Organic compound containing phenanthrene benzofuran, organic electroluminescent device containing organic compound, display device and lighting device

Abstract

The invention discloses an organic compound containing phenanthrene benzofuran, and an organic electroluminescent device, a display device and a lighting device comprising the same. The structural general formula of the organic compound is as shown in formula I; wherein L1 and L2 each independently represent any one of a single bond and an arylene group with a carbon atom number of C6-C12; ar1 represents a substituted or unsubstituted aryl group having a carbon atom number of C6-C60; ar2 represents a group represented by formula II, and ring A represents phenanthryl. By introducing a phenanthrene benzofuran substituent substituted by a specific site into the structure, the molecular high-energy linear state energy level can be adjusted while the molecular polarity is adjusted, and the carrier injection and energy level difference are improved, so that the internal quantum efficiency of the material is improved. And the phenanthrene benzofuran substituent at the specific site and anthryl present a rigid structure, which is beneficial for ordered arrangement of molecules according to a certain orientation, so that the light extraction efficiency is improved, and the device performance can be significantly improved. I; iI

Description

Technical Field

[0001] This invention belongs to the field of OLED technology, specifically including an organic compound containing phenanthrene-benzofuran and an organic electroluminescent device, display device and lighting device containing the same. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a highly popular display technology. Due to innovations in OLED structure and the use of efficient transport, host, luminescent, and injection materials, OLED-based display and lighting applications have become one of the most competitive technologies available. OLED technology has attracted worldwide attention due to its high efficiency, lightweight design, high color quality, near 180° viewing angle, ultra-fast response time, and potential for achieving pure black displays.

[0003] Currently, almost all blue organic light-emitting devices use host-guest doped light-emitting systems for their luminescent layers. This means that electroluminescence is achieved by doping the host material with a guest dopant. Commonly used blue fluorescent devices primarily employ anthracene-based host materials. However, the anthracene-based host materials currently used still have some problems that need to be solved in terms of lifetime, color purity, and device efficiency.

[0004] Therefore, it is very important to develop a blue light host material with superior performance. Summary of the Invention

[0005] In view of the above-mentioned problems existing in the prior art, the present invention provides an organic compound containing phenanthrene benzofuran and an organic electroluminescent device, display device and lighting device containing the same.

[0006] To achieve the above objectives, the technical solution adopted by the present invention includes: A first aspect of the present invention provides an organic compound containing phenanthrenebenzofuran, the general structural formula of which is shown in Formula I: I; II; Wherein, L1 and L2 each independently represent any one of the aryl groups with a single bond and a carbon number of C6 to C12; Ar1 represents a substituted or unsubstituted aryl group with 6 to 60 carbon atoms; Ar2 represents the group shown in formula II, and ring A represents a phenanthrene group; In Formula I, any hydrogen atom can be substituted with deuterium.

[0007] Furthermore, when Ar1 contains substituents, the substituents are selected from one or more of deuterium, phenyl, biphenyl, naphthyl, and phenanthrene.

[0008] Furthermore, Ar2 represents one of the following structures: , , , , , .

[0009] Furthermore, L1 and L2 each independently represent any one of a single bond, a phenylene group, or a naphthylene group; for example, L1 and L2 can each independently represent a single bond, a phenylene group, or a naphthylene group. , , , One of them.

[0010] Furthermore, L1 represents a single bond, , , , One of them, where L2 represents a single bond.

[0011] Furthermore, Ar1 represents a substituted or unsubstituted aryl group with a carbon number of C6 to C30.

[0012] Furthermore, Ar1 represents a substituted or unsubstituted aryl group with a carbon number of C6 to C20.

[0013] Furthermore, Ar1 represents any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0014] Furthermore, the organic compound is selected from the structures shown below:

[0015]

[0016]

[0017]

[0018]

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031] ; Where Dn represents n hydrogen atoms being replaced by deuterium, and n is a positive integer, ranging from 1 to the maximum deuterium algebra.

[0032] by To explain, it can represent The case where any hydrogen is replaced by deuterium, for example , , , wait.

[0033] A second aspect of the present invention provides the use of the organic compound described above in the preparation of organic electroluminescent devices.

[0034] A third aspect of the present invention provides an organic electroluminescent device comprising an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode sequentially disposed on a substrate; wherein the light-emitting layer comprises a host material and a guest material, and the host material comprises one or more organic compounds as described above.

[0035] A fourth aspect of the present invention provides a display device comprising the organic electroluminescent device as described above.

[0036] A fifth aspect of the present invention provides a lighting device comprising the organic electroluminescent device as described above.

[0037] Beneficial effects of this invention: This invention provides a blue light-emitting host material with a phenanthrene-benzofuran structure. By introducing phenanthrene-benzofuran substituents at specific sites, the high-energy line state energy level of the molecule can be adjusted while regulating molecular polarity, improving carrier injection and energy level difference, thereby enhancing the internal quantum efficiency of the material. Furthermore, these phenanthrene-benzofuran substituents at specific sites, along with the anthracene group, exhibit a rigid structure, which facilitates the orderly arrangement of molecules in a certain orientation, further improving light extraction efficiency and thus significantly enhancing device performance. Attached Figure Description

[0038] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device of the present invention. In the diagram, 1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-light-emitting auxiliary layer, 6-light-emitting layer, 7-hole blocking layer, 8-electron transport layer, 9-electron injection layer, 10-cathode, and 11-capping layer.

[0039] Figure 2 This is the NMR spectrum of compound C11.

[0040] Figure 3 This is a schematic diagram of the intersystem crossing from the high-energy triplet exciton (T2) of compound C1 to the first singlet exciton (S1) of compound DB04. Detailed Implementation

[0041] To better understand the content of this invention, it will be described in detail with reference to the accompanying drawings and embodiments.

[0042] The compounds of this invention are applicable to light-emitting elements, display panels, and electronic devices, particularly organic electroluminescent devices. The electronic devices described in this invention are devices comprising a layer of at least one organic compound, and may also comprise layers of inorganic materials or layers formed entirely of inorganic materials. Preferably, the electronic devices are organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic dye-sensitized solar cells (O-DSSCs), organic optical detectors, organic photosensors, organic field quenching devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), and organic plasma emitting devices. Organic electroluminescent devices (OLEDs) are particularly preferred. A schematic diagram of an exemplary organic electroluminescent device is shown below. Figure 1 As shown.

[0043] Experimental Section To better understand the content of this invention, the polycyclic compound, the preparation method of the compound, and the luminescent properties of the device will be explained in detail with reference to embodiments. Various chemical reactions can be applied to the synthesis method of the compound according to one embodiment of this invention. However, it should be noted that the synthesis method of the compound according to one embodiment of this invention is not limited to the synthesis method described below. Unless otherwise stated, subsequent synthesis is carried out in an anhydrous solvent under a protective gas atmosphere. Solvents and reagents can be purchased from conventional reagent suppliers.

[0044] Example 1

[0045] 1) Preparation of compound A1-3 Compounds A1-1 (29.24 g, 0.17 mol) and A1-2 (55.93 g, 0.17 mol) were added to 600 mL of THF, stirred, and refluxed. Then, potassium carbonate (72.16 g, 0.51 mol) was dissolved in 216.5 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium (3.93 g, 34 mmol) was added. After 3 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then subjected to reduced pressure to remove the solvent. It was then completely dissolved in ethyl acetate, washed with water, and subjected to reduced pressure again to remove approximately 80% of the solvent. Recrystallization from n-heptane yielded 39.15 g of compound A1-3, 70% yield. MS (m / z) (M+): 329.

[0046] 2) Preparation of compound A1-4 Compound A1-3 (39.15 g, 0.12 mol) and potassium carbonate (49.68 g, 0.36 mol) were added to 800 mL of DMAC and stirred under reflux. After 3 hours, the reactants were poured into 1 L of water and stirred for 10 min, resulting in an insoluble solid, which was then filtered. The filtered solid was completely dissolved in dichloromethane and washed with water. Anhydrous magnesium sulfate was added to the organic phase, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from ethyl acetate to give 33.59 g of compound A1-4, in 90% yield. MS (m / z) (M+): 309.

[0047] 3) Preparation of compound A1-6 Compounds A1-4 (33.59 g, 0.11 mol) and A1-5 (16.50 g, 0.11 mol) were added to 650 mL of THF, stirred, and refluxed. Then, potassium carbonate (45.54 g, 0.33 mol) was dissolved in 130 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium (2.54 g, 22 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in dichloromethane, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from ethyl acetate to give 27.64 g of compound A1-6, yield 75%. MS (m / z) (M+): 335.

[0048] 4) Preparation of compound A1-7 Compound A1-6 (27.64 g, 0.08 mol) and hydrazine monohydrate (4.00 g, 0.08 mol) were added to 550 mL of AcOH and stirred under reflux. After 2 hours, when the reaction was complete, the solvent was removed under reduced pressure. The compound was then completely dissolved in toluene, washed with water, and the solvent was removed again under reduced pressure. The concentrated compound was recrystallized from toluene to give 15.76 g of compound A1-7, yield 65%. MS (m / z) (M+): 303.

[0049] 5) Preparation of compound A1 Compound A1-7 (15.76 g, 0.05 mol) and bis(pinacol)diboron (13.21 g, 0.05 mol) were refluxed in 300 mL of 1,4-dioxane with stirring. Then, potassium acetate (21.53 g, 0.15 mol) was added, and after thorough stirring, bis(dibenzylacetone)palladium (0.57 g, 1 mmol) and tricyclohexylphosphine (0.57 g, 2 mmol) were added. After reacting for 7 hours, the mixture was distilled under reduced pressure, redissolved in dichloromethane, and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene to give 14.81 g of compound A1, in 75% yield. MS (m / z) (M+): 395.

[0050]

[0051] In a 250 mL three-necked flask, under nitrogen protection, 50 mL of toluene, 25 mL of ethanol, and 25 mL of water were added. Then, compound A1 (3.94 g; 10 mmol), compound B1 (3.41 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol) were added. The mixture was heated to 80 °C and reacted for 12 h. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was dissolved in toluene and filtered to remove the solid insoluble matter. The product C1 was then recrystallized to give product C1: 4.23 g, yield: 80%, MS (m / z) (M+): 529.

[0052] Example 2

[0053] 1) Preparation of compound A2-3 Similar to the preparation of compound A1-3, compounds A1-1 and A1-2 were replaced with compounds A2-1 (29.24 g, 0.17 mol) and A2-2 (55.93 g, 0.17 mol), respectively, to obtain 40.83 g of compound A2-3, with a yield of 73%. MS (m / z)(M+): 329.

[0054] 2) Preparation of compound A2-4 Similar to the preparation of compound A1-4, compound A1-3 was replaced with compound A2-3 (39.15, 0.12 mol) to obtain 33.74 g of compound A2-4, with a yield of 91%. MS (m / z) (M+): 309.

[0055] 3) Preparation of compound A2-6 Similar to the preparation of compound A1-6, compounds A1-4 and A1-5 were replaced with compounds A2-4 (33.59 g, 0.11 mol) and A2-5 (16.50 g, 0.11 mol) to obtain 26.53 g of compound A2-6, with a yield of 72%. MS (m / z) (M+): 335.

[0056] 4) Preparation of compound A2-7 Similar to the preparation of compound A1-7, compound A1-6 was replaced with compound A2-6 (27.64 g, 0.08 mol) to obtain 17.94 g of compound A2-7, with a yield of 74%. MS (m / z) (M+): 303.

[0057] 5) In a 250 mL reaction flask, compound A2-7 (17.94 g, 0.06 mol), 60 mL LD2O and 30 mL isopropanol were added. Under an argon atmosphere, catalyst Pt / C (0.72 g, 0.36 mmol) was added, the temperature was raised to 180 °C, and the reaction was carried out for 12 h. The temperature was lowered to room temperature, the catalyst Pt / C was removed, and the mixture was distilled under reduced pressure to obtain 15.07 g of compound A2-8, yield 80%, MS (m / z) (M+): 314.

[0058] 6) Preparation of compound A2 Similar to the preparation of compound A1, compound A1-7 was replaced with compound A2-8 (15.70 g, 0.05 mol) to obtain 12.18 g of compound A2, with a yield of 60%. MS (m / z) (M+): 406.

[0059]

[0060] The preparation method was the same as in Example 1, except that compounds A1 and B1 were replaced with compounds A2 (4.05 g; 10 mmol) and B2 (3.46 g; 10 mmol), and the final product C2 was obtained: 4.96 g, yield: 91%, MS (m / z) (M+): 545.

[0061] Example 3

[0062] 1) Synthesis of intermediate A3-3 Under a nitrogen atmosphere, compound A3-1 (14.35 g, 50 mmol), compound A3-2 (9.74 g, 55 mmol), tetra(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed overnight. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by recrystallization from dichloromethane / n-heptane to give 12.75 g of compound A3-3, yield 75%, MS (m / z) (M+): 340.

[0063] 2) Synthesis of intermediate A3-4 Under a nitrogen atmosphere, compound A3-3 (10.20 g, 30 mmol) and dry dichloromethane (100 mL) were added to a 500 mL three-necked flask. The system was cooled to 0 ± 5 °C, and a dichloromethane solution of boron tribromide (60 mL, 1 mol / L) was added dropwise using a constant-pressure dropping funnel, with the temperature strictly controlled within the range of 0 ± 5 °C during the addition. After the addition was complete, the system was kept at 0 ± 5 °C for 2 h, and then allowed to warm naturally to room temperature, stirring overnight. The system was then cooled to -78 °C again, and the reaction was quenched by slowly adding methanol (5 mL) dropwise using a constant-pressure dropping funnel. After the system warmed to room temperature, the reaction solution was extracted with dichloromethane (100 mL × 3 times), and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain the crude product. Recrystallization from n-heptane / dichloromethane yielded 7.34 g of compound A3-4, with a yield of 75% and MS (m / z) (M+): 326.

[0064] 3) Synthesis of intermediate A3-5 Under a nitrogen atmosphere, compound A3-4 (6.52 g, 20 mmol), cesium carbonate (13.03 g, 40 mmol), and DMSO (70 mL) were added to a 250 mL three-necked flask. Stirring and heating were initiated, and the reaction was carried out at 80 °C for 4 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain 5.51 g of compound A3-5, yield 90%, MS (m / z) (M+): 306.

[0065] 4) Synthesis of intermediate A3 Under a nitrogen atmosphere, compound A3-5 (3.06 g, 10 mmol), pinacol diborate (2.80 g, 11 mmol), potassium acetate (2.16 g, 22 mmol), and 1,4-dioxane (30 mL) were added sequentially to a 100 mL three-necked flask. Stirring and heating were started, and when the system reached 40 °C, tris(dibenzylacetone)dipalladium (0.09 g, 0.10 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (0.10 g, 0.20 mmol) were quickly added. The temperature was further increased to reflux, and the reaction was stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system, and the mixture was stirred thoroughly for 30 min. The filter cake was obtained by vacuum filtration under reduced pressure. The filter cake was recrystallized from dichloromethane / n-heptane to obtain 3.10 g of compound A3 (yield 78%), MS (m / z) (M+): 398.

[0066]

[0067] The preparation method was the same as in Example 1, except that compounds A1 and B1 were replaced with compounds A3 (3.97 g; 10 mmol) and B3 (3.83 g; 10 mmol), and the final product C3 was obtained: 4.71 g, yield: 82%, MS (m / z) (M+): 574.

[0068] Example 4

[0069] 1) Preparation of compound A4-3 Similar to the preparation of compound A1-3, compounds A1-1 and A1-2 were replaced with compounds A4-1 (29.24 g, 0.17 mol) and A4-2 (55.93 g, 0.17 mol), respectively, to obtain 38.59 g of compound A4-3, with a yield of 69%. MS (m / z) (M+): 329.

[0070] 2) Preparation of compound A4-4 Similar to the preparation of compound A1-4, compound A1-3 was replaced with compound A4-3 (39.15, 0.12 mol) to give 35.23 g of compound A4-4, with a yield of 95%. MS (m / z) (M+): 309.

[0071] 3) Preparation of compound A4-6 Similar to the preparation of compound A1-6, compounds A1-4 and A1-5 were replaced with compounds A4-4 (33.59 g, 0.11 mol) and A4-5 (16.50 g, 0.11 mol) to obtain 28.74 g of compound A4-6, with a yield of 78%. MS (m / z) (M+): 335.

[0072] 4) Preparation of compound A4-7 Similar to the preparation of compound A1-7, compound A1-6 was replaced with compound A4-6 (27.64 g, 0.08 mol) to give 17.45 g of compound A4-7, with a yield of 72%. MS (m / z) (M+): 303.

[0073] 5) Preparation of compound A4 Similar to the preparation of compound A1, compound A1-7 was replaced with compound A4-7 (15.76 g, 0.05 mol) to give 12.84 g of compound A4, with a yield of 65%. MS (m / z) (M+): 395.

[0074]

[0075] The preparation method was the same as in Example 1, except that compound A4 (3.94 g; 10 mmol) and compound B4 (4.14 g; 10 mmol) were used to replace compounds A1 and B1, and the final product C4 was obtained: 5.12 g, yield: 85%, MS (m / z) (M+): 602.

[0076] Example 5

[0077] 1) Preparation of compound A5-3 Similar to the preparation of compound A1-3, compounds A1-1 and A1-2 were replaced with compounds A5-1 (29.24 g, 0.17 mol) and A5-2 (55.93 g, 0.17 mol), respectively, to obtain 40.27 g of compound A5-3, with a yield of 72%. MS (m / z)(M+): 329.

[0078] 2) Preparation of compound A5-4 Similar to the preparation of compound A1-4, compound A1-3 was replaced with compound A5-3 (39.15, 0.12 mol) to give 34.11 g of compound A5-4, with a yield of 92%. MS (m / z) (M+): 309.

[0079] 3) Preparation of compound A5-6 Similar to the preparation of compound A1-6, compounds A1-4 and A1-5 were replaced with compounds A5-4 (33.59 g, 0.11 mol) and A5-5 (16.50 g, 0.11 mol) to obtain 26.90 g of compound A5-6, with a yield of 73%. MS (m / z) (M+): 335.

[0080] 4) Preparation of compound A5-7 Similar to the preparation of compound A1-7, compound A1-6 was replaced with compound A5-6 (27.64 g, 0.08 mol) to give 16.97 g of compound A5-7, with a yield of 70%. MS (m / z) (M+): 303.

[0081] 5) Preparation of compound A5 Similar to the preparation of compound A1, compound A1-7 was replaced with compound A5-7 (15.76 g, 0.05 mol) to obtain 13.83 g of compound A5, with a yield of 70%. MS (m / z) (M+): 395.

[0082]

[0083] The preparation method was the same as in Example 1, except that compound A5 (3.94 g; 10 mmol) and compound B5 (4.09 g; 10 mmol) were used to replace compounds A1 and B1, and the final product C5 was obtained: 5.25 g, yield: 88%, MS (m / z) (M+): 597.

[0084] The preparation methods for compound A6 and compound A1 are the same, and will not be repeated here.

[0085] Example 6

[0086] The preparation method was the same as in Example 1, except that compounds A1 and B1 were replaced with compounds A6 (3.94 g; 10 mmol) and B6 (3.98 g; 10 mmol), and the final product C6 was obtained: 4.57 g, yield: 78%, MS (m / z) (M+): 586.

[0087] Example 7 Preparation method of A7 Compound A7-7 was prepared in the same manner as compound A2-7.

[0088]

[0089] Similar to the preparation of compound A1, replacing compound A1-7 with compound A7-7 (15.15 g, 0.05 mol) yielded 12.81 g of compound A7, with a yield of 65%. MS (m / z) (M+): 394

[0090] The preparation method was the same as in Example 1, except that compounds A1 and B1 were replaced with compounds A7 (3.94 g; 10 mmol) and B7 (4.26 g; 10 mmol), and the final product C7 was obtained: 4.97 g, yield: 81%, MS (m / z) (M+): 614.

[0091] Example 8

[0092] Synthesis of intermediate A8-3 Similar to the preparation of compound A3-3, compounds A3-1 and A3-2 were replaced with compounds A8-1 (14.75 g, 50 mmol) and A8-2 (9.57 g, 55 mmol) to obtain 12.77 g of compound A8-3, yield 74%, MS (m / z) (M+): 345.

[0093] Synthesis of intermediate A8-4 Similar to the preparation of compound A3-4, compound A8-3 (10.35 g, 30 mmol) was substituted to give 7.54 g of compound A8-4, yield 76%, MS (m / z) (M+): 331.

[0094] Synthesis of intermediate A8-5 Similar to the preparation of compound A3-5, compound A8-4 (6.62 g, 20 mmol) was substituted to give 5.52 g of compound A8-5, yield 89%, MS (m / z) (M+): 311.

[0095] Synthesis of intermediate A8 Similar to the preparation of compound A3, compound A3-5 was replaced with compound A8-5 (3.11 g, 10 mmol) to give 3.18 g of compound A8, yield 79%, MS (m / z) (M+): 403.

[0096]

[0097] The preparation method was the same as in Example 1, except that compound A8 (4.02 g; 10 mmol) and compound B8 (4.09 g; 10 mmol) were used to replace compounds A1 and B1, and the final product C8 was obtained: 5.02 g, yield: 83%, MS (m / z) (M+): 605.

[0098] Example 9

[0099] Compound A9-7 was prepared using the same method as compound A4-7. Then, compound A9-8 was prepared using the same method as compound A2-8. When compound A2-7 was replaced with compound A9-7 (17.94 g, 0.06 mol), 14.13 g of compound A9-8 was obtained, with a yield of 75% and MS (m / z) (M+): 314.

[0100] Subsequently, compound A9 was prepared in a similar manner to compound A1, by replacing compound A1-7 with compound A9-8 (15.70 g, 0.05 mol), yielding 12.38 g of compound A9, with a yield of 61%. MS (m / z) (M+): 406.

[0101]

[0102] The preparation method was the same as in Example 1, except that compound A9 (4.05 g; 10 mmol) and compound B9 (4.14 g; 10 mmol) were used to replace compounds A1 and B1, and the final product C9 was obtained: 4.90 g, yield: 80%, MS (m / z) (M+): 613.

[0103] Example 10 Compound A10-7 was prepared using the same method as compound A5-7. Compound A10-8 was then prepared using the same method as compound A2-8. Compound A2-7 was replaced with compound A10-7 (17.94 g, 0.06 mol) to give 13.38 g of compound A10-8, yield 71%, MS (m / z) (M+): 314.

[0104] Subsequently, compound A10 was prepared in a similar manner to compound A1, by replacing compound A1-7 with compound A10-8 (15.70 g, 0.05 mol), yielding 12.79 g of compound A10, with a yield of 63%. MS (m / z) (M+): 406.

[0105]

[0106] The preparation method was the same as in Example 1, except that compound A10 (4.05 g; 10 mmol) and compound B10 (4.09 g; 10 mmol) were used to replace A1 and B1, and the final product C10 was obtained: 5.23 g, yield: 86%, MS (m / z) (M+): 608.

[0107] Example 11

[0108] The preparation method was the same as in Example 1, except that compound A11 (3.94 g; 10 mmol) and compound B11 (3.33 g; 10 mmol) were used to replace compounds A1 and B1, and the final product C11 was obtained: 3.91 g, yield: 75%, MS (m / z) (M+): 521.

[0109] See the NMR spectrum of compound C11. Figure 2 .

[0110] Comparative compounds

[0111] Compound properties To illustrate the beneficial effects of introducing a phenanthrene-benzofuran structure at a specific site, the following experiments were conducted: 1. Using ORCA 6.0.1 software, the density functional theory (DFT) method was used to calculate the basis set level as B3LYP-d3 / 6-63G(d). (With a charge number of 0), the high-energy triplet state of the molecule is obtained; when the energy of the high-energy triplet state approaches 3.0 eV (blue light energy), the thermal exciton effect will exist, allowing the high-energy triplet exciton to transition to the singlet state through reverse intersystem crossing, thereby improving the internal quantum efficiency.

[0112] 2. Giant surface potential (GSP) gradient The giant surface polarization (GSP) gradient (GSP_slope) was determined by measuring the film thickness dependence of the surface potential. The chamber was designed to be light-shielded. To ensure the object being measured does not receive light, the vacuum level is set to 10. -5 The target material was deposited on an ITO substrate at a deposition rate of 2 Å / s, with a film thickness of 20 nm, and the surface potential (mV) of the deposited film was measured. This operation was repeated five times. The surface potential (mV) was plotted on the vertical axis, and the film thickness (nm) on the horizontal axis. The graphs were fitted to a straight line using the least squares method, and the slope was calculated as the giant surface potential (GSP) gradient (mV / nm). The surface potential under vacuum was measured using a Kelvin probe apparatus (Tokyo Instruments Co., Ltd., "Ultra-high Vacuum Kelvin Probe").

[0113] Deposition and surface potential measurements were performed under vacuum and light-shielding conditions. Throughout the repeated deposition and measurement processes, the sample remained in the same chamber (under light-shielding and in a vacuum). "Repeated five times" refers to: depositing 20 nm on the sample (ITO substrate) and measuring the surface potential; depositing another 20 nm on the same sample (total film thickness 40 nm) and measuring the surface potential; depositing another 20 nm on the same sample (total film thickness 60 nm) and measuring the surface potential; depositing another 20 nm on the same sample (total film thickness 80 nm) and measuring the surface potential; and depositing another 20 nm on the same sample (total film thickness 100 nm) and measuring the surface potential.

[0114] 3. Molecular orientation was measured using angle-dependent fluorescence spectroscopy to determine the transition dipole moment orientation of molecules in the luminescent layer. A molecular orientation testing system manufactured by Hamamatsu Corporation, Japan, was used for measurement. The testing method involved co-depositing compounds C1-C10 and BD01 provided in this invention onto a high-transmittance quartz glass slide to form an organic film. The guest material (BD01) had a doping concentration of 2%, and the host material (one of compounds C1-C10) had a doping concentration of 98%. The sample was then excited with 365 nm ultraviolet light, emitting emission light. The p-polarized light in the emission light was detected by a polarizer and received by a detector. The fluorescence intensity distribution of the organic film as a function of the test angle was measured, and the anisotropy factor Θ (dimensionless) was determined using optical fitting software, as shown in the following formula: ; In the formula, p z denoted by , where p represents the vertical dipole electrode moment. This represents the total vertical dipole's emission power. This represents the total emission power of all dipoles. The smaller the value, the higher the probability that the molecules are arranged in a horizontal orientation, indicating that the material has a better molecular orientation. It also indicates that there are more horizontal photon components in the organic film guest material, and the higher the utilization rate of the guest material's radiative emission.

[0115] The structure of compound BD01 is as follows .

[0116] The results of the compound performance are summarized in Table 1.

[0117] Table 1

[0118] The results above show that, due to the use of specific substitution sites, this invention exhibits a relatively larger GSP (Gross Space Slope) compared to the comparative example. This is a comprehensive result of the specific substitution sites adopted in this invention and the combined effect of phenanthrenebenzofuran on the rigidity, symmetry, and polarity of the molecule. The larger GSP-slope of this invention improves carrier injection and increases the recombination probability of the host material, thereby improving device efficiency. This structure also facilitates host-guest interactions and improves energy transfer, resulting in better molecular orientation and further enhancing device efficiency. Compared to the comparative example, the phenanthrenebenzofuran substituent in this invention makes the T2 energy level of the material closer to and further away from the S1 energy level, thereby further improving the utilization rate of triplet excitons.

[0119] The S1 and T1 energy levels of anthracene-based host materials typically do not vary significantly due to light color limitations. For ease of understanding, the energy level configurations of host materials C1 and DB04 are used as examples, and the following diagrams are drawn. Figure 3 To be explained. Figure 3 It is known that the S1 energy level of compound C1 is 2.91 eV and the high-energy triplet energy level (T2) is 2.61 eV, while the high-energy triplet energy level (T2) of compound DB04 is 2.48 eV. The high-energy triplet energy level of compound C1 is closer to the S1 energy level, and the energy difference between T2 and T1 of compound C1 is greater. This indicates that compound C1 is more likely to undergo transitions from the high-energy triplet exciton to S1, which is beneficial to improving the utilization rate of triplet excitons.

[0120] OLED manufacturing and characterization Device Examples The organic electroluminescent device provided by the present invention includes an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode sequentially disposed on a substrate. Furthermore, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer; the electron transport region includes an electron transport layer and an electron injection layer.

[0121] Furthermore, the light-emitting layer is composed of a host material and a guest material, and the host material of the light-emitting layer can be composed of one molecular material or multiple molecular materials.

[0122] The composition described in this invention can be used in the light-emitting layer of the aforementioned organic electroluminescent device.

[0123] In this embodiment, the anode uses a commonly used anode material in the art, such as ITO, Ag, or their multilayer structures. The hole injection layer uses a commonly used hole injection material in the art, with F4TCNQ, HATCN, NDP-9, etc., added for doping. The hole transport layer uses a commonly used hole transport material in the art. The light-emitting layer uses the host and guest material composition provided by this invention. The electron transport layer uses a commonly used electron transport material in the art. The electron injection layer uses a commonly used electron injection material in the art, such as LiQ, LiF, Yb, etc. The cathode uses a commonly used material in the art, such as metallic Al, Ag, or metal mixtures (Ag-doped Mg, Ag-doped Ca, etc.).

[0124] The electrode fabrication method and the deposition method of each functional layer in this embodiment are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, and will not be described in detail here. Only some process details and testing methods in the fabrication process are supplemented as follows: Device Example 1 The substrates used in this invention are all subjected to the following operations: the ITO substrate is patterned to give it a light-emitting area of ​​3mm × 3mm, then ultrasonicated with water / isopropanol, irradiated with UV / ozone, and then dried at 100°C. Afterwards, the ITO substrate is mounted on the substrate support of a vacuum deposition apparatus, and the pressure is adjusted to make the vacuum rate 1 × 10⁻⁶. -7 torr. The following operations are then performed: First, a hole injection layer is formed on the ITO layer (anode) formed on the substrate by vacuum deposition of compounds HT01 and PD01 (mass ratio of HT01 to PD01 is 97:3) with a thickness of 10 nm; second, a hole transport layer is formed on the hole injection layer by vacuum deposition of compound HT01 with a thickness of 100 nm; third, a light-emitting auxiliary layer is formed on the hole transport layer by vacuum deposition of compound BP01 with a thickness of 5 nm; fourth, a light-emitting layer is formed on the light-emitting auxiliary layer by vacuum deposition of a mixture of compound C1 and compound BD01 provided by the present invention with a thickness of 20 nm, wherein compound C1 is used as the host material and compound BD01 is used as the guest material, with a mass ratio of host material to guest material of 98:2; then, a hole blocking layer is formed on the light-emitting layer by vacuum deposition of compound HB01 with a thickness of 5 nm; then… On the aforementioned hole-blocking layer, an electron transport layer is formed by vacuum-depositing compounds ET01 and LiQ (ET01 to LiQ in a 1:1 mass ratio) with a thickness of 30 nm. Then, an electron injection layer is formed by vacuum-depositing Yb with a thickness of 1 nm on the electron transport layer. Next, a cathode is formed by depositing Mg and Ag (Mg to Ag in a 1:9 mass ratio) with a thickness of 15 nm on the electron injection layer. Finally, a capping layer is formed by depositing compound CP01 with a thickness of 50 nm on the cathode. The vapor-deposited substrate is then encapsulated. A UV adhesive coating process is used to coat the cleaned cover plate. The coated cover plate is then moved to the lamination section, and the vapor-deposited substrate is placed on top of the cover plate. Finally, the substrate and cover plate are laminated using a bonding device, while simultaneously curing the UV adhesive under light. This process produces a top-emitting organic light-emitting device. The device structure is described in [reference needed]. Figure 1 .

[0125] Except for the guest material of the luminescent layer, the molecular structural formulas of the other layers are as follows:

[0126]

[0127]

[0128] Device Example 2-11 Organic electroluminescent devices were fabricated using the compounds described in other embodiments in Table 2 using the above method. Specifically, blue organic electroluminescent devices Examples 2-11 were fabricated by replacing C1 in Device Example 1 with the main material shown in the Device Examples in Table 2.

[0129] Device Comparison Examples 1-6 Organic electroluminescent devices were fabricated using the compounds described in the comparative examples in Table 2 using the above method. Specifically, blue organic electroluminescent devices (Comparative Examples 1-6) were fabricated by replacing C1 in Device Example 1 with the main material shown in the comparative examples in Table 2.

[0130] The OLED devices described above were tested using standard methods. For this purpose, J = 10 mA / cm² was used. 2 The driving voltage and luminous efficiency of the organic electroluminescent device were determined at a current density of J = 20 mA / cm². LT97 indicates that the fabricated blue light-emitting device is capable of operating at this current density. 2 When operating, the luminous intensity drops to 97% of its initial value L0 after time LT97.

[0131] The testing instruments and methods used to perform performance testing on the OLED devices of the above embodiments and comparative examples are as follows: Luminous efficacy (CE) (cd / A) and chromaticity coordinates (CIEy) were measured using a PhotoResearch PR-735 spectral scanner. Current density and turn-on voltage: tested using a Keithley 2400 digital source meter; The luminous efficiency of blue light devices is greatly affected by chromaticity. The industry generally uses the BI value as the basis for the efficiency of blue light devices. BI (Blue index) is obtained by dividing the luminous efficiency CE (cd / A) by the chromaticity coordinate (CIEy). Lifetime testing: Using a silicon photonics-based OLED device lifetime testing system.

[0132] The performance test results of the above devices are listed in Table 2.

[0133] Table 2 Performance test results of blue light devices

[0134] The device evaluation results above show that organic light-emitting devices containing the phenanthrene-benzofuran blue light-emitting host material provided by this invention have significant advantages in driving voltage and luminous efficiency, and also have certain advantages in device lifetime. This is because the blue light-emitting host material provided by this invention contains phenanthrene-benzofuran substituents, resulting in comprehensive advantages in molecular polarity, molecular energy levels, and molecular orientation.

[0135] Specifically addressing DB06, the introduction of benzimidazole groups significantly increases its polarity. Benzimidazole also significantly improves electron transport and injection, deepening energy levels and is frequently used in electron transport materials. As a host material, while it improves molecular orientation and polarity to some extent, the bond energy of the introduced CN bond is close to the excitation energy of the blue light host material, leading to material stability issues. Furthermore, the excessive polarity of the CN bond results in very high molecular polarity. Although this has a beneficial effect on host-guest energy transport, excessive molecular polarity can easily lead to molecular aggregation and crystallization, resulting in dead pixels and concentration quenching, and poor device lifetime performance.

[0136] Obviously, the above embodiments of the present invention are merely examples for clearly illustrating the present invention, and are not intended to limit the implementation of the present invention. For those skilled in the art, other variations or modifications can be made based on the above description. It is impossible to exhaustively list all the implementation methods here. All obvious variations or modifications derived from the technical solutions of the present invention are still within the protection scope of the present invention.

Claims

1. An organic compound containing phenanthrenebenzofuran, characterized in that, The general structural formula of the organic compound is shown in Formula I: I； Ⅱ； Wherein, L1 and L2 each independently represent any one of the aryl groups with a single bond and a carbon number of C6 to C12; Ar1 represents a substituted or unsubstituted aryl group with 6 to 60 carbon atoms; Ar2 represents the group shown in formula II, and ring A represents a phenanthrene group; In Formula I, any hydrogen atom can be substituted with deuterium.

2. The organic compound according to claim 1, characterized in that, Ar2 represents one of the following structures: 、 、 、 、 、 。 3. The organic compound according to claim 1, characterized in that, L1 and L2 each independently represent any one of a single bond, phenylene, or naphthylene.

4. The organic compound according to claim 1, characterized in that, Ar1 represents a substituted or unsubstituted aryl group with a carbon number of C6 to C30.

5. The organic compound according to claim 1 or 4, characterized in that, Ar1 represents any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

6. The organic compound according to claim 1, characterized in that, The organic compound is selected from the following structures: ； Where Dn represents n hydrogen atoms being replaced by deuterium, and n is a positive integer, ranging from 1 to the maximum deuterium algebra.

7. The use of the organic compound as described in any one of claims 1-6 in the preparation of organic electroluminescent devices.

8. An organic electroluminescent device, characterized in that, It includes an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode sequentially disposed on a substrate; wherein the light-emitting layer includes a host material and a guest material, and the host material includes one or more organic compounds as described in any one of claims 1 to 6.

9. A display device, characterized in that, Including the organic electroluminescent device as described in claim 8.

10. A lighting device, characterized in that, Including the organic electroluminescent device as described in claim 8.

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