A heteroaryl organic compound, and a preparation method and application thereof

Abstract

The application provides a heteroaryl organic compound and a preparation method and application thereof, and belongs to the technical field of semiconductors. The heteroaryl organic compound provided by the application has a structure shown in general formula (1), the structure contains both nitrogen heterobenzene and benzoxazole or benzothiazole, and the nitrogen heterobenzene is connected to a heteroaryl structure at three specific sites, has a high visible light refractive index in the visible light field, and can effectively improve the light extraction efficiency of an OLED device when applied to the OLED device as a cover layer. The results of examples show that when the heteroaryl organic compound provided by the application is used as a cover layer of an electroluminescent device, the current efficiency of the device is 140.5-158.4@10mA / cm 2 Compared with the existing CP-1, CP-2, CP-3, CP-4 and CP-5 as a cover layer, the current efficiency is obviously improved.

Description

Technical Field

[0001] This invention relates to the field of semiconductor technology, and in particular to a heteroaryl organic compound, its preparation method, and its application. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a technology that uses organic materials to emit light through carrier injection and recombination under the influence of an electric field. They convert electrical energy into light energy through organic light-emitting materials. Essentially, an OLED is a thin-film stacked device. Theoretically, when both the anode and cathode are transparent electrodes, the light emitted from the light-emitting layer can propagate from either the anode or the cathode to the outside of the device. Therefore, based on the different light propagation paths, devices can be classified as bottom-emitting devices and top-emitting devices.

[0003] In a bottom-emitting device, light propagates from the anode through the substrate to the outside of the device, while in a top-emitting device, light propagates through the cathode to the outside of the device. The different light emission methods of these two devices lead to vastly different applications. If a bottom-emitting device is used in an active matrix structure, its light emission path is organic layer-anode-TFT-substrate. The TFT is a mesh array switch deposited on the substrate. The presence of the TFT further reduces the aperture ratio of the device, causing the emitted light to be reflected and scattered at this point, preventing it from propagating to the outside of the device and severely impacting the display effect. In contrast, the top-emitting device emits light from the cathode side, bypassing the substrate and thus avoiding the TFT structure. This successfully avoids the reduced aperture ratio problem seen in bottom-emitting devices, resulting in a more detailed and clearer image with higher color vibrancy.

[0004] In top-emitting organic electroluminescent devices, the metal cathode layer and the bottom metal reflective layer form a resonant cavity (also called a microcavity), resulting in both constructive and destructive interference. As the viewing angle changes, the distance between the metal cathode layer and the bottom metal reflective layer (i.e., the cavity length of the microcavity) changes accordingly. This leads to significant differences in brightness and color observed at different viewing angles, severely impacting product performance.

[0005] In such light-emitting elements, when light emitted from the light-emitting layer is incident on other films at an angle greater than a certain value, total internal reflection will occur at the interface between the light-emitting layer and the other films. Therefore, only a portion of the emitted light can be utilized. In recent years, to improve light extraction efficiency and reduce color shift, light-emitting elements with a high-refractive-index "coating layer" placed on the outside of a semi-transparent electrode with a low refractive index have been proposed.

[0006] The currently used capping layers are mainly CP-1, CP-2, CP-3, CP-4, and CP-5. Their main problem is that they have low light extraction efficiency, and when applied to OLED devices, the improvement in device luminous efficiency is limited.

[0007] Summary of the Invention

[0008] In view of this, the present invention aims to provide a heteroaryl organic compound, its preparation method, and its application. The heteroaryl organic compound provided by the present invention can improve light extraction efficiency and enhance the performance of OLED devices.

[0009] To achieve the above-mentioned objectives, the present invention provides the following technical solution:

[0010] This invention provides a heteroaryl organic compound having the structure shown in general formula (1):

[0011]

[0012] In general formula (1), X and X1 are independently CH or N; and there is only one of X and X1 that is N;

[0013] L, L1, and L2 are independently single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted diphenylene, or substituted or unsubstituted naphthylene;

[0014] R, R1, and R2 are independently general formulas (2), (3), or substituted or unsubstituted C6-C6. 30 aryl, substituted or unsubstituted C2-C containing one or more heteroatoms 30 Heteroaryl; at least one of R, R1, and R2 is represented by the structure shown in general formula (2);

[0015]

[0016] In general formula (2), X2 is represented as -O- or -S-;

[0017] In general formula (3), Ar1 and Ar2 are independently substituted or unsubstituted C6 to C6. 30 aryl, substituted or unsubstituted C2-C containing one or more heteroatoms 30 Mixed aromatic compounds.

[0018] Preferably, it has the structure shown in general formula (I-1) or general formula (I-2):

[0019]

[0020] Preferably, it has the structure shown in any one of general formulas (Ⅱ-1) to (Ⅱ-4):

[0021]

[0022] Preferably, it has the structure shown in any one of general formulas (Ⅲ-1) to (Ⅲ-4):

[0023]

[0024] Preferably, the structure of the general formula (2) is as follows: The structure of general formula (3) is as follows:

[0025] This invention provides a method for preparing the above-mentioned aryl organic compounds, comprising the following steps:

[0026] Under the action of inorganic base and catalyst, a compound having the structure shown in formula a undergoes a substitution reaction with compounds having the structures shown in formulas b, c and d to obtain aryl organic compounds.

[0027] B(OH)2-LR formula b; B(OH)2-L1-R1 formula c;

[0028] B(OH)2-L2-R2 formula d;

[0029] In formula a, K, K1, and K2 are independently one of F, Cl, Br, and I.

[0030] This invention provides the application of the above-mentioned aryl organic compounds in organic electroluminescent devices or display devices.

[0031] The present invention provides an organic electroluminescent device, comprising a substrate layer, a first electrode layer, an organic light-emitting functional layer, a second electrode layer and a capping layer stacked sequentially, wherein the capping layer is one or more of the above-mentioned aryl organic compounds.

[0032] The present invention provides a display, wherein the cover layer of the display is one or more of the above-mentioned aryl organic compounds.

[0033] This invention provides a heteroaryl organic compound having the structure shown in general formula (1). The heteroaryl organic compound provided by this invention contains both azirbenzene and benzoxazolyl or benzothiazolyl groups, and the azirbenzene is linked at three specific sites in the heteroaryl structure, which has a high visible light refractive index in the visible light field. When used as a capping layer in OLED devices, it can effectively improve the light extraction efficiency of OLED devices.

[0034] Meanwhile, the heteroaryl organic compounds provided by this invention have high glass transition temperatures and molecular thermal stability, requiring lower temperatures for vapor deposition. Furthermore, the decomposition temperature of the material is higher than the vapor deposition temperature, thus effectively avoiding decomposition during vapor deposition and making it suitable for long-term vapor deposition. At the same time, it ensures that no crystallization occurs after the material is formed.

[0035] The results of the examples show that when the heteroaryl organic compounds provided by the present invention are used as a capping layer for electroluminescent devices, the current efficiency of the devices is 140.5–158.4 @ 10 mA / cm². 2 Compared with existing CP-1, CP-2, CP-3, CP-4, and CP-5 as cover layers, the current efficiency is significantly improved.

[0036] This invention provides a method for preparing the above-mentioned heteroaryl organic compounds. This method is simple to operate, low in cost, and easy to implement for industrial mass production. Attached Figure Description

[0037] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device. Detailed Implementation

[0038] This invention provides a heteroaryl organic compound having the structure shown in general formula (1):

[0039]

[0040] In general formula (1), X and X1 are independently CH or N; and there is only one of X and X1 that is N;

[0041] L, L1, and L2 are independently single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted diphenylene, or substituted or unsubstituted naphthylene; L, L1, and L2 may be the same or different;

[0042] R, R1, and R2 are independently general formulas (2), (3), or substituted or unsubstituted C6-C6. 30 aryl, substituted or unsubstituted C2-C containing one or more heteroatoms 30 Heteroaryl; at least one of R, R1, and R2 is represented by the structure shown in general formula (2); R, R1, and R2 may be the same or different;

[0043]

[0044] In general formula (2), X2 is represented as -O- or -S-;

[0045] In general formula (3), Ar1 and Ar2 are each independently represented as substituted or unsubstituted C6~C6. 30 aryl, substituted or unsubstituted C2-C containing one or more heteroatoms30 Mixed aromatic compounds.

[0046] In this invention, Indicates the connection site.

[0047] In this invention, the substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 Among heteroaryl, substituted or unsubstituted phenylene, substituted or unsubstituted diphenylene, and substituted or unsubstituted naphthylene, the substituent is selected from protium, deuterium, halogen, cyano, C1-C2. 20 Alkyl groups, C1-C 20 alkoxy groups, C6-C 20 aryl, C2-C with one or more heteroatoms 20 One or more heteroaryl groups; the heteroatom in the heteroaryl group is nitrogen, oxygen or sulfur.

[0048] In this invention, the heteroaryl organic compound preferably has the structure shown in general formula (I-1) or general formula (I-2):

[0049] The selectable ranges of R, R1, R2, L, L1, and L2 are the same as those mentioned above.

[0050] In this invention, the heteroaryl organic compound preferably has the structure shown in any one of general formulas (II-1) to (II-4):

[0051]

[0052] The selectable ranges of X, X1, R, R1, R2, L, L1, and L2 are the same as those mentioned above.

[0053] In this invention, the heteroaryl organic compound preferably has the structure shown in any one of general formulas (Ⅲ-1) to (Ⅲ-4):

[0054]

[0055] The selectable ranges of X1, X2, R, R1, R2, L, L1, and L2 are the same as those mentioned above.

[0056] In this invention, the heteroaryl organic compound preferably has the structure shown in any one of general formulas (Ⅳ-1) to (Ⅳ-6):

[0057]

[0058] The selectable ranges of R, R1, R2, L, L1, L2, and X2 are the same as those mentioned above.

[0059] In this invention, the heteroaryl organic compound preferably has the structure shown in any one of the general formulas (V-1) to (V-6):

[0060]

[0061] The selectable ranges of R, R1, R2, L, L1, L2, and X2 are the same as those described above.

[0062] In this invention, R, R1, and R2 are independently preferably substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or substituted phenanthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted benzo[a]phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, or substituted or unsubstituted N-phenylcarbazolyl. Azolyl, substituted or unsubstituted N-diphenylcarbazolyl, substituted or unsubstituted N-naphthylcarbazolyl, substituted or unsubstituted N-dibenzofuranylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxolinyl, substituted or unsubstituted quinoxolinyl, substituted or unsubstituted cyclophosphine, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazolyl, substituted or unsubstituted naphridinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoisoxazolyl, substituted or unsubstituted benzoisothiazolyl, substituted or unsubstituted azaindolyl, or one of the general formula (3);

[0063] In this invention, in general formula (3), Ar1 and Ar2 are each independently represented as substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted N-phenylcarbazoyl; Ar1 ​​and Ar2 can also be connected to form a polycyclic ring;

[0064] In this invention, the substituents of the "substituted or unsubstituted" group are selected from one or more of the following: protium atom, deuterium atom, halogen atom, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, phenyl, naphthyl, diphenyl, terphenyl, fluorenyl, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinylbenzimidazolyl, quinoxalinyl, quinazolinyl, cyclolinyl, naphthidyl, fluorenyl, dibenzofuranyl, N-phenylcarbazoyl, and dibenzothiophene.

[0065] In this invention, the structure of general formula (2) is as follows: The preferred structure of general formula (3) is

[0066] The C6~C used in this invention 30 Aryl groups are monovalent groups in carbocyclic aromatic systems comprising 6 to 30 carbon atoms as cyclic atoms, C6 to C4. 30 Non-limiting examples of aryl groups include phenyl, biphenyl, phenanthryl, triphenyl, and naphthyl. When C6–C6… 30 When an aryl group comprises two or more rings, these rings can fused together.

[0067] The C2~C used in this invention 30 A heteroaryl group is a monovalent group comprising a carbocyclic aromatic system having at least one heteroatom selected from N, O, P, and S as a cyclic atom and 2 to 30 carbon atoms. (C2~C) 30 Non-limiting examples of heteroaryl groups include pyridyl, dibenzofuranyl, benzoxazolyl, bisbenzoxazolyl, carbazoleyl, and N-phenylcarbazoleyl. (C2-C2) 30 Non-limiting examples of heteroaryl groups may include divalent groups of the above-mentioned groups. When C2~C 30 When a heteroaryl group comprises two or more rings, these rings can fused together.

[0068] In this invention, C6~C are used. 20 Aryl groups are monovalent groups in carbocyclic aromatic systems comprising 6 to 20 carbon atoms as cyclic atoms, C6 to C6. 20 Non-limiting examples of aryl groups may include phenyl, biphenyl, phenanthryl, triphenyl, and naphthyl. When C6–C6… 20 When an aryl group comprises two or more rings, these rings can fused together.

[0069] In this invention, C2 to C are used 20 A heteroaryl group is a monovalent group comprising a carbocyclic aromatic system having at least one heteroatom selected from N, O, P, and S as the cyclic atom and 2 to 20 carbon atoms. (C2~C) 20 Non-limiting examples of heteroaryl groups include pyridyl, oxadiazolyl, triazinyl, pyrimidinyl, furanyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, bisbenzoxazolyl, carbazoleyl, and N-phenylcarbazoleyl. When C2~C 20 When a heteroaryl group comprises two or more rings, these rings can fused together.

[0070] In this invention, C1~C 20Alkyl groups are groups consisting of 1 to 20 carbon atoms in saturated aliphatic hydrocarbons, which can be branched or straight-chained. (C1-C2) 20 Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, and hexyl. Among these alkyl groups, C1 to C4 alkyl groups are particularly preferred.

[0071] In this invention, C1~C 20 Alkyl groups are alkyl groups with 1 to 20 carbon atoms connected by oxygen bridges, and can be branched or straight-chain, C1 to C2. 20 Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, pentooxy, 2-pentoxy, isopentoxy, neopentoxy, hexoxy, 2-hexoxy, 3-hexoxy, and 3-methylpentoxy.

[0072] In this invention, the heteroaryl organic compound preferably has the structure shown in any one of formulas (1) to (343):

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] This invention provides a method for preparing the above-mentioned aryl organic compounds, comprising the following steps:

[0085] In the presence of inorganic bases and catalysts, compounds with structures shown in formulas a, b, c, and d undergo substitution reactions to yield aryl organic compounds.

[0086] B(OH)2-LR formula b; B(OH)2-L1-R1 formula c;

[0087] B(OH)2-L2-R2 formula d;

[0088] In formula a, K, K1, and K2 are independently one of F, Cl, Br, and I.

[0089] In this invention, the inorganic base is preferably potassium carbonate; the catalyst is preferably Pd(PPh3)4.

[0090] In this invention, the substitution reaction is preferably carried out in an organic solvent, preferably toluene or xylene.

[0091] In this invention, the temperature of the substitution reaction is preferably 110°C and the time is preferably 40 h.

[0092] In this invention, when formulas b, c, and d are different, it is preferred to first perform a first substitution reaction on any one of the compounds with the structures shown in formulas b, c, and d to obtain a first intermediate.

[0093] The first intermediate is then subjected to a second substitution reaction and a third substitution reaction in sequence with the remaining two compounds with the structures shown in formulas b, c, and d to obtain aryl organic compounds.

[0094] In this invention, after the substitution reaction, the resulting substitution reaction solution is preferably post-treated, and the post-treatment preferably includes the following steps:

[0095] The substitution reaction solution was subjected to solid-liquid separation to remove the organic solvent from the resulting liquid. The remaining phase was then separated by silica gel column chromatography to obtain pure aryl organic compounds.

[0096] In this invention, the solid-liquid separation method is preferably filtration; the organic solvent removal method is preferably vacuum rotary evaporation, wherein the vacuum rotary evaporation pressure is preferably -0.09 MPa and the temperature is preferably 85°C. In this invention, the mobile phase for silica gel column separation is ethyl acetate and petroleum ether, wherein the volume ratio of ethyl acetate to petroleum ether is preferably 2:1.

[0097] This invention provides the application of the above-mentioned aryl organic compounds in organic electroluminescent devices or display devices.

[0098] The present invention provides an organic electroluminescent device comprising a substrate layer, a first electrode layer, an organic light-emitting functional layer, a second electrode layer and a capping layer stacked sequentially, wherein the capping layer is one or more of the above-mentioned aryl organic compounds, for improving light extraction efficiency and visual deviation problems.

[0099] In this invention, the organic light-emitting functional layer preferably includes a light-emitting layer, and more preferably includes one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport layer, and an electron injection layer. This invention does not have special requirements regarding the specific materials of the light-emitting layer, hole transport layer, hole injection layer, electron blocking layer, electron transport layer, and electron injection layer; components well-known in the art can be used.

[0100] In this invention, the materials of the first electrode layer and the second electrode layer are preferably metal oxides or combinations of metals and metal oxides. In this invention, the metal oxide is preferably one or more of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2). The combination of metals and metal oxides is preferably ITO / Ag / ITO, IGO / Al / IGO, or AZO / Ag / AZO.

[0101] The present invention does not have any special requirements on the thickness of the substrate layer, the first electrode layer, the organic light-emitting functional layer, and the second electrode layer; thicknesses known to those skilled in the art can be used.

[0102] In this invention, the thickness of the covering layer is preferably 10-1000 nm, preferably 40-140 nm, more preferably 50-90 nm, more preferably 60-80 nm, and most preferably 65-75 nm.

[0103] In this invention, the capping layer is preferably deposited onto the surface of the second electrode layer. The deposition thickness is preferably 60–80 nm, more preferably 60–70 nm. Devices obtained by depositing the compound of this invention within this thickness range as a capping layer exhibit higher quality, greater stability, and higher product yield compared to conventional compound capping layers.

[0104] In this invention, the vapor deposition temperature is preferably 300–370°C, more preferably 330–365°C. By performing vapor deposition at the above temperatures, the compound of this invention, as a coating layer, can effectively improve the light extraction efficiency of the device.

[0105] As a specific embodiment of the present invention, the structural schematic diagram of the organic electroluminescent device is shown below. Figure 1 As shown, Figure 1 In the diagram, 1-substrate layer, 2-anode layer, 3-hole injection layer, 4-hole transport layer, 5-electron blocking layer, 6-light emitting layer, 7-electron transport layer, 8-electron injection layer, 9-cathode layer, and 10-capping layer.

[0106] This invention provides a display, wherein the cover layer of the display is one or more of the aforementioned aryl organic compounds. In this invention, the thickness of the cover layer is preferably 50–80 nm.

[0107] The following detailed description of the heteroaryl organic compounds provided by the present invention, in conjunction with the embodiments, should not be construed as limiting the scope of protection of the present invention.

[0108] Example 1 Synthesis of compound (4)

[0109]

[0110] In a 500 mL three-necked flask, under nitrogen protection, add 0.01 mol of raw material A-1, 0.05 mol of raw material D-1, and 150 mL of toluene. After stirring thoroughly, add 10 mL of 0.02 mol / mL NaOH aqueous solution, and finally add 5 × 10⁻⁶ ppm of NaOH. -5 mol of Pd(PPh3)4 was heated to 110℃ and reacted for 48 h. A sample was spotted onto a TLC plate, showing no remaining starting material A-1, indicating complete reaction. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was subjected to rotary evaporation under reduced pressure (-0.09 MPa, 85℃) until no fraction remained. The filtrate was then passed through a neutral silica gel column (mobile phase: ethyl acetate: petroleum ether = 2:1 volume ratio) to obtain compound (4). Elemental analysis of the structure (molecular formula C) 44 H 26 N4O3): Theoretical values: C, 80.23; H, 3.98; N, 8.51; Measured values: C, 80.26; H, 3.96; N, 8.52. LC-MS: Theoretical value: 658.20, Measured value: 658.14. 1 HNMR(400MHz,Chloroform-d)δ8.87(d,1H),8.10–8.05(m,4H),8.04–8.00(m,2H),7.8 5–7.80(m,2H),7.77(d,1H),7.68–7.64(m,2H),7.61–7.54(m,5H),7.49–7.40(m,9H).

[0111] Examples 2-16

[0112] Synthesis of compound (8)

[0113]

[0114] 1) In a 500mL three-necked flask, under nitrogen protection, add 0.01mol of raw material A-2, 0.012mol of raw material B-1, and 150mL of toluene. After stirring thoroughly, add 10mL of 4mol / L K2CO3 aqueous solution, and finally add 5×10 -5mol of Pd(PPh3)4 was heated to 110℃ and reacted for 24 h. A sample was spotted onto a TLC plate, showing no remaining starting material A-2, indicating complete reaction. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09 MPa, 85℃) until no fraction remained. The filtrate was then passed through a neutral silica gel column (mobile phase: dichloromethane:petroleum ether = 5:3 volume ratio) to obtain intermediate C-1. Elemental analysis of the structure (molecular formula C) is required. 17 H 11 Cl2N): Theoretical values: C, 68.02; H, 3.69; N, 4.67; Measured values: C, 68.04; H, 3.67; N, 4.64. LC-MS: Theoretical value: 299.03, Measured value: 299.11.

[0115] 2) In a 500mL three-necked flask, under nitrogen protection, add 0.01mol of intermediate C-1, 0.03mol of raw material D-1, and 150mL of toluene. After stirring thoroughly, add 2mL of 0.02mol / mL NaOH aqueous solution, and finally add 5×10⁻⁶ NaOH solution. -5 mol of Pd(PPh3)4 was heated to 110℃ and reacted for 40 h. A TLC sample was taken, showing no intermediate C-1 remaining, indicating complete reaction. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09 MPa, 85℃) until no fraction remained. The filtrate was then passed through a neutral silica gel column (mobile phase: ethyl acetate: petroleum ether = 1:1 volume ratio) to give compound 8. Elemental analysis of the structure (molecular formula C) is also provided. 43 H 27 N3O2): Theoretical values: C, 83.61; H, 4.41; N, 6.80; Measured values: C, 83.60; H, 4.40; N, 6.83. LC-MS: Theoretical value: 617.21, Measured value: 617.14. 1 HNMR(400MHz,Chloroform-d)δ8.87(d,1H),8.11–8.04(m,4H),7.82–7.75(m,3 H),7.69–7.63(m,2H),7.62–7.52(m,8H),7.49–7.40(m,8H),7.39–7.33(m,1H).

[0116] Compounds 192 and 284 of this invention were prepared using a similar synthetic procedure to that of compound 4, the difference being the reactants. The reactants A and D used, and the corresponding products, are shown in Table 1.

[0117] Table 1 Raw materials A and D and their corresponding products

[0118]

[0119] Other compounds of the present invention were prepared using a similar synthetic procedure to that of compound 8, except that the reactants A, B, C, and D and the corresponding products are shown in Table 2.

[0120] Table 2 Raw materials A, B, C, and D and their corresponding products

[0121]

[0122]

[0123]

[0124]

[0125] The amount of raw materials B and D used in the synthesis of compound 343 was 0.012 mol each.

[0126] Furthermore, it was determined using 400MHz NMR (JEOL 400MHz) with deuterated chloroform (CDCl3) as the solvent. 1 The results of H-NMR are shown in Table 3.

[0127] Table 3. Proton NMR data of the compounds

[0128]

[0129]

[0130] Application examples

[0131] The following describes in detail the application effects of the OLED material synthesized in the device through Device Examples 1-16 and Device Comparative Examples 1-5. The device fabrication processes of Device Examples 1-16 and Device Comparative Examples 1-5 are completely identical, and the same substrate material and electrode material are used. The film thickness of the electrode material is also kept consistent. The difference lies in the change of the capping layer material in Device Examples 1-16 and Device Comparative Examples 2-5. The performance test results of the devices obtained in each example are shown in Table 4.

[0132] Fabrication process of device comparative example 1:

[0133] a) The substrate layer 1 is transparent glass, and an anode layer 2 (Ag, with a thickness of 100nm) is deposited on the surface of the substrate layer 1 by vacuum evaporation.

[0134] b) HAT-CN with a thickness of 10 nm is deposited on the anode layer 2 by vacuum evaporation to serve as the hole injection layer 3;

[0135] c) HT-1 with a thickness of 140 nm is deposited on hole injection layer 3 by vacuum evaporation to serve as hole transport layer 4.

[0136] d) EB-1 with a thickness of 30 nm is deposited on top of hole transport layer 4 by vacuum evaporation to serve as electron blocking layer 5.

[0137] e) A light-emitting layer 6 is deposited on top of the electron blocking layer 5, with GH-2 and GH-1 as the host materials and GD-1 as the dopant material. The mass ratio of GH-2, GH-1 and GD-1 is 45:45:10 and the thickness is 40nm.

[0138] f) On the light-emitting layer 6, ET-1 and Liq with a mass ratio of 1:1 are vapor-deposited by vacuum evaporation, with a thickness of 40 nm, to serve as the electron transport layer 7.

[0139] g) On top of the electron transport layer 7, LiF with a thickness of 1 nm is vacuum-deposited as the electron injection layer 8;

[0140] h) Above the electron injection layer 8, a Mg:Ag layer with a mass ratio of 1:9 and a thickness of 15 nm is vacuum-deposited as the cathode layer 9.

[0141] i) CP-1 with a thickness of 70 nm is deposited on the cathode layer 9 by vacuum evaporation and used as the capping layer 10.

[0142] After completing the fabrication of the electroluminescent device according to the above steps, the current efficiency of the device was measured, and the results are shown in Table 4. The molecular structural formulas of the relevant materials are shown below:

[0143]

[0144] Table 4 Current efficiency of the devices

[0145]

[0146]

[0147]

[0148] The test data of the obtained electroluminescent devices are shown in Table 5.

[0149] Table 5 shows the test data of the electroluminescent devices.

[0150]

[0151]

[0152] Note: Current efficiency was tested using an IVL (current-voltage-luminance) testing system at a current density of 10 mA / cm². 2 .

[0153] As can be seen from the results in Table 5, when the organic compound provided by the present invention is applied to the fabrication of OLED light-emitting devices, the light extraction is significantly improved compared with devices in Comparative Examples 1 to 5, and the device efficiency is improved at the same current density.

[0154] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A heteroaryl organic compound, said heteroaryl organic compound having any one of the following structures: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。 2. The use of the aryl organic compounds of claim 1 in organic electroluminescent devices or display devices.

3. An organic electroluminescent device, comprising a substrate layer, a first electrode layer, an organic light-emitting functional layer, a second electrode layer, and a capping layer stacked sequentially, characterized in that, The coating layer is an aryl organic compound as described in claim 1.

4. A display, characterized in that, The cover layer of the display is an aryl organic compound as described in claim 1.

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