Material containing naphthofuran structure as well as preparation method and application thereof

Abstract

The invention relates to a material containing a naphthofuran structure and a preparation method and application thereof, and belongs to the technical field of OLED materials. The structure of the material containing the naphthofuran structure is shown in the specification, and Ar is one of a C6-C30 aryl group, a heterocyclic aryl group, a deuterated aryl group or a deuterated heterocyclic aryl group. The material containing the naphthofuran structure is applied to luminescent materials in OLED devices. Due to the special structure, the material containing the naphthofuran structure has better compound energy level and stacking structure, better thermal stability and higher electron mobility, and shows excellent performance in an OLED device, including prolonging the service life, improving the luminous efficiency and reducing the driving pressure.

Description

TECHNICAL FIELD

[0001] The present application relates to a material containing naphthofuran structure and its preparation method and application, and belongs to the technical field of OLED materials. BACKGROUND

[0002] Organic light emitting diode (OLED) has the advantages of self-luminescence, wide viewing angle, short response time, high luminous efficiency, thin panel, low energy consumption, wide temperature range of use, etc., and has gradually replaced LCD display and become the mainstream display. The core material layer in the OLED device is the light-emitting layer, the electron transport layer and the hole transport layer, among which the most core part is the light-emitting layer, and the organic electroluminescent material used therein determines the light-emitting efficiency, film-forming property and carrier transport property of the OLED device.

[0003] The light-emitting layer of the OLED device is excited by the recombination of injected carriers, and then emits light with high efficiency. Therefore, the light-emitting layer must use a compound with very strong fluorescence or phosphorescence. Although other layers can use inorganic substances, the light-emitting layer must be an organic substance.

[0004] Although the OLED display screen has many advantages, there are still many aspects that need to be improved, such as the poor light-emitting efficiency, poor stability and short service life of the OLED device, which are one of the problems. Therefore, it is of great value to develop new materials that can improve the performance and service life of the OLED device. SUMMARY

[0005] The present application provides a material containing naphthofuran structure and its preparation method and application, which solves the problems in the prior art. The special structure of naphthofuran in the material makes it thermally stable, with high electron affinity. The material containing naphthofuran structure has excellent performance in optoelectronic materials.

[0006] The technical scheme for solving the above technical problems is as follows: a material containing naphthofuran structure, the structure of the material containing naphthofuran structure is shown in general formula I: General formula I; Ar is any one of C6-C30 aryl, heterocyclic aryl, deuterium-substituted aryl or deuterium-substituted heterocyclic aryl; The heteroatom in the heterocyclic aryl is selected from N, S and O.

[0007] Further, Ar is selected from any one of the following structures: .

[0008] Further, the material containing naphthofuran structure is selected from any one of the following structural formula: .

[0009] The application further discloses a preparation method of the material containing naphthofuran structure. In inert gas protection, the intermediate and the raw material compound are heated to react under the action of a catalyst under alkaline conditions, after the reaction is completed, the material containing naphthofuran structure is obtained through post-treatment; The structural formula of the intermediate is: X is selected from halogen and ; When X is selected from halogen, the structural formula of the raw material compound is Ar-Y, Y is any one of a boronic acid group, a boronic ester group and an imine structure group; When X is , the structural formula of the raw material compound is Ar-Cl, Ar-Br or Ar-I.

[0010] Further, the base is at least one of potassium carbonate, sodium carbonate and sodium tert-butoxide.

[0011] Further, the catalyst is at least one of tetrakis triphenylphosphine palladium, palladium acetate and tris (dibenzylideneacetone) dipalladium.

[0012] The application further discloses an application of the material containing naphthofuran structure.

[0013] Further, the material containing naphthofuran structure is applied to an organic functional layer of an OLED device.

[0014] Further, the material containing naphthofuran structure is applied to a light-emitting layer material.

[0015] Further, the OLED device comprises a transparent substrate layer, an anode electrode layer, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode reflection electrode layer.

[0016] The application has the following beneficial effects: The material containing the naphthofuran structure has excellent photophysical properties, as a weak acceptor, can be combined with a strong donor to construct a wide energy gap blue light material, and constitutes a narrow spectrum blue light device with high efficiency; the properties can be accurately "tailored", the molecule can have hybrid local charge transfer characteristics by adjusting the substituent group, thereby utilizing the triplet exciton, breaking through the upper limit of the exciton utilization rate of traditional fluorescent materials; the thermal stability is good, the rigid fused ring structure helps to improve the thermal decomposition temperature of the material, and helps to realize low driving voltage and long service life; the low temperature mutual solubility is good, which can provide a relatively wide use environment temperature range, further improving the stability of the material as a light emitting layer material. The naphthofuran material successfully occupies a key position in the development of high-efficiency, high-color-purity blue light materials due to its unique rigid fused ring skeleton, and also shows comprehensive advantages in device stability and molecular design flexibility. It is a very promising core structural unit in the field of organic optoelectronic materials. The OLED device using the structure as a light emitting layer has obvious improvement in luminous efficiency and service life, and has good stability and wide application prospect. BRIEF DESCRIPTION OF DRAWINGS

[0017] Figure 1 A schematic diagram of the multi-layer structure of the OLED light emitting device described in the examples; In the figure, 1 is a transparent substrate layer; 2 is an anode electrode layer; 3 is a hole injection layer; 4 is a hole transport layer; 5 is an electron blocking layer; 6 is a light emitting layer; 7 is a hole blocking layer; 8 is an electron transport layer; 9 is an electron injection layer; 10 is a cathode reflection electrode layer. DETAILED DESCRIPTION

[0018] In order to make the above-mentioned purposes, features and advantages of the present application more obvious and easy to understand, the specific embodiments of the present application are described in detail below. In the following description, a large number of specific details are set forth in order to fully understand the present application. However, the present application can be implemented in many other ways different from those described herein, and those skilled in the art can make similar improvements without departing from the scope of the present application, therefore the present application is not limited by the specific examples disclosed below.

[0019] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the present application belongs. The terms used in the specification of the present application herein are only for the purpose of describing the specific embodiments and are not intended to limit the present application.

[0020] Synthesis method of parent structure general intermediate: ; (1) Synthesis of intermediate 1: A reaction flask was charged with 50 mmol of starting material 1 (CAS: 1195572-81-6), 100 g of dichloroethane (as solvent), and 50 mmol of NBS (CAS: 128-08-5) was added dropwise at -10-0 °C under nitrogen control. The reaction was maintained for 5 h, and after the reaction was completed, the reaction system was hydrolyzed, washed with water, and desolvated. The product was obtained by recrystallization using toluene, with a yield of 81%. Mass spectrum: m / z = 275.98; Hydrogen spectrum: 1H NMR (400 MHz, chloroform-d) δ 8.08 (dd, J = 7.4, 1.7 Hz, 1H), 7.82 (s, 1H), 7.74 (dt, J = 7.4, 1.7 Hz, 1H), 7.49 (td, J = 7.3, 1.6 Hz, 1H), 7.42 (td, J = 7.4, 1.5 Hz, 1H), 7.20 (d, J = 1.5 Hz, 1H), 3.98 (s, 3H).

[0021] (2) Synthesis of intermediate 2: A reaction flask was charged with 60 mmol of intermediate 1, 80 g of tetrahydrofuran (as solvent), and then nitrogen was passed. 60 mmol of n-butyllithium (CAS: 109-72-8) was added dropwise at -80-90 °C, and the reaction was maintained for 2 h. 60 mmol of triisopropyl borate (CAS: 5419-55-6) was then added dropwise, and the reaction was maintained for 2 h. The reaction liquid was added to water, hydrolyzed, washed with water, extracted with ethyl acetate, and desolvated to obtain the product, with a yield of 93%. Mass spectrum: m / z = 242.08; Hydrogen spectrum: 1H NMR (400 MHz, chloroform-d) δ 8.10 - 8.02 (m, 1H), 7.77 - 7.70 (m, 1H), 7.65 (s, 1H), 7.53 - 7.44 (m, 2H), 7.20 (d, J = 1.5 Hz, 1H), 6.97 (s, 2H), 3.96 (s, 3H).

[0022] (3) Synthesis of intermediate 3: A reaction flask was charged with 38.5 mmol of starting material 2 (CAS: 6630-33-7), 77 mmol of potassium carbonate, 25 g of water, and 100 g of tetrahydrofuran, and purged with nitrogen. 0.385 mmol of palladium acetate and 0.77 mmol of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were added, and then the mixture was warmed to 55-60 °C. A solution of 38.5 mmol of intermediate 2 in 50 g of tetrahydrofuran was added dropwise, and then the dropwise addition was completed. The mixture was incubated for 8 h, hydrolyzed, and then extracted with toluene, washed with water, passed through a silica gel column, desolvated, and recrystallized with toluene to obtain intermediate 3 in a yield of 72%. Mass spectrum: m / z = 302.09; hydrogen spectrum:1H NMR (400 MHz, Chloroform-d) δ 10.01 (s, 1H), 8.02 (dd, J = 7.7, 1.5 Hz, 1H), 7.90 (d, J = 7.8 Hz, 2H), 7.80 - 7.71 (m, 2H), 7.63 (td, J = 7.4, 1.5 Hz, 1H), 7.49 (tt, J = 7.6, 1.9 Hz, 2H), 7.40 (td, J = 7.4, 1.5 Hz, 1H), 7.19 (d, J = 1.5 Hz, 1H), 3.96 (s, 3H).

[0023] (4) Synthesis of intermediate 4: A reaction flask was charged with 47.2 mmol of intermediate 3, 81.9 mmol of (methoxymethyl)triphenylphosphonium chloride (CAS: 4009-98-7), and 100 g of toluene, and purged with nitrogen. The mixture was cooled to 0-5 °C, and a solution of 70.8 mmol of sodium tert-butoxide in 100 g of tetrahydrofuran was added dropwise. The mixture was incubated for 4 h, hydrolyzed by adding water, washed with water, passed through a silica gel column, desolvated, and recrystallized with toluene to obtain intermediate 4 in a yield of 91%. Mass spectrum: m / z = 330.13; hydrogen spectrum:1H NMR (400 MHz, Chloroform-d) δ 8.00 (dd, J = 7.5, 1.7 Hz, 1H), 7.78 - 7.72 (m, 1H), 7.66 (s, 1H), 7.62 (dd, J = 7.0, 2.0 Hz, 1H), 7.47 (ddd, J = 9.3, 7.2, 1.8 Hz, 2H), 7.43 - 7.35 (m, 3H), 7.19 (d, J = 1.5 Hz, 1H), 6.53 - 6.46 (m, 1H), 6.00 (d, J = 14.9 Hz, 1H), 3.98 (s, 3H), 3.56 (d, J = 1.1 Hz, 3H).

[0024] (5) Synthesis of intermediate 5: A reaction flask was charged with 220 mmol of methanesulfonic acid (CAS: 75-75-2), 80 g of dichloroethane, then nitrogen was bubbled, and the temperature was raised to 80-90 °C, and a solution of 44 mmol of intermediate 4 dissolved in 80 g of dichloroethane was added dropwise, and the temperature was maintained for 2 h, then hydrolysis, water washing, desolvation, and recrystallization using toluene were performed to obtain intermediate 5 with a yield of 72%. Mass spectrum: m / z = 298.10; Hydrogen spectrum:1H NMR (400 MHz, Chloroform-d) δ 8.33 - 8.27 (m, 1H), 8.05 (dd, J = 7.1, 1.4 Hz, 1H), 7.95 (dt, J = 6.9, 1.7 Hz, 1H), 7.88 (dd, J = 7.4, 1.4 Hz, 1H), 7.75 (dt, J = 7.8, 1.7 Hz, 1H), 7.56 - 7.46 (m, 3H), 7.43 - 7.36 (m, 2H), 7.23 (d, J = 1.5 Hz, 1H), 3.97 (s, 3H).

[0025] (6) Synthesis of intermediate 6: A reaction flask was charged with 40.0 mmol of intermediate 5, 100 g of dichloroethane, and 60.0 mmol of boron tribromide (CAS: 10294-33-4) was added to the reaction system while controlling the temperature to 0-10 °C, and then the temperature was maintained for 5 h, and hydrolysis, water washing, silica gel column, desolvation, and recrystallization using dichloroethane were performed to obtain intermediate 6. Yield: 79%. Mass spectrum: m / z = 257.0; Hydrogen spectrum:1H NMR (400 MHz, Chloroform-d) δ 10.30 (s, 1H), 8.34 - 8.26 (m, 1H), 8.03 (dd, J = 7.7, 1.4 Hz, 1H), 7.98 - 7.90 (m, 2H), 7.75 - 7.70 (m, 1H), 7.56 - 7.47 (m, 3H), 7.44 - 7.36 (m, 2H), 7.22 (d, J = 1.5 Hz, 1H).

[0026] (7) Synthesis of Intermediate 7: A reaction flask was charged with 70.0 mmol of Intermediate 6, 70.0 mmol of starting material 3 (CAS: 2641900-32-3), 210.0 mmol of potassium carbonate, 200 g of DMF. The temperature was raised to 130-135 °C and held for 10 h, hydrolyzed, filtered, washed with hot water, passed through a silica gel column, desolvated, and recrystallized using toluene to obtain Intermediate 7. Yield: 75%. Mass spectrum: m / z = 524.00; Hydrogen spectrum:1H NMR (400 MHz, Chloroform-d) δ 8.31 (dd, J = 6.6, 2.1 Hz, 1H), 8.18 - 8.12 (m, 1H), 8.09 (dd, J = 7.7, 1.5 Hz, 1H), 7.95 (dt, J = 6.5, 1.6 Hz, 1H), 7.88 (dd, J = 7.6, 1.5 Hz, 1H), 7.72 (ddt, J = 19.1, 7.6, 1.9 Hz, 2H), 7.61 (d, J = 1.4 Hz, 1H), 7.49 (dddd, J = 11.7, 9.9, 4.9, 2.2 Hz, 5H), 7.44 - 7.35 (m, 2H), 6.99 (d, J = 1.5 Hz, 1H).

[0027] (8) Synthesis of intermediate 8: In a reaction bottle, 38.6 mmol of intermediate 7, 96.5 mmol of cesium carbonate and 100 g of N-methyl pyrrolidone were added, then nitrogen was passed, 0.4 mmol of palladium acetate, 0.8 mmol of tri-tert-butyl phosphine tetrafluoroborate were added, and the temperature was raised to 155-160°C for reaction, and the temperature was kept for 12 h, then hydrolysis, filtration, silica gel column after dissolving with toluene, desolvation, using o-dichlorobenzene for recrystallization, to obtain high-quality intermediate 8, the final yield is 73%.Mass spectrum: m / z = 442.08; Hydrogen spectrum: 1H NMR (400 MHz, Chloroform-d) δ 8.30 (td, 2H), 8.06 (dd, 1H), 7.93 (ddt, 2H), 7.87 (dd, 1H), 7.74 (dt, 1H), 7.61 (d, 1H), 7.56 - 7.43 (m, 5H), 7.38 (d, 1H), 7.32 (td, 1H); Carbon spectrum: 13C NMR (125 MHz, Chloroform-d) δ 153.85, 150.86, 150.27, 150.22, 148.07, 131.58, 131.57, 130.30, 130.24, 130.19, 130.13, 129.80, 129.01, 128.98, 128.96, 128.92, 128.90, 127.90, 127.85, 127.84, 127.78, 127.61, 127.60, 127.58, 127.57, 127.55, 127.54, 127.52, 127.51, 127.39, 127.33, 127.31, 127.29, 127.28, 127.26, 127.23, 127.22, 127.14, 127.12, 127.11, 127.08, 127.06, 127.05, 127.03, 127.02, 127.00, 126.98, 125.87, 125.85, 125.84, 125.81, 125.79, 125.78, 125.50, 125.48, 125.43, 124.96, 124.95, 124.90, 124.88, 124.75, 124.70, 123.88, 123.82, 123.77, 123.76, 123.23, 123.18, 123.01, 122.99, 122.95, 122.94, 122.89, 122.88, 122.27, 120.33, 120.27, 118.66, 117.67, 108.45, 108.43, 107.67.

[0028] (09) Synthesis of Intermediate 9: In a reaction flask, 43.8 mmol of Intermediate 9, 65.7 mmol of pinacol diborane, 52.6 mmol of potassium acetate and 100 g of xylene were added, then nitrogen was passed, 0.5 mmol of tris(dibenzylideneacetone)dipalladium, 1.0 mmol of tricyclohexylphosphine were added, the temperature was raised to 130-135 °C, and the reaction was kept for 12 h, then hydrolysis, water washing, silica gel column, desolvation, using xylene for recrystallization, to obtain high-quality Intermediate 9, the final yield was 85%. Mass spectrum: m / z = 534.20; Hydrogen spectrum:1HNMR (400 MHz, chloroform-d) δ 8.34 - 8.28 (m, 2H), 7.97 - 7.89 (m, 2H), 7.89 - 7.79 (m, 3H), 7.60 (d, 1H), 7.56 - 7.46 (m, 4H), 7.45 - 7.36 (m, 2H), 7.30 (td, 1H), 1.24 (s, 12H).

[0029] Carbon Spectrum: 13C NMR (125 MHz, chloroform-d) δ 154.98, 153.09, 149.83, 149.82, 149.81, 149.77, 149.76, 149.03, 132.69, 132.68, 131.38, 131.37, 131.36, 131.32, 131.31, 131.30, 130.28, 130.22, 130.21, 130.16, 129.85, 129.65, 129.09, 129.04, 129.03, 129.02, 128.98, 128.97, 128.34, 128.33, 128.29, 128.28, 128.25, 128.24, 128.23, 127.92, 127.92, 127.91, 127.87, 127.85, 127.53, 127.52, 127.52, 127.51, 127.50, 127.48, 127.47, 127.46, 127.45, 127.42, 127.40, 127.24, 127.23, 127.22, 127.21, 127.21, 127.20, 127.16, 127.15, 127.15, 127.14, 127.10, 127.09, 127.07, 127.05, 127.02, 127.01, 127.00, 127.00, 126.95, 126.23, 126.21, 126.20, 126.17, 126.15, 126.13, 125.62, 125.61, 125.57, 125.55, 125.55, 125.54, 125.49, 125.39, 125.38, 125.38, 125.33, 125.32, 125.31, 124.80, 124.79, 124.74, 124.72, 124.29, 124.24, 124.06, 124.05, 122.57, 122.56, 122.51, 122.50, 122.49, 122.46, 122.44, 121.91, 121.90, 121.85, 121.84, 121.80, 121.79, 119.40, 119.35, 119.35, 118.60, 108.52, 108.51, 108.50, 108.49, 106.28, 83.76, 24.83.

[0030] The parent compound is structured by coupling with intermediate 8 and Ar-Y (at this time, Y is a boronic acid group, a boronic ester group, an imine structure group, etc. which can react with a halogen group) or by coupling with intermediate 9 and Ar-Y (at this time, Y is a common halogen group and other structure groups which can react with a boronic ester). The following are several synthesis examples of compounds: Example 1 A structural formula of a compound 1 applied to an OLED device: ; A specific synthesis route of the compound 1 is as follows: ; Preparation of compound 1: In a reaction flask, 35 mmol of intermediate 8, 87.5 mmol of potassium carbonate, 30 g of water and 120 g of toluene were added, then nitrogen was passed, 0.35 mmol of palladium tetraphenylphosphine was added, the temperature was raised to 60-65 °C, and a solution of phenylboronic acid (36.8 mmol of phenylboronic acid (CAS: 98-80-6) and 20 g of tetrahydrofuran) was added dropwise, and after the dropwise addition was completed, the temperature was maintained for 5 h, then the water phase was separated, the organic phase was washed with water until it was about neutral, then passed through a silica gel column, desolvated, and recrystallized with toluene to obtain the product, with a yield of 79%. Mass spectrum: m / z = 484.15.Hydrogen spectrum:1H NMR (400 MHz, chloroform-d) δ 8.33 (ddd, J = 10.3, 7.0, 1.9 Hz, 2H), 7.97 - 7.84 (m, 4H), 7.79 (dt, J = 8.4, 2.1 Hz, 3H), 7.61 (d, J = 1.4 Hz, 1H), 7.55 - 7.35 (m, 9H), 7.31 (td, J = 7.5, 1.6 Hz, 1H); Carbon spectrum:13C NMR (125 MHz, chloroform-d) δ 154.63, 151.97, 150.51, 150.45, 148.49, 135.56, 135.51, 133.03, 131.93, 131.92, 130.43, 130.38, 130.29, 130.12, 130.07, 130.06, 130.05, 130.00, 129.78, 128.32, 128.31, 128.26, 128.24, 128.15, 128.13, 128.10, 128.08, 127.97, 127.96, 127.94, 127.93, 127.90, 127.89, 127.88, 127.84, 127.82, 127.69, 127.67, 127.63, 127.62, 127.61, 127.55, 127.43, 127.41, 127.37, 127.35, 127.32, 127.31, 127.29, 127.27, 127.25, 127.18, 127.12, 127.06, 127.00, 126.99, 126.94, 126.92, 126.09, 126.07, 126.05, 126.02, 126.01, 125.99, 125.66, 125.65, 125.64, 125.59, 124.87, 124.82, 124.77, 124.62, 124.60, 124.56, 124.54, 124.43, 124.37, 123.91, 123.86, 122.43, 122.38, 122.37, 122.36, 122.32, 122.30, 121.91, 119.73, 119.43, 119.38, 118.66, 108.52, 108.50, 105.53.

[0031] Example 2 A compound 2 applied to an OLED device has a structural formula: ; A specific synthesis route of the compound 2 is as follows: ; Preparation of the compound 2: a reaction bottle is added with 35 mmol of intermediate 8, 87.5 mmol of potassium carbonate, 30 g of water and 120 g of toluene, then nitrogen is passed, 0.35 mmol of palladium acetate and 0.7 mmol of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene are added, then the temperature is raised to 70-75°C, and a 2-biphenylboronic acid solution (36.8 mmol of 2-biphenylboronic acid (CAS: 4688-76-0) and 20 g of ethanol are prepared into a solution) is added dropwise, and after the dropwise addition is completed, the temperature is kept for 5 h, then the water phase is separated, the organic phase is washed to about neutral, then a silica gel column is passed, desolvated, and toluene is used for recrystallization to obtain the product, with a yield of 78%. Mass spectrum: m / z = 560.18. Hydrogen spectrum: 1H NMR (400 MHz, chloroform-d) δ 8.33 (ddd, J = 10.8, 6.5, 2.5 Hz, 2H), 7.97 - 7.84 (m, 4H), 7.81 (dt, J = 7.4, 1.7 Hz, 1H), 7.63 - 7.57 (m, 3H), 7.56 - 7.42 (m, 10H), 7.42 - 7.36 (m, 2H), 7.36 - 7.26 (m, 2H); Carbon spectrum: 13C NMR (125 MHz, chloroform-d) δ 155.37, 150.99, 148.96, 148.88, 140.52, 139.48, 133.67, 133.49, 132.40, 130.28, 130.00, 129.56, 129.35, 128.51, 128.45, 128.43, 128.36, 128.21, 128.09, 128.06, 127.87, 127.80, 127.57, 126.87, 126.64, 126.59, 126.35, 125.66, 125.47, 124.93, 124.23, 124.01, 123.86, 121.76, 120.58, 120.36, 111.29, 109.27.

[0032] Example 3 A compound 6 applied to an OLED device has a structural formula: ; A specific synthesis route of the compound 6 is as follows: ; Preparation of compound 6: In a reaction flask, 42.1 mmol of intermediate 9, 46.3 mmol of 3,5-diphenylchlorobenzene (CAS: 126866-34-0), 105.3 mmol of potassium carbonate, 25 g of water and 150 g of toluene were added, then nitrogen was passed, 0.4 mmol of palladium acetate and 0.8 mmol of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were added. Reaction was kept at 75~80℃ for 12 h, then the aqueous phase was separated, the organic phase was washed with water until about neutral, then passed through a silica gel column, desolvated, recrystallized with toluene to obtain the product, the yield was 81%. Mass spectrum: m / z = 636.21. Hydrogen spectrum:1H NMR (400 MHz, chloroform-d) δ 8.33 (td, J = 7.7, 1.9 Hz, 2H), 7.97 - 7.87 (m, 5H), 7.86 (dd, J = 7.6, 1.6 Hz, 1H), 7.84 - 7.76 (m, 2H), 7.64 - 7.44 (m, 9H), 7.44 - 7.33 (m, 8H), 7.29 (td, J = 7.4, 1.5 Hz, 1H); Carbon spectrum:13C NMR (125 MHz, chloroform-d) δ 155.73, 151.23, 148.62, 147.60, 139.50, 136.39, 133.76, 132.95, 132.41, 132.10, 130.60, 129.52, 129.18, 129.06, 129.00, 128.42, 128.30, 127.84, 127.80, 127.52, 127.33, 127.15, 126.92, 126.44, 126.33, 126.17, 125.91, 125.48, 124.88, 124.86, 123.46, 122.87, 122.50, 120.58, 120.41, 111.33, 109.14. Example 4 A compound 5 applied to an OLED device has a structural formula as follows: ; A specific synthesis route of compound 5 is as follows: ; Preparation of compound 5: In a reaction flask, 35 mmol of intermediate 8, 87.5 mmol of potassium carbonate, 30 g of water and 120 g of tetrahydrofuran were added, then nitrogen was passed, 0.35 mmol of palladium tetra-triphenylphosphine was added, then the temperature was raised to 60-65 °C, 1-naphthalene boronic acid solution (36.8 mmol of 1-naphthalene boronic acid (CAS: 13922-41-3) and 20 g of tetrahydrofuran were prepared into a solution) was added dropwise, after the dropwise addition was completed, it was kept for 5 h, then toluene was added for extraction, the organic phase was washed with water until it was about neutral, then it was passed through a silica gel column, desolvated, and recrystallized with dichloroethane to obtain the product, with a yield of 76%. Mass spectrum: m / z = 534.16. Hydrogen spectrum:1H NMR (400 MHz, chloroform-d) δ 8.37 - 8.30 (m, 2H), 7.98 - 7.91 (m, 4H), 7.91 - 7.79 (m, 4H), 7.58 - 7.43 (m, 8H), 7.39 (td, J = 7.5, 1.8 Hz, 2H), 7.30 (td, J = 7.4, 1.5 Hz, 1H); Carbon spectrum:13C NMR (125 MHz, chloroform-d) δ 155.37, 151.28, 148.96, 148.88, 133.68, 133.49, 133.39, 133.25, 132.49, 132.38, 130.85, 129.68, 129.25, 128.43, 128.36, 128.28, 128.12, 127.68, 127.55, 126.97, 126.87, 126.70, 126.59, 126.51, 126.35, 126.33, 126.30, 126.05, 126.03, 125.85, 125.50, 124.84, 124.28, 124.25, 123.87, 121.86, 120.85, 120.36, 111.29, 109.27.

[0033] Example 5 A compound 8 applied to an OLED device has a structural formula as follows: ; A specific synthesis route of compound 8 is as follows: ; Preparation of compound 8: In a reaction flask, 42.1 mmol of intermediate 9, 46.3 mmol of 9-bromoanthracene (CAS: 1564-64-3), 105.3 mmol of potassium carbonate, 20 g of water and 200 g of toluene were added, then nitrogen was passed, 0.4 mmol of palladium tetraphenylphosphine was added, 75-80 °C was incubated for 12 h, then the aqueous phase was separated, the organic phase was washed with water until about neutral, then passed through a silica gel column, desolvated, and recrystallized with DMF to obtain the product, with a yield of 69%. Mass spectrum: m / z = 584.18. Hydrogen spectrum: 1H NMR (400 MHz, chloroform-d) δ 8.37 (d, J = 1.5 Hz, 1H), 8.38 - 8.29 (m, 2H), 8.07 (ddd, J = 7.6, 4.2, 1.9 Hz, 4H), 7.94 (dt, J = 5.7, 1.8 Hz, 1H), 7.95 - 7.89 (m, 1H), 7.91 - 7.84 (m, 3H), 7.82 (dt, J = 7.8, 1.8 Hz, 1H), 7.63 (d, J = 1.5 Hz, 1H), 7.57 - 7.35 (m, 11H), 7.30 (td, J = 7.4, 1.5 Hz, 1H); Carbon spectrum: 13C NMR (125 MHz, chloroform-d) δ 155.37, 151.34, 148.69, 148.29, 133.76, 133.47, 133.40, 132.32, 131.92, 130.06, 129.98, 129.03, 128.64, 128.61, 128.56, 128.30, 128.17, 127.64, 126.84, 126.81, 126.76, 126.71, 126.66, 126.50, 126.40, 126.10, 125.81, 125.45, 125.24, 124.72, 124.52, 123.86, 120.58, 120.31, 111.29, 109.27.

[0034] Example 6 A compound 10 applied to an OLED device has the following structural formula: ; A specific synthesis route of compound 10 is as follows: ; Preparation of compound 10: In a reaction flask was added 35 mmol of intermediate 8, 87.5 mmol of sodium carbonate, 30 g of water and 120 g of dioxane, then nitrogen was bubbled, 0.35 mmol of palladium tetra-triphenylphosphine was added, then the temperature was raised to 80-85 °C, 2-benzofuran boronic acid solution (36.8 mmol of 2-benzofuran boronic acid (CAS: 98437-24-2) and 20 g of dioxane were prepared into a solution) was added dropwise, after the dropwise addition was completed, it was kept for 5 h, then toluene was added for extraction, the organic phase was washed with water until it was about neutral, then it was passed through a silica gel column, desolvated, recrystallized with toluene to obtain the product, the yield was 71%. Mass spectrum: m / z = 524.14. Hydrogen spectrum:1H NMR (400 MHz, Chloroform-d) δ 8.38 - 8.27 (m, 2H), 8.05 (dd, J = 7.2, 1.5 Hz, 1H), 7.96 - 7.89 (m, 2H), 7.87 (dd, J = 7.7, 1.6 Hz, 1H), 7.81 (dt, J = 7.5, 1.5 Hz, 1H), 7.68 (d, J = 1.5 Hz, 1H), 7.58 - 7.46 (m, 5H), 7.46 - 7.35 (m, 3H), 7.34 - 7.24 (m, 3H), 7.07 (d, J = 1.6 Hz, 1H); Carbon spectrum:13C NMR (125 MHz, Chloroform-d) δ 155.06, 154.77, 152.20, 151.79, 151.73, 149.76, 149.71, 148.33, 148.32, 130.85, 130.79, 130.39, 130.38, 130.22, 129.94, 129.07, 129.04, 129.03, 129.01, 128.98, 127.97, 127.96, 127.93, 127.91, 127.90, 127.86, 127.84, 127.48, 127.47, 127.46, 127.42, 127.40, 127.35, 127.34, 127.29, 127.28, 127.22, 127.20, 127.17, 127.16, 127.14, 127.11, 127.10, 127.09, 127.04, 127.03, 127.02, 126.98, 126.96, 126.13, 126.11, 126.10, 126.07, 126.05, 126.04, 125.63, 125.62, 125.59, 125.57, 125.56, 125.29, 125.28, 125.26, 125.25, 125.23, 125.22, 125.20, 125.18, 125.17, 124.41, 124.36, 124.35, 124.31, 124.30, 124.02, 123.93, 123.91, 123.87, 123.06, 123.01, 122.96, 122.91, 122.79, 122.78, 122.43, 122.38, 122.37, 122.36, 121.94, 121.89, 121.43, 121.41, 121.37, 121.36, 121.35, 121.31, 121.29, 119.91, 119.86, 118.60, 112.05, 112.03, 111.99, 111.97, 108.52, 108.50, 108.49, 105.81, 105.80, 104.05, 103.99.

[0035] Example 7 A compound 19 applied to an OLED device has a structural formula: ; A specific synthesis route of the compound 19 is as follows: ; Preparation of compound 19: In a reaction flask, 42.1 mmol of intermediate 9, 46.3 mmol of 3-chloro-9-phenyl-9H-carbazole (CAS: 193686-61-2), 105.3 mmol of potassium carbonate, 20 g of water and 200 g of toluene were added, then nitrogen was passed, 0.4 mmol of palladium acetate and 0.8 mmol of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were added, and the reaction was kept at 80~85°C for 20 h. Then the aqueous phase was separated, the organic phase was washed with water until it was about neutral, then it was passed through a silica gel column, desolvated, and recrystallized with xylene to obtain the product, with a yield of 78%. Mass spectrum: m / z = 649.20. Hydrogen spectrum: 1H NMR (500 MHz, chloroform-d) δ 8.33 (td, J = 7.7, 1.9 Hz, 2H), 8.13 - 8.06 (m, 1H), 7.97 - 7.84 (m, 4H), 7.81 (tt, J = 3.4, 1.8 Hz, 2H), 7.66 (dd, J = 7.6, 1.5 Hz, 1H), 7.66 - 7.58 (m, 2H), 7.56 - 7.43 (m, 9H), 7.43 - 7.23 (m, 6H); Carbon spectrum: 13C NMR (125 MHz, chloroform-d) δ 155.73, 151.26, 148.44, 147.53, 140.35, 140.16, 139.40, 133.76, 133.55, 133.42, 132.40, 130.68, 130.60, 129.64, 129.28, 128.30, 128.27, 127.96, 127.94, 127.91, 127.83, 127.47, 127.10, 126.44, 126.21, 126.07, 125.91, 125.82, 125.32, 124.88, 124.27, 123.87, 123.46, 123.23, 123.20, 122.97, 122.74, 121.72, 120.85, 120.58, 120.41, 115.15, 111.33, 111.03, 109.14.

[0036] Example 8 A compound 26 applied to an OLED device has a structural formula as follows: ; A specific synthesis route of compound 26 is as follows: ; Preparation of compound 26: A reaction bottle was charged with 42.1 mmol of intermediate 9, 46.3 mmol of 4-bromo-9,9'-spirobi[fluorene] (CAS: 1161009-88-6), 105.3 mmol of potassium carbonate, 16 g of water, and 150 g of tetrahydrofuran, then nitrogen was passed, and 0.4 mmol of palladium tetra-triphenylphosphine was added. The reaction was incubated at 65-70 °C for 10 h, toluene was added for extraction, and then the aqueous phase was separated, the organic phase was washed with water until about neutral, then passed through a silica gel column, desolvated, and recrystallized with toluene to obtain the product, with a yield of 81%. Mass spectrum: m / z = 722.22. Hydrogen spectrum:1H NMR (400 MHz, Chloroform-d) δ 8.36 (dt, J = 7.1, 2.3 Hz, 2H), 7.94 (dt, J = 7.0, 1.9 Hz, 1H), 7.92 - 7.86 (m, 3H), 7.86 - 7.83 (m, 2H), 7.80 (dt, J = 7.2, 1.6 Hz, 1H), 7.68 (dd, J = 7.6, 1.5 Hz, 1H), 7.63 (dd, J = 8.0, 1.5 Hz, 2H), 7.57 - 7.44 (m, 6H), 7.43 - 7.29 (m, 6H), 7.29 - 7.25 (m, 2H), 6.99 (dd, J = 7.4, 1.5 Hz, 1H), 6.93 (dd, J = 7.1, 1.6 Hz, 1H), 6.81 (dd, J = 7.2, 1.6 Hz, 2H).

[0037] Carbon spectrum:13C NMR (125 MHz, Chloroform-d) δ 156.24, 149.89, 148.52, 147.40, 142.29, 141.33, 139.63, 137.11, 136.44, 134.26, 133.76, 132.41, 130.90, 129.55, 129.47, 129.41, 128.72, 128.25, 127.98, 127.87, 127.85, 127.82, 127.33, 127.13, 126.96, 126.88, 126.75, 126.21, 126.13, 126.05, 126.03, 125.74, 124.40, 124.38, 124.33, 124.07, 123.79, 123.49, 123.47, 122.73, 121.96, 120.82, 120.36, 112.81, 110.27, 65.55.

[0038] Example 9 A structural formula of a compound 32 applied to an OLED device: ; A specific synthesis route of the compound 32 is as follows: ; Preparation of compound 32: In a reaction flask, 42.1 mmol of intermediate 9, 46.3 mmol of 2-biphenyl-4-chloro-6-phenyl-1,3,5-triazine (CAS: 1472062-94-4), 105.3 mmol of potassium carbonate, 25 g of water and 200 g of toluene were added, then nitrogen was passed, and 0.4 mmol of palladium tetra-triphenylphosphine was added. The reaction was incubated at 80-85 °C for 18 h, then the aqueous phase was separated, the organic phase was washed with water until it was about neutral, then it was passed through a silica gel column, desolvated, and recrystallized with xylene and ethyl acetate to obtain the product with a yield of 78%. Mass spectrum: m / z = 715.23. Hydrogen spectrum:1H NMR (400 MHz, chloroform-d) δ 8.59 - 8.52 (m, 2H), 8.44 (dd, J = 7.5, 1.5 Hz, 1H), 8.36 (dd, J = 6.7, 2.1 Hz, 1H), 7.94 (dt, J = 6.9, 1.9 Hz, 1H), 7.93 - 7.80 (m, 4H), 7.76 - 7.69 (m, 3H), 7.63 (d, J = 1.5 Hz, 1H), 7.64 - 7.53 (m, 3H), 7.56 - 7.33 (m, 12H), 7.36 - 7.27 (m, 1H); Carbon spectrum:13C NMR (125 MHz, chloroform-d) δ 167.87, 167.41, 166.67, 156.24, 151.80, 148.81, 147.53, 145.47, 139.30, 134.25, 133.78, 131.91, 131.79, 131.70, 131.22, 130.90, 130.09, 129.47, 129.09, 128.92, 128.73, 128.72, 128.68, 128.46, 128.25, 128.10, 127.77, 127.33, 127.00, 126.96, 126.89, 126.21, 126.18, 126.13, 126.05, 126.03, 125.10, 124.40, 124.07, 123.47, 122.60, 120.85, 120.43, 111.93, 109.53.

[0039] Example 10 A compound 39 applied to an OLED device has a structural formula: ; A specific synthesis route of compound 39 is: Preparation of compound 39: In a reaction flask, 42.1 mmol of intermediate 10, 46.3 mmol of 9-chloro-2-phenyl-phenanthro[3,4-d]oxazole (CAS: 2085325-16-0), 105.3 mmol of potassium carbonate, 25 g of water and 200 g of toluene were added, then nitrogen was passed, and 0.4 mmol of palladium tetra-triphenylphosphine was added. The reaction was incubated at 80-85°C for 15 h, then the aqueous phase was separated, the organic phase was washed with water until it was about neutral, then it was passed through a silica gel column, desolvated, and recrystallized with xylene to obtain the product with a yield of 82%. Mass spectrum: m / z = 701.20. Hydrogen spectrum:1H NMR (400 MHz, Chloroform-d) δ 9.61 (d, J = 1.8 Hz, 1H), 8.82 (s, 1H), 8.38 - 8.28 (m, 3H), 8.13 - 8.05 (m, 3H), 7.98 - 7.77 (m, 7H), 7.66 (dd, J = 7.7, 1.5 Hz, 1H), 7.62 (d, J = 1.5 Hz, 1H), 7.56 - 7.35 (m, 9H), 7.30 (td, J = 7.5, 1.6 Hz, 1H). Carbon spectrum:13C NMR (125 MHz, Chloroform-d) δ 161.05, 156.24, 151.26, 150.62, 148.44, 147.53, 137.92, 135.36, 133.92, 133.77, 133.65, 133.22, 133.08, 132.41, 131.28, 130.90, 129.38, 129.24, 128.72, 128.48, 128.30, 127.85, 127.54, 127.33, 126.96, 126.80, 126.79, 126.70, 126.50, 126.33, 126.17, 126.13, 126.08, 125.88, 125.81, 124.40, 124.07, 123.47, 123.13, 122.74, 120.85, 120.46, 111.93, 110.27, 109.75, 104.75.

[0040] Example 11 A compound 43 applied to an OLED device has a structural formula as follows: A specific synthesis route of compound 43 is as follows: ​​; Preparation of compound 43: 35 mmol of intermediate 8, 35 mmol of diphenylamine (CAS: 37055-51-9), 52.5 mmol of sodium tert-butoxide, and 200 g of toluene were added to a reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.35 mmol of tris(dibenzylacetone)dipalladium and 0.7 mmol of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene. The reaction was maintained at 100–105 °C for 15 h, then cooled to below 80 °C, followed by hydrolysis. The aqueous phase was separated, and the organic phase was washed with water until approximately neutral. The solution was then passed through a silica gel column, the solvent was removed, and recrystallized from xylene to obtain the product in 81% yield. Mass spectrometry: m / z = 582.25. 1H NMR: 500 MHz, chloroform-d) δ 8.36 – 8.26 (m, 2H), 8.06 (dd, J = 7.2, 1.5 Hz, 1H), 7.98 – 7.88 (m, 2H), 7.83 (dd, J = 7.8, 1.6 Hz, 1H), 7.75 (dt, J = 7.3, 1.7 Hz, 1H), 7.56 – 7.45 (m, 4H), 7.42 – 7.35 (m, 3H), 7.31 (td, J = 7.4, 1.5 Hz, 1H); 13C NMR: 125 MHz, chloroform-d) δ 156.36, 148.41, 148.27, 145.43, 142.67, 136.57, 133.78, 133.50, 132.59, 130.90, 129.66, 129.64, 129.07, 128.44, 128.25, 127.16, 127.01, 126.93, 126.64, 126.59, 126.42, 125.94, 125.89, 124.52, 124.27, 123.47, 122.18, 122.00, 120.58, 119.10, 112.78, 111.33, 110.53.

[0041] Example 12 The structural formula of compound 49 for use in OLED devices: ; The specific synthetic route for compound 49 is as follows: ; Preparation of compound 49: In a reaction bottle, 35 mmol of intermediate 8, 35 mmol of deuterated carbazole (CAS: 38537-24-5), 52.5 mmol of sodium tert-butoxide, 200 g of toluene were added, then nitrogen was passed, 0.35 mmol of tris(dibenzylideneacetone)dipalladium, 0.7 mmol of 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl were added. Reaction at 100-105°C for 12h, then cooled to below 80°C, then hydrolyzed, the aqueous phase was separated, the organic phase was washed with water until about neutral, then passed through a silica gel column, desolvated, recrystallized with toluene to obtain the product, the yield was 85%. Mass spectrum: m / z = 581.22. Hydrogen spectrum: 1H NMR (400 MHz, Chloroform-d) δ 8.36 - 8.30 (m, 1H), 8.26 (dd, J = 7.5, 1.6 Hz, 1H), 8.00 - 7.88 (m, 3H), 7.84 (dd, J = 7.1, 1.5 Hz, 1H), 7.77 (dt, J = 7.3, 1.8 Hz, 1H), 7.72 (d, J = 1.5 Hz, 1H), 7.56 - 7.45 (m, 4H), 7.39 (td, J = 7.5, 1.5 Hz, 2H), 7.31 (td, J = 7.4, 1.5 Hz, 1H). Carbon spectrum: 13C NMR (125 MHz, Chloroform-d) δ 156.36, 149.24, 148.41, 145.43, 139.36, 134.76, 133.52, 133.49, 132.69, 130.60, 129.78, 129.64, 128.44, 128.25, 127.16, 127.13, 127.01, 126.93, 126.53, 126.42, 125.97, 125.94, 124.52, 124.48, 124.20, 124.07, 123.89, 122.18, 122.12, 121.49, 120.58, 119.05, 112.29, 111.44, 111.33, 110.53.

[0042] The material based on benzofuran structure can have any one of the following structures: .

[0043] The compounds in Tables 1-8 were prepared according to the synthetic methods of the above examples. The same reaction types and reaction conditions were repeated, and the reactants, products and yields involved are summarized in Tables 1-8.

[0044] Table 1 Preparation table of compounds 1-7

[0045] Table 2 Preparation table of compounds 8-13

[0046] Table 3 Preparation table of compounds 14-19

[0047] Table 4 Preparation table of compounds 20-25

[0048] Table 5 Preparation table of compounds 26-31

[0049] Table 6 Preparation table of compounds 32-37

[0050] Table 7 Preparation table of compounds 38-44

[0051] Table 8 Preparation table of compounds 45-50

[0052] Device Example 1: The structure of the OLED device is as shown in Figure 1The preparation of the device of the OLED material is shown: (1) ITO substrate anode: the transparent anode electrode layer 2 (ITO) on the transparent substrate layer 1 is first cleaned with distilled water for 15 minutes, then ultrasonic cleaned with isopropanol and acetone for 15 minutes respectively, and finally treated with a plasma cleaner for 5 minutes, and then the hole injection layer 3 material 2-TNATA is evaporated by vacuum evaporation method with a thickness of 300 Å. Then the hole transport layer 4 is a-NPD with a thickness of 200 Å. The electron blocking layer 5 uses TCTA (4,4',4''-tris (carbazol-9-yl) triphenylamine) 200 Å, and then the light-emitting layer 6 uses DPF-NA (N3,N9-di([1,1'-biphenyl]-4-yl)-N3,N9-di(naphthalen-1-yl) dinaphtho[2,3-b:2',3'-d]furan-3,9-diamine) (reference from DOI: 10.37188 / CJL.20240143) as the host material mixed with the dopant material TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine) 5% with a thickness of 200 Å, followed by the electron transport layer 8 and the electron injection layer 9 TPBi 300 Å, the cathode reflective electrode layer 10 (LiF 2000 Å); the evaporation speed of the above-mentioned organic matter is maintained at 1 Å / sec, the evaporation speed of LiF is 0.2 Å / sec, and the evaporation speed of Al is 3-7 Å / sec, and then the OLED light-emitting device is prepared.

[0053] Device Example 2 The difference between this example and Device Example 1 is that the light-emitting layer host material of the electroluminescent device is the compound 1 of Synthetic Example 1 of the application.

[0054] Device Example 3 The difference between this example and Device Example 1 is that the light-emitting layer host material of the electroluminescent device is the compound 2 of Synthetic Example 2 of the application.

[0055] Device Example 4 The difference between this example and Device Example 1 is that the light-emitting layer host material of the electroluminescent device is the compound 6 of Synthetic Example 3 of the application.

[0056] Device Example 5 The difference between this example and Device Example 1 is that the light-emitting layer host material of the electroluminescent device is the compound 5 of Synthetic Example 4 of the application.

[0057] Device Example 6 The difference between this example and Device Example 1 is that the light-emitting layer host material of the electroluminescent device is the compound 8 of Synthetic Example 5 of the application.

[0058] Device Example 7 This example differs from Device Example 1 in that the light-emitting layer host material of the electroluminescent device is compound 10 of Synthesis Example 6 of the present invention.

[0059] Device Example 8: This example differs from Device Example 1 in that the light-emitting layer host material of the electroluminescent device is compound 19 of Synthesis Example 7 of the present invention.

[0060] Device Example 9: This example differs from Device Example 1 in that the light-emitting layer host material of the electroluminescent device is compound 26 of Synthesis Example 8 of the present invention.

[0061] Device Example 10: This example differs from Device Example 1 in that the light-emitting layer host material of the electroluminescent device is compound 32 of Synthesis Example 9 of the present invention.

[0062] Device Example 11: This example differs from Device Example 1 in that the light-emitting layer host material of the electroluminescent device is compound 39 of Synthesis Example 10 of the present invention.

[0063] Device Example 12: This example differs from Device Example 1 in that the light-emitting layer host material of the electroluminescent device is compound 43 of Synthesis Example 11 of the present invention.

[0064] Device Example 13: This example differs from Device Example 1 in that the light-emitting layer host material of the electroluminescent device is compound 49 of Synthesis Example 12 of the present invention.

[0065] Device Comparative Example 1: This comparative example differs from Device Example 1 in that the light-emitting layer host material of the electroluminescent device is compound x as follows: .

[0066] Device Comparative Example 2: This comparative example differs from Device Example 1 in that the light-emitting layer host material of the electroluminescent device is compound y as follows: .

[0067] Device Examples were tested for device performance, see the OLED device performance test data in Table 9 below.

[0068] Table 9 OLED device performance test data

[0069] Note: The test is performed by using a KEITHLEY 2400 source measurement unit and a CS-2000 spectroradiometer.

[0070] The device performance test takes device example 1 as a reference, and the performance indicators of device example 1 are set to 1.0. As can be seen from the test results in the above table, the device life of the new material applied in the application is longer, and the luminous efficiency is also improved. The OLED device prepared by the new material involving naphthofuran structure in the application has excellent performance in all aspects, and has great potential in application.

[0071] From the data comparison of device comparative example 1, device comparative example 2 and device example 2-device example 13, it can be seen that the material containing naphthofuran structure in the application has better application performance in OLED device, which is due to the characteristics of naphthofuran structure material as a weak electron acceptor and the ability of energy level adjustment, so that they can better match the energy level of hole transport layer and light emitting layer, optimize the hole transport layer and block the excitation diffusion, thereby improving the efficiency and life of OLED device.

[0072] The technical features of the above-described embodiments can be combined arbitrarily, and in order to make the description simple, all possible combinations of the technical features in the above-described embodiments are not described, however, as long as the combination of the technical features does not exist contradictory, it should be considered as the scope of the present application.

[0073] The above-described embodiments only express several embodiments of the present application, and the description is more specific and detailed, but it should not be understood as a limitation on the scope of the patent. It should be pointed out that for ordinary skilled in the art, without departing from the concept of the present application, a number of variations and improvements can be made, which are within the scope of the present application. Therefore, the protection scope of the patent of the present application should be subject to the appended claims.

Claims

1. A material comprising a naphthofuran structure, characterized in that, The structure of the material containing naphthofuran structure is shown in general formula I: Formula I; Ar is any one of C6-C30 aryl, heterocyclic aryl, deuterium-substituted aryl or deuterium-substituted heterocyclic aryl; The heteroatom in the heterocyclic aryl is selected from N, S and O.

2. The material containing a naphthofuran structure according to claim 1, characterized by Ar is selected from any one of the following structures: 。 3. The material containing a naphthofuran structure according to claim 1, characterized by, The material containing naphthofuran structure is selected from any one of the following structural formulae: 。 4. A method for preparing a material containing a naphthofuran structure according to any one of claims 1 to 3, characterized in that, The preparation method is: In inert gas protection, the intermediate and the raw material compound are heated to react under the action of a base and a catalyst, after the reaction is completed, the material containing naphthofuran structure is obtained through post-treatment; The intermediate has the structural formula: X is selected from the group consisting of halogen and ; When X is selected from halogen, the structure of the raw material compound is Ar-Y, Y is any one of a boronic acid group, a boronic ester group and an imine structure group; When X is Ar-Cl, Ar-Br or Ar-I.

5. The method for preparing a material containing a naphthofuran structure according to claim 4, characterized in that, The base is at least one of potassium carbonate, sodium carbonate and sodium tert-butoxide.

6. The method for preparing a material containing a naphthofuran structure according to claim 4, characterized in that, The catalyst is at least one of tetrakis triphenylphosphine palladium, palladium acetate and tris (dibenzalacetone) dipalladium.

7. Use of a material comprising a naphthofuran structure according to any one of claims 1 to 3, characterized in that, The material containing naphthofuran structure is applied to an OLED device.

8. Use of a material containing a naphthofuran structure according to claim 7, characterized in that, The material containing naphthofuran structure is applied to an organic functional layer of an OLED device.

9. The use of a material containing a naphthofuran structure according to claim 7, characterized in that, The material containing naphthofuran structure is applied to a light-emitting layer material.

10. The use of a material containing a naphthofuran structure according to claim 7, characterized in that, The OLED device comprises a transparent substrate layer, an anode electrode layer, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode reflection electrode layer.

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