A material containing a naphthofuran structure, and a preparation method and application thereof

Abstract

This invention relates to a material containing a naphthofuran structure, its preparation method, and its application, belonging to the field of OLED material technology. The structure of the naphthofuran-containing material is as follows: Ar is one of C6-C30 aryl, heterocyclic aryl, deuterated substituted aryl, or deuterated heterocyclic aryl. The naphthofuran-containing material is used as a luminescent material in OLED devices. Due to its special structure, the naphthofuran-containing material possesses better compound energy levels and packing structure, better thermal stability, and higher electron mobility, exhibiting excellent performance in OLED devices, including extended lifetime, improved luminous efficiency, and reduced driving pressure.

Description

Technical Field

[0001] This invention relates to a material containing a naphthalene-furan structure, its preparation method, and its application, belonging to the field of OLED material technology. Background Technology

[0002] Organic light-emitting diodes (OLEDs) have advantages such as self-illumination, wide viewing angle, short response time, high luminous efficiency, thin panel, low power consumption, and wide operating temperature range. They have gradually replaced LCD displays and become the mainstream display technology. The core material layers in an OLED device are the light-emitting layer, electron transport layer, and hole transport layer. Among these, the most crucial part is the light-emitting layer, and the organic electroluminescent material used in it determines the luminous efficiency, film-forming properties, and carrier transport properties of the OLED device.

[0003] In OLED devices, the emissive layer is excited by recombination of injected charge carriers, resulting in high-efficiency light emission. Therefore, the emissive layer must use compounds with very strong fluorescence or phosphorescence. Although other layers can use inorganic materials, the emissive layer must be an organic material.

[0004] While OLED displays offer numerous advantages, there are still many areas for improvement. For example, poor luminous efficiency, instability, and short lifespan are among the problems. Therefore, developing new materials that can enhance the performance and lifespan of OLED devices is of great value. Summary of the Invention

[0005] This invention addresses the shortcomings of existing technologies by providing a material containing a naphthofuran structure, its preparation method, and its applications. The special structural design of the naphthofuran in the material results in good thermal stability and high electron affinity. The material containing the naphthofuran structure exhibits excellent performance in optoelectronic materials.

[0006] The technical solution of the present invention to solve the above-mentioned technical problems is as follows: a material containing a naphthofuran structure, wherein the structure of the material containing the naphthofuran structure is shown in general formula I:

[0007] General Formula I;

[0008] Ar is any one of C6-C30 aryl, heterocyclic aryl, deuterated substituted aryl, or deuterated substituted heterocyclic aryl;

[0009] The heteroatom in the heterocyclic aryl group is selected from N, S, and O.

[0010] Furthermore, Ar is selected from any of the following structures:

[0011] .

[0012] Furthermore, the material containing the naphthofuran structure is selected from any of the following structural formulas:

[0013] .

[0014] This invention also discloses a method for preparing a material containing a naphthofuran structure, the preparation method being as follows:

[0015] In an inert gas atmosphere, the intermediate and the raw material compound react under alkaline conditions and with the aid of a catalyst. After the reaction is complete, the material containing the naphthanofuran structure is obtained through post-processing.

[0016] The structural formula of the intermediate is: X is selected from halogens and ;

[0017] When X is selected from halogens, the structural formula of the raw material compound is: Ar-Y, where Y is any one of boric acid group, borate ester group, and imine structural group;

[0018] When X is When the raw material compound has the structural formula of Ar-Cl, Ar-Br or Ar-I.

[0019] Furthermore, the alkali is selected from at least one of potassium carbonate, sodium carbonate, and sodium tert-butoxide.

[0020] Furthermore, the catalyst is selected from at least one of tetrakis(triphenylphosphine)palladium, palladium acetate, and tris(dibenzylideneacetone)palladium.

[0021] The present invention also discloses the application of a material containing a naphthofuran structure, wherein the material containing the naphthofuran structure is used in OLED devices.

[0022] Furthermore, the material containing the naphthalene-furan structure is applied to the organic functional layer of OLED devices.

[0023] Furthermore, the material containing the naphthalene-furan structure is used in the luminescent layer material.

[0024] Furthermore, the OLED device includes 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 reflective electrode layer.

[0025] The beneficial effects of this invention are:

[0026] The naphthofuran-containing material described in this invention possesses excellent photophysical properties. As a weak dot acceptor, it can be combined with a strong donor to construct a wide-bandgap blue light-emitting material, forming a highly efficient narrow-spectrum blue light-emitting device. Its properties can be precisely "tailored"; by adjusting the substituents, the molecule can possess characteristics such as hybridized local charge transfer, thereby utilizing triplet excitons to break through the exciton utilization limit of traditional fluorescent materials. It exhibits good thermal stability; its rigid fused-ring structure helps to increase the thermal decomposition temperature of the material, contributing to low driving voltage and long lifespan. Its good low-temperature miscibility provides a relatively wide operating temperature range, further improving its stability as a light-emitting layer material. Naphthofuran-based materials, with their unique rigid fused-ring framework, have successfully occupied a key position in the development of high-efficiency, high-color-purity blue light-emitting materials, while also demonstrating comprehensive advantages in device stability and molecular design flexibility. They are a very promising core structural unit in the current field of organic optoelectronic materials. OLED devices using this structure as the light-emitting layer show significantly improved luminous efficiency and lifespan, good stability, and broad application prospects. Attached Figure Description

[0027] Figure 1 This is a schematic diagram of the multilayer structure of the OLED light-emitting device described in the embodiment;

[0028] In the figure, 1 is the transparent substrate layer; 2 is the anode electrode layer; 3 is the hole injection layer; 4 is the hole transport layer; 5 is the electron blocking layer; 6 is the light-emitting layer; 7 is the hole blocking layer; 8 is the electron transport layer; 9 is the electron injection layer; and 10 is the cathode reflective electrode layer. Detailed Implementation

[0029] To make the above-mentioned objects, features, and advantages of the present invention more apparent and understandable, specific embodiments of the present invention are described in detail below. Many specific details are set forth in the following description to provide a thorough understanding of the present invention. However, the present invention can be practiced in many other ways different from those described herein, and those skilled in the art can make similar modifications without departing from the spirit of the present invention. Therefore, the present invention is not limited to the specific embodiments disclosed below.

[0030] 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 this invention pertains. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.

[0031] Synthesis method of general intermediates for parent structure:

[0032] ;

[0033] (1) Synthesis of intermediate 1: 50 mmol of raw material 1 (CAS: 1195572-81-6) and 100 g of dichloroethane (as solvent) were added to a reaction flask. Nitrogen gas was purged and the temperature was controlled at -10 to 0℃. 50 mmol of NBS (CAS: 128-08-5) was added and kept at this temperature for 5 h. After the reaction was complete, the reaction system was hydrolyzed, washed with water, and the solvent was removed. The product was obtained by recrystallization using toluene, with a yield of 81%. Mass spectrometry: m / z = 275.98; 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).

[0034] (2) Synthesis of intermediate 2: 60 mmol of intermediate 1 and 80 g of tetrahydrofuran (as solvent) were added to the reaction flask and nitrogen gas was introduced. 60 mmol of n-butyllithium (CAS: 109-72-8) was added dropwise at -80 to -90 °C. After addition, the temperature was maintained for 2 h. Then, 60 mmol of triisopropyl borate (CAS: 5419-55-6) was added dropwise and the temperature was maintained for 2 h. The reaction solution was added to water for hydrolysis, washed with water, extracted with ethyl acetate, and the solvent was removed to obtain the product with a yield of 93%. Mass spectrometry: m / z = 242.08; Proton NMR: 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).

[0035] (3) Synthesis of intermediate 3: 38.5 mmol of raw material 2 (CAS: 6630-33-7), 77 mmol of potassium carbonate, 25 g of water and 100 g of tetrahydrofuran were added to the reaction flask. Nitrogen gas was introduced and 0.385 mmol of palladium acetate and 0.77 mmol of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene were added. The temperature was then raised to 55-60 °C and the solution was added dropwise (38.5 mmol of intermediate 2 was dissolved in 50 g of tetrahydrofuran). After the addition was complete, the temperature was maintained for 8 h. After hydrolysis, toluene was added for extraction, water was washed, silica gel column chromatography was performed, solvent was removed, and intermediate 3 was obtained by recrystallization with toluene, with a yield of 72%. Mass spectrometry: m / z = 302.09; Proton NMR: 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).

[0036] (4) Synthesis of intermediate 4: 47.2 mmol of intermediate 3, 81.9 mmol of (methoxymethyl)triphenylphosphine chloride (CAS:4009-98-7), and 100 g of toluene were added to the reaction flask. Nitrogen gas was introduced, and the temperature was lowered to 0-5 °C. The solution (70.8 mmol of sodium tert-butoxide dissolved in 100 g of tetrahydrofuran) was added dropwise. The temperature was maintained for 4 h. The reaction solution was added to water for hydrolysis, washed with water, passed through a silica gel column, and the solvent was removed to obtain intermediate 4 with a yield of 91%. Mass spectrometry: m / z = 330.13; Proton NMR: 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).

[0037] (5) Synthesis of intermediate 5: 220 mmol of methanesulfonic acid (CAS: 75-75-2) and 80 g of dichloroethane were added to the reaction flask, and then nitrogen gas was introduced. The temperature was raised to 80-90℃ and the solution (44 mmol of intermediate 4 dissolved in 80 g of dichloroethane) was added dropwise. The temperature was maintained for 2 h. Then, after hydrolysis, washing with water, solvent removal, and recrystallization with toluene, intermediate 5 was obtained with a yield of 72%. Mass spectrometry: m / z = 298.10; Proton NMR: 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).

[0038] (6) Synthesis of intermediate 6: 40.0 mmol of intermediate 5 and 100 g of dichloroethane were added to a reaction flask. 60.0 mmol of boron tribromide (CAS: 10294-33-4) was added to the reaction system at a controlled temperature of 0-10 °C. The mixture was then kept at this temperature for 5 h. After hydrolysis, washing with water, passing through a silica gel column, solvent removal, and recrystallization using dichloroethane, intermediate 6 was obtained. The yield was 79%. Mass spectrometry: m / z = 257.0; Proton NMR: 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).

[0039] (7) Synthesis of intermediate 7: 70.0 mmol of intermediate 6, 70.0 mmol of starting material 3 (CAS: 2641900-32-3), 210.0 mmol of potassium carbonate, and 200 g of DMF were added to a reaction flask. The mixture was heated to 130-135 °C and held at that temperature for 10 h. After hydrolysis, the mixture was filtered, washed with hot water, passed through a silica gel column, desolventized, and recrystallized from toluene to obtain intermediate 7. Yield: 75%. Mass spectrometry: m / z = 524.00; 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).

[0040] (8) Synthesis of intermediate 8: 38.6 mmol of intermediate 7, 96.5 mmol of cesium carbonate and 100 g of N-methylpyridinone were added to the reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.4 mmol of palladium acetate and 0.8 mmol of tri-tert-butylphosphine tetrafluoroborate. The reaction was heated to 155-160 °C and kept at that temperature for 12 h. After hydrolysis, filtration, dissolution in toluene, and silica gel column chromatography, solvent removal and recrystallization using o-dichlorobenzene were performed to obtain the refined intermediate 8 with a final yield of 73%.Mass spectrometry: m / z = 442.08; 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); 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.

[0041] (09) Synthesis of intermediate 9: 43.8 mmol of intermediate 9, 65.7 mmol of pinacol diborate, 52.6 mmol of potassium acetate and 100 g of xylene were added to the reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.5 mmol of tris(dibenzylacetone)dipalladium and 1.0 mmol of tricyclohexylphosphine. The mixture was heated to 130-135 °C and kept at that temperature for 12 h. After hydrolysis, washing with water, passing through a silica gel column, solvent removal, and recrystallization with xylene, the refined intermediate 9 was obtained with a final yield of 85%. Mass spectrometry: m / z = 534.20; Proton NMR: 1H NMR (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).

[0042] Carbon NMR 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.

[0043] The parent compound is synthesized by coupling intermediate 8 with an Ar-Y compound (where Y is a borate group, borate ester group, imine group, or other structural group that can react with halogen groups), or by coupling intermediate 9 with an Ar-Y compound (where Y is a common halogen group or other structural group that can react with borate esters). Examples of the synthesis of several compounds are given below:

[0044] Example 1

[0045] The structural formula of compound 1 for use in OLED devices:

[0046] ;

[0047] The specific synthetic route for compound 1 is as follows:

[0048] ;

[0049] Preparation of Compound 1: 35 mmol of intermediate 8, 87.5 mmol of potassium carbonate, 30 g of water, and 120 g of toluene were added to a reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.35 mmol of tetra(triphenylphosphine)palladium. The temperature was raised to 60–65 °C, and a phenylboronic acid solution (a solution prepared from 36.8 mmol of phenylboronic acid (CAS: 98-80-6) and 20 g of tetrahydrofuran) was added dropwise. The mixture was kept at this temperature for 5 h after the addition was complete. The aqueous phase was then separated by standing, 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 toluene to obtain the product, with a yield of 79%. Mass spectrometry: m / z = 484.15.1H 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); 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.

[0050] Example 2

[0051] The structural formula of compound 2 for use in OLED devices:

[0052] ;

[0053] The specific synthetic route for compound 2 is as follows:

[0054] ;

[0055] Preparation of Compound 2: 35 mmol of intermediate 8, 87.5 mmol of potassium carbonate, 30 g of water, and 120 g of toluene were added to a reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.35 mmol of palladium acetate and 0.7 mmol of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene. The temperature was then raised to 70–75 °C, and a solution of 2-biphenylboronic acid (prepared from 36.8 mmol of 2-biphenylboronic acid (CAS: 4688-76-0) and 20 g of ethanol) was added dropwise. The mixture was kept at this temperature for 5 h after the addition was complete. The aqueous phase was then separated by standing, 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 toluene to obtain the product in 78% yield. Mass spectrometry: m / z = 560.18. 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); 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.

[0056] Example 3

[0057] The structural formula of compound 6 for use in OLED devices:

[0058] ;

[0059] The specific synthetic route for compound 6 is as follows:

[0060] ;

[0061] Preparation of Compound 6: 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 to a reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.4 mmol of palladium acetate and 0.8 mmol of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene. The reaction was maintained at 75–80 °C for 12 h. The aqueous phase was then 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 recrystallization was performed using toluene to obtain the product, with a yield of 81%. Mass spectrometry: m / z = 636.21. 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); 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.

[0062] Example 4

[0063] The structural formula of compound 5 for use in OLED devices:

[0064] ;

[0065] The specific synthetic route for compound 5 is as follows:

[0066] ;

[0067] Preparation of compound 5: 35 mmol of intermediate 8, 87.5 mmol of potassium carbonate, 30 g of water, and 120 g of tetrahydrofuran were added to a reaction flask. Nitrogen gas was then purged, followed by the addition of 0.35 mmol of tetratriphenylphosphine palladium. The temperature was then raised to 60–65 °C, and a solution of 1-naphthoboric acid (prepared from 36.8 mmol of 1-naphthoboric acid (CAS: 13922-41-3) and 20 g of tetrahydrofuran) was added dropwise. The mixture was kept at this temperature for 5 h after the addition was complete. Toluene was then added for extraction, and the organic phase was washed with water until approximately neutral. The mixture was passed through a silica gel column, the solvent was removed, and the product was recrystallized using dichloroethane in 76% yield. Mass spectrometry: m / z = 534.16. 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); 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.

[0068] Example 5

[0069] The structural formula of compound 8 for use in OLED devices:

[0070] ;

[0071] The specific synthetic route for compound 8 is as follows:

[0072] ;

[0073] Preparation of compound 8: 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 to a reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.4 mmol of tetra(triphenylphosphine)palladium. The reaction was maintained at 75–80 °C for 12 h. The aqueous phase was then separated, and the organic phase was washed with water until approximately neutral. The mixture was then passed through a silica gel column, the solvent was removed, and recrystallized using DMF to obtain the product, with a yield of 69%. Mass spectrometry: m / z = 584.18. 1H NMR spectrum: 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). ¹H); Carbon NMR: 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.

[0074] Example 6

[0075] A structural formula of compound 10 for use in OLED devices:

[0076] ;

[0077] The specific synthetic route for compound 10 is as follows:

[0078] ;

[0079] Preparation of Compound 10: 35 mmol of intermediate 8, 87.5 mmol of sodium carbonate, 30 g of water, and 120 g of dioxane were added to a reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.35 mmol of tetra-triphenylphosphine palladium. The temperature was raised to 80–85 °C, and a solution of 2-benzofuranboronic acid (prepared from 36.8 mmol of 2-benzofuranboronic acid (CAS: 98437-24-2) and 20 g of dioxane) was added dropwise. The mixture was kept at this temperature for 5 h after the addition was complete. Toluene was then added for extraction. The organic phase was washed with water until approximately neutral. The solution was passed through a silica gel column, the solvent was removed, and recrystallization was performed using toluene to obtain the product, with a yield of 71%. Mass spectrometry: m / z = 524.14. 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); 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...

[0080] Example 7

[0081] The structural formula of compound 19 for use in OLED devices:

[0082] ;

[0083] The specific synthetic route for compound 19 is as follows:

[0084] ;

[0085] Preparation of compound 19: 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 to a reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.4 mmol of palladium acetate and 0.8 mmol of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene. The reaction was maintained at 80–85 °C for 20 h. The aqueous phase was then 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 recrystallization was performed using xylene to obtain the product, with a yield of 78%. Mass spectrometry: m / z = 649.20. 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); 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.

[0086] Example 8

[0087] The structural formula of compound 26 for use in OLED devices:

[0088] ;

[0089] The specific synthetic route for compound 26 is as follows:

[0090] ;

[0091] Preparation of compound 26: 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 were added to a reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.4 mmol of tetra-triphenylphosphine palladium. The reaction was maintained at 65–70 °C for 10 h. Toluene was added for extraction, and the aqueous phase was separated. The organic phase was washed with water until approximately neutral, then passed through a silica gel column, and the solvent was removed. Recrystallization was performed using toluene to obtain the product, with a yield of 81%. Mass spectrometry: m / z = 722.22. 1H NMR spectrum: 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).

[0092] Carbon NMR 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.

[0093] Example 9

[0094] The structural formula of compound 32 for use in OLED devices:

[0095] ;

[0096] The specific synthetic route for compound 32 is as follows:

[0097] ;

[0098] Preparation of compound 32: 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 to a reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.4 mmol of tetra-triphenylphosphine palladium. The reaction was maintained at 80–85 °C for 18 h. The aqueous phase was then separated, and the organic phase was washed with water until approximately neutral. The solution was then passed through a silica gel column, and the solvent was removed. Recrystallization was performed using xylene and ethyl acetate to obtain the product in 78% yield. Mass spectrometry: m / z = 715.23. 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); 13C NMR: 125 MHz, Chloroform-d) δ167.87, 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.

[0099] Example 10

[0100] The structural formula of compound 39 for use in OLED devices:

[0101] ;

[0102] The specific synthetic route for compound 39 is as follows:

[0103] ;

[0104] Preparation of compound 39: 42.1 mmol of intermediate 10, 46.3 mmol of 9-chloro-2-phenyl-phenanthroline[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 to a reaction flask. Nitrogen gas was then introduced, followed by the addition of 0.4 mmol of tetra-triphenylphosphine palladium. The reaction was maintained at 80–85 °C for 15 h. The aqueous phase was then 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 recrystallization was performed using xylene to obtain the product in 82% yield. Mass spectrometry: m / z = 701.20. 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). 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.

[0105] Example 11

[0106] The structural formula of compound 43 for use in OLED devices:

[0107] ;

[0108] The specific synthetic route for compound 43 is as follows:

[0109] ;

[0110] 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.

[0111] Example 12

[0112] The structural formula of compound 49 for use in OLED devices:

[0113] ;

[0114] The specific synthetic route for compound 49 is as follows:

[0115] ;

[0116] Preparation of compound 49: 35 mmol of intermediate 8, 35 mmol of deuterated carbazole (CAS: 38537-24-5), 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)palladium and 0.7 mmol of 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl. The reaction was maintained at 100–105 °C for 12 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 toluene to obtain the product in 85% yield. Mass spectrometry: m / z = 581.22. 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). 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.

[0117] Materials based on the benzofuran structure can have any of the following structural formulas:

[0118] .

[0119] The compounds listed in Tables 1-8 were prepared using the synthesis methods described in the above embodiments. The same reaction types and reaction conditions were repeatable. A summary of the reactants, products, and yields involved is shown in Tables 1-8.

[0120] Table 1. Preparation of Compounds 1 through 7

[0121]

[0122] Table 2. Preparation of compounds 8-13

[0123]

[0124] Table 3. Preparation of compounds 14-19

[0125]

[0126] Table 4. Preparation of Compounds 20-25

[0127]

[0128] Table 5. Preparation of compounds 26-31

[0129]

[0130] Table 6. Preparation of compounds 32-37

[0131]

[0132] Table 7. Preparation of compounds 38-44

[0133]

[0134] Table 8. Preparation of compounds 45-50

[0135]

[0136] Device Example 1:

[0137] The structure of OLED devices is as follows Figure 1As shown, the fabrication of OLED material devices is as follows: (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 ultrasonically cleaned with isopropanol and acetone for 15 minutes respectively, and finally treated with a plasma cleaner for 5 minutes. Then, the hole injection layer 3 material 2-TNATA with a thickness of 300 Å is deposited by vacuum evaporation. Then, the hole transport layer 4 is formed by a-NPD with a thickness of 200 Å. Electron blocking layer 5 uses TCTA (4,4',4''-tris(carbazole-9-yl)triphenylamine) at a thickness of 200 Å. Then, luminescent layer 6 uses DPF-NA (N3,N9-bis([1,1'-biphenyl]-4-yl)-N3,N9-bis(naphthyl-1-yl)dinaphtho[2,3-b:2',3'-d]furan-3,9-diamine) as the host material, mixed with 5% dopant TPDA (N1,N1,N6,N6-tetraphenylpyrene-1,6-diamine) at a thickness of 200 Å by vapor deposition. This is followed by electron transport layer 8 and electron injection layer 9 (TPBi 300 Å), and cathode reflective electrode layer 10 (LiF 2000 Å). The deposition rate for organic materials in the above process is maintained at 1 Å / sec, and for LiF at 0.2 Å / sec. Å / sec, A1 is 3 to 7 Å / sec, and then OLED light-emitting devices are fabricated.

[0138] Device Example 2:

[0139] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 1 of the synthesis embodiment 1 of this invention.

[0140] Device Example 3:

[0141] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 2 from synthesis embodiment 2 of the present invention.

[0142] Device Example 4:

[0143] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 6 of the synthesis embodiment 3 of this invention.

[0144] Device Example 5:

[0145] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 5 from synthesis embodiment 4 of this invention.

[0146] Device Example 6:

[0147] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 8 of the synthesis embodiment 5 of this invention.

[0148] Device Example 7:

[0149] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 10 of the synthesis embodiment 6 of this invention.

[0150] Device Example 8:

[0151] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 19 of the synthesis embodiment 7 of this invention.

[0152] Device Example 9:

[0153] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 26 of the synthesis embodiment 8 of this invention.

[0154] Device Example 10:

[0155] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 32 of the synthesis embodiment 9 of this invention.

[0156] Device Example 11:

[0157] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 39 of synthesis embodiment 10 of the present invention.

[0158] Device Example 12:

[0159] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 43 of the synthesis embodiment 11 of this invention.

[0160] Device Example 13:

[0161] The difference between this embodiment and device embodiment 1 is that the main material of the light-emitting layer of the electroluminescent device is compound 49 of the synthesis embodiment 12 of this invention.

[0162] Device Comparison Example 1:

[0163] The difference between this comparative example and device example 1 is that the main material of the light-emitting layer of the electroluminescent device is the following compound x:

[0164] .

[0165] Device Comparison Example 2:

[0166] The difference between this comparative example and device example 1 is that the main material of the light-emitting layer of the electroluminescent device is the following compound y:

[0167] .

[0168] The device performance of the test device embodiment is shown in Table 9 below, which contains the OLED device performance test data.

[0169] Table 9 OLED Device Performance Test Data

[0170]

[0171] Note: The test was conducted using a KEITHLEY 2400 source measurement unit and a CS-2000 spectroradiometer.

[0172] Device performance testing was conducted with reference to Device Example 1, where all performance indicators were set to 1.0. The test results in the table above show that the novel material involved in this invention results in devices with longer lifespans and improved luminous efficiency. This invention relates to OLED devices prepared from novel materials with a naphthofuran structure, exhibiting excellent performance in all aspects and possessing great potential for application.

[0173] The data comparison of Device Comparative Example 1, Device Comparative Example 2 and Device Examples 2-13 shows that the material containing the naphthanofuran structure described in this invention has better application performance in OLED devices. This is due to the characteristics of the naphthanofuran structure material as a weak electron acceptor and its energy level tuning ability, which allows it to better match the energy levels of the hole transport layer and the light-emitting layer, optimize the hole transport layer and block exciton diffusion, thereby improving the efficiency and lifespan of OLED devices.

[0174] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0175] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these all fall within the protection scope of the present invention. Therefore, the protection scope of this invention patent should be determined by the appended claims.

Claims

1. A material comprising a naphthofuran structure, characterized in that, The material containing naphthofuran structure has a structure as shown in general formula I: Formula I; Ar is selected from any one of the following structures: 。 2. A material comprising a naphthofuran structure, characterized in that, The material containing naphthofuran structure is selected from any one of the following structures: 。 3. A method for preparing a material containing a naphthofuran structure according to any one of claims 1-2, characterized by, 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.

4. The method for preparing a material containing a naphthofuran structure according to claim 3, characterized in that, The base is selected from at least one of potassium carbonate, sodium carbonate and sodium tert-butoxide.

5. The method of claim 3, wherein the material having a naphthofuran structure is prepared by the reaction of a compound represented by formula (2) with a compound represented by formula (3) in the presence of a base. The catalyst is selected from at least one of tetrakis triphenylphosphine palladium, palladium acetate and tris(dibenzylideneacetone)dipalladium.

6. Use of a material comprising a naphthofuran structure according to any one of claims 1 to 2, characterized in that, The material containing naphthofuran structure is applied to an OLED device.

7. Use of a material containing a naphthofuran structure according to claim 6, characterized in that, The material containing naphthofuran structure is applied to an organic functional layer of an OLED device.

8. The use of a material containing a naphthofuran structure according to claim 6, characterized in that, The material containing naphthofuran structure is applied to a light-emitting layer material.

9. The use of a material containing a naphthofuran structure according to claim 6, 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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