97; Se9.83; found value: C 77.72; H 5.16; B 1.34; O 5.96; Se 9.85.

[0059] Figure 5 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 5 in toluene solution.

[0060] (6) Example 6: Preparation of Z6 Intermediate A2 (0.49 g, 1 mmol), compound B3 (0.58 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 72 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 65%).

[0061] Elemental analysis theoretical value C52H41BO3Se (%): C 77.71; H 5.14; B 1.35; O 5.97; Se9.83; found value: C 77.73; H 5.15; B 1.36; O 5.95; Se 9.84.

[0062] Figure 6 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 6 in toluene solution.

[0063] (7) Example 7: Preparation of Z7 Intermediate A1 (0.49 g, 1 mmol), compound B4 (0.54 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 72 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 75%).

[0064] Elemental analysis theoretical value C52H41BO2S2 (%): C 80.82; H 5.35; B 1.40; O 4.14; S8.30; found value: C 80.83; H 5.34; B 1.38; O 4.16; S 8.30.

[0065] Figure 7 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 7 in toluene solution.

[0066] Fig.10 This is a transient photoinduced spectrum decay curve of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 7 in a toluene solution.

[0067] (8) Example 8: Preparation of Z8 Intermediate A2 (0.49 g, 1 mmol), compound B4 (0.54 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 72 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 73%).

[0068] Elemental analysis theoretical value C52H41BO2S2 (%): C 80.82; H 5.35; B 1.40; O 4.14; S8.30; found value: C 80.84; H 5.32; B 1.39; O 4.17; S 8.32.

[0069] Figure 8 This is the fluorescence spectrum of the organic light-emitting material with both chiral and narrow-band emission properties prepared in Example 8 in toluene solution.

[0070] (9) Example 9: Preparation of Z9 Intermediate A1 (0.49 g, 1 mmol), compound B5 (0.60 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 66%).

[0071] Elemental analysis theoretical value C52H41BO2SSe (%): C 76.19; H 5.04; B 1.32; O 3.90; S3.91; Se 9.63; found value: C 76.17; H 5.01; B 1.30; O 3.92; S 3.90; Se 9.61.

[0072] (10) Example 10: Preparation of Z10 Intermediate A2 (0.49 g, 1 mmol), compound B5 (0.60 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 60%).

[0073] Elemental analysis theoretical value C52H41BO2SSe (%): C 76.19; H 5.04; B 1.32; O 3.90; S3.91; Se 9.63; found value: C 76.18; H 5.05; B 1.34; O 3.91; S 3.89; Se 9.63.

[0074] (11) Example 11: Preparation of Z11 Intermediate A1 (0.49 g, 1 mmol), compound B6 (0.65 g, 1.1 mmol), palladium acetate (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 36 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 58%).

[0075] Elemental analysis theoretical value C62H52BNO3 (%): C 85.60; H 6.03; B 1.24; N 1.61; O 5.52; found value: C 85.63; H 6.00; B 1.21; N 1.64; O 5.52.

[0076] (12) Example 12: Preparation of Z12 Intermediate A2 (0.49 g, 1 mmol), compound B6 (0.65 g, 1.1 mmol), palladium acetate (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 36 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 57%).

[0077] Elemental analysis theoretical value C62H52BNO3 (%): C 85.60; H 6.03; B 1.24; N 1.61; O 5.52; found value: C 85.61; H 6.02; B 1.25; N 1.61; O 5.52.

[0078] (13) Example 13: Preparation of Z13 Intermediate A1 (0.49 g, 1 mmol), compound B7 (0.67 g, 1.1 mmol), palladium acetate (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 72 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 63%).

[0079] Elemental analysis theoretical value C62H52BNO2S (%): C 84.05; H 5.92; B 1.22; N 1.58; O3.61; S 3.62; found value: C 84.03; H 5.90; B 1.23; N 1.57; O 3.63; S 3.60.

[0080] (14) Example 14: Preparation of Z14 Intermediate A2 (0.49 g, 1 mmol), compound B7 (0.67 g, 1.1 mmol), palladium acetate (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 72 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 63%).

[0081] Elemental analysis theoretical value C62H52BNO2S (%): C 84.05; H 5.92; B 1.22; N 1.58; O3.61; S 3.62; found value: C 84.07; H 5.88; B 1.21; N 1.59; O 3.63; S 3.64.

[0082] (15) Example 15: Preparation of Z15 Intermediate A1 (0.49 g, 1 mmol), compound B8 (0.72 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 36 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 60%).

[0083] Elemental analysis theoretical values ​​C62H52BNO2Se (%): C 79.83; H 5.62; B 1.16; N 1.50; O3.43; Se 8.47; found values: C 79.85; H 5.61; B 1.16; N 1.52; O 3.45; Se 8.45.

[0084] (16) Example 16: Preparation of Z16 Intermediate A2 (0.49 g, 1 mmol), compound B8 (0.72 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 36 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 60%).

[0085] Elemental analysis theoretical values ​​C62H52BNO2Se (%): C 79.83; H 5.62; B 1.16; N 1.50; O3.43; Se 8.47; found values: C 79.81; H 5.63; B 1.14; N 1.49; O 3.41; Se 8.48.

[0086] (17) Example 17: Preparation of Z17 Intermediate A1 (0.49 g, 1 mmol), compound B9 (0.65 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, and the mixture was heated under reflux for 72 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material having both chiral and narrow-band emission properties (yield 80%).

[0087] Elemental analysis theoretical value C52H41BO2Se2 (%): C 72.07; H 4.77; B 1.25; O 3.69; Se18.22; found value: C 72.06; H 4.75; B 1.23; O 3.67; Se 18.25.

[0088] (18) Example 18: Preparation of Z18 Intermediate A2 (0.49 g, 1 mmol), compound B9 (0.65 g, 1.1 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and potassium carbonate (0.28 g, 2 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 72 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 76%).

[0089] Elemental analysis theoretical value C52H41BO2Se2 (%): C 72.07; H 4.77; B 1.25; O 3.69; Se18.22; found value: C 72.05; H 4.77; B 1.24; O 3.70; Se 18.21.

[0090] (19) Example 19: Preparation of Z19 Intermediate A3 (0.62 g, 1 mmol), compound B1 (1.15 g, 2.4 mmol), tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 75%).

[0091] Elemental analysis theoretical value C78H66B2O6 (%): C 83.57; H 5.93; B 1.93; O 8.56; found value: C 83.56; H 5.95; B 1.94; O 8.54.

[0092] (20) Example 20: Preparation of Z20 Intermediate A4 (0.62 g, 1 mmol), compound B1 (1.15 g, 2.4 mmol), tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 75%).

[0093] Elemental analysis theoretical value C78H66B2O6 (%): C 83.57; H 5.93; B 1.93; O 8.56; found value: C 83.56; H 5.93; B 1.91; O 8.57.

[0094] (21) Example 21: Preparation of Z21 Intermediate A3 (0.62 g, 1 mmol), compound B2 (1.19 g, 2.4 mmol), tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 70%).

[0095] Elemental analysis theoretical value C78H66B2O4S2 (%): C 81.25; H 5.77; B 1.87; O 5.55; S5.56; found value: C 81.27; H 5.76; B 1.86; O 5.53; S 5.58.

[0096] (22) Example 22: Preparation of Z22 Intermediate A4 (0.62 g, 1 mmol), compound B2 (1.19 g, 2.4 mmol), tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 70%).

[0097] Elemental analysis theoretical value C78H66B2O4S2 (%): C 81.25; H 5.77; B 1.87; O 5.55; S5.56; found value: C 81.25; H 5.79; B 1.88; O 5.54; S 5.59.

[0098] (23) Example 23: Preparation of Z23 Intermediate A3 (0.62 g, 1 mmol), compound B3 (1.31 g, 2.4 mmol), tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 36 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 65%).

[0099] Elemental analysis theoretical value C78H66B2O4Se2 (%): C 75.13; H 5.34; B 1.73; O 5.13; Se12.67; found value: C 75.14; H 5.35; B 1.70; O 5.12; Se 12.68.

[0100] (24) Example 24: Preparation of Z24 Intermediate A4 (0.62 g, 1 mmol), compound B3 (1.31 g, 2.4 mmol), tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 36 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 61%).

[0101] Elemental analysis theoretical value C78H66B2O4Se2 (%): C 75.13; H 5.34; B 1.73; O 5.13; Se12.67; found value: C 75.13; H 5.36; B 1.74; O 5.11; Se 12.69.

[0102] (25) Example 25: Preparation of Z25 Intermediate A3 (0.62 g, 1 mmol), compound B4 (1.23 g, 2.4 mmol), palladium acetate (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 72 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 60%).

[0103] Elemental analysis theoretical value C78H66B2O2S4 (%): C 79.04; H 5.61; B 1.82; O 2.70; S10.82; found value: C 79.05; H 5.62; B 1.80; O 2.71; S 10.83.

[0104] (26) Example 26: Preparation of Z26 Intermediate A4 (0.62 g, 1 mmol), compound B4 (1.23 g, 2.4 mmol), palladium acetate (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 72 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 65%).

[0105] Elemental analysis theoretical value C78H66B2O2S4 (%): C 79.04; H 5.61; B 1.82; O 2.70; S10.82; found value: C 79.03; H 5.60; B 1.81; O 2.72; S 10.81.

[0106] (27) Example 27: Preparation of Z27 Intermediate A3 (0.62 g, 1 mmol), compound B5 (1.35 g, 2.4 mmol), palladium acetate (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 62%).

[0107] Elemental analysis theoretical value C78H66B2O2S2Se2 (%): C 73.25; H 5.20; B 1.69; O 2.50; S5.01; Se 12.35; found value: C 73.24; H 5.18; B 1.71; O 2.52; S 5.04; Se 12.31.

[0108] (28) Example 28: Preparation of Z28 Intermediate A4 (0.62 g, 1 mmol), compound B5 (1.35 g, 2.4 mmol), palladium acetate (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 56%).

[0109] Elemental analysis theoretical value C78H66B2O2S2Se2 (%): C 73.25; H 5.20; B 1.69; O 2.50; S5.01; Se 12.35; found value: C 73.27; H 5.19; B 1.66; O 2.51; S 5.02; Se 12.36.

[0110] (29) Example 29: Preparation of Z29 Intermediate A3 (0.62 g, 1 mmol), compound B6 (1.47 g, 2.4 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, and the mixture was heated under reflux for 36 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material having both chiral and narrow-band emission properties (yield 75%).

[0111] Elemental analysis theoretical value C98H88B2N2O4 (%): C 85.33; H 6.43; B 1.57; N 2.03; O4.64; found value: C 85.35; H 6.41; B 1.56; N 2.03; O 4.66.

[0112] (30) Example 30: Preparation of Z30 Intermediate A4 (0.62 g, 1 mmol), compound B6 (1.47 g, 2.4 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, and the mixture was heated under reflux for 36 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material having both chiral and narrow-band emission properties (yield 74%).

[0113] Elemental analysis theoretical value C98H88B2N2O4 (%): C 85.33; H 6.43; B 1.57; N 2.03; O4.64; found value: C 85.36; H 6.40; B 1.55 N 2.01; O 4.61.

[0114] (31) Example 31: Preparation of Z31 Intermediate A3 (0.62 g, 1 mmol), compound B7 (1.57 g, 2.4 mmol), tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, and the mixture was heated under reflux for 72 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material having both chiral and narrow-band emission properties (yield 65%).

[0115] Elemental analysis theoretical value C98H88B2N2O2S2 (%): C 83.39; H 6.28; B 1.53; N 1.98; O2.27; S 4.54; found value: C 83.37; H 6.29; B 1.51; N 1.99; O 2.25; S 4.53.

[0116] (32) Example 32: Preparation of Z32 Intermediate A4 (0.62 g, 1 mmol), compound B7 (1.57 g, 2.4 mmol), tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 72 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material having both chiral and narrow-band emission properties (yield 66%).

[0117] Elemental analysis theoretical value C98H88B2N2O2S2 (%): C 83.39; H 6.28; B 1.53; N 1.98; O2.27; S 4.54; found value: C 83.36; H 6.30; B 1.54; N 1.97; O 2.25; S 4.51.

[0118] (33) Example 33: Preparation of Z33 Intermediate A3 (0.62 g, 1 mmol), compound B8 (1.63 g, 2.4 mmol), tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 69%).

[0119] Elemental analysis theoretical value C98H88B2N2O2Se2 (%): C 78.19; H 5.89; B 1.44; N 1.86; O2.13; Se 10.49; found value: C 78.17; H 5.88; B 1.41; N 1.89; O 2.12; Se 10.47.

[0120] (34) Example 34: Preparation of Z34 Intermediate A4 (0.62 g, 1 mmol), compound B8 (1.63 g, 2.4 mmol), tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, heated under reflux for 48 hours, and the solvent was removed by distillation under reduced pressure. The mixture was extracted with dichloromethane and water, and purified by column chromatography to obtain an organic light-emitting material with both chiral and narrow-band emission properties (yield 66%).

[0121] Elemental analysis theoretical value C98H88B2N2O2Se2 (%): C 78.19; H 5.89; B 1.44; N 1.86; O2.13; Se 10.49; found value: C 78.18; H 5.87; B 1.42; N 1.87; O 2.11; Se 10.46.

[0122] (35) Example 35: Preparation of Z35 Intermediate A3 (0.62 g, 1 mmol), compound B9 (1.47 g, 2.4 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, and the mixture was heated under reflux for 72 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material having both chiral and narrow-band emission properties (yield 85%).

[0123] Elemental analysis theoretical value C78H66B2O2Se4 (%): C 68.24; H 4.85; B 1.57; O 2.33; Se23.01; found value: C 68.23; H 4.86; B 1.55; O 2.35; Se 23.02.

[0124] (36) Example 36: Preparation of Z36 Intermediate A4 (0.62 g, 1 mmol), compound B9 (1.47 g, 2.4 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.12 g, 0.10 mmol) and potassium carbonate (0.56 g, 4 mmol) were dissolved in 60 mL of toluene solvent, followed by the addition of 30 mL of ethanol and 15 mL of water, and the mixture was heated under reflux for 72 hours. The solvent was removed by distillation under reduced pressure, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material having both chiral and narrow-band emission properties (yield 79%).

[0125] Elemental analysis theoretical value C78H66B2O2Se4 (%): C 68.24; H 4.85; B 1.57; O 2.33; Se23.01; found value: C 68.24; H 4.83; B 1.59; O 2.32; Se 23.03.

[0126] Application Example 1 The structure of the organic electroluminescent device made using the organic light-emitting material having both chirality and narrow-band emission performance is: ITO / MoO3 (8nm) / TAPC (50nm) / mcP: 2% Emitters (compounds of the present invention) / TmPyPB (40nm) / LiF (1nm) / Al (100nm).

[0127] like Fig.11 As shown, the organic electroluminescent device made of the organic light-emitting material with both chirality and narrow-band emission performance includes a conductive glass substrate 1, a hole injection layer 2 (molybdenum trioxide MoO3), a hole transport layer 3 (4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline]TAPC), an organic light-emitting layer 4 (mCP main material and the organic light-emitting material with both chirality and narrow-band emission performance prepared by the present invention), an electron transport layer 5 (3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1''-terphenyl]-3,3''-diyl]bipyridine TmPyPB), an electron injection layer 6 (lithium fluoride LiF), and 7 is a cathode layer (aluminum Al).

[0128] The device preparation process is as follows: the electroluminescent device is made according to methods known in the art, such as the method disclosed in reference (Adv. Mater. 2004, 16, 537.); the specific method is: under high vacuum conditions, 8 nm of MoO3, 50 nm of TAPC, 20 nm of light-emitting layer, 40 nm of TmPyPB, 1 nm of LiF and 100 nm of Al are sequentially evaporated on a cleaned conductive glass (ITO) substrate.

[0129] The device performance test data is shown in Table 1 below: Table 1 Organic electroluminescent device performance test results As can be seen from the above table, the maximum current efficiency of the device using the compound of the present invention can reach 24.9 cd / A, the lowest starting voltage is only 3.1 V, the efficiency decay performance is good, and the quantum efficiency is higher than that of the device using traditional fluorescent materials.

[0130] The embodiments described above provide a detailed description of the technical solutions of the present invention. It should be understood that the above are only specific embodiments of the present invention and are not intended to limit the present invention. Any modifications, supplements or similar substitutions made within the scope of the principles of the present invention should be included in the protection scope of the present invention.

Claims

1. An organic light-emitting material having both chirality and narrow-band emission performance, characterized in that: The structure of the organic light-emitting material is one of the structures shown in the following formulas Ⅰ, Ⅱ, Ⅲ, Ⅳ, V, Ⅵ, Ⅶ, and Ⅷ: Among them, R1 is selected from one of H, methyl, cyano, and methoxy; R2 is selected from one of H, methyl, ethyl, and tert-butyl; X1, X2, X3, and X4 are independently selected from one of O, S, and Se atoms.

2. A method for preparing an organic light-emitting material having both chirality and narrow-band emission performance as claimed in claim 1, characterized in that: The preparation method comprises the following steps: Step (1), adding compound C, compound D and a base together into an organic solvent, reacting at 60-140° C. for 36-72 hours, separating and purifying to obtain a product, dissolving it in o-dichlorobenzene, adding n-butyl lithium, boron tribromide and N,N-diethylpropylethylamine at 0° C. respectively, reacting at 160-200° C. for 12-24 hours, separating and purifying to obtain compound B; The compound B is selected from one of the following structural formulas: , , , , , , , or , wherein X5 is one of Br, Cl, and I; R2 is one of H, methyl, ethyl, and tert-butyl; The compound C is selected from one of the following structural formulas: , , , , wherein R2 is one of methyl, ethyl, and tert-butyl; The compound D is , wherein X5 is one of Br, Cl and I; Step (2), adding compound A, compound B, a base and a palladium catalyst into a mixed solvent of toluene, ethanol and water, reacting at 80-120° C. for 36-72 hours, and obtaining an organic light-emitting material having structures shown in I-VIII and having both chirality and narrow-band emission performance after separation; The compound A is selected from one of the following structural formulas: , , or , wherein R1 is selected from one of H, methyl, cyano and methoxy.

3. The preparation method according to claim 2, characterized in that: The base is an alkali metal hydride, an alkali metal hydroxide or a metal carbonate.

4. The preparation method according to claim 3, characterized in that: The base is one of NaH, NaOH, KOH, Na2CO3, K2CO3, and Cs2CO3.

5. The preparation method according to claim 2, characterized in that: The molar ratio of compound C to compound D in step (1) is 1:1.1-3.

0.

6. The preparation method according to claim 2, characterized in that: In step (2), the molar ratio of compound A to compound B is 1:1.5-4.

0.

7. The preparation method according to claim 2, characterized in that: The palladium catalyst is tetrakis(triphenylphosphine)palladium, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride or palladium acetate.

8. The preparation method according to claim 2, characterized in that: The organic solvent is toluene, N,N-dimethylformamide or N-methylpyrrolidone.

9. Use of the organic light-emitting material having both chirality and narrow-band emission performance as claimed in claim 1 as an organic light-emitting layer in the optoelectronic field.

10. An organic electroluminescent device, comprising glass, a conductive glass substrate layer, a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer, an electron injection layer, and a cathode layer connected in sequence from bottom to top, characterized in that: The organic light-emitting layer contains the organic light-emitting material having both chirality and narrow-band emission properties as claimed in claim 1.

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