Boron-nitrogen compound with macrocyclic structure and organic electroluminescent device thereof
By designing boron nitrogen compounds with macrocyclic structure, the problem of the aggregation and quenching effect of existing MR-TADF luminescent materials at high voltage is solved, and the narrow spectrum band characteristics are maintained under high doping concentration is achieved, and the efficiency of the device is improved and lifespan.
Patent Information
- Application Number
- CN202411676150.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-11-22
- Publication Date
- 2025-02-25
AI Technical Summary
The rigid planar structure of existing MR-TADF luminescent materials leads to high production difficulties and there is aggregation quenching effect at high voltages, resulting in widening spectral and roll-off efficiency, limiting its commercial applications.
A boron nitrogen compound with a macrocyclic structure was designed, and its non-planarity effectively prevents close packing between molecules, weakens the aggregation quenching effect, and maintains the narrow band characteristics under high doping concentrations.
By introducing boron nitrogen compounds with macrocyclic structures, the narrow spectrum band characteristics are maintained at high doping concentrations, the aggregation quenching effect is reduced, and the efficiency and lifetime of the device are improved.
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Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a boron nitrogen compound with a macrocyclic structure and an organic electroluminescent device thereof. Background Art
[0002] The CIE (Commission Internationale de L'Eclairage, 1931) color coordinates of the three primary colors of red, green, and blue are respectively (0.708, 0.292), (0.170, 0.797), and (0.131, 0.046) in the various parameter index requirements of BT2020 (Broadcast Television 2020) for ultra-high-definition video display in the broadcasting, television, and consumer electronics industries. This undoubtedly poses greater challenges to organic electroluminescent (OLED) materials, such as narrow spectrum and no shoulder peak. Luminescent materials with multiple resonance thermally activated delayed luminescence (MR-TADF) effect can narrow the half-peak width (FWHM), meet the above three primary color spectrum requirements, and achieve efficient luminescence. However, its rigid planar structure requires a low device doping concentration and is difficult to prepare; at the same time, under high voltage, there is a more obvious aggregation quenching effect, which will cause the spectrum to become wider and the efficiency to roll off, restricting the commercial application of MR-TADF luminescent materials. Summary of the invention
[0003] In order to solve the problems existing in the background technology, the first object of the present invention is to provide a boron nitrogen compound having a MR-TADF effect containing a macrocycle, and the technical scheme is as follows:
[0004] A boron nitrogen compound with a macrocyclic structure has a structure shown in the following general formula:
[0005]
[0006] Wherein, the A rings are the same or different and are independently selected from a benzene ring, a furan ring or a thiophene ring; Y is N or O; the dotted line Indicates the presence or absence of a bonding relationship; X is the same or different and is independently selected from O, S, Se, C=O, S(=O) 2 , CR 1 R 2 , R 1 , R 2 are independently selected from hydrogen or alkyl; R are the same or different and are independently selected from alkyl, alkoxy, and aromatic groups, and n is an integer from 0 to 4;
[0007] When ring A is a benzene ring, there may or may not be a bond relationship with the dotted line X; when ring A is a furan ring or a thiophene ring, there is no bond relationship with the dotted line X; when Y is N, there is a bond relationship with the dotted line Y; when Y is O, ring A is a benzene ring, and there is no bond relationship with the dotted line Y.
[0008] As a preferred embodiment of the present invention, the A rings are the same, and are all benzene rings, furan rings or thiophene rings.
[0009] As a preference of the present invention, when the A ring is a benzene ring, the two Ys adjacent to the A ring are the same, and if there is a bonding relationship of X, the two Xs adjacent to the A ring are the same.
[0010] As a preferred embodiment of the present invention, the R 1 , R 2 Same, selected from hydrogen or C 1 ~C 4 of alkyl.
[0011] As a preferred embodiment of the present invention, the R are the same or different and are independently selected from hydrogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy groups, phenyl groups, and adjacent R groups can be bonded to form a ring.
[0012] As a preferred embodiment of the present invention, the structure of the compound is selected from one of the following structures:
[0013]
[0014]
[0015]
[0016]
[0017]
[0018]
[0019]
[0020]
[0021]
[0022]
[0023]
[0024]
[0025]
[0026]
[0027]
[0028]
[0029]
[0030] Another object of the present invention is to provide an organic electroluminescent device, comprising a cathode, an anode and one or more organic layers arranged therebetween, characterized in that at least one of the organic layers is a light-emitting layer, and the light-emitting layer contains one or more of the above-mentioned boron nitrogen compounds with a macrocyclic structure.
[0031] As a preferred embodiment of the present invention, the light-emitting layer includes a host material and a guest material, and the guest material is the above-mentioned boron nitrogen compound with a macrocyclic structure.
[0032] As a preferred embodiment of the present invention, the organic electroluminescent device is used to manufacture display devices, lighting sources, signal lights, and signboards. The display devices include mobile phone displays, computer displays, television displays, smart watch displays, smart car display panels, VR or AR helmet displays.
[0033] The beneficial effects of the present invention are as follows:
[0034] The boron-nitrogen compound with a macrocyclic structure provided by the present invention has a macrocyclic structure with more than 10 atoms in a single ring, which can not only maintain a rigid structure, but also has a non-planar structure (see Figure 1 ) can effectively prevent the close packing (interaction) of molecules, which greatly weakens the aggregation quenching effect. In addition, the method of introducing macrocycles into MR-TADF materials is simple, and the prepared devices can maintain narrow-band characteristics at high doping concentrations. BRIEF DESCRIPTION OF THE DRAWINGS
[0035] The drawings described herein are used to provide a further understanding of the present invention and constitute a part of the present invention. The exemplary embodiments of the present invention and their descriptions are used to explain the present invention and do not constitute an improper limitation of the present invention. In the drawings:
[0036] Figure 1 These are the chem3D renderings of compound 10 in the present invention at two different angles. DETAILED DESCRIPTION
[0037] The technical solution of the present invention will be clearly and completely described below in conjunction with the embodiments. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.
[0038] If the specific conditions are not specified in the embodiments, they are carried out under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used without indicating the manufacturer are all conventional products that can be purchased commercially. Some reaction compounds are purchased from commodity suppliers (Zhengzhou Alpha Chemical Co., Ltd.), and some compounds that cannot be directly purchased are prepared by simple reactions of commercially available raw materials. The percentages all refer to mass percentages, and the temperatures are degrees Celsius (℃). Such method principles, operating procedures, conventional post-treatments, silica gel columns, recrystallization purification and other means are well known to synthesizers in the art, and the synthesis process can be fully realized to obtain the target product. The reactions in each preparation embodiment are generally carried out under positive pressure of nitrogen or argon.
[0039] Preparation Example
[0040] Preparation Example 1: Synthesis of Compound 3
[0041]
[0042] Synthesis of compound 3-3: Compound 3-1 (3.4 g, 32 mmol), compound 3-2 (4.4 g, 16 mmol), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 ) (0.9 g, 1 mmol), sodium tert-butoxide (BuONa) (2.4 g, 32 mmol), bis(diphenylphosphino)-1,1'-binaphthyl (BINPA) (0.6 g, 1 mmol) and toluene (45 mL) were placed in a 100 mL reactor. The mixture was refluxed for 24 h under stirring. After the reaction was completed, the reaction mixture was filtered, and the filtrate was concentrated and purified by column chromatography to obtain compound 3-3 (4.3 g, yield 82%);
[0043] Synthesis of compound 3-5: Compound 3-3 (5.2 g, 16 mmol), compound 3-4 (9.0 g, 32 mmol), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3) (0.9 g, 1 mmol), sodium tert-butoxide (BuONa) (2.4 g, 32 mmol), 1,1'-ferrocenyldiyl-bis(diphenylphosphine) (dppf) (0.6 g, 1 mmol) and toluene (45 mL) were placed in a 100 mL reactor. The mixture was refluxed for 24 h under stirring. After the reaction was completed, the reaction mixture was filtered, and the filtrate was concentrated and purified by column chromatography to obtain compound 3-5 (8.7 g, yield 85%);
[0044] Synthesis of compound 3-7: Compound 3-5 (4.6 g, 7.2 mmol), compound 3-6 (3.6 g, 14.2 mmol), potassium acetate (AcOK) (4.7 g, 48 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (Pd(dppf) 2 Cl 2 )(0.13g, 0.18mmol) was put into a dry reaction bottle with a condenser, and after vacuuming and nitrogen ventilation for more than three times, it was dissolved in 200mL of dry dioxane. Then the temperature was raised to 100°C and reacted for 12h. After the reaction was completed, the reaction mixture was put into water, and the aqueous phase was extracted three times with dichloromethane (500mL). The obtained dichloromethane phase was washed once with water and dried over anhydrous sodium sulfate. After dichloromethane was removed by reduced pressure distillation, the crude product was washed twice with methanol to obtain compound 3-7 (2.5g, yield 47%);
[0045] Synthesis of compound 3-8: Compound 3-7 (11.0 g, 15 mmol) and compound 3-5 (9.6 g, 15 mmol) were completely dissolved in tetrahydrofuran (THF) (50 mL), and 2M potassium carbonate aqueous solution (30 mL) and tetrakis-(triphenylphosphine)palladium (Pd(PPh 3 ) 4 ) (0.6 g, 0.5 mmol), the mixture was heated and stirred for 2 h. Then, the mixture was cooled to room temperature to complete the reaction, and after removing the potassium carbonate solution, the solid was filtered out, and the solid was washed once with tetrahydrofuran and ethanol to obtain compound 3-8 (13.0 g, yield 90%);
[0046] Synthesis of compound 3: Compound 3-8 (22.0 g, 23 mmol) and tert-butylbenzene (120 mL) were placed in a 300 mL reactor, and n-butyl lithium (42.5 mL, 68 mmol) was added thereto at -78 ° C, the mixture was stirred at 60 ° C for 3 h, boron tribromide (11.3 g, 45 mmol) was added thereto at -78 ° C, the mixture was stirred at room temperature for 1 h, N, N-diisopropylethylamine (DIEA) (5.9 g, 45 mmol) was added thereto at 0 ° C, and the mixture was stirred at 120 ° C for 2 h. After the reaction was completed, sodium acetate aqueous solution was added to the reaction mixture at room temperature, stirred, and extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography to obtain compound 3 (3.1 g, yield 15%), MS: 904.43.
[0047] Preparation Example 2: Synthesis of Compound 10
[0048]
[0049] The synthesis of compound 10-3 is the same as that of compound 3-3, except that compound 3-1 is replaced by compound 10-1, and compound 3-2 is replaced by compound 10-2; the synthesis of compound 10-4 is the same as that of compound 3-5, except that compound 3-3 is replaced by compound 10-3; the synthesis of compound 10-5 is the same as that of compound 3-7, except that compound 3-5 is replaced by compound 10-4; the synthesis of compound 10-6 is the same as that of compound 3-8, except that compound 3-7 is replaced by compound 10-5, and compound 3-5 is replaced by compound 10-4; the synthesis of compound 10 is the same as that of compound 3, except that compound 3-8 is replaced by compound 10-6, MS: 936.19.
[0050] Preparation Example 3: Synthesis of Compound 39
[0051]
[0052] The synthesis of compound 39-2 is the same as that of compound 3-7, except that compound 39-1 is used to replace compound 3-5; the synthesis of compound 39-3 is the same as that of compound 3-8, except that compound 39-2 is used to replace compound 3-7, and compound 39-1 is used to replace compound 3-5; the synthesis of compound 39 is the same as that of compound 3, except that compound 39-3 is used to replace compound 3-8, MS: 536.27.
[0053] Preparation Example 4: Synthesis of Compound 62
[0054]
[0055] The synthesis of compound 62-3 is the same as that of compound 3-3, except that compound 3-1 is replaced by compound 62-1, and compound 3-2 is replaced by the compound 62-2; the synthesis of compound 62-4 is the same as that of compound 3-5, except that compound 3-3 is replaced by compound 62-3; the synthesis of compound 62-5 is the same as that of compound 3-7, except that compound 3-5 is replaced by compound 62-4; the synthesis of compound 62-6 is the same as that of compound 3-8, except that compound 3-7 is replaced by compound 62-5, and compound 3-5 is replaced by compound 62-4; the synthesis of compound 62 is the same as that of compound 3, except that compound 3-8 is replaced by the compound 62-6, MS: 1036.23.
[0056] Preparation Example 5: Synthesis of Compound 89
[0057]
[0058] Synthesis of compound 89-2: Compound 89-1 (9.3 g, 16 mmol), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 ) (0.9 g, 1 mmol), sodium tert-butoxide (BuONa) (2.4 g, 32 mmol), bis(diphenylphosphino)-1,1'-binaphthyl (BINPA) (0.6 g, 1 mmol) and toluene (45 mL) were placed in a 100 mL reactor. The mixture was refluxed for 24 h under stirring. After the reaction was completed, the reaction mixture was filtered, and the filtrate was concentrated and purified by column chromatography to obtain compound 89-2 (5.7 g, yield 85%);
[0059] The synthesis of compound 89-3 is the same as that of compound 3-5, except that compound 89-2 is used to replace compound 3-3; the synthesis of compound 89-4 is the same as that of compound 3-7, except that compound 89-3 is used to replace compound 3-5; the synthesis of compound 89-5 is the same as that of compound 3-8, except that compound 89-4 is used to replace compound 3-7, and compound 89-3 is used to replace compound 3-5; the synthesis of compound 89 is the same as that of compound 3, except that compound 89-5 is used to replace compound 3-8, MS: 1092.61.
[0060] Preparation Example 6: Synthesis of Compound 210
[0061]
[0062] The synthesis of compound 210-2 is the same as that of compound 89-2, except that compound 210-1 is used to replace compound 89-1; the synthesis of compound 210-3 is the same as that of compound 3-5, except that compound 210-1 is used to replace compound 3-3; the synthesis of compound 210-4 is the same as that of compound 3-8, except that compound 210-3 is used to replace compound 3-5, and compound 62-5 is used to replace compound 3-7; the synthesis of compound 210-5 is the same as that of compound 3, except that compound 210-4 is used to replace compound 3-8;
[0063] Synthesis of compound 210: Compound 210-5 (0.73 g, 0.69 mmol) was dispersed in a mixed solvent of dichloromethane (DCM) (10 mL), dioxane (Diox) (5 mL) and water (1 mL), cooled to 0 ° C, and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (0.94 g, 4.14 mmol) was slowly added, and then naturally warmed to room temperature and stirred overnight. The reaction was quenched with saturated sodium bicarbonate solution, and the aqueous layer was washed three times with DCM. The organic layer solvent was removed by rotary evaporation, and the crude product was purified by silica gel column chromatography (ethyl acetate / DCM, 2:1), and recrystallized from DCM and methanol to obtain compound 210 (0.47 g, 63%), MS: 1088.47.
[0064] Preparation Example 7: Synthesis of Compound 226
[0065]
[0066]
[0067] The synthesis of compound 226-2 is the same as that of compound 89-2, except that compound 89-1 is replaced by compound 226-1; the synthesis of compound 226-3 is the same as that of compound 3-5, except that compound 3-3 is replaced by compound 226-2; the synthesis of compound 226-4 is the same as that of compound 3-7, except that compound 3-5 is replaced by compound 226-3; the synthesis of compound 226-6 is the same as that of compound 89-2, except that compound 89-1 is replaced by compound 226-5; The synthesis of 7 is the same as that of compound 3-5, except that compound 226-6 is used to replace compound 3-3; the synthesis of compound 226-8 is the same as that of compound 3-8, except that compound 226-7 is used to replace compound 3-5, and compound 226-4 is used to replace compound 3-7; the synthesis of compound 226-9 is the same as that of compound 3, except that compound 226-8 is used to replace compound 3-8; the synthesis of compound 226-10 is the same as that of compound 210, except that compound 226-9 is used to replace compound 210-5;
[0068] Synthesis of compound 226: mCBPA (2.32 g, 13.4 mmol) was slowly added to a DCM (10 mL) solution of compound 226-10 (1.44 g, 1.34 mmol) and stirred at room temperature overnight. The reaction was quenched with saturated sodium hydroxide solution, the aqueous phase was washed three times with DCM, the organic phases were combined, the organic layer solvent was removed by rotary evaporation, and the crude product was purified by silica gel column chromatography (ethyl acetate / DCM, 2:1), and recrystallized with DCM and methanol to obtain compound 226 (12.68 g, 83%), MS: 1140.06.
[0069] Preparation Example 8: Synthesis of Compound 242
[0070]
[0071] The synthesis of compound 242-2 is the same as that of compound 89-2, except that compound 242-1 is used to replace compound 89-1; the synthesis of compound 242-3 is the same as that of compound 3-5, except that compound 242-2 is used to replace compound 3-3; the synthesis of compound 242-4 is the same as that of compound 3-7, except that compound 242-3 is used to replace compound 3-5; the synthesis of compound 242-6 is the same as that of compound 89-2, except that compound 242-1 is used to replace compound 3-3; Compound 242-5 replaced compound 89-1; the synthesis of compound 242-7 was the same as that of compound 3-5, except that compound 242-6 replaced compound 3-3; the synthesis of compound 242-8 was the same as that of compound 3-8, except that compound 242-4 replaced compound 3-7, and compound 242-7 replaced compound 3-5; the synthesis of compound 242 was the same as that of compound 3, except that compound 242-8 replaced compound 3-8, MS: 980.39.
[0072] Preparation Example 9: Synthesis of Compound 270
[0073]
[0074] The synthesis of compound 270-2 is the same as that of compound 89-2, except that compound 270-1 is used to replace compound 89-1; the synthesis of compound 270-3 is the same as that of compound 3-5, except that compound 270-2 is used to replace compound 3-3; the synthesis of compound 270-4 is the same as that of compound 3-7, except that compound 270-3 is used to replace compound 3-5; the synthesis of compound 270-5 is the same as that of compound 3-3, except that compound 270-4 is used to replace compound 3-5; Compound 62-2 replaced compound 3-2; the synthesis of compound 270-6 was the same as that of compound 3-5, except that compound 270-5 replaced compound 3-3; the synthesis of compound 270-7 was the same as that of compound 3-8, except that compound 270-6 replaced compound 3-5, and compound 270-4 replaced compound 3-7; the synthesis of compound 270 was the same as that of compound 3, except that compound 270-7 replaced compound 3-8, MS: 1044.57.
[0075] Preparation Example 10: Synthesis of Compound 322
[0076]
[0077]
[0078] The synthesis of compound 322-2 is the same as that of compound 89-2, except that compound 89-1 is replaced by compound 322-1; the synthesis of compound 322-3 is the same as that of compound 3-5, except that compound 3-3 is replaced by compound 322-2; the synthesis of compound 322-4 is the same as that of compound 3-8, except that compound 3-5 is replaced by compound 322-3, and compound 3-7 is replaced by compound 226-4; the synthesis of compound 322 is the same as that of compound 3, except that compound 3-8 is replaced by compound 322-4, MS: 1104.51.
[0079] In addition, it should be noted that other compounds of the present application can be obtained by referring to the preparation methods of the above-mentioned embodiments, so they will not be listed one by one here.
[0080] Device Embodiment
[0081] The preparation method of device embodiment 1 is as follows:
[0082] The glass substrate containing the ITO (thickness 185nm) transparent conductive layer was ultrasonically treated in a commercial cleaning agent (30min / 2 times), rinsed in deionized water; then ultrasonically treated in acetone and isopropanol solvents (30min / 2 times), baked in a clean environment until the solvent was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam. The ITO transparent conductive layer after the above treatment was used as the anode layer, and the glass plate with the anode layer was placed in the vacuum chamber of the evaporation equipment and evacuated to 1×10 -5 Pa, HT10:HI2 (95:5wt%) was vacuum evaporated on the anode layer as a hole injection layer, and HT10 was used as a hole transport layer, with the thickness of the evaporated films being 10nm and 40nm respectively. BFH5:Compound 3 (90:10wt%) was vacuum evaporated on the hole transport layer as a light-emitting layer, with a thickness of 30nm. ET8 was vacuum evaporated on the light-emitting layer as an electron transport layer, with a thickness of 20nm. 1nm of LiF was vacuum evaporated on the electron transport layer as an electron injection layer and 100nm of Al as a cathode.
[0083] The device structure of the device embodiment 1 is briefly summarized as follows: ITO (185nm) / HT10: HI2 (10nm, 95:5wt%) / HT10 (40nm) / BFH5: Compound 3 (30nm, 10%wt) / ET8 (20nm) / LiF (1nm) / Al (100nm); the compound structure used in the device junction structure is as follows:
[0084]
[0085] The difference between device examples 2-22 and device example 1 is that the light-emitting layer guest material compound 3 is replaced by compound 5, compound 10, compound 20, compound 25, compound 39, compound 58, compound 62, compound 71, compound 80, compound 85, compound 89, compound 114, compound 126, compound 167, compound 210, compound 220, compound 226, compound 242, compound 270, compound 302, and compound 322.
[0086] At the same brightness, the driving voltage, current efficiency and device life of the organic electroluminescent devices in device embodiments 1 to 22 were measured using a digital source meter and a brightness meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the brightness of the organic electroluminescent device was measured when it reached 1000 cd / m 2 The voltage at this time is the driving voltage, and the current density at this time is measured at the same time. The ratio of brightness to current density is the current efficiency; LT95 life test: use a brightness meter at 1000cd / m 2 At the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to drop to 950cd / m 2 The time in hours.
[0087] Table 1
[0088]
[0089] As can be seen from Table 1 above, the compounds of the present invention have MR-TADF effect, which achieves narrow-band luminescence. At the same time, the macrocyclic ring with 16 atoms in the molecular structure not only retains a large rigidity, but also suppresses the vibration coupling between the ground state and the first excited singlet state and the relaxation of the excited state structure, which leads to the broadening of the spectrum and the reduction of the fluorescence quantum yield (PLQY). Figure 1 ) enables the device prepared by the compound of the present invention to still obtain a lower operating voltage, higher efficiency and longer life when the doping ratio is 10wt%.
Claims
1. A boron-nitrogen compound having a macrocyclic structure, characterized in that: It has the structure shown in the following general formula I: Wherein, the A rings are the same or different and are independently selected from a benzene ring, a furan ring or a thiophene ring; Y is N or O; the dotted line Indicates the presence or absence of a bonding relationship; X is the same or different and is independently selected from O, S, Se, C=O, S(=O)2, CR1R2, R1 and R2 are independently selected from hydrogen or alkyl; R is the same or different and is independently selected from alkyl, alkoxy, and aromatic, and n is an integer of 0 to 4; When ring A is a benzene ring, there may or may not be a bond relationship with the dotted line X; when ring A is a furan ring or a thiophene ring, there is no bond relationship with the dotted line X; when Y is N, there is a bond relationship with the dotted line Y; when Y is O, ring A is a benzene ring, and there is no bond relationship with the dotted line Y.
2. The boron-nitrogen compound having a macrocyclic structure according to claim 1, characterized in that: The A rings are the same, and are all benzene rings, furan rings or thiophene rings.
3. The boron-nitrogen compound having a macrocyclic structure according to claim 1, characterized in that: When the A ring is a benzene ring, two Ys adjacent to the A ring are the same, and if there is a bonding relationship with X, two Xs adjacent to the A ring are also the same.
4. The boron-nitrogen compound having a macrocyclic structure according to claim 1, characterized in that: The R1 and R2 are the same and are selected from hydrogen or C1-C4 alkyl.
5. The boron-nitrogen compound having a macrocyclic structure according to claim 1, characterized in that: The R's are the same or different and are independently selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, and phenyl, and adjacent R's may be bonded to form a ring.
6. The boron nitrogen compound having a macrocyclic structure according to claim 1, characterized in that: The structure of the compound is selected from one of the following structures:
7. An organic electroluminescent device, characterized in that: The invention comprises a cathode, an anode and one or more organic layers arranged therebetween, wherein at least one of the organic layers is a light-emitting layer, and the light-emitting layer contains one or more of the boron nitrogen compounds with a macrocyclic structure as described in any one of claims 1 to 6.
8. The organic electroluminescent device according to claim 7, characterized in that: The light-emitting layer comprises a host material and a guest material, and the guest material is the boron nitrogen compound with a macrocyclic structure as claimed in any one of claims 1 to 6.
9. The organic electroluminescent device according to claim 8, characterized in that: The organic electroluminescent device is used to manufacture display devices, lighting sources, signal lights, and signboards. The display devices include mobile phone display screens, computer display screens, television display screens, smart watch display screens, smart car display panels, and VR or AR helmet display screens.