Organic compound, electroluminescent device and display device

Abstract

The invention provides an organic compound, an electroluminescent device and a display device, and relates to the technical field of display, the organic compound has a structural formula as shown in a general formula I, L1 and L2 are independently selected from substituted or unsubstituted arylene of C6-C36 and substituted or unsubstituted heteroarylene of C2-C36, and m and n are independently selected from integers of 0-4.

Description

Technical Field

[0001] This application relates to the field of display technology, and more specifically, to an organic compound, an electroluminescent device, and a display apparatus. Background Technology

[0002] In recent years, Organic Light Emitting Devices (OLEDs) have seen their applications expand from mobile phones to other high-quality information display devices due to their self-emissive nature, wide material selection, high brightness and efficiency, wide color gamut and viewing angle, fast response, and flexibility. With the development of product types and the increasing demands of various display devices, the requirements for OLED devices are becoming increasingly stringent, necessitating the development of devices with higher resolution, higher efficiency, lower voltage, and longer lifespan.

[0003] When light propagates between different media, it is lost at the interface due to differences in refractive index. To improve the luminous efficiency of OLED devices, a simple and effective method is to form a light extraction layer (also called a capping layer, CPL) on the transparent electrode as a functional layer. By adding a high-refractive-index light extraction layer to the device, the external quantum efficiency can be significantly improved, and light loss within the device can be reduced, thereby increasing the light extraction efficiency. Therefore, providing a high-refractive-index light extraction material to improve the light extraction efficiency of organic electronic components has become a pressing problem in this field. Summary of the Invention

[0004] This application provides an organic compound, an electroluminescent device, and a display device, aiming to solve the problem of how to improve the light extraction efficiency of organic electronic components.

[0005] The first aspect of this application provides an organic compound having the structural formula shown in general formula I:

[0006]

[0007] Wherein, L1 and L2 are each independently selected from substituted or unsubstituted C6-C36 arylene groups and substituted or unsubstituted C2-C36 heteroarylene groups, and m and n are each independently selected from integers from 0 to 4;

[0008] R1 and R2 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6.

[0009] In one alternative implementation, Ar1 has the structural formula shown in general formula II:

[0010]

[0011] in, Indicates the linkage site of the functional group;

[0012] Z is selected from C(R3) or N, and X1 is selected from any one of O, S, C(R4R5) and N(R6).

[0013] In one alternative implementation, Ar2 has the structural formula shown in general formula III:

[0014]

[0015] in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

[0016] In one alternative implementation, Ar3 has the structural formula shown in general formula IV:

[0017]

[0018] in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

[0019] In one alternative implementation, Ar4 has the structural formula shown in general formula V:

[0020]

[0021] in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

[0022] In one alternative implementation, Ar5 has the structural formula shown in general formula VI:

[0023]

[0024] in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

[0025] In one alternative implementation, Ar6 has the structural formula shown in general formula VII:

[0026]

[0027] in, Indicates the linkage site of the functional group;

[0028] Y is selected from any one of O, S, C(R4R5) and N(R6);

[0029] Ring A and ring B are each independently selected from any one of the following: substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, or substituted or unsubstituted phenanthrene ring.

[0030] In one alternative embodiment, R3 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0031] In one optional embodiment, R4 and R5 are each independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; R4 and R5 are not connected to each other or are connected to form substituted or unsubstituted rings;

[0032] R6 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0033] In one alternative embodiment, Ar1 is selected from any of the substituents in the following structural formulas:

[0034]

[0035]

[0036] In one alternative embodiment, Ar2 is selected from any of the substituents in the following structural formulas:

[0037]

[0038] In one alternative implementation, Ar3 is selected from any of the substituents in the following structural formulas:

[0039]

[0040] In one alternative embodiment, Ar4 is selected from any of the substituents in the following structural formulas:

[0041]

[0042] In one alternative implementation, Ar5 is selected from any of the substituents in the following structural formulas:

[0043]

[0044] In one alternative implementation, Ar6 is selected from any of the substituents in the following structural formulas:

[0045]

[0046]

[0047]

[0048] In one alternative embodiment, the organic compound comprises any one of the following structural formulas:

[0049]

[0050]

[0051] In one alternative embodiment, the organic compound has a refractive index at a wavelength of 460 nm that is greater than or equal to 2.08 and less than or equal to 2.5.

[0052] The refractive index of the organic compound at a wavelength of 530 nm is greater than or equal to 1.98 and less than or equal to 2.24.

[0053] The organic compound has a refractive index at a wavelength of 620 nm that is greater than or equal to 1.93 and less than or equal to 2.14.

[0054] A second aspect of this application provides an electroluminescent device, the electroluminescent device comprising:

[0055] A light-emitting layer, a cathode, and an anode are stacked together, with the light-emitting layer disposed between the cathode and the anode;

[0056] A light extraction layer is disposed on the side of the cathode opposite to the anode, and the material of the light extraction layer includes an organic compound as described in any one of the first aspects.

[0057] In one alternative embodiment, the electroluminescent device further includes at least one of the following:

[0058] A hole injection layer, a hole transport layer, and an electron blocking layer are stacked sequentially between the anode and the light-emitting layer along a first direction, wherein the first direction is the direction from the anode to the cathode;

[0059] A hole blocking layer, an electron transport layer, and an electron injection layer are stacked sequentially between the light-emitting layer and the cathode along the first direction.

[0060] A third aspect of this application provides a display device, the display device including the electroluminescent device as described in the second aspect.

[0061] Beneficial effects:

[0062] This application provides an organic compound, an electroluminescent device, and a display device. The organic compound has a structural formula as shown in Formula I, wherein L1 and L2 are each independently selected from substituted or unsubstituted C6-C36 arylene groups and substituted or unsubstituted C2-C36 heteroarylene groups, and m and n are each independently selected from integers from 0 to 4. The organic compound provided in this application uses fluorene-anthraquinone as the core group. Due to its relatively large conjugated fused ring group, it has strong rigidity. Furthermore, the core group is connected to side chains with aromatic amine structures, which, in conjunction with the core group, gives the organic compound a high refractive index. When this organic compound is used as a layer material for organic electronic components, the light extraction efficiency of the organic electronic components can be improved. Attached Figure Description

[0063] To more clearly illustrate the technical solutions of the embodiments of this application, the drawings used in the description of the embodiments of this application will be briefly introduced below. Obviously, the drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0064] Figure 1This is a schematic diagram of the hierarchical structure of an electroluminescent device according to an embodiment of this application.

[0065] Explanation of reference numerals in the attached figures: 101, substrate; 102, anode; 103, hole transport region; 1031, hole injection layer; 1032, hole transport layer; 1033, electron blocking layer; 104, light-emitting layer; 105, electron transport region; 1051, electron injection layer; 1052, electron transport layer; 1053, hole blocking layer; 106, cathode; 107, light extraction layer; 108, light-assisted layer; 109, encapsulation layer. Detailed Implementation

[0066] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application.

[0067] In the accompanying drawings, the size of constituent elements, the thickness of layers, or areas may sometimes be exaggerated for clarity. Therefore, any implementation of this disclosure is not necessarily limited to the dimensions shown in the drawings, and the shapes and sizes of the components in the drawings do not reflect true proportions. Furthermore, the drawings schematically illustrate ideal examples, and any implementation of this disclosure is not limited to the shapes or values ​​shown in the drawings.

[0068] In recent years, Organic Light Emitting Devices (OLEDs) have seen their applications expand from mobile phones to other high-quality information display devices due to their self-emissive nature, wide material selection, high brightness and efficiency, wide color gamut and viewing angle, fast response, and flexibility. An OLED device consists of an emissive layer and a pair of electrodes on either side of it. When an electric field is applied between the two electrodes, electrons are injected from the negative electrode and holes from the positive electrode. These electrons and holes combine in the emissive layer to form an excited state. When the excited state returns to the ground state, the energy emitted emits light, achieving self-emissive emission from the OLED device. With the development of product types and the increasing demands of various display devices, the requirements for OLED devices are becoming increasingly stringent, necessitating the development of devices with higher resolution, higher efficiency, lower voltage, and longer lifespan.

[0069] When light travels between different media, it is lost at the interface due to differences in refractive index. To improve the luminous efficiency of OLED devices, a simple and effective method is to form a light extraction layer (also called a capping layer, CPL) on the transparent electrode as a functional layer. By adding a high-refractive-index light extraction layer to the device, the external quantum efficiency of the device can be significantly improved, and the light loss inside the device can be reduced, thereby improving the light extraction efficiency of the device.

[0070] In view of this, embodiments of this application propose an organic compound having the structural formula shown in general formula I:

[0071]

[0072] Wherein, L1 and L2 are each independently selected from substituted or unsubstituted C6-C36 arylene groups and substituted or unsubstituted C2-C36 heteroarylene groups, and m and n are each independently selected from integers from 0 to 4;

[0073] R1 and R2 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6.

[0074] The organic compounds provided in this application embodiment are based on fluorenanthraquinone as the core group. Since fluorenanthraquinone is a large conjugated fused ring group, it has strong rigidity. At the same time, as shown in general formula I, the fluorenanthraquinone core group is connected to a branched structure. The branched structure is a substituted aromatic amine-like structure (e.g., the substituent is a benzo[a]heterocyclic ring or an aromatic ring, etc.), which has more lone pair electrons. Therefore, the organic compounds based on the core group and the branched structure have a large polarizability. When used as the light extraction layer of an electroluminescent device, it can effectively improve the light extraction efficiency and device performance.

[0075] It should be noted that, in the embodiments of this application, the aryl group includes, but is not limited to, phenyl, naphthyl, anthraceneyl, acenaphtheneyl, indeneyl, phenanthryl, azulel, pyreneyl, fluorenyl, peryleneyl, spirofluorenyl, and spirobisfluorenyl. Benzyl, benzo[phenanthryl], benzo[anthryl], fluoranyl, fenyl, tetraphenyl, indenephenyl.

[0076] It should be noted that the term "hetero" used in heteroaryl refers to the substitution of at least one carbon atom in the aromatic ring by a heteroatom, wherein the heteroatom is selected from any one or more of nitrogen (N), oxygen (O), and sulfur (S). In the embodiments of this disclosure, the heteroaryl group includes, but is not limited to, benzoxazolyl, benzothiazolyl, indolyl, benzimidazolyl, pyrroleyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, imidazolyl, pyrazolyl, carbazoleyl, thiopheneyl, thiazolyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, indocarbazoleyl, quinolinyl, isoquinolinyl, phthalaziny, and quinoxalyl. (inyl), cinnolinyl, quinazolinyl, phthalazinyl, benzoquinolinyl, benzoisoquinolinyl, benzoquinazolinyl, benzoquinoxalinyl, acridineyl, phenanthrolinel, furanyl, pyranyl, oxazinyl, oxadiazolyl, triazolyl, dioxynyl, benzofuranyl, dibenzofuranyl, thiopyranyl, thiazinyl, phenylthioyl, and N-substituted spirofluorene.

[0077] In some alternative implementations, Ar1 has the structural formula shown in General Formula II:

[0078]

[0079] in, Indicates the linkage site of the functional group;

[0080] Z is selected from C(R3) or N, and X1 is selected from any one of O, S, C(R4R5) and N(R6).

[0081] In some alternative implementations, Ar2 has the structural formula shown in general formula III:

[0082]

[0083] in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

[0084] In some alternative implementations, Ar3 has the structural formula shown in general formula IV:

[0085]

[0086] in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

[0087] In some alternative implementations, Ar4 has the structural formula shown in general formula V:

[0088]

[0089] in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

[0090] In some alternative implementations, Ar5 has the structural formula shown in general formula VI:

[0091]

[0092] in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

[0093] In some alternative implementations, Ar6 has the structural formula shown in general formula VII:

[0094]

[0095] in, Indicates the linkage site of the functional group;

[0096] Y is selected from any one of O, S, C(R4R5) and N(R6);

[0097] Ring A and ring B are each independently selected from any one of the following: substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, or substituted or unsubstituted phenanthrene ring.

[0098] In some alternative embodiments, R3 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0099] In some optional embodiments, R4 and R5 are each independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; R4 and R5 are not connected to each other or are connected to form substituted or unsubstituted rings.

[0100] In some alternative embodiments, R6 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0101] In some alternative embodiments, Ar1 is selected from any of the substituents in the following structural formulas:

[0102]

[0103] It should be noted that the Ar1 disclosed in the embodiments of this application includes, but is not limited to, the various groups mentioned above.

[0104] In some alternative embodiments, Ar2 is selected from any of the substituents in the following structural formulas:

[0105]

[0106] It should be noted that the Ar2 disclosed in the embodiments of this application includes, but is not limited to, the various groups mentioned above.

[0107] In some alternative implementations, Ar3 is selected from any of the substituents in the following structural formulas:

[0108]

[0109] It should be noted that the Ar3 disclosed in the embodiments of this application includes, but is not limited to, the various groups mentioned above.

[0110] In some alternative embodiments, Ar4 is selected from any of the substituents in the following structural formulas:

[0111]

[0112] It should be noted that the Ar4 disclosed in the embodiments of this application includes, but is not limited to, the various groups mentioned above.

[0113] In some alternative embodiments, Ar5 is selected from any of the substituents in the following structural formulas:

[0114]

[0115] It should be noted that the Ar5 disclosed in the embodiments of this application includes, but is not limited to, the various groups mentioned above.

[0116] In some alternative embodiments, Ar6 is selected from any of the substituents in the following structural formulas:

[0117]

[0118]

[0119]

[0120] It should be noted that the Ar6 disclosed in the embodiments of this application includes, but is not limited to, the various groups mentioned above.

[0121] In some alternative embodiments, the organic compound comprises any one of the following structural formulas:

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] It should be noted that the structures of the organic compounds disclosed in the embodiments of this application include, but are not limited to, the various structural formulas mentioned above.

[0211] In some alternative embodiments, the refractive index of the organic compound at a wavelength of 460 nm is greater than or equal to 2.08 and less than or equal to 2.5; the refractive index of the organic compound at a wavelength of 530 nm is greater than or equal to 1.98 and less than or equal to 2.24; and the refractive index of the organic compound at a wavelength of 620 nm is greater than or equal to 1.93 and less than or equal to 2.14.

[0212] In some optional embodiments, the glass transition temperature (Tg) of the organic compound determines the thermal stability of the material during vapor deposition; a higher Tg indicates better thermal stability. The glass transition temperature (Tg) of the organic compound is greater than or equal to 123°C and less than or equal to 142°C.

[0213] Optionally, the organic compound includes any one of the following structural formulas:

[0214]

[0215] Next, this application will take the above-mentioned organic compounds E1-E12 as examples to describe in detail the preparation method of the organic compounds provided in the embodiments of this application. It is easy to understand that the preparation method of organic compounds E1-E12 is only an optional implementation method provided to enable those skilled in the art to better understand the scheme of this application. The preparation method of the organic compounds provided in the embodiments of this application includes, but is not limited to, the following synthesis examples.

[0216] In some optional embodiments, the synthesis of the organic compound E1 includes the following steps:

[0217]

[0218] In the specific preparation of compound E1, toluene solvent was added to a flask, followed by compound E0 (2.1 eq) and intermediate 1 (1 eq) in sequence. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), palladium acetate (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration, dried in a vacuum oven for 3 h, and then sublimated to obtain compound E1.

[0219] Mass spectrometry m / z: 743.91, elemental composition (%): C55H37NO2, C, 88.80; H, 5.01; O, 4.03; N, 1.88.

[0220] 1 H NMR (300MHz, DMSO): 8.38(1H),8.32(2H),8.29(2H),8.06-8.09(5H),7.99(2H),7.86 (1H),7.63(2H),7.6(2H),7.55(6H),7.37-7.38(6H),7.33(1H),7.16(1H),1.69(6H).

[0221] In some alternative embodiments, the synthesis of the organic compound E2 includes the following steps:

[0222] Step 1:

[0223]

[0224] In specific implementation step 1, toluene solvent was added to a bottle, followed by compound E0 (1 eq) and intermediate 2 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), palladium acetate (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain intermediate 3.

[0225] Step 2:

[0226]

[0227] In specific step 2, toluene solvent was added to the bottle, followed by intermediate 3 (1 eq) and intermediate 4 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain the solid. Sublimation of the solid yielded compound E₂.

[0228] Mass spectrometry m / z: 750.92, elemental composition (%): C52H34N2O2S, C, 83.17; H, 4.56; O, 4.26; N, 3.73; S, 4.27.

[0229] 1 H NMR (300MHz, DMSO): 8.38(1H),8.32(2H),8.29(2H),8.18(1H),8.02-8.09(4H),7.99(1H),7.85-7.86 (3H),7.63(1H),7.6(1H),7.55(3H),7.51-7.53(2H),7.37-7.38(5H),7.33(1H),7.16(1H),1.69(6H).

[0230] In some optional embodiments, the synthesis of the organic compound E3 includes the following steps:

[0231]

[0232] In the specific preparation of compound E3, toluene solvent was added to a flask, followed by intermediate 3 (1 eq) and intermediate 5 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration, dried in a vacuum oven for 3 h, and then sublimated to obtain compound E3.

[0233] Mass spectrometry m / z: 734.86, elemental composition (%): C52H34N2O3, C, 84.99; H, 4.66; O, 6.53; N, 3.81.

[0234] 1 H NMR (300MHz, DMSO): 8.38(1H),8.32(2H),8.29(2H),8.06-8.09(3H),7.99(1H),7.86(1H),7. 73-7.74(4H),7.63(1H),7.6(1H),7.55(3H),7.37-7.38(7H),7.33(1H),7.16(1H),1.69(6H).

[0235] In some alternative embodiments, the synthesis of the organic compound E4 includes the following steps:

[0236]

[0237] In the specific preparation of compound E4, toluene solvent was added to a flask, followed by intermediate 3 (1 eq) and intermediate 6 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration, dried in a vacuum oven for 3 h, and then sublimated to obtain compound E4.

[0238] Mass spectrometry m / z: 734.86, elemental composition (%): C52H34N2O3, C, 84.99; H, 4.66; O, 6.53; N, 3.81.

[0239] 1 H NMR (300MHz, DMSO): 8.43(1H),8.38(1H),8.32(2H),8.29(2H),8.06-8.09(3H),7.99(1H),7.86(1H), 7.63(3H),7.6(1H),7.55(3H),7.37-7.38(5H),7.33(2H),7.21(1H),7.16(1H),6.56(1H),1.69(6H).

[0240] In some optional embodiments, the synthesis of the organic compound E5 includes the following steps:

[0241] Step 1:

[0242]

[0243] In specific implementation step 1, toluene solvent was added to a flask, followed by compound E0 (1 eq) and intermediate 7 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), palladium acetate (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain intermediate 8.

[0244] Step 2:

[0245]

[0246] In specific step 2, toluene solvent was added to the bottle, followed by intermediate 8 (1 eq) and intermediate 4 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration and dried in a vacuum oven for 3 h to obtain the solid. Sublimation of the solid yielded compound E5.

[0247] Mass spectrometry m / z: 741.87, elemental composition (%): C49H31N3O3S, C, 79.33; H, 4.21; O, 6.47; N, 5.66; S, 4.32.

[0248] 1 H NMR (300MHz, DMSO): 8.43(1H),8.38(1H),8.32(2H),8.29(2H),8.18(1H),8.09(1H),8.02(1H),7.85- 7.86(3H),7.63(2H),7.51-7.53(2H),7.37(4H),7.33(2H),7.21(1H),7.16(1H),6.56(1H),1.69(6H).

[0249] In some alternative embodiments, the synthesis of the organic compound E6 includes the following steps:

[0250]

[0251] In the specific preparation of compound E6, toluene solvent was added to a flask, followed by compound E0 (2.1 eq) and intermediate 7 (1 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration, dried in a vacuum oven for 3 h, and then sublimated to obtain compound E6.

[0252] Mass spectrometry m / z: 725.80, elemental composition (%): C49H31N3O4, C, 81.09; H, 4.31; O, 8.82; N, 5.79.

[0253] 1 H NMR (300MHz, DMSO): 8.43(2H),8.38(1H),8.32(2H),8.29(2H),8.09(1H),7.86( 1H),7.63(4H),7.37(4H),7.33(3H),7.21(2H),7.16(1H),6.56(2H),1.69(6H).

[0254] In some alternative embodiments, the synthesis of the organic compound E7 includes the following steps:

[0255] Step 1:

[0256]

[0257] In specific implementation step 1, toluene solvent was added to a bottle, followed by compound E0 (1 eq) and intermediate 9 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain intermediate 10.

[0258] Step 2:

[0259]

[0260] In specific implementation step 2, toluene solvent was added to the bottle, followed by intermediate 11 (1 eq) and intermediate 10 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain the solid. Sublimation of the solid yielded compound E7.

[0261] Mass spectrometry m / z: 846.99, elemental composition (%): C61H38N2O3, C, 86.50; H, 4.52; O, 5.67; N, 3.31.

[0262] 1 H NMR (300MHz, DMSO): 8.38(1H),8.32(2H),8.29(2H),8.09(1H),7.9-8.89(3H),7.86(2H),7.73-7 .74(4H),7.55(1H),7.45(2H),7.37-7.38(5H),7.33(2H),7.27-7.28(5H),7.16(2H),1.69(6H).

[0263] In some alternative embodiments, the synthesis of the organic compound E8 includes the following steps:

[0264]

[0265] In the specific preparation of compound E8, toluene solvent was added to a flask, followed by intermediate 12 (1 eq) and intermediate 8 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration, dried in a vacuum oven for 3 h, and then sublimated to obtain compound E8.

[0266] Mass spectrometry m / z: 814.96, elemental composition (%): C56H34N2O3S, C, 82.53; H, 4.21; O, 5.89; N, 3.44; S, 3.93.

[0267] 1 H NMR (300MHz, DMSO): 8.87(1H),8.43-8.45(2H),8.38(1H),8.32(2H),8.29(2H),8.09(1H),8.05(1H),8.01(3H),7.91( 1H),7.86(1H),7.63-7.64(3H),7.54(2H),7.43(1H),7.37(2H),7.33(2H),7.21(1H),7.16(1H),6.56(1H),1.69(6H).

[0268] In some alternative embodiments, the synthesis of the organic compound E9 includes the following steps:

[0269] Step 1:

[0270]

[0271] In specific implementation step 1, toluene solvent was added to a bottle, followed by compound E0 (1 eq) and intermediate 13 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain intermediate 14.

[0272] Step 2:

[0273]

[0274] In specific step 2, toluene solvent was added to the bottle, followed by intermediate 14 (1 eq) and intermediate 15 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration and dried in a vacuum oven for 3 h to obtain the solid. Sublimation of the solid yielded compound E9.

[0275] Mass spectrometry m / z: 834.29, elemental composition (%): C60H38N2O3, C, 86.31; H, 4.59; O, 5.75; N, 3.36.

[0276] 1 H NMR (300MHz, DMSO): 9.27(1H),8.79(1H),8.37-8.38(2H),8.32-8.33(4H),8.3(1H),8.29(2H),8.12-8.13(3H),8.09(1H),7 .86(1H),7.82(1H),7.7(2H),7.64(2H),7.55(2H),7.52(1H),7.47(1H),7.37(4H),7.33(1H),7.16(1H),6.3(1H),1.69(6H).

[0277] In some optional embodiments, the synthesis of the organic compound E10 includes the following steps:

[0278]

[0279] In the specific preparation of compound E10, toluene solvent was added to a flask, followed by intermediate 10 (1 eq) and intermediate 16 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration, dried in a vacuum oven for 3 h, and then sublimated to obtain compound E10.

[0280] Mass spectrometry m / z: 784.91, elemental composition (%): C56H36N2O3, C, 85.69; H, 4.62; O, 6.11; N, 3.57.

[0281] 1 H NMR (300MHz, DMSO): 9.11(1H),8.7(1H),8.46(1H),8.43(1H),8.38(1H),8.32(2H),8.29(2H),8.09(1H),7.9-7.92 (2H),7.86(1H),7.73-7.75(5H),7.68(1H),7.63(1H),7.55(2H),7.37-7.38(6H),7.33(1H),7.16(1H),1.69(6H).

[0282] In some optional embodiments, the synthesis of the organic compound E11 includes the following steps:

[0283] Step 1:

[0284]

[0285] In specific implementation step 1, toluene solvent was added to a bottle, followed by compound E0 (1 eq) and intermediate 17 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain intermediate 18.

[0286] Step 2:

[0287]

[0288] In specific step 2, toluene solvent was added to the bottle, followed by intermediate 18 (1 eq) and intermediate 19 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain the solid. Sublimation of the solid yielded compound E11.

[0289] Mass spectrometry m / z: 800.98, elemental composition (%): C56H36N2O2S, C, 83.97; H, 4.53; O, 3.99; N, 3.50; S, 4.00.

[0290] 1 H NMR (300MHz, DMSO): 8.38-8.39(2H),8.32(2H),8.29(2H),8.18-8.19(3H),8.09(1H),8.02-8.03(3H), 7.85-7.86(3H),7.55(2H),7.51-7.53(2H),7.42-7.43(4H),7.37(4H),7.33(1H),7.16(1H),1.69(6H).

[0291] In some optional embodiments, the synthesis of the organic compound E12 includes the following steps:

[0292]

[0293] In the specific preparation of compound E12, toluene solvent was added to a flask, followed by intermediate 3 (1 eq) and intermediate 20 (1.05 eq) sequentially. Nitrogen gas was then introduced, and the mixture was heated under reflux for 0.5 h. Sodium tert-butoxide (1.5 eq), Pd₂(Dba)₃ (0.01 eq), and X-Phos (0.02 eq) were then added. Nitrogen gas was then introduced again, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. The filtrate was concentrated, heated, and a small amount of ethanol was added. The mixture was allowed to stand at room temperature for recrystallization twice. The recrystallized solid was obtained by suction filtration, dried in a vacuum oven for 3 h, and then sublimated to obtain compound E12.

[0294] Mass spectrometry m / z: 782.94, elemental composition (%): C57H38N2O2, C, 87.44; H, 4.89; O, 4.09; N, 3.58.

[0295] 1 H NMR (300MHz, DMSO): 8.55(1H),8.38(1H),8.32(2H),8.29(2H),8.19(1H),8.09(2H),8.06(1H),7.99(1H),7.94(1H),7.86(1H) ,7.69(2H),7.63(1H),7.6(1H),7.58(1H),7.55(3H),7.5(1H),7.37-7.38(3H),7.32-7.35(4H),7.2(1H),7.16(2H),1.69(6H).

[0296] It should be noted that, in the preparation of different types of organic compounds in the embodiments of this application, the reactants and reaction conditions can be adjusted according to actual needs. It is easy to understand that when the intermediates are different, the reactants used may be different.

[0297] Table 1 shows the refractive index and Tg data of organic compounds E1-E12 at different wavelengths. As shown in Table 1, on the one hand, compared with comparative compound 1 and comparative compound 2, the organic compounds provided in this application have higher refractive indices at different wavelengths. Therefore, when the organic compounds provided in this application are used as the light extraction layer material of electroluminescent devices, the light extraction efficiency of the device can be significantly improved, higher external quantum efficiency can be obtained, light loss inside the device can be reduced, and the device efficiency can be effectively improved. On the other hand, compared with comparative compound 1 and comparative compound 2, the organic compounds provided in this application have a higher glass transition temperature Tg because the core group (fluorenanthraquinone) is a larger conjugated fused ring group, which effectively increases the thermal stability of the material.

[0298] Table 1. Refractive index and Tg data of organic compounds E1-E12 at different wavelengths.

[0299]

[0300]

[0301] This application provides an organic compound having the structural formula shown in general formula I, wherein L1 and L2 are each independently selected from substituted or unsubstituted C6-C36 arylene groups and substituted or unsubstituted C2-C36 heteroarylene groups, and m and n are each independently selected from integers from 0 to 4. The organic compound provided in this application uses fluorene-anthraquinone as the core group, which has strong rigidity due to its relatively large conjugated fused ring group; and the core group is connected to side chains with aromatic amine structures, so that the side chains cooperate with the core group to give the organic compound a high refractive index. When this organic compound is used as a layer material for organic electronic devices, the light extraction efficiency of the organic electronic devices can be improved.

[0302] Based on the same inventive concept, this application discloses an electroluminescent device, which includes: an emitting layer (EML), a cathode, and an anode stacked together, wherein the emitting layer is disposed between the cathode and the anode; and a capping layer (CPL) disposed on the side of the cathode away from the anode, wherein the material of the capping layer includes the organic compounds described in the embodiments of this application.

[0303] In some optional embodiments, the electroluminescent device can be a top-emitting device or a bottom-emitting device. Taking a top-emitting device as an example, the electroluminescent device further includes at least one of the following: a hole transport region, wherein the hole transport region comprises any one or more of a hole injection layer (HIL), a hole transport layer (HTL), and an electron block layer (EBL), wherein the hole injection layer, the hole transport layer, and the electron block layer are sequentially stacked between the anode and the light-emitting layer along a first direction, wherein the first direction is the direction from the anode to the cathode; and an electron transport region, wherein the electron transport region comprises any one or more of a hole block layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), wherein the hole block layer, the electron transport layer, and the electron injection layer are sequentially stacked between the light-emitting layer and the cathode along the first direction.

[0304] Figure 1 This illustration shows a schematic diagram of the hierarchical structure of an electroluminescent device according to an embodiment of this application, as follows: Figure 1 As shown, the electroluminescent device includes: an anode 102; a hole transport region 103, the hole transport region 103 including a hole injection layer 1031, a hole transport layer 1032, and an electron blocking layer 1033 stacked sequentially, wherein the hole injection layer 1031 is disposed on one side of the anode 102, the hole transport layer 1032 is disposed on the side of the hole injection layer 1031 opposite to the anode 102, and the electron blocking layer 1033 is disposed on the side of the hole transport layer 1032 opposite to the anode 102; a light-emitting layer 104, the light-emitting layer 104 being disposed on the side of the electron blocking layer 1033 opposite to the anode 102; and an electron transport region 105, the electron transport region... The light-emitting region 105 includes a hole-blocking layer 1053, an electron transport layer 1052, and an electron injection layer 1051 stacked sequentially. The hole-blocking layer 1053 is disposed on the side of the light-emitting layer 104 away from the anode 102, the electron transport layer 1052 is disposed on the side of the hole-blocking layer 1053 away from the anode 102, and the electron injection layer 1051 is disposed on the side of the electron transport layer 1052 away from the anode 102. A cathode 106 is disposed on the side of the electron injection layer 1051 away from the anode 102. A light extraction layer 107 is disposed on the side of the cathode 106 away from the anode 102.

[0305] In some optional embodiments, the electroluminescent device further includes a light-assisted layer 108, which is disposed on the side of the light extraction layer 107 away from the anode 102. The refractive index of the light-assisted layer 108 is lower than that of the light extraction layer 107. Through the difference in refractive index between the light-assisted layer and the light extraction layer, a high-low refractive index structure is formed on the light-emitting side, thereby further improving the light extraction efficiency of the electroluminescent device.

[0306] In some optional embodiments, the electroluminescent device further includes an encapsulation layer 109 and a substrate 101, the substrate 101 being disposed on the side of the anode 102 away from the cathode 106; the encapsulation layer 109 being disposed on the side of the light extraction layer 107 away from the anode 102; and when the electroluminescent device further includes the light-assisted layer 108, the encapsulation layer 109 being disposed on the side of the light-assisted layer 108 away from the anode 102.

[0307] In some alternative embodiments, the electroluminescent device may include one or more light extraction layers, wherein, in the case where the electroluminescent device includes multiple light extraction layers, at least one of the multiple light extraction layers is made of the organic compound described in the embodiments of this application.

[0308] In some optional embodiments, the anode 102 can be a high work function electrode material, such as transparent oxide ITO, IZO, etc.; the anode 102 can also be a composite electrode material, such as ITO / Ag / ITO, Ag / IZO, CNT / ITO, CNT / IZO, GO / ITO, GO / IZO, etc.

[0309] In some optional embodiments, the hole injection layer 1031 can be an inorganic oxide, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc.; the hole injection layer 1031 can also be a p-type dopant of a strong electron-withdrawing system or a dopant of a hole transport material, such as hexacyanohexaazatriphenylene, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-p-quinone dimethyl ether (F4TCNQ), 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane, etc.

[0310] In some optional embodiments, the hole transport layer 1032 is a hole transport material with good hole transport characteristics, which can be an aromatic amine, dimethylfluorene or carbazole material and its derivatives, such as NPB, TPD, BAFLP, DFLDPBi, etc.

[0311] In some optional embodiments, the electron blocking layer 1033 (i.e., the light-emitting auxiliary layer) also has good hole transport characteristics and can be a red light-emitting auxiliary layer, a green light-emitting auxiliary layer, or a blue light-emitting auxiliary layer. The electron blocking layer 1033 can be an aromatic amine, dimethylfluorene, or carbazole material, such as CBP, PCzPA, etc.

[0312] In some optional embodiments, the hole blocking layer 1053 and the electron transport layer 1052 can be aromatic heterocyclic compounds, such as imidazole derivatives, imidazopyridine derivatives, benzimidazole-phenanthridine derivatives, and other imidazole derivatives; pyrimidine derivatives, triazine derivatives, and other azine derivatives; quinoline derivatives, isoquinoline derivatives, phenanthrene derivatives, and other compounds containing a nitrogen-containing six-membered ring structure (including compounds with phosphine oxide substituents on the heterocycle, such as OXD-7, TAZ, p-EtTAZ), BPhen, BCP, etc.).

[0313] In some alternative embodiments, the electron injection layer 1051 may be a metal or alkali metal, such as LiF, Yb, Mg, Ca, or their compounds.

[0314] In some alternative implementations, the light-assisted layer 108 may be LiF.

[0315] In some optional embodiments, the electroluminescent device is a blue electroluminescent device, a red electroluminescent device, or a green electroluminescent device. The blue electroluminescent device includes a blue light-emitting layer, the red electroluminescent device includes a red light-emitting layer, and the green electroluminescent device includes a green light-emitting layer.

[0316] The luminescent layer 104 can be a phosphorescent host material and a red phosphorescent dopant; the luminescent layer 104 can also be a phosphorescent host material and a green phosphorescent dopant; the luminescent layer 104 can also be a fluorescent host material and a fluorescent dopant. Each host material can be a single material or a mixture of two or more materials.

[0317] The host material (GH) of the blue luminescent layer can be selected from anthracene derivatives such as ADN and MADN; the guest material (GD) can be pyrene derivatives, fluorene derivatives, perylene derivatives, styrene-amine derivatives, metal complexes, etc., such as TBPe, BDAVBi, DPAVBi, FIrpic, etc.

[0318] The host material (GH) of the green luminescent layer can be selected from coumarin dyes, quinacrine copper derivatives, polycyclic aromatic hydrocarbons, diamine anthracene derivatives, carbazole derivatives, etc., such as DMQA, BA-NPB, Alq3, etc.; the guest material (GD) can be metal complexes, such as Ir(ppy)3, Ir(ppy)2(acac), etc.

[0319] The host material (GH) of the red luminescent layer can be selected from DCM series materials, such as DCM, DCJTB, DCJTI, etc.; the guest material (GD) can be a metal complex, such as Ir(piq)2(acac), PtOEP, Ir(btp)2(acac), etc.

[0320] To enable those skilled in the art to better understand the performance of the organic compounds provided in the embodiments of this application, the performance of electroluminescent devices through some exemplary embodiments will be tested and compared below:

[0321] The electroluminescent device may include: a glass substrate, and an anode, a hole injection layer HIL, a hole transport layer HTL, an electron blocking layer EBL, a light emitting layer EML, a hole blocking layer HBL, an electron transport layer ETL, an electron injection layer EIL, a cathode, and a light extraction layer, which are sequentially stacked on the glass substrate.

[0322] In some optional embodiments, the fabrication process of the electroluminescent device under test is as follows:

[0323] (1) The glass plate with ITO was ultrasonically treated in a cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone-ethanol mixed solvent, and baked in a clean environment until all moisture was removed.

[0324] (2) Place the glass substrate with the anode into the vacuum chamber and evacuate to 1×10⁻⁶. -5 ~1×10 -6 Hole injection material is vacuum-deposited onto the aforementioned anodic layer film to form a hole injection material.

[0325] (3) Hole transport material is vapor-deposited on the hole injection layer to form a hole transport layer.

[0326] (4) Vacuum evaporation deposition of an electron blocking layer for the hole transport device on top of the hole transport layer;

[0327] (5) A light-emitting layer of the device is vacuum-deposited on top of the electron blocking layer. The light-emitting layer includes a host material and a guest material. The weight ratio of the host material to the guest material is 90:10 using a multi-source co-evaporation method.

[0328] (6) A hole blocking layer of the device is vacuum-deposited on top of the light-emitting layer;

[0329] (7) Electron transport layer of a vacuum-deposited device above a hole blocking layer;

[0330] (8) Vacuum evaporation of an electron injection layer on an electron transport layer (ETL).

[0331] (9) Evaporate the cathode onto the electron injection layer.

[0332] (10) A light-extracting layer is deposited on the cathode by evaporation.

[0333] Table 2 shows the chemical structures of some of the materials used in the embodiments of the electroluminescent devices. As shown in Table 2, the organic electroluminescent devices to be tested and the comparative electroluminescent devices were fabricated by evaporating the materials shown in Table 2 into different functional layers using the above embodiments.

[0334] Table 2 shows the chemical structures of some materials used in the embodiments of electroluminescent devices.

[0335]

[0336]

[0337]

[0338] Table 3 shows the performance data of an embodiment of the blue electroluminescent device. The hierarchical structure of the blue electroluminescent device under test is: ITO / m-MTDATA:F4TCNQ (3%, 10nm) / m-MTDATA (110nm) / CBP (5nm) / BH:BD (5%, 20nm) / TPBI (5nm) / BCP:Liq (1:1, 30nm) / Yb (1nm) / Mg:Ag (13nm) / CPL (65nm). As shown in Table 3:

[0339] Table 3 Performance data of embodiments of blue electroluminescent devices

[0340]

[0341]

[0342] As shown in Table 3, the blue electroluminescent device using the organic compound provided in the embodiments of this application as the light extraction layer material has higher light extraction efficiency and stability compared to Comparative Example 1 and Comparative Example 2, and also has greater luminous efficiency and device lifespan, thus having better practical value.

[0343] Table 4 shows the performance data of an embodiment of the green electroluminescent device. The hierarchical structure of the green electroluminescent device under test is: ITO / m-MTDATA:F4TCNQ (3%, 10nm) / m-MTDATA (110nm) / CBP (5nm) / GH:GD (10%, 40nm) / TPBI (5nm) / BCP:Liq (1:1, 30nm) / Yb (1nm) / Mg:Ag (13nm) / CPL (65nm). As shown in Table 4:

[0344] Table 4 Performance data of embodiments of green electroluminescent devices

[0345]

[0346]

[0347] As shown in Table 4, the green electroluminescent device using the organic compound provided in the embodiments of this application as the light extraction layer material has higher light extraction efficiency and stability compared to Comparative Example 1 and Comparative Example 2, and also has greater luminous efficiency and device lifespan, thus having better practical value.

[0348] Table 5 shows the performance data of an embodiment of the red electroluminescent device. The hierarchical structure of the red electroluminescent device under test is: ITO / m-MTDATA:F4TCNQ (3%, 10nm) / m-MTDATA (110nm) / CBP (5nm) / RH:RD (3%, 45nm) / TPBI (5nm) / BCP:Liq (1:1, 30nm) / Yb (1nm) / Mg:Ag (13nm) / CPL (65nm). As shown in Table 5:

[0349] Table 5 Performance data of embodiments of red electroluminescent devices

[0350]

[0351]

[0352] As shown in Table 5, the red electroluminescent device using the organic compound provided in the embodiments of this application as the light extraction layer material has higher light extraction efficiency and stability compared to Comparative Example 1 and Comparative Example 2, and also has greater luminous efficiency and device lifespan, thus having better practical value.

[0353] A third aspect of this application provides a display device, the display device including the electroluminescent device as described in the second aspect.

[0354] In one alternative implementation, the display device may include a plurality of electroluminescent devices. For example, the display device may include a red electroluminescent device, a blue electroluminescent device, and a green electroluminescent device.

[0355] It should be noted that the display device can be any product or component with display function. For example, the display device can be a mobile phone, tablet computer, laptop computer, television, monitor, smart bracelet, or other products or components.

[0356] The various embodiments in this specification are described in a progressive manner, with each embodiment focusing on the differences from other embodiments. The same or similar parts between the various embodiments can be referred to each other.

[0357] While preferred embodiments of the present disclosure have been described, those skilled in the art, upon learning the basic inventive concept, can make other changes and modifications to these embodiments. Therefore, the appended claims are intended to be interpreted as including both the preferred embodiments and all changes and modifications falling within the scope of the present disclosure.

[0358] Finally, it should be noted that in this document, relational terms such as "first" and "second" are used only to distinguish one entity or operation from another, and do not necessarily require or imply any such actual relationship or order between these entities or operations. Furthermore, the terms "comprising," "including," or any other variations thereof are intended to cover non-exclusive inclusion, such that a process, method, article, or terminal device that comprises a list of elements includes not only those elements but also other elements not expressly listed, or elements inherent to such a process, method, article, or terminal device. Without further limitations, an element defined by the phrase "comprising one..." does not exclude the presence of other identical elements in the process, method, article, or terminal device that includes said element.

[0359] The above provides a detailed description of an organic compound, an electroluminescent device, and a display device provided in this application. Specific examples have been used to illustrate the principles and implementation methods of this application. The descriptions of the above embodiments are only for the purpose of helping to understand the method and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An organic compound, characterized in that, The organic compound has the structural formula shown in general formula I: Wherein, L1 and L2 are each independently selected from substituted or unsubstituted C6-C36 arylene groups and substituted or unsubstituted C2-C36 heteroarylene groups, and m and n are each independently selected from integers from 0 to 4; R1 and R2 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6.

2. The organic compound according to claim 1, characterized in that, Ar1 has the following structural formula as shown in General Formula II: in, Indicates the linkage site of the functional group; Z is selected from C(R3) or N, and X1 is selected from any one of O, S, C(R4R5) and N(R6).

3. The organic compound according to claim 1, characterized in that, Ar2 has the following structural formula as shown in general formula III: in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

4. The organic compound according to claim 1, characterized in that, Ar3 has the following structural formula as shown in general formula IV: in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

5. The organic compound according to claim 1, characterized in that, Ar4 has the following structural formula as shown in general formula V: in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

6. The organic compound according to claim 1, characterized in that, Ar5 has the following structural formula as shown in general formula VI: in, Z represents the linkage site of the group, and Z is selected from C(R3) or N.

7. The organic compound according to claim 1, characterized in that, Ar6 has the following structural formula as shown in general formula VII: in, Indicates the linkage site of the functional group; Y is selected from any one of O, S, C(R4R5) and N(R6); Ring A and ring B are each independently selected from any one of the following: substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, or substituted or unsubstituted phenanthrene ring.

8. The organic compound according to any one of claims 2 to 6, characterized in that, R3 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

9. The organic compound according to claim 2 or 7, characterized in that, R4 and R5 are each independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; R4 and R5 are not linked together or are linked to form substituted or unsubstituted rings; R6 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

10. The organic compound according to claim 1, characterized in that, Ar1 is selected from any of the substituents in the following structural formulas:

11. The organic compound according to claim 1, characterized in that, Ar2 is selected from any of the substituents in the following structural formulas:

12. The organic compound according to claim 1, characterized in that, Ar3 is selected from any of the substituents in the following structural formulas:

13. The organic compound according to claim 1, characterized in that, Ar4 is selected from any of the substituents in the following structural formulas:

14. The organic compound according to claim 1, characterized in that, Ar5 is selected from any of the substituents in the following structural formulas:

15. The organic compound according to claim 1, characterized in that, Ar6 is selected from any of the substituents in the following structural formulas:

16. The organic compound according to claim 1, characterized in that, The organic compound includes any one of the following structural formulas:

17. The organic compound according to claim 1, characterized in that, The refractive index of the organic compound at a wavelength of 460 nm is greater than or equal to 2.08 and less than or equal to 2.

5. The refractive index of the organic compound at a wavelength of 530 nm is greater than or equal to 1.98 and less than or equal to 2.

24. The organic compound has a refractive index at a wavelength of 620 nm that is greater than or equal to 1.93 and less than or equal to 2.

14.

18. An electroluminescent device, characterized in that, The electroluminescent device includes: A light-emitting layer, a cathode, and an anode are stacked together, with the light-emitting layer disposed between the cathode and the anode; A light extraction layer is disposed on the side of the cathode opposite to the anode, and the material of the light extraction layer includes an organic compound as described in any one of claims 1 to 17.

19. The electroluminescent device according to claim 18, characterized in that, The electroluminescent device further includes at least one of the following: A hole injection layer, a hole transport layer, and an electron blocking layer are stacked sequentially between the anode and the light-emitting layer along a first direction, wherein the first direction is the direction from the anode to the cathode; A hole blocking layer, an electron transport layer, and an electron injection layer are stacked sequentially between the light-emitting layer and the cathode along the first direction.

20. A display device, characterized in that, The display device includes the electroluminescent device as described in claim 18 or 19.

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