Boron-nitrogen fused ring compound and organic photoelectric element containing same

Abstract

The invention discloses a boron-nitrogen fused ring compound and an organic photoelectric element containing the same, and belongs to the field of organic photoelectricity. The boron-nitrogen fused ring compound has a structure as shown in a chemical formula (1), a chemical formula (2) or a chemical formula (3). According to the compound disclosed by the invention, by expanding molecular pi conjugation, while the emission spectrum of the material is sharpened, the anti-intersystem crossing rate of the material is increased, and when the compound is applied to an organic light-emitting diode, the light-emitting color purity of a device can be obviously improved, the stability of the device is improved, the service life of the device is prolonged, and the compound has a good commercialization prospect. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the field of organic photoelectric technology, and particularly relates to a boron-nitrogen condensed ring compound and an organic photoelectric element containing the same. Background Art

[0002] With its unique advantages of full color, ultra-thin, and wide viewing angle, a new type of light-emitting technology, organic light-emitting diodes (OLEDs), has quickly become a research focus in the fields of display and lighting. As the core of the entire OLED device, the research and development of compounds will become a key factor affecting the performance of the device. Currently, the third-generation thermally activated delayed fluorescence (TADF) materials that do not contain metal can fully utilize triplet excitons to achieve efficient light emission through the reverse intersystem crossing (RISC) process, and are hailed as the most promising third-generation OLED compounds.

[0003] In order to meet people's production and living needs, the spectrum narrowing engineering of organic compounds has become an important research direction for achieving ultra-high-definition display. Based on this, TADF materials with multi-resonance (MR) effect have attracted widespread attention in the field of OLEDs due to their narrow-band emission characteristics.

[0004] However, accelerating the RISC process of compounds and improving device stability and lifespan are still issues that need to be addressed by MR-TADF materials. Recently, a fusion ring expansion strategy to extend the π conjugation of MR-TADF molecules has been proposed, which integrates multiple MR units into a rigid molecular skeleton. Due to the good positioning between heteroatoms, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of this type of organic polycyclic aromatic hydrocarbons (PAHs) are well separated, resulting in a smaller singlet-triplet energy level difference (ΔE ST ), which accelerates the upconversion of triplet excitons to singlet excitons, effectively alleviates the efficiency roll-off, and achieves an improvement in device performance. Summary of the invention

[0005] In order to solve the problems of slow RISC rate of current MR-TADF materials, which easily cause large efficiency roll-off and short service life of devices, the purpose of the present invention is to provide a boron-nitrogen fused ring compound and an organic optoelectronic element containing the same, which increases the RISC rate of the material by extending the molecular π conjugation, significantly improves the stability of the material in organic electroluminescent devices, and prolongs the life of the device.

[0006] In order to achieve the above object, the present invention provides a boron-nitrogen fused ring compound, the specific general formula of the compound is shown in chemical formulas (1) to (3):

[0007]

[0008] In the chemical formulas (1) to (3), X1 To X 4 Each independently selected from one of O, S or Se;

[0009] In the chemical formula (1), Ar is selected from any one of the following formulae:

[0010]

[0011] Among them, the X a and X b are independently selected from one of O, S or Se; R a and R b One selected from hydrogen, deuterium, trifluoromethyl, cyano, halogen, or substituted or unsubstituted one of the following groups: C1-C10 alkyl, C6-C60 arylalkyl, alkoxy, C6-C60 aryl, C5-C60 heteroaryl, alkylamino, C6-C60 arylamino;

[0012] The R 1 To R 6 One selected from hydrogen, deuterium, trifluoromethyl, cyano, halogen, or substituted or unsubstituted one of the following groups: C1-C10 alkyl, C6-C60 arylalkyl, alkoxy, C6-C60 aryl, C5-C60 heteroaryl, alkylamino, C6-C60 arylamino;

[0013] Wherein, the above-mentioned substituent groups are independently selected from one of deuterium, halogen, and C1-C10 alkyl.

[0014] Furthermore, the chemical formula (1) of the present invention has the structures of the following chemical formulas (1-1) and (1-2):

[0015]

[0016] In the chemical formula (1-1) and the chemical formula (1-2), X 1 , X 2 are independently selected from one of O, S or Se, R 1 , R 2 , R 3 , R a , R b It is selected from hydrogen, deuterium, trifluoromethyl, cyano, halogen or one of the following substituted or unsubstituted groups: C1-C10 alkyl, C6-C60 arylalkyl, alkoxy, C6-C60 aryl, C5-C60 heteroaryl, alkylamino, C6-C60 arylamino.

[0017] Preferably, in the chemical formula of the present invention, R 1 To R 6 , R a , Rb Each is independently selected from one of the following formulae, wherein * represents a connection site;

[0018] *-H*-D*-CF*-CN*-F*-Cl*-Br*-CH3

[0019] More preferably, the specific structure of the compound of the present invention is any one of the following structures;

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028] On the other hand, the present invention also provides the application of the above narrow-band compound, which is used as a host material or a sensitizer material or a guest material of a light-emitting layer to prepare an organic electroluminescent device.

[0029] Specifically, the organic electroluminescent device provided by the present invention comprises a first electrode, a second electrode and one or more organic functional layers sandwiched between the first electrode and the second electrode, wherein the organic functional layer comprises at least one of the above-mentioned compounds.

[0030] Compared with the prior art, the beneficial effects of the present invention are:

[0031] (1) The compounds of the present invention can effectively sharpen the emission spectrum of the material and improve the color purity of the device;

[0032] (2) The compounds of the present invention have efficient multiple resonance thermally activated delayed fluorescence characteristics, which can effectively promote better separation of HOMO and LUMO distribution at the atomic level, improve the anti-intersystem crossing process, and accelerate the up-conversion of triplet excitons, thereby improving the efficiency and stability of the device and extending the device life, showing good commercial application prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 This is the H NMR spectrum of compound 15 prepared in the example of the present invention;

[0034] Figure 2 This is the H NMR spectrum of compound 28 prepared in Example of the present invention;

[0035] Figure 3 This is the H NMR spectrum of compound 51 prepared in Example of the present invention;

[0036] Figure 4 This is the fluorescence spectrum of compound 15 prepared in the embodiment of the present invention;

[0037] Figure 5 This is the fluorescence spectrum of compound 28 prepared in Example of the present invention;

[0038] Figure 6 It is a schematic structural diagram of the organic electroluminescent device of the present invention. DETAILED DESCRIPTION

[0039] In order to enable those skilled in the art to better understand the solution of the present application, the technical solution in the embodiments of the present application will be clearly and completely described below in conjunction with the drawings in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of this application.

[0040] Synthesis of compounds:

[0041] Based on the technical foundation in this field, the synthesis of the compound involved in the present invention is briefly described below.

[0042] Synthesis Example

[0043] Representative synthetic route 1, taking the synthesis of compound 15 as an example.

[0044] Example 1

[0045] Synthesis of compound 15

[0046]

[0047] Under nitrogen flow, 4.0 mmol of 15-S1, 4.0 mmol of o-chloroaniline, 0.2 mmol of tri(dibenzylideneacetone)dipalladium, 0.4 mmol of tri-tert-butylphosphine tetrafluoroborate and 8.0 mmol of sodium tert-butoxide were dissolved in a three-necked flask with 50 mL of toluene (tol). The reaction system was stirred at 90° C. for 12 hours, then cooled to room temperature, and toluene was removed by distillation under reduced pressure. 200 mL of distilled water was added, and the mixture was extracted with dichloromethane (50 mL×3). The organic phase was collected, dried over anhydrous sodium sulfate, and distilled under reduced pressure to obtain a crude reaction product, which was then purified by silica gel column chromatography to obtain a white solid 15-S2 (1.6 g, 78.8%). 1 HNMR (400MHz, CDCl 3 )δ8.71(d,J=2.5Hz,2H),7.73(dd,J=8.8,2.5Hz,2H),7.65(dd,J=8.2,1.4Hz,1H),7.44(t,J =7.5Hz,3H),7.32–7.27(m,1H),7.04–6.97(m,1H),6.87(s,2H),6.44(s,1H),1.48(s,18H).

[0048] Under nitrogen flow, 2.0 mmol of 15-S2, 0.2 mmol of palladium acetate, 0.4 mmol of tri-tert-butylphosphine tetrafluoroborate and 8.0 mmol of potassium carbonate were dissolved in a three-necked flask with 30 mL of N,N-dimethylacetamide (DMAc). The reaction system was stirred at 150°C for 6 hours, cooled to room temperature, and then poured into 200 mL of ice water, and a gray precipitate appeared. The gray precipitate was filtered, washed with n-hexane, and then transferred to a flask, and a small amount of dichloromethane and methanol were added for slurrying, filtered, and dried to obtain an off-white solid 15-S3 (0.5 g, 53.2%). 1 H NMR (400 MHz, CDCl 3 )δ8.80(dd,J=15.2,2.5Hz,2H),8.61(d,J=7.4Hz,1H),8.30(s,1H),7.83(dd,J=8.7,2 .5Hz,1H),7.78–7.70(m,2H),7.52–7.34(m,4H),7.15(s,1H),1.52(d,J=7.9Hz,18H).

[0049] Under nitrogen flow, 2.0 mmol of 15-S3, 2.0 mmol of 15-S2, 0.1 mmol of tri(dibenzylideneacetone)dipalladium, 0.2 mmol of tri-tert-butylphosphine tetrafluoroborate and 4.0 mmol of sodium tert-butoxide were dissolved in a three-necked flask with 30 mL of toluene. The reaction system was stirred at 110° C. for 12 hours, then cooled to room temperature, and toluene was removed by distillation under reduced pressure. 100 mL of distilled water was added, and the mixture was extracted with dichloromethane (20 mL×3). The organic phase was collected, dried over anhydrous sodium sulfate, and distilled under reduced pressure to obtain a crude reaction product, which was then purified by silica gel column chromatography to obtain a white solid product 15 (1.4 g, 82.4%). 1 H NMR (400 MHz, CDCl 3 )δ8.85(d,J=2.4Hz,1H),8.80(dd,J=4.5,2.5Hz,3H),8.72–8.66(m,1H),7.88–7.76(m,4H),7.75–7.64(m, 2H),7.51(t,J=4.4Hz,4H),7.48–7.44(m,2H),7.44–7.40(m,2H),1.54(s,9H),1.53(s,18H),1.50(s,9H).

[0050] Example 2

[0051] Synthesis of compound 28

[0052]

[0053] Referring to the representative synthesis route 1, under a nitrogen flow, 2.0 mmol of 15-S3, 2.0 mmol of 28-S1, 0.1 mmol of tris(dibenzylideneacetone)dipalladium, 0.2 mmol of tri-tert-butylphosphine tetrafluoroborate and 4.0 mmol of sodium tert-butoxide were dissolved in a three-necked flask with 30 mL of toluene. The reaction system was stirred at 110° C. for 12 hours, then cooled to room temperature, and toluene was removed by distillation under reduced pressure. 100 mL of distilled water was added, and the mixture was extracted with dichloromethane (20 mL×3). The organic phase was collected, dried over anhydrous sodium sulfate, and distilled under reduced pressure to obtain a crude reaction product, which was then purified by silica gel column chromatography to obtain a white solid product 28 (1.0 g, 71.4%). 1 H NMR (400 MHz, CDCl 3)δ8.87(d,J=2.4Hz,1H),8.83–8.73(m,2H),8.25(s,2H),8.14(d,J=7.7Hz,2H),8.00(d,J=8.1Hz,2 H),7.91–7.80(m,2H),7.72–7.61(m,3H),7.51–7.34(m,6H),7.12(s,1H),1.55(s,9H),1.49(s,9H).

[0054] Example 3

[0055] Synthesis of compound 51

[0056]

[0057] Referring to the representative synthesis route 1, under a nitrogen flow, 2.0 mmol of 51-S1, 2.0 mmol of 2,6-dichloroaniline, 0.1 mmol of tris(dibenzylideneacetone)dipalladium, 0.2 mmol of tri-tert-butylphosphine tetrafluoroborate and 4.0 mmol of sodium tert-butoxide were dissolved in a three-necked flask with 30 mL of toluene. The reaction system was stirred at 110° C. for 12 hours, then cooled to room temperature and filtered to obtain a gray-green solid. The solid was ultrasonically cleaned with methanol and recrystallized in hot toluene to obtain an off-white solid product 51 (0.3 g, 35.7%). 1 H NMR (400 MHz, CDCl 3 )δ8.75(d,J=2.4Hz,2H),8.71(s,2H),8.17(d,J=7.3Hz,2H),7.80(d,J=8.8Hz,2H),7. 75–7.71(m,2H),7.69–7.60(m,5H),7.49(d,J=8.7Hz,2H),1.53(s,18H),1.49(s,18H).

[0058] Representative synthetic route 2, taking the synthesis of compound 113 as an example.

[0059] Example 4

[0060] Synthesis of compound 113

[0061]

[0062] Under nitrogen flow, 10.0 mmol of o-chloroaniline, 5.0 mmol of 1,4-dibromo-2,5-diiodobenzene, 0.5 mmol of tris(dibenzylideneacetone)dipalladium, 1.0 mmol of 1,1'-bis(diphenylphosphino)ferrocene (DPPF) and 10.0 mmol of sodium tert-butoxide were dissolved in a three-necked flask with 50 mL of toluene. The reaction system was stirred at 90°C for 12 hours, then cooled to room temperature, filtered, and washed with distilled water to obtain a dark purple solid, which was purified by silica gel column chromatography to obtain a light purple solid product 113-S1 (2.2 g, 90.3%). 1 H NMR (400 MHz, CDCl 3 )δ7.54(s,2H),7.41(dd,J=8.0,1.4Hz,2H),7.24–7.14(m,4H),6.91(ddd,J=7.8,6.9,2.0Hz,2H),6.23(s,2H).

[0063] Under nitrogen flow, 4.0 mmol of 113-S1, 0.4 mmol of palladium acetate, 0.8 mmol of tri-tert-butylphosphine tetrafluoroborate and 8.0 mmol of potassium carbonate were dissolved in a three-necked flask with 30 mL of N,N-dimethylacetamide (DMAc). The reaction system was stirred at 150°C for 6 hours, cooled to room temperature, and then poured into 200 mL of ice water, resulting in a brown precipitate. The brown precipitate was filtered and purified by silica gel column chromatography to obtain a light yellow solid product 113-S2 (0.4 g, 30.8%). 1 H NMR (400 MHz, DMSO-d 6 ) δ11.44 (s, 2H), 8.23 ​​(d, J = 7.1Hz, 4H), 7.49 (dd, J = 7.8, 0.9Hz, 2H), 7.17 (t, J = 7.7Hz, 2H).

[0064] Under nitrogen flow, 2.0 mmol of 113-S2, 4.0 mmol of 113-S3, 0.1 mmol of tris(dibenzylideneacetone)dipalladium, 0.2 mmol of tri-tert-butylphosphine tetrafluoroborate and 4.0 mmol of sodium tert-butoxide were dissolved in a three-necked flask with 50 mL of toluene. The reaction system was stirred at 110°C for 12 hours, then cooled to room temperature, toluene was removed by vacuum distillation, 100 mL of distilled water was added, and the mixture was extracted with dichloromethane (20 mL×3). The organic phase was collected, dried over anhydrous sodium sulfate, and vacuum distilled to obtain a crude reaction product, which was then purified by silica gel column chromatography to obtain a yellow solid product 113-S4 (0.8 g, 46.4%). LC-MS: Measured value: 861.35 ([M+H] + ); Theoretical value: 860.16.

[0065] Under nitrogen flow, 1.0 mmol of 113-S4, 0.1 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine tetrafluoroborate and 2.0 mmol of potassium carbonate were dissolved in a three-necked flask with 20 mL of N,N-dimethylacetamide (DMAc). The reaction system was stirred at 150°C for 6 hours, cooled to room temperature, and then poured into 200 mL of ice water, and a gray precipitate appeared. The gray precipitate was filtered and purified by silica gel column chromatography to obtain a white solid product 113 (0.2 g, 25.4%). LC-MS: Measured value: 789.50 ([M+H] + ); Theoretical value: 788.21.

[0066] Example 5

[0067] Synthesis of compound 138

[0068]

[0069] Referring to representative synthesis route 2, under nitrogen flow, 10.0 mmol of 4-bromo-2-chloroaniline, 5.0 mmol of 1,4-dibromo-2,5-diiodobenzene, 0.5 mmol of tris(dibenzylideneacetone)dipalladium, 1.0 mmol of 1,1'-bis(diphenylphosphino)ferrocene (DPPF) and 10.0 mmol of sodium tert-butoxide were dissolved in a three-necked flask with 50 mL of toluene. The reaction system was stirred at 90°C for 12 hours, then cooled to room temperature, filtered, and washed with distilled water to obtain a purple solid, which was purified by silica gel column chromatography to obtain a light purple solid product 138-S1 (2.1 g, 65.1%).

[0070] Under nitrogen flow, 2.0 mmol of 138-S1, 0.2 mmol of palladium acetate, 0.4 mmol of tri-tert-butylphosphine tetrafluoroborate and 4.0 mmol of potassium carbonate were dissolved in a three-necked flask with 30 mL of N,N-dimethylacetamide (DMAc). The reaction system was stirred at 150°C for 6 hours, cooled to room temperature, and then poured into 200 mL of ice water, resulting in a brown precipitate. The brown precipitate was filtered and purified by silica gel column chromatography to obtain a light yellow solid product 138-S2 (0.3 g, 31.1%).

[0071] Under nitrogen flow, 2.0 mmol of 138-S2, 4.0 mmol of 138-S3, 0.1 mmol of tri(dibenzylideneacetone)dipalladium, 0.2 mmol of tri-tert-butylphosphine tetrafluoroborate and 4.0 mmol of sodium tert-butoxide were dissolved in a three-necked flask with 50 mL of toluene. The reaction system was stirred at 110°C for 12 hours, then cooled to room temperature, and toluene was removed by distillation under reduced pressure. 100 mL of distilled water was added, and the mixture was extracted with dichloromethane (20 mL×3). The organic phase was collected, dried over anhydrous sodium sulfate, and distilled under reduced pressure to obtain a crude reaction product, which was then purified by silica gel column chromatography to obtain a yellow solid product 138-S4 (1.5 g, 58.1%).

[0072] Under nitrogen flow, 1.0 mmol of 113-S4, 0.1 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine tetrafluoroborate and 2.0 mmol of potassium carbonate were dissolved in a three-necked flask with 20 mL of N,N-dimethylacetamide (DMAc). The reaction system was stirred at 150°C for 6 hours, cooled to room temperature, and then poured into 200 mL of ice water, resulting in a gray precipitate. The gray precipitate was filtered and purified by silica gel column chromatography to obtain a white solid product 138-S5 (0.4 g, 32.8%).

[0073] Under nitrogen flow, 1.0 mmol of 138-S5, 2.0 mmol of 138-S3, 0.1 mmol of tris(dibenzylideneacetone)dipalladium, 0.2 mmol of tri-tert-butylphosphine tetrafluoroborate and 2.0 mmol of sodium tert-butoxide were dissolved in a three-necked flask with 30 mL of toluene. The reaction system was stirred at 110°C for 12 hours, then cooled to room temperature, toluene was removed by vacuum distillation, 100 mL of distilled water was added, and the mixture was extracted with dichloromethane (20 mL×3). The organic phase was collected, dried over anhydrous sodium sulfate, and vacuum distilled to obtain a crude reaction product, which was then purified by silica gel column chromatography to obtain a white solid product 138 (0.8 g, 49.5%). LC-MS: Measured value: 1615.59 ([M+H] + ); Theoretical value: 1614..21.

[0074] The target product obtained by the above synthesis is purified by column chromatography, then purified by recrystallization, and finally purified by high vacuum sublimation for use in preparing an organic electroluminescent device.

[0075] In order to make the purpose, technical solution and advantages of the present invention more clearly understood, the present invention is further described in detail below in conjunction with specific electroluminescent device embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.

[0076] In a preferred embodiment of the present invention, the organic electroluminescent device of the present invention contains a hole transport layer, and the hole transport material may preferably be a reported or unknown material, and is particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures:

[0077]

[0078] Further, in a preferred embodiment of the present invention, the hole injection layer contained in the organic electroluminescent device of the present invention comprises one or more p-type dopants. The preferred p-type dopant of the present invention is the following structure, but it does not mean that the present invention is limited to the following structure:

[0079]

[0080] Furthermore, in a preferred embodiment of the present invention, the electron transport layer can be selected from at least one of compounds ET-1 to ET-12, but it does not mean that the present invention is limited to the following structure:

[0081]

[0082] Furthermore, the electron injection layer may be formed of an organic material and one or more n-type dopants (eg, LiQ).

[0083] Preferably, in a preferred embodiment of the present invention, the organic electroluminescent device comprises an organic light-emitting layer, and the material of the organic light-emitting layer is the above-mentioned narrow-band compound as a guest material doped in a 1,3-bis(9H-carbazole-9-yl)benzene (mCP) host material.

[0084] like Figure 6 As shown, the organic electroluminescent device is composed of a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, and a cathode 110.

[0085] In a preferred embodiment disclosed in the present invention, an organic electroluminescent device based on the above narrow-band compound has a specific structure: indium tin oxide (ITO) is an anode, HT-6:P-2 (97:3 v / v%) is a hole injection layer (HIL), HT-6 is a hole transport layer (HTL), HT-12 is an electron blocking layer (EBL), the above narrow-band compound is used as a guest material doped with an mCP host material and used together as a light-emitting layer (EML), ET-2:LiQ (50:50 v / v%) is an electron transport layer (ETL), and aluminum (Al) is a cathode; the specifications of each layer of the organic electroluminescent device are: ITO / HT-6:P-2 (97:3 v / v%) (10nm) / HT-6 (90nm) / HT-12 (10nm) / mCP: guest material (5wt%) (30nm) / ET-2:LiQ (50:50 v / v%) (35nm) / Al (40nm). The specific preparation process is conventional technology, and is prepared by vacuum evaporation method.

[0086] The luminescence peak and full width at half maximum (FWHM) of the organic electroluminescent device based on the compounds prepared in the above-mentioned embodiments are shown in Table 1, and the specific testing method is the existing technology.

[0087] Table 1

[0088] Example EML EL(nm) FWHM(nm) Device Example 1 mCP:1 433 48 Device Example 2 mCP:8 435 50 Device Example 3 mCP:15 440 49 Device Example 4 mCP:28 441 48 Device Example 5 mCP:51 430 40 Device Example 6 mCP:58 433 42 Device Example 7 mCP:61 435 39 Device Example 8 mCP:113 445 28 Device Example 9 mCP:123 452 25 Device Example 10 mCP:138 455 30

[0089] The above experimental data show that the compound prepared by the present invention can achieve good narrow-band blue light emission after being applied to an organic electroluminescent device. At the same time, with the introduction of boron nitrogen fused ring, the electroluminescent spectrum of the device is significantly sharpened, the color purity is further improved, and the overall performance of the device is significantly improved. The present invention provides a narrow-band boron nitrogen fused ring compound that can achieve a blue light organic electroluminescent device with high color purity, and the overall performance of the device is significantly improved.

[0090] The above detailed description of the embodiments of the present invention will easily lead to other embodiments of the present application by those skilled in the art after considering the invention disclosed in the specification and specific examples. The present application is intended to cover any modification, use or adaptation of the present application, which follows the general principles of the present application and includes common knowledge or customary technical means in the art that are not disclosed in the present disclosure. The specification and examples are only to be regarded as exemplary, and the true scope and spirit of the present application are indicated by the following claims.

[0091] It should be understood that the present application is not limited to the precise structure described and shown above, and various modifications and changes can be made without departing from the scope thereof. The scope of the present application is limited only by the appended claims. The above description is only a preferred embodiment of the present application and is not intended to limit the present application. Any modification, equivalent substitution, improvement, etc. made within the spirit and principle of the present application shall be included in the protection scope of the present application.

Claims

1. A boron-nitrogen fused ring compound, wherein the boron-nitrogen fused ring compound has the following general structural formulas (1) to (3): In the chemical formulae (1) to (3), X1 to X4 are independently selected from O, S or Se; In the chemical formula (1), Ar is selected from any one of the following formulae: in, The X a and X b are independently selected from O, S or Se; R a and R b One selected from hydrogen, deuterium, trifluoromethyl, cyano, halogen, or substituted or unsubstituted one of the following groups: C1-C10 alkyl, C6-C60 arylalkyl, alkoxy, C6-C60 aryl, C5-C60 heteroaryl, alkylamino, C6-C60 arylamino; The R1 to R6 are selected from hydrogen, deuterium, trifluoromethyl, cyano, halogen or one of the following substituted or unsubstituted groups: C1-C10 alkyl, C6-C60 arylalkyl, alkoxy, C6-C60 aryl, C5-C60 heteroaryl, alkylamine, C6-C60 arylamine; Wherein, the substituent groups are independently selected from one of deuterium, halogen and C1-C10 alkyl.

2. The boron-nitrogen fused ring compound according to claim 1, characterized in that: The compound of the chemical formula (1) has the following structures of the chemical formula (1-1) and the chemical formula (1-2): Wherein, X1 and X2 are independently selected from O, S or Se; R1, R2, R3, R a , R b It is selected from hydrogen, deuterium, trifluoromethyl, cyano, halogen or one of the following substituted or unsubstituted groups: C1-C10 alkyl, C6-C60 arylalkyl, alkoxy, C6-C60 aryl, C5-C60 heteroaryl, alkylamino and C6-C60 arylamino.

3. The boron-nitrogen fused ring compound according to any one of claims 1 to 2, characterized in that: In the chemical formula (1), the chemical formula (2), the chemical formula (3), the chemical formula (1-1) and the chemical formula (1-2), R1 to R6, R a , R b Each independently selected from one of the following formulae; Wherein, * represents the attachment site.

4. The compound according to any one of claims 1 to 3, characterized in that The specific structure of the compound is any one of the following structures:

5. A boron-nitrogen fused ring compound according to any one of claims 1 to 3 used as a host material, a sensitizer material or a guest material of a light-emitting layer in an organic electroluminescent device.

6. An organic electroluminescent device, characterized in that: The device comprises a first electrode, a second electrode and one or more organic functional layers sandwiched between the first electrode and the second electrode, wherein the organic functional layer comprises at least one boron-nitrogen condensed ring compound according to any one of claims 1 to 3.

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