An organic light-emitting material with chiral and narrow-band emission performance, a preparation method and application thereof

Abstract

The application discloses an organic light-emitting material with chiral and narrow-band emission performance, a preparation method and application thereof, and the core is that multiple resonance structures can effectively inhibit the vibration coupling between S1-S0 transition and excited state structure relaxation, form significant narrow-band emission, and simultaneously utilize the axial chirality characteristics of BINOL, utilize a chiral disturbance strategy to form circularly polarized luminescence. The application further provides a preparation method of the material, wherein compound B is obtained by reacting compound C with compound D, and the organic light-emitting material is obtained by reacting compound A with compound B. The material has the characteristics of thermal activated delayed fluorescence induced by multiple resonance effect, and simultaneously has the characteristics of circularly polarized luminescence, and can be applied to the fields of 3D display, molecular probe, spin information, optical data storage and processing and optoelectronic devices, and the like. The synthesis process is simple, raw materials are widely sourced and inexpensive, and the material is suitable for wide application.

Description

Technical Field

[0001] This invention belongs to the field of organic optoelectronic materials technology, and particularly relates to an organic light-emitting material that combines chirality and narrow-band emission performance, its preparation method and application. Background Technology

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

[0003] Traditional organic fluorescent materials suffer from a limited quantum efficiency (IQE) of only 25% for OLED fluorescent materials due to the "forbidden principle," which restricts 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 utilize singlet and triplet excitons for emission, achieving an IQE of 100%; however, the triplet emission depends on transition metal complexes, making it unsuitable for large-scale OLED production. (JM Teng, YF Wang and CF Chen, J. Mater. Chem. C, 2020, 8, 11340.) Thermally activated delayed fluorescence (TADF) materials are purely organic molecules that utilize the reverse intersystem crossing (RISC) process to convert triplet excitons into singlet excitons, achieving an IQE of 100%. TADF materials maintain the high internal quantum efficiency of organic phosphors and the stability of traditional organic fluorescent materials. At the same time, TADF materials eliminate the cost and resource limitations of organic phosphors and the low internal quantum efficiency of traditional organic fluorescent materials, making them one of the most promising candidate materials for next-generation OLEDs and a research hotspot in recent years.

[0004] OLEDs with TADF molecules have been widely used in display and lighting technologies. However, OLEDs require the use of polarizers to achieve high image contrast, typically suffering at least 50% brightness and energy loss. CP-OLEDs, on the other hand, emit circularly polarized light, which does not suffer brightness loss when passing through a polarizer, enabling more energy-efficient OLED displays. By introducing chiral structures (chiral centers, axial chirality, planar chirality, and helical chirality, etc.) onto luminescent groups, not only can small organic molecules be induced to generate circularly polarized light emission (CPL) signals, but the corresponding chiral aggregates can also 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 resulting chiral aggregates can achieve synergistic amplification of chiral signals, which is an effective method for constructing high-performance organic light-emitting materials.

[0005] However, the preparation of chiral materials for circularly polarized luminescence is often complicated and costly. Furthermore, how to achieve high efficiency and high color purity narrow-band emission while maintaining excellent circular polarization performance remains a challenge in current technological research. Summary of the Invention

[0006] The first objective of this invention is to address the shortcomings of existing technologies by providing an organic light-emitting material that combines chirality and narrow-band emission performance. This material is simple and efficient to synthesize, has a high fluorescence quantum yield, is easy to mass-produce, and its corresponding devices have better luminous efficiency than traditional fluorescent material devices. It exhibits significant narrow-band emission and chiral luminescence phenomena and can be widely used in organic optoelectronic materials and 3D display fields.

[0007] The specific technical solution adopted is as follows:

[0008] An organic light-emitting material possessing both chirality and narrow-band emission properties has one of the structures shown in formulas I, II, III, IV, V, VI, VII, and VIII:

[0009]

[0010]

[0011]

[0012]

[0013] R1 is selected from H, methyl, cyano, and methoxy; R2 is selected from H, methyl, ethyl, and tert-butyl; X1, X2, X3, and X4 are each independently selected from O, S, and Se atoms, and X1, X2, X3, and X4 can be the same or different.

[0014] This describes an organic light-emitting material that combines chirality and narrow-band emission properties. Utilizing the chiral synergistic amplification effect of BINOL, narrow-band emitting luminescent groups are introduced into its framework, resulting in a novel type of circularly polarized light-emitting material with narrow-band emission. This allows the same molecule to simultaneously exhibit the TADF properties of circularly polarized emission and narrow-band emission. It enables the introduction of circularly polarized light into the molecule while maintaining high color purity due to a small FHWM (Frequency High-Wave Micrometer), thereby reducing brightness loss caused by polarizers and filters.

[0015] The second objective of this invention is to provide a method for preparing an organic light-emitting material that combines chirality and narrow-band emission properties, wherein the organic light-emitting material that combines 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;

[0016] Compound A is selected from one of the following structural formulas:

[0017] , , or R1 is selected from H, methyl, cyano, and methoxy.

[0018] The compound B is selected from one of the following structural formulas: , , , , , , , or X5 is one of Br, Cl, and I; R2 is one of H, methyl, ethyl, and tert-butyl.

[0019] The compound C is selected from one of the following structural formulas: , , , R2 is one of H, methyl, ethyl, or tert-butyl.

[0020] The compound D is X5 is one of Br, Cl and I.

[0021] Specifically, the preparation method includes the following steps:

[0022] (1) Compound C and compound D were added to an organic solvent along with a base at a molar ratio of 1:1.1~3.0 and reacted at 60~140°C for 36~72 hours. After separation and purification, the product was dissolved in o-dichlorobenzene. At 0°C, n-butyllithium, boron tribromide and N,N-diisopropylethylamine were added respectively and reacted at 160~200°C for 12~24 hours. After separation and purification, compound B was obtained.

[0023] (2) Compound A and compound B are added together with base and palladium catalyst in a molar ratio of 1:1.5~4.0 to a mixed solvent of toluene, ethanol and water. The mixture is reacted at 80~120°C for 36~72 hours. After separation, an organic light-emitting material with both chirality and narrow band emission performance with the structure shown in I~VIII is obtained.

[0024] Preferably, the alkali is an alkali metal hydride, an alkali metal hydroxide, or a metal carbonate; more preferably, the alkali is one of NaH, NaOH, KOH, Na2CO3, K2CO3, and Cs2CO3.

[0025] Preferably, the palladium catalyst is tetra(triphenylphosphine)palladium, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride, or palladium acetate; the organic solvent is toluene, N,N-dimethylformamide (DMF), or N-methylpyrrolidone (NMP).

[0026] The third objective of this invention is to provide an organic light-emitting material that combines chirality and narrow-band emission properties as an organic light-emitting layer material for use in the optoelectronic field.

[0027] A fourth objective of this invention is to provide an organic electroluminescent device comprising a glass, a conductive glass substrate, 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 an organic light-emitting material that combines chirality and narrow-band emission performance.

[0028] Compared with the prior art, the advantages of the present invention are as follows:

[0029] (1) This invention provides a novel organic light-emitting material that combines chirality and narrow-band emission properties. Utilizing a multiple resonance structure, it effectively suppresses the vibrational coupling between the S1-S0 transition and the excited-state structural relaxation, resulting in significant narrow-band emission. Simultaneously, through the chiral synergistic amplification effect of BINOL, a chiral perturbation strategy enables the entire molecule to emit circularly polarized light, and narrow-band emitting luminescent groups are introduced into its framework, thus obtaining a novel type of circularly polarized light-emitting material with narrow-band emission. This allows the same molecule to simultaneously exhibit the TADF properties of circularly polarized emission and narrow-band emission.

[0030] (2) The organic light-emitting material prepared by the present invention has both chirality and narrow band emission performance. The raw materials are readily available, the synthesis is simple, and it has high quantum efficiency. It can be used for large-scale production in the field of organic electroluminescence.

[0031] (3) The organic electroluminescent devices made by the organic light-emitting materials with both chirality and narrow band emission performance of the present invention generally have higher efficiency than those using traditional fluorescent materials. The highest device efficiency can reach 14.6%. Attached Figure Description

[0032] Figure 1 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 1 in toluene solution is shown.

[0033] Figure 2 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 2 in toluene solution is shown.

[0034] Figure 3 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 3 in toluene solution is shown.

[0035] Figure 4 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 4 is shown in toluene solution.

[0036] Figure 5 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 5 in toluene solution is shown.

[0037] Figure 6 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 6 in toluene solution is shown.

[0038] Figure 7 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 7 in toluene solution is shown.

[0039] Figure 8The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 8 in toluene solution is shown.

[0040] Figure 9 The transient photoluminescent spectral decay curve of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 4 in toluene solution is shown.

[0041] Figure 10 The transient photoluminescent spectral decay curve of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 7 in toluene solution is shown.

[0042] Figure 11 This is a schematic diagram of the structure of an organic electroluminescent device. Detailed Implementation

[0043] The present invention will be further illustrated below with reference to the accompanying drawings and embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention.

[0044] Unless otherwise specified, all raw materials used in the following examples can be purchased from commercial channels both domestically and internationally. For example, compounds A, C, and D are all readily available. Compound B was prepared using the following method:

[0045] , , , , , , , , .

[0046] (1) Synthesis of compound B1

[0047]

[0048] 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 of NMP solvent in an Ar atmosphere. The mixture was heated and stirred at 140 °C for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The resulting intermediate compound was purified by column chromatography. The intermediate compound was then dissolved in anhydrous o-dichlorobenzene solvent in an Ar atmosphere. After stirring at 0 °C for 30 minutes, 2.5 M n-butyllithium (0.44 mL, 1.1 mmol) was added dropwise at 2 s / drop, and the mixture was stirred at room temperature for 1 hour after 30 minutes. Subsequently, 2 M boron tribromide (1 mL, 2 mmol) was added dropwise at 2 s / drop at -17 °C, and the mixture was stirred at room temperature for 30 minutes after 30 minutes. The mixture was then stirred at 50 °C for 1 hour. Finally, N,N-diisopropylethylamine (0.26 g, 2 mmol) was added dropwise at 0 °C at 2 s / drop. After stirring at room temperature for 30 minutes (mmol), the mixture was stirred at 180 °C for 12 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The product was purified by column chromatography to give compound B1 as a white solid (yield 40%).

[0049] (2) Synthesis of compound B2

[0050]

[0051] D2 (0.27 g, 1 mmol) was dissolved in 30 mL of anhydrous DMF in an Ar atmosphere and added to a bottle containing sodium hydride (0.06 g, 2.5 mmol). Then, compound D1 (0.27 g, 1 mmol) and compound C1 (0.15 g, 1 mmol) were added to the above mixed solvent. The mixture was heated and stirred at 60 °C for 8 hours. The solvent was removed by vacuum distillation, followed by extraction with dichloromethane and water, and purification by column chromatography to obtain an intermediate compound. This intermediate compound was then dissolved in anhydrous o-dichlorobenzene in an Ar atmosphere. After stirring at 0 °C for 30 minutes, 2.5 M n-butyllithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop, and the mixture was stirred at room temperature for 1 hour after 30 minutes. Subsequently, 2 M boron tribromide (1 mL, 2 mmol) was added at -17 °C at a rate of 2 s / drop, and the mixture was stirred at room temperature for 30 minutes. Finally, the mixture was heated at 50 °C... The mixture was stirred at °C for 1 hour; then N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at 0 °C at a rate of 2 s / drop. 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 vacuum distillation, and the mixture was extracted with dichloromethane and water. The product was purified by column chromatography to give compound B2 as a yellow solid (yield 25%).

[0052] (3) Synthesis of compound B3

[0053]

[0054] D1 (0.27 g, 1 mmol), compound C1 (0.15 g, 1 mmol), compound C3 (0.21 g, 1 mmol), and potassium carbonate (0.42 g, 3 mmol) were dissolved in 30 mL of anhydrous DMF in an Ar atmosphere. The mixture was heated and stirred at 140 °C for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The resulting intermediate compound was purified by column chromatography. The intermediate compound was then dissolved in anhydrous o-dichlorobenzene in an Ar atmosphere. After stirring at 0 °C for 30 minutes, 2.5 M n-butyllithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop, and the mixture was stirred at room temperature for 1 hour after 30 minutes. Subsequently, 2 M boron tribromide (1 mL, 2 mmol) was added at -17 °C at a rate of 2 s / drop, and the mixture was stirred at room temperature for 30 minutes after 30 minutes. The mixture was then stirred at 50 °C for 1 hour. N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at °C at a rate of 2 s / drop. After 30 minutes, the mixture was stirred at room temperature for 30 minutes, followed by stirring at 190 °C for 12 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The product was purified by column chromatography to give compound B3 as a yellow solid (yield 20%).

[0055] (4) Synthesis of compound B4

[0056]

[0057] D1 (0.27 g, 1 mmol) was dissolved in 30 mL of anhydrous DMF in an Ar atmosphere and added to a flask containing sodium hydride (0.06 g, 2.5 mmol). Compound C2 (0.42 g, 2.5 mmol) was then added to the mixture. The mixture was heated and stirred at 60 °C for 4 hours. The solvent was removed by vacuum distillation, followed by extraction with dichloromethane and water, and purification by column chromatography to obtain an intermediate compound. This intermediate compound was then dissolved in anhydrous o-dichlorobenzene in an Ar atmosphere. After stirring at 0 °C for 30 minutes, 2.5 M n-butyllithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop, and the mixture was stirred at room temperature for 1 hour after 30 minutes. Subsequently, 2 M boron tribromide (1 mL, 2 mmol) was added at -17 °C at a rate of 2 s / drop, and the mixture was stirred at room temperature for 30 minutes, followed by stirring at 50 °C for 1 hour. Finally, the mixture was stirred at 0 °C for 1 hour. N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at °C at a rate of 2 s / drop. After 30 minutes, the mixture was stirred at room temperature for 30 minutes, followed by stirring at 170 °C for 16 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The product was purified by column chromatography to give compound B4 as a yellow solid (yield 50%).

[0058] (5) Synthesis of compound B5

[0059]

[0060] D2 (0.27 g, 1 mmol) was dissolved in 30 mL of anhydrous DMF in an Ar atmosphere and added to a flask containing sodium hydride (0.06 g, 2.5 mmol). Compounds C2 (0.18 g, 1.1 mmol) and C3 (0.24 g, 1.1 mmol) were then added to the mixed solvent. The mixture was heated and stirred at 100 °C for 12 hours. The solvent was removed by vacuum distillation, followed by extraction with dichloromethane and water, and purification by column chromatography to obtain an intermediate compound. This intermediate compound was then dissolved in anhydrous o-dichlorobenzene in an Ar atmosphere. After stirring at 0 °C for 30 minutes, 2.5 M n-butyllithium (0.44 mL, 1.1 mmol) was added dropwise at 2 s / drop, and the mixture was stirred at room temperature for 1 hour after 30 minutes. Subsequently, 2 M boron tribromide (1 mL, 2 mmol) was added dropwise at 2 s / drop at -17 °C, and the mixture was stirred at room temperature for 30 minutes. Finally, the mixture was heated at 50 °C... The mixture was stirred at °C for 1 hour; then N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at 0 °C at a rate of 2 s / drop. 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 vacuum distillation, and the mixture was extracted with dichloromethane and water. The product was purified by column chromatography to give compound B5 as a yellow solid (yield 24%).

[0061] (6) Synthesis of compound B6

[0062]

[0063] 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 in an Ar atmosphere. The mixture was heated and stirred at 100 °C for 40 hours. The solvent was removed by vacuum distillation, followed by extraction with dichloromethane and water, and purification by column chromatography to obtain an intermediate compound. The obtained intermediate compound was then dissolved in anhydrous o-dichlorobenzene in an Ar atmosphere. After stirring at 0 °C for 30 minutes, 2.5 M n-butyllithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop, and the mixture was stirred at room temperature for 1 hour after 30 minutes. Subsequently, 2 M boron tribromide (1 mL, 2 mmol) was added at -17 °C at a rate of 2 s / drop, and the mixture was stirred at room temperature for 30 minutes after 30 minutes. Then, the mixture was stirred at 50 °C for 1 hour. Finally, the mixture was stirred at 0 °C for 1 hour. N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at °C at a rate of 2 s / drop. After 30 minutes, the mixture was stirred at room temperature for 30 minutes, followed by stirring at 160 °C for 24 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The product was purified by column chromatography to give compound B6 as a white solid (yield 35%).

[0064] (7) Synthesis of compound B7

[0065]

[0066] D2 (0.27 g, 1 mmol) was dissolved in 30 mL of anhydrous DMF in an Ar atmosphere and added to a flask containing sodium hydride (0.06 g, 2.5 mmol). Compounds C2 (0.18 g, 1.1 mmol) and C4 (0.31 g, 1.1 mmol) were then added to the mixed solvent. The mixture was heated and stirred at 90 °C for 6 hours. The solvent was removed by vacuum distillation, followed by extraction with dichloromethane and water, and purification by column chromatography to obtain an intermediate compound. This intermediate compound was then dissolved in anhydrous o-dichlorobenzene in an Ar atmosphere. After stirring at 0 °C for 30 minutes, 2.5 M n-butyllithium (0.44 mL, 1.1 mmol) was added dropwise at 2 s / drop, and the mixture was stirred at room temperature for 1 hour after 30 minutes. Subsequently, 2 M boron tribromide (1 mL, 2 mmol) was added dropwise at 2 s / drop at -17 °C, and the mixture was stirred at room temperature for 30 minutes. Finally, the mixture was heated at 50 °C... The mixture was stirred at °C for 1 hour; then N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at 0 °C at a rate of 2 s / drop. 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 vacuum distillation, and the mixture was extracted with dichloromethane and water. The product was purified by column chromatography to give compound B5 as a yellow solid (yield 34%).

[0067] (8) Synthesis of compound B8

[0068]

[0069] 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 in an Ar atmosphere. The mixture was heated and stirred at 80 °C for 60 h. The solvent was removed by vacuum distillation, followed by extraction with dichloromethane and water, and purification by column chromatography to obtain an intermediate compound. The obtained intermediate compound was then dissolved in anhydrous o-dichlorobenzene in an Ar atmosphere. After stirring at 0 °C for 30 min, 2.5 M n-butyllithium (0.44 mL, 1.1 mmol) was added at a rate of 2 s / drop, and stirred at room temperature for 1 h after 30 min. Subsequently, 2 M boron tribromide (1 mL, 2 mmol) was added at -17 °C at a rate of 2 s / drop, and stirred at room temperature for 30 min after 30 min, followed by stirring at 50 °C for 1 h. N,N-diisopropylethylamine (0.26 g, 2 mmol) was added at °C at a rate of 2 s / drop. After 30 minutes, the mixture was stirred at room temperature for 30 minutes, followed by stirring at 190 °C for 16 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The product was purified by column chromatography to give compound B8 as a yellow solid (yield 30%).

[0070] (9) Synthesis of compound B9

[0071]

[0072] 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 of DMF in an Ar atmosphere. The mixture was heated and stirred at 120 °C for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The resulting intermediate compound was purified by column chromatography. The intermediate compound was then dissolved in anhydrous o-dichlorobenzene in an Ar atmosphere. After stirring at 0 °C for 30 minutes, 2.5 M n-butyllithium (0.44 mL, 1.1 mmol) was added dropwise at 2 s / drop, followed by stirring at room temperature for 1 hour after 30 minutes. Subsequently, 2 M boron tribromide (1 mL, 2 mmol) was added dropwise at 2 s / drop at -17 °C, followed by stirring at room temperature for 30 minutes, and then stirring at 50 °C for 1 hour. Finally, N,N-diisopropylethylamine (0.26 g, 2 mmol) was added dropwise at 0 °C for 2 s / drop. After stirring at room temperature for 30 minutes (mmol), the mixture was stirred at 200 °C for 18 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The product was purified by column chromatography to give compound B9 as a white solid (yield 36%).

[0073] The present invention will be further described below with reference to specific embodiments.

[0074] (1) Example 1: Preparation of Z1

[0075]

[0076] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 80%). Figure 1 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 1 in toluene solution is shown.

[0077] Elemental analysis theoretical values ​​of C52H41BO4 (%): C 84.32; H 5.58; B 1.46; O 8.64; Found values: C 84.34; H 5.57; B 1.45; O 8.63.

[0078] (2) Example 2: Preparation of Z2

[0079]

[0080] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 82%).

[0081] Elemental analysis theoretical values ​​of C52H41BO4 (%): C 84.32; H 5.58; B 1.46; O 8.64; Found values: C 84.33; H 5.55; B 1.44; O 8.65.

[0082] Figure 2 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 2 in toluene solution is shown.

[0083] (3) Example 3: Preparation of Z3

[0084]

[0085] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 75%).

[0086] Elemental analysis theoretical values ​​of C52H41BO3S (%): C 82.53; H 5.46; B 1.43; O 6.34; S 4.24; Found values: C 82.54; H 5.45; B 1.41; O 6.34; S 4.26.

[0087] Figure 3 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 3 in toluene solution is shown.

[0088] (4) Example 4: Preparation of Z4

[0089]

[0090] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 70%).

[0091] Elemental analysis theoretical values ​​of C52H41BO3S (%): C 82.53; H 5.46; B 1.43; O 6.34; S 4.24; Found values: C 82.51; H 5.44; B 1.43; O 6.35; S 4.25.

[0092] Figure 4 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 4 is shown in toluene solution. Figure 9The transient photoluminescent spectral decay curve of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 4 in toluene solution is shown.

[0093] (5) Example 5: Preparation of Z5

[0094]

[0095] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 65%).

[0096] Elemental analysis theoretical values ​​of C52H41BO3Se (%): C 77.71; H 5.14; B 1.35; O 5.97; Se 9.83; Found values: C 77.72; H 5.16; B 1.34; O 5.96; Se 9.85.

[0097] Figure 5 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 5 in toluene solution is shown.

[0098] (6) Example 6: Preparation of Z6

[0099]

[0100] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 65%).

[0101] Elemental analysis theoretical values ​​of C52H41BO3Se (%): C 77.71; H 5.14; B 1.35; O 5.97; Se 9.83; Found values: C 77.73; H 5.15; B 1.36; O 5.95; Se 9.84.

[0102] Figure 6 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 6 in toluene solution is shown.

[0103] (7) Example 7: Preparation of Z7

[0104]

[0105] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 75%).

[0106] Elemental analysis theoretical values ​​of C52H41BO2S2 (%): C 80.82; H 5.35; B 1.40; O 4.14; S 8.30; Found values: C 80.83; H 5.34; B 1.38; O 4.16; S 8.30.

[0107] Figure 7 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 7 in toluene solution is shown.

[0108] Figure 10 The transient photoluminescent spectral decay curve of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 7 in toluene solution is shown.

[0109] (8) Example 8: Preparation of Z8

[0110]

[0111] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The solution was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 73%).

[0112] Elemental analysis theoretical values ​​of C52H41BO2S2 (%): C 80.82; H 5.35; B 1.40; O 4.14; S 8.30; Found values: C 80.84; H 5.32; B 1.39; O 4.17; S 8.32.

[0113] Figure 8 The fluorescence spectrum of the organic light-emitting material with both chirality and narrow-band emission properties prepared in Example 8 in toluene solution is shown.

[0114] (9) Example 9: Preparation of Z9

[0115]

[0116] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The solution was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 66%).

[0117] Elemental analysis theoretical values ​​of C52H41BO2SSe (%): C 76.19; H 5.04; B 1.32; O 3.90; S 3.91; Se 9.63; Found values: C 76.17; H 5.01; B 1.30; O 3.92; S 3.90; Se 9.61.

[0118] (10) Example 10: Preparation of Z10

[0119]

[0120] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The solution was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 60%).

[0121] Elemental analysis theoretical values ​​of C52H41BO2SSe (%): C 76.19; H 5.04; B 1.32; O 3.90; S 3.91; Se 9.63; Found values: C 76.18; H 5.05; B 1.34; O 3.91; S 3.89; Se 9.63.

[0122] (11) Example 11: Preparation of Z11

[0123]

[0124] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 58%).

[0125] Elemental analysis theoretical values ​​of C62H52BNO3 (%): C 85.60; H 6.03; B 1.24; N 1.61; O 5.52; Found values: C 85.63; H 6.00; B 1.21; N 1.64; O 5.52.

[0126] (12) Example 12: Preparation of Z12

[0127]

[0128] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 57%).

[0129] Elemental analysis theoretical values ​​of C62H52BNO3 (%): C 85.60; H 6.03; B 1.24; N 1.61; O 5.52; Found values: C 85.61; H 6.02; B 1.25; N 1.61; O 5.52.

[0130] (13) Example 13: Preparation of Z13

[0131]

[0132] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 63%).

[0133] Elemental analysis theoretical values ​​of C62H52BNO2S (%): C 84.05; H 5.92; B 1.22; N 1.58; O 3.61; S 3.62; Found values: C 84.03; H 5.90; B 1.23; N 1.57; O 3.63; S 3.60.

[0134] (14) Example 14: Preparation of Z14

[0135]

[0136] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The solution was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 63%).

[0137] Elemental analysis theoretical values ​​of C62H52BNO2S (%): C 84.05; H 5.92; B 1.22; N 1.58; O 3.61; S 3.62; Found values: C 84.07; H 5.88; B 1.21; N 1.59; O 3.63; S 3.64.

[0138] (15) Example 15: Preparation of Z15

[0139]

[0140] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 60%).

[0141] Elemental analysis theoretical values ​​of C62H52BNO2Se (%): C 79.83; H 5.62; B 1.16; N 1.50; O 3.43; Se 8.47; Found values: C 79.85; H 5.61; B 1.16; N 1.52; O 3.45; Se 8.45.

[0142] (16) Example 16: Preparation of Z16

[0143]

[0144] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 60%).

[0145] Elemental analysis theoretical values ​​of C62H52BNO2Se (%): C 79.83; H 5.62; B 1.16; N 1.50; O 3.43; Se 8.47; Found values: C 79.81; H 5.63; B 1.14; N 1.49; O 3.41; Se 8.48.

[0146] (17) Example 17: Preparation of Z17

[0147]

[0148] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 80%).

[0149] Elemental analysis theoretical values ​​of C52H41BO2Se2 (%): C 72.07; H 4.77; B 1.25; O 3.69; Se 18.22; Found values: C 72.06; H 4.75; B 1.23; O 3.67; Se 18.25.

[0150] (18) Example 18: Preparation of Z18

[0151]

[0152] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 76%).

[0153] Elemental analysis theoretical values ​​of C52H41BO2Se2 (%): C 72.07; H 4.77; B 1.25; O 3.69; Se 18.22; Found values: C 72.05; H 4.77; B 1.24; O 3.70; Se 18.21.

[0154] (19) Example 19: Preparation of Z19

[0155]

[0156] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 75%).

[0157] Elemental analysis theoretical values ​​of C78H66B2O6 (%): C 83.57; H 5.93; B 1.93; O 8.56; Found values: C 83.56; H 5.95; B 1.94; O 8.54.

[0158] (20) Example 20: Preparation of Z20

[0159]

[0160] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The solution was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 75%).

[0161] Elemental analysis theoretical values ​​of C78H66B2O6 (%): C 83.57; H 5.93; B 1.93; O 8.56; Found values: C 83.56; H 5.93; B 1.91; O 8.57.

[0162] (21) Example 21: Preparation of Z21

[0163]

[0164] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 70%).

[0165] Elemental analysis theoretical values ​​of C78H66B2O4S2 (%): C 81.25; H 5.77; B 1.87; O 5.55; S 5.56; Found values: C 81.27; H 5.76; B 1.86; O 5.53; S 5.58.

[0166] (22) Example 22: Preparation of Z22

[0167]

[0168] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 70%).

[0169] Elemental analysis theoretical values ​​of C78H66B2O4S2 (%): C 81.25; H 5.77; B 1.87; O 5.55; S 5.56; Found values: C 81.25; H 5.79; B 1.88; O 5.54; S 5.59.

[0170] (23) Example 23: Preparation of Z23

[0171]

[0172] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 65%).

[0173] Elemental analysis theoretical values ​​of C78H66B2O4Se2 (%): C 75.13; H 5.34; B 1.73; O 5.13; Se 12.67; Found values: C 75.14; H 5.35; B 1.70; O 5.12; Se 12.68.

[0174] (24) Example 24: Preparation of Z24

[0175]

[0176] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 61%).

[0177] Elemental analysis theoretical values ​​of C78H66B2O4Se2 (%): C 75.13; H 5.34; B 1.73; O 5.13; Se 12.67; Found values: C 75.13; H 5.36; B 1.74; O 5.11; Se 12.69.

[0178] (25) Example 25: Preparation of Z25

[0179]

[0180] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 60%).

[0181] Elemental analysis theoretical values ​​of C78H66B2O2S4 (%): C 79.04; H 5.61; B 1.82; O 2.70; S 10.82; Found values: C 79.05; H 5.62; B 1.80; O 2.71; S 10.83.

[0182] (26) Example 26: Preparation of Z26

[0183]

[0184] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 65%).

[0185] Elemental analysis theoretical values ​​of C78H66B2O2S4 (%): C 79.04; H 5.61; B 1.82; O 2.70; S 10.82; Found values: C 79.03; H 5.60; B 1.81; O 2.72; S 10.81.

[0186] (27) Example 27: Preparation of Z27

[0187]

[0188] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The solution was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 62%).

[0189] Elemental analysis theoretical values ​​C78H66B2O2S2Se2 (%): C 73.25; H 5.20; B 1.69; O 2.50; S 5.01; Se 12.35; Found values: C 73.24; H 5.18; B 1.71; O 2.52; S 5.04; Se 12.31.

[0190] (28) Example 28: Preparation of Z28

[0191]

[0192] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 56%).

[0193] Elemental analysis theoretical values ​​C78H66B2O2S2Se2 (%): C 73.25; H 5.20; B 1.69; O 2.50; S 5.01; Se 12.35; Found values: C 73.27; H 5.19; B 1.66; O 2.51; S 5.02; Se 12.36.

[0194] (29) Example 29: Preparation of Z29

[0195]

[0196] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 75%).

[0197] Elemental analysis theoretical values ​​of C98H88B2N2O4 (%): C 85.33; H 6.43; B 1.57; N 2.03; O 4.64; Found values: C 85.35; H 6.41; B 1.56; N 2.03; O 4.66.

[0198] (30) Example 30: Preparation of Z30

[0199]

[0200] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 36 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 74%).

[0201] Elemental analysis theoretical values ​​of C98H88B2N2O4 (%): C 85.33; H 6.43; B 1.57; N 2.03; O 4.64; Found values: C 85.36; H 6.40; B 1.55; N 2.01; O 4.61.

[0202] (31) Example 31: Preparation of Z31

[0203]

[0204] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 65%).

[0205] Elemental analysis theoretical values ​​of C98H88B2N2O2S2 (%): C 83.39; H 6.28; B 1.53; N 1.98; O 2.27; S 4.54; Found values: C 83.37; H 6.29; B 1.51; N 1.99; O 2.25; S 4.53.

[0206] (32) Example 32: Preparation of Z32

[0207]

[0208] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was then purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 66%).

[0209] Elemental analysis theoretical values ​​of C98H88B2N2O2S2 (%): C 83.39; H 6.28; B 1.53; N 1.98; O 2.27; S 4.54; Found values: C 83.36; H 6.30; B 1.54; N 1.97; O 2.25; S 4.51.

[0210] (33) Example 33: Preparation of Z33

[0211]

[0212] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 69%).

[0213] Elemental analysis theoretical values ​​C98H88B2N2O2Se2 (%): C 78.19; H 5.89; B 1.44; N 1.86; O 2.13; Se 10.49; Found values: C 78.17; H 5.88; B 1.41; N 1.89; O 2.12; Se 10.47.

[0214] (34) Example 34: Preparation of Z34

[0215]

[0216] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 48 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The solution was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 66%).

[0217] Elemental analysis theoretical values ​​of C98H88B2N2O2Se2 (%): C 78.19; H 5.89; B 1.44; N 1.86; O 2.13; Se 10.49; Found values: C 78.18; H 5.87; B 1.42; N 1.87; O 2.11; Se 10.46.

[0218] (35) Example 35: Preparation of Z35

[0219]

[0220] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The mixture was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 85%).

[0221] Elemental analysis theoretical values ​​of C78H66B2O2Se4 (%): C 68.24; H 4.85; B 1.57; O 2.33; Se 23.01; Found values: C 68.23; H 4.86; B 1.55; O 2.35; Se 23.02.

[0222] (36) Example 36: Preparation of Z36

[0223]

[0224] 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. Then, 30 mL of ethanol and 15 mL of water were added, and the mixture was heated under reflux for 72 hours. The solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The solution was purified by column chromatography to obtain an organic light-emitting material with both chirality and narrow-band emission properties (yield 79%).

[0225] Elemental analysis theoretical values ​​of C78H66B2O2Se4 (%): C 68.24; H 4.85; B 1.57; O 2.33; Se 23.01; Found values: C 68.24; H 4.83; B 1.59; O 2.32; Se 23.03.

[0226] Application Example 1

[0227] The structure of the organic electroluminescent device made using the organic light-emitting material with both chirality and narrow band emission performance is as follows: ITO / MoO3 (8nm) / TAPC (50nm) / mcP:2%Emitters (compound of this invention) / TmPyPB (40nm) / LiF (1nm) / Al (100nm).

[0228] like Figure 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-di(4-methylphenyl)aniline]TAPC), an organic light-emitting layer 4 (mCP host material and the organic light-emitting material with both chirality and narrow band emission performance prepared in this invention), an electron transport layer 5 (3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1''-terphenyl]-3,3''-diyl]dipyridine TmPyPB), an electron injection layer 6 (lithium fluoride LiF), and a cathode layer (aluminum Al).

[0229] The device fabrication process is as follows: The electroluminescent device is fabricated according to methods known in the art, such as the method disclosed in reference (Adv. Mater. 2004, 16, 537). Specifically, 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 deposited on a cleaned conductive glass (ITO) substrate.

[0230] The device performance test data are shown in Table 1 below:

[0231] Table 1 Performance test results of organic electroluminescent devices

[0232]

[0233] As shown in the table above, the devices using the compounds of this invention have a maximum current efficiency of 24.9 cd / A, a minimum start-up voltage of only 3.1 V, good efficiency decay performance, and higher quantum efficiency than devices using traditional fluorescent materials.

[0234] The embodiments described above provide a detailed explanation of the technical solutions of the present invention. It should be understood that the above descriptions are merely specific embodiments of the present invention and are not intended to limit the present invention. Any modifications, additions, or similar substitutions made within the scope of the principles of the present invention should be included within the protection scope of the present invention.

Claims

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

2. A method for preparing an organic light-emitting material with both chirality and narrow-band emission properties as described in claim 1, characterized in that, The preparation method includes the following steps: Step (1): Compound C, compound D and base are added to an organic solvent and reacted at 60-140°C for 36-72 hours. After separation and purification, the product is dissolved in o-dichlorobenzene. At 0°C, n-butyllithium, boron tribromide and N,N-diisopropylethylamine are added respectively and reacted at 160-200°C for 12-24 hours. After separation and purification, compound B is obtained. Compound B is selected from one of the following structural formulas: , , , , , , , or Among them, 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: , , , R2 is one of H, methyl, ethyl, or tert-butyl. The compound D is X5 is one of Br, Cl and I; Step (2): Compound A, Compound B, base, and palladium catalyst are added to a mixed solvent of toluene, ethanol, and water, and reacted at 80-120°C for 36-72 hours. After separation, an organic light-emitting material with both chirality and narrow-band emission performance is obtained with the structure shown in I-VIII. Compound A is selected from one of the following structural formulas: , , or R1 is selected from H, methyl, cyano, and methoxy.

3. The preparation method according to claim 2, characterized in that, The alkali 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 alkali is one of NaH, NaOH, KOH, Na2CO3, K2CO3, and Cs2CO3.

5. The preparation method according to claim 2, characterized in that, In step (1), the molar ratio of compound C to compound D 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 tetra(triphenylphosphine)palladium, [1,1'-bis(diphenylphosphine)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. The application of the organic light-emitting material with both chirality and narrow-band emission properties as described in claim 1 as an organic light-emitting layer material in the optoelectronic field.

10. An organic electroluminescent device, comprising, from bottom to top, a glass layer, 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, characterized in that, The organic light-emitting layer contains the organic light-emitting material with both chirality and narrow-band emission properties as described in claim 1.

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