Oligoether and amide substituted aromatic hydrocarbon derivative, preparation method therefor and use thereof

Abstract

An oligoether and amide substituted aromatic hydrocarbon derivative, a preparation method therefor and a use thereof, belonging to the field of light-emitting diodes. The oligoether and amide substituted aromatic hydrocarbon derivative has a structure as shown in formula (I). The aromatic hydrocarbon derivative can be doped in a zinc oxide solution, and during the process of forming the solution into a film, the oligoether and amide substituted aromatic hydrocarbon derivative and zinc oxide nanoparticles form a uniform film by means of interaction between amide bonds and ether bonds. The functional oligoether and amide substituted aromatic hydrocarbon derivative can be used to regulate electron transport, and balance device carrier injection.

Description

Oligoether and amide substituted aromatic derivatives and their preparation method and application Technical Field

[0001] The present application relates to an oligoether and amide substituted aromatic derivative and a preparation method and application thereof, belonging to the field of light emitting diodes. Background Art

[0002] Quantum dot light-emitting diodes are currently the most promising application direction for quantum dot materials. In quantum dot light-emitting diodes, since the potential barrier for holes injected through the anode is much higher than that for electrons injected through the cathode, when the device is working, the excess electrons injected will interfere with the normal exciton radiative transition process, generating non-radiative recombination paths such as Auger recombination, reducing the device's luminous efficiency and accelerating device aging.

[0003] At present, the main organic components used in the hole transport layer are: N,N,N',N'-tetrakis(4-methoxyphenyl)-benzidine, polyvinylcarbazole, [N,N'-(4-n-butylphenyl)-N,N'-diphenyl-p-phenylenediamine]-[9,9-di-n-octylfluorenyl-2,7-diyl] copolymer (PFB), etc. However, these organic components and zinc oxide nanoparticles will produce phase separation, and the carrier injection balance cannot be controlled.

[0004] Summary of the Invention

[0005] According to one aspect of the present application, an alcohol-soluble oligoether and amide-substituted aromatic derivative is provided. The aromatic derivative can be doped in a zinc oxide solution. During the film formation process of the solution, the oligoether and amide-substituted aromatic derivative interacts with zinc oxide nanoparticles through amide bonds and ether bonds to form a uniform thin film. The functional oligoether and amide-substituted aromatic derivative can be used to regulate electron transport and balance device carrier injection.

[0006] The oligoether and amide substituted aromatic derivatives have the following structures:

[0007] Wherein, R1 is an oligoether group;

[0008] The oligoether group structure is as follows:

[0009] n is any integer from 1 to 16;

[0010] Ar1 and Ar2 are each independently selected from at least one of a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group.

[0011] Optionally, the number of ring atoms of the arylene and heteroarylene groups is independently 5-50.

[0012] The number of ring atoms in this application refers to the number of atoms constituting the ring.

[0013] Optionally, the arylene group is selected from one or more of the following groups:

[0014] Naphthylene, anthrylene, phenanthrenyl, fluorenylene, spirofluorenylene, biphenylene, diphenylenefluorenyl, 9-9 dioctylfluorenylene, phenylene;

[0015] The heteroarylene group is selected from one or more of the following groups:

[0016] pyridylene, carbazolylene, diphenylamino, triphenylamino, azaanthrylene, benzimidazolylene, benzocarbazolylene, furylene, pyrrolylene, benzofuranylene, pyrazinylene, spirofluorenyloxanthrylene.

[0017] Examples of the biphenylene group in the present application include diphenylene and terphenylene.

[0018] Optionally, Ar1 and Ar2 are each selected from one or more of the following substituted or unsubstituted groups:

[0019] Optionally, the heteroatoms in the heteroarylene group are selected from any one or more of nitrogen, oxygen, sulfur and silicon.

[0020] Optionally, the substituents in the arylene group and heteroarylene group are independently selected from any one or more of cyano, halogen, nitro, and phenyl.

[0021] Optionally, n is any integer from 1 to 2.

[0022] In another aspect, the present application provides a method for preparing the oligoether and amide-substituted aromatic derivatives, comprising the following steps:

[0023] (1) reacting a mixture 1 comprising a substance 1, a catalyst 1, and a solvent 1 to obtain a substance 2;

[0024] (2) reacting a mixture 2 comprising a substance 2, a solvent 2, and a substance 3 to obtain a substance 4;

[0025] (3) reacting a mixture 3 comprising a substance 4, a borate ester, a catalyst 2, a base substance, and a solvent 3 to obtain a substance 5;

[0026] (4) reacting a mixture 4 comprising substance 5, substance 6, catalyst 3, solvent 4, and alkaline solution to obtain the oligoether and amide-substituted aromatic derivatives.

[0027] The structure of substance 1 is as follows:

[0028] Wherein, n is any integer from 1 to 16.

[0029] Optionally, in step (1), the reaction temperature is 20-50° C. and the reaction time is 40-60 h;

[0030] Optionally, in step (2), the reaction conditions are: ice-water bath reaction for 20-28 h;

[0031] Optionally, in step (3), the reaction temperature is 70-90° C. and the reaction time is 40-55 h;

[0032] Optionally, in step (4), the reaction temperature is 70-95° C., and the reaction time is 20-30 h.

[0033] Optionally, in step (1), the reaction temperature is 30-40°C, and the reaction time is 45-55h; preferably, in step (1), the reaction temperature is 35°C, and the reaction time is 48h.

[0034] Optionally, in step (1), the added amounts of substance 1, catalyst 1, and solvent 1 are: (5-15) g: (1-10) mg: 100 mL; preferably, in step (1), the added amounts of substance 1, catalyst 1, and solvent 1 are: 10 g: 5 mg: 100 mL.

[0035] Optionally, solvent 1 is aqueous ammonia.

[0036] Optionally, catalyst 1 is 4-dimethylaminopyridine.

[0037] Optionally, in step (2), the reaction time is 24 hours.

[0038] Optionally, solvent 2 is dichloromethane.

[0039] Optionally, in step (2), the added amounts of substance 2, solvent 2, and substance 3 are: (1-10) g: (40-60) mL: (5-15) g; preferably, the added amounts of substance 2, solvent 2, and substance 3 are: 6 g: 50 mL: 11.1 g.

[0040] Optionally, the borate ester is pinacol diborate.

[0041] Optionally, the alkaline substance is potassium acetate.

[0042] Optionally, the catalyst 2 is palladium chloride.

[0043] Optionally, the solvent 3 is toluene.

[0044] Optionally, in step (3), the added amounts of substance 4, borate ester, catalyst 2, alkaline substance, and solvent 3 are: (1-5) g: (1-5 g): (0.1-0.5) g: (1-5) g: 60 mL; preferably, in step (3), the added amounts of substance 4, borate ester, catalyst 2, alkaline substance, and solvent 3 are: 3.2 g: 3 g: 0.22 g: 2 g: 60 mL.

[0045] Optionally, in step (3), the reaction temperature is 80° C. and the reaction time is 48 h.

[0046] Optionally, the catalyst 3 is 4-triphenylphosphine palladium.

[0047] Optionally, the solvent 4 is toluene.

[0048] Optionally, the alkaline solution is a potassium carbonate solution.

[0049] Optionally, the concentration of the potassium carbonate solution is 0.5-1.5M; preferably, the concentration of the potassium carbonate solution is 1M.

[0050] Optionally, in step (4), the added amounts of substance 5, substance 6, catalyst 3, solvent 4, and alkaline solution are (0.5-2) g: (0.1-0.8) g: (15-25) mg: (15-25) mL: (1-5) mL; preferably, the added amounts of substance 5, substance 6, catalyst 3, solvent 4, and alkaline solution are 0.9 g: 0.4 g: 18 mg: 20 mL: 2 mL.

[0051] Optionally, in step (4), the reaction temperature is 85° C. and the reaction time is 24 h.

[0052] Optionally, substance 3 and substance 6 are independently aromatic hydrocarbons and / or heteroaromatic hydrocarbons;

[0053] The aromatic hydrocarbon and heteroaromatic hydrocarbon are independently substituted by halogen and / or acyl halide groups.

[0054] Optionally, the hydrocarbon and heteroaromatic hydrocarbon are independently substituted by any one or more of cyano, nitro and phenyl.

[0055] Optionally, the number of ring atoms of substance 3 and substance 6 is independently 5-50.

[0056] Optionally, the heteroatom in the heteroaromatic hydrocarbon is selected from any one or more of nitrogen, oxygen, sulfur and silicon.

[0057] Optionally, substance 3 and substance 6 are independently selected from one or more of the following substances substituted with halogen and / or acyl halide groups:

[0058] Pyridine, carbazole, diphenylamine, triphenylamine, naphthalene, anthracene, azaanthracene, benzimidazole, phenanthrene, fluorene, spirofluorene, biphenyl, terphenyl, benzocarbazole, furan, pyrrole, benzofuran, pyrazine, spirofluorene xanthene, diphenylfluorene, 9-9 dioctylfluorene, benzene.

[0059] In another aspect, the present application provides a QLED device, comprising a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a second electrode stacked in sequence; wherein the electron transport layer comprises a functional material;

[0060] The functional material comprises zinc oxide nanoparticles and the above-mentioned oligoether and amide-substituted aromatic hydrocarbon derivatives.

[0061] Optionally, the QLED device further comprises an electron injection layer;

[0062] The electron injection layer is located between the second electrode and the electron transport layer.

[0063] In one embodiment, as shown in FIG1 , the QLED device includes, from bottom to top, a first electrode A10 , a hole injection layer A20 , a hole transport layer A30 , a light-emitting layer A40 , an electron transport layer A50 , an electron injection layer A60 , and a second electrode A70 .

[0064] In one embodiment, as shown in FIG2 , the QLED device includes, from bottom to top, a first electrode B 100 , a hole injection layer B 200 , a hole transport layer B 300 , a light emitting layer B 400 , an electron transport layer B 500 , and a second electrode B 700 .

[0065] In one embodiment, as shown in FIG3 , the QLED device includes, from bottom to top, a first electrode C1000, an electron injection layer C2000, an electron transport layer C3000, a light-emitting layer C4000, a hole transport layer C5000, a hole injection layer C6000, and a second electrode C7000.

[0066] In one embodiment, as shown in FIG4 , the QLED device includes, from bottom to top, a first electrode D 10000 , an electron transport layer D 30000 , a light emitting layer D 40000 , a hole transport layer D 50000 , a hole injection layer D 60000 , and a second electrode D 70000 .

[0067] Optionally, the zinc oxide nanoparticles are further doped with metal elements;

[0068] The metal element is selected from any one or more of magnesium, aluminum, indium and tin.

[0069] Optionally, the doping amount of the metal element in the zinc oxide nanoparticles is 0-15 wt %.

[0070] Optionally, the content of the oligoether and amide-substituted aromatic hydrocarbon derivatives in the zinc oxide nanoparticles is 0-10 wt %, and the content does not include 0.

[0071] Preferably, the content of the oligoether and amide-substituted aromatic hydrocarbon derivatives in the zinc oxide nanoparticles is 0.5-5 wt %; further preferably, the content of the oligoether and amide-substituted aromatic hydrocarbon derivatives in the zinc oxide nanoparticles is 0.5-3 wt %.

[0072] Optionally, the percentage of the oligoether and amide-substituted aromatic derivatives in the zinc oxide nanoparticles is independently selected from any value of 0.5wt%, 1wt%, 1.5wt%, 2wt%, 2.5wt%, 3wt%, 4wt%, 5wt%, 8wt%, 10wt% or any two of the above ranges.

[0073] The beneficial effects of this application include:

[0074] 1) The oligoether and amide substituted aromatic derivatives provided in this application are added to the electron transport layer to avoid phase separation between zinc oxide nanoparticles and additives, and can also regulate the carrier injection balance.

[0075] 2) The oligoether and amide-substituted aromatic derivatives provided in this application are doped in a zinc oxide solution. During the film formation process of the solution, the oligoether and amide-substituted aromatic derivatives interact with zinc oxide nanoparticles to form a uniform film through amide bonds and ether bonds. BRIEF DESCRIPTION OF THE DRAWINGS

[0076] FIG1 is a schematic structural diagram of a QLED device in one embodiment of the present application;

[0077] FIG2 is a schematic structural diagram of a QLED device in another embodiment of the present application;

[0078] FIG3 is a schematic structural diagram of a QLED device in another embodiment of the present application;

[0079] FIG4 is a schematic structural diagram of a QLED device in another embodiment of the present application.

[0080] List of parts and reference numerals:

[0081] 10 First electrode A 20 Hole injection layer A 30 Hole transport layer A

[0082] 40 light-emitting layer A 50 electron transport layer A 60 electron injection layer A

[0083] 70 second electrode A

[0084] 100 First electrode B 200 Hole injection layer B 300 Hole transport layer B

[0085] 400 light-emitting layer B 500 electron transport layer B 700 second electrode B

[0086] 1000 first electrode C 2000 electron injection layer C 3000 electron transport layer C

[0087] 4000 light-emitting layer C 5000 hole transport layer C 6000 hole injection layer C

[0088] 7000 Second Electrode C

[0089] 10000 first electrode D 30000 electron transport layer D 40000 light-emitting layer D

[0090] 50000 hole transport layer D 60000 hole injection layer D 70000 second electrode D DETAILED DESCRIPTION

[0091] The present application is described in detail below with reference to embodiments, but the present application is not limited to these embodiments.

[0092] Unless otherwise specified, the raw materials in the examples of this application were purchased through commercial channels.

[0093] The instrument conditions and instrument used for the NMR test in this application are: 500 MHz, JNM-ECZ500R / S1.

[0094] The performance test instrument of quantum dot light-emitting diodes in this application is an IVL test system built by combining Keithley 2400 SourceMeter and SR-3A spectroradiometer.

[0095] Example 1

[0096] 100 mL of ammonia water was added to a round-bottom flask, followed by the addition of 10 g (75 mmol) of (1), 5 mg of the catalyst 4-dimethylaminopyridine (DMAP), and a magnet. The mixture was sealed and heated and stirred at 35°C for 48 hours. After the reaction, the reaction solution was extracted with dichloromethane, the organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain approximately 6 g of the intermediate product (2) with a yield of approximately 60%. 1 H NMR (500MHz, Chloroform-d) δ3.74(t,J=4.4Hz,1H),3.61(s,2H),3.55(q,J=8.1Hz,1H),2.82(t,J=4.4Hz,1H),1.31–1.21(m,3H).

[0097] Take a round-bottom flask, weigh 6 g of intermediate product (2) (45 mmol) and dissolve it in 50 mL of dry dichloromethane, add 11.1 g (54 mmol) of p-bromobenzoyl chloride and a magnet, place it in an ice-water bath and stir for 24 hours. After the reaction is completed, the reaction solution is washed with water and separated. The organic phase is dried over anhydrous sodium sulfate, and the solvent is removed under reduced pressure by a rotary evaporator and then passed through a silica gel column to obtain about 12.8 g of intermediate product (4) with a yield of 90%; 1 H NMR(500MHz,Chloroform-d)δ7.76–7.70(m,1H),7.71–7.65(m,1H),3.78(t,J=4.1Hz, 1H), 3.61 (s, 2H), 3.55 (q, J = 8.0Hz, 1H), 3.37 (t, J = 4.0Hz, 1H), 1.25 (t, J = 8.0Hz, 2H).

[0098] A three-necked flask was charged with 3.2 g (10 mmol) of the intermediate product (4), 3 g (12 mmol) of biboronic acid pinacol ester (5), 0.22 g (0.3 mmol) of the catalyst PdCl2 (dppf), 2 g of potassium acetate, and a magnet. The flask was sealed and evacuated with nitrogen three times. 60 mL of toluene was injected and the reaction was carried out at 80°C for 48 h. After the reaction was completed, the solid was removed by filtration, and the organic phase was dried over anhydrous sodium sulfate and the organic solvent was removed by rotary evaporation. Petroleum ether / ethyl acetate was used as the column chromatography eluent to obtain 3.4 g of a white solid with a yield of approximately 95%. 1 H NMR(500MHz,Chloroform-d)δ7.96–7.90(m,1H),7.76–7.70(m,1H),3.78(t,J=4.2Hz,1H),3 .61(s,2H),3.55(q,J=8.1Hz,1H),3.37(t,J=4.2Hz,1H),1.40(s,6H),1.25(t,J=8.0Hz,2H).

[0099] 0.9 g (0.25 mmol) (6), 0.48 g (0.1 mmol) 2,7-dibromospirobifluorene (7) and 18 mg (0.0015 mmol) 4-triphenylphosphine palladium were added to a three-necked flask, which was sealed and evacuated with nitrogen three times and protected with nitrogen. 20 mL toluene and 2 mL 1 M potassium carbonate solution were then added. The reaction solution was heated at 85°C for 24 hours. After the reaction was completed, the solid was removed by filtration and the organic phase was dried over anhydrous sodium sulfate, and then the organic solvent was removed by rotary evaporation. Petroleum ether / ethyl acetate was used as column chromatography eluent to obtain 0.7 g of white product (8) with a yield of 89%. 1H NMR(500MHz,Chloroform-d)δ8.05(d,J=7.5Hz,1H),7.95–7.81(m,4H),7.78(ddd,J=9.0,7.4,1.5Hz,1H),7.71–7.51(m,4H),7 .44(dtd,J=20.9,7.5,1.6Hz,1H),6.75(s,1H),3.68–3.41(m,6H),3.40–3.31(m,1H),3.28–3.05(m,2H),1.25(t,J=8.0Hz,3H).

[0100] Example 2

[0101] The synthetic steps of product (6) and the previous products are the same as those in Example 1. The synthetic steps of product (8) are as follows:

[0102] To a three-necked flask, 0.9 g (6) (0.25 mmol), 0.43 g (0.1 mmol) dibromotriphenylamine (7) and 18 mg (0.0015 mmol) 4-triphenylphosphine palladium were added. After sealing, the flask was evacuated with nitrogen three times and protected with nitrogen. Subsequently, 20 mL of toluene and 2 mL of 1 M potassium carbonate solution were added. The reaction solution was heated at 85°C for 24 hours. After the reaction was completed, the solid was removed by filtration and the organic phase was dried over anhydrous sodium sulfate, and then the organic solvent was removed by rotary evaporation. Petroleum ether / ethyl acetate was used as the column chromatography eluent to obtain 0.7 g of white product (8) with a yield of 90%. 1 H NMR(500MHz,Chloroform-d)δ7.86–7.77(m,2H),7.74–7.67(m,2H),7.40–7.27(m,2H),7.30–7.18(m,3H),7.11–7.04(m, 1H), 6.75 (s, 1H), 3.78 (t, J = 4.1Hz, 2H), 3.61 (s, 4H), 3.55 (q, J = 8.0Hz, 2H), 3.37 (t, J = 4.1Hz, 2H), 1.25 (t, J = 8.0Hz, 3H).

[0103] Example 3

[0104] The product (8) in Example 1 was added to a 30 mg / mL ethanol solution of zinc oxide nanoparticles and stirred to prepare solutions containing 3 wt%, 2 wt%, 1 wt%, and 0 wt% (mass percentage of (8) in the zinc oxide nanoparticles), respectively, which were used as raw materials for preparing the electron transport layer of the QLED device. The structure of the prepared QLED device was ITO / PEDOT:PSS / TFB / QDs / ZnO: (8) / Ag, wherein ITO was used as the anode, PEDOT:PSS was used as the hole injection layer, TFB was used as the hole transport layer, QDs was used as the light-emitting layer, ZnO:(8) was used as the electron transport layer, and Ag was used as the cathode.

[0105] The specific steps are as follows:

[0106] Step 1: Cleaning, drying, and surface treatment of the ITO substrate: Ultrasonicate the ITO substrate in pure water for 15 minutes, then ultrasonicate it in ethanol for 15 minutes, then ultrasonicate it in isopropyl alcohol for 15 minutes, and then dry it in an oven for 1 hour. The dried substrate is then transferred to a UV-OZONE device for surface treatment for 15 minutes.

[0107] Step 2: Preparation of functional layers: Spin-coat a layer of PEDOT:PSS on the cleaned ITO substrate and anneal at 150°C for 30 min to a thickness of 45 nm.

[0108] Step 3: Spin-coat the TFB solution onto PEDOT:PSS and anneal at 150 °C for 30 min to a thickness of 25 nm.

[0109] Step 4: Spin-coat the QDs solution onto TFB with a thickness of 30 nm.

[0110] Step 5: Spin-coat the mixed solution of zinc oxide nanoparticles (8) on the QDs layer respectively, and maintain the pressure for 10 minutes under a vacuum environment of 10 Pa to remove the solvent, with a thickness of 30 nm. Devices containing 3wt%, 2wt%, 1wt%, and 0wt% (mass percentage in zinc oxide nanoparticles) of substance (8) as the raw material of the electron transport layer of the QLED device are obtained, and are numbered as sample 1, sample 2, sample 3 and comparison sample 1 respectively.

[0111] Step 6: Finally, transfer the substrate to the evaporation machine and evaporate a layer of Ag with a thickness of 100nm.

[0112] Table 1 Relevant performance tests of quantum dot light-emitting diodes prepared by samples 1, 2, 3 and comparative sample 1

[0113] From the test results in Table 1, it can be seen that when the aromatic hydrocarbon derivatives provided in the present application are used as the electron transport layer for preparing quantum dot light-emitting diodes, the quantum dot light-emitting diodes prepared have better current efficiency and external quantum efficiency. It can be seen that when the aromatic hydrocarbon derivatives proposed in the present application are used as the functional layer of the light-emitting device, they can better control the injection of carriers, achieve device carrier balance, and thus improve the efficiency of the device, which has obvious advantages.

[0114] The above descriptions are merely a few embodiments of the present application and do not constitute any form of limitation to the present application. Although the present application discloses the preferred embodiments as above, they are not intended to limit the present application. Any technical personnel familiar with the present profession, without departing from the scope of the technical solution of the present application, using the technical content disclosed above to make slight changes or modifications are equivalent to equivalent implementation cases and fall within the scope of the technical solution.

Claims

1. An oligoether and amide substituted aromatic derivative, characterized in that: Its structure is shown below: Wherein, R1 is an oligoether group; The oligoether group structure is as follows: n is any integer from 1 to 16; Ar1 and Ar2 are independently selected from at least one of a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group.

2. The oligoether and amide substituted aromatic derivatives according to claim 1, characterized in that: The number of ring atoms of the arylene group and the heteroarylene group is independently 5-50; The arylene group is selected from one or more of the following groups: Naphthylene, anthrylene, phenanthrylene, fluorenylene, spirofluorenylene, biphenylene, diphenylenefluorenylene, 9-9 dioctylfluorenylene, phenylene; The heteroarylene group is selected from one or more of the following groups: pyridylene, carbazolylene, diphenylamino, triphenylamino, azaanthrylene, benzimidazolylene, benzocarbazolylene, furylene, pyrrolylene, benzofuranylene, pyrazinylene, spirofluorenyloxanthrylene.

3. The oligoether and amide substituted aromatic derivative according to claim 1 or 2, characterized in that: The heteroatom in the heteroarylene group is selected from any one or more of nitrogen, oxygen, sulfur and silicon.

4. The oligoether and amide substituted aromatic derivative according to any one of claims 1 to 3, characterized in that: The substituents in the arylene group and the heteroarylene group are independently selected from any one or more of cyano, halogen, nitro and phenyl.

5. A method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 1 to 4, characterized in that: The following steps are included: (1) reacting a mixture 1 including a substance 1, a catalyst 1, and a solvent 1 to obtain a substance 2; (2) reacting a mixture 2 comprising a substance 2, a solvent 2, and a substance 3 to obtain a substance 4; (3) reacting a mixture 3 including a substance 4, a boric acid ester, a catalyst 2, a base substance, and a solvent 3 to obtain a substance 5; (4) reacting a mixture 4 including a substance 5, a substance 6, a catalyst 3, a solvent 4, and an alkaline solution to obtain the oligoether and amide-substituted aromatic derivatives; The structure of substance 1 is as follows: Wherein, n is any integer from 1 to 16; Substance 3 and substance 6 are independently aromatic hydrocarbons and / or heteroaromatic hydrocarbons; The aromatic hydrocarbons and heteroaromatic hydrocarbons are independently substituted by halogen and / or acyl halide groups.

6. The method for preparing oligoether and amide substituted aromatic derivatives according to claim 5, characterized in that: The number of ring atoms in substance 3 and substance 6 is independently 5-50.

7. The method for preparing the oligoether and amide substituted aromatic derivatives according to claim 5 or 6, characterized in that: Substance 3 and substance 6 are independently selected from one or more of the following substances substituted with halogen and / or acyl halide groups: Pyridine, carbazole, diphenylamine, triphenylamine, naphthalene, anthracene, azaanthracene, benzimidazole, phenanthrene, fluorene, spirofluorene, biphenyl, terphenyl, benzocarbazole, furan, pyrrole, benzofuran, pyrazine, spirofluorene xanthene, diphenylfluorene, 9-9 dioctylfluorene, benzene.

8. The method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 5 to 7, characterized in that: The heteroatom in the heteroaromatic hydrocarbon is selected from any one or more of nitrogen, oxygen, sulfur and silicon.

9. The method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 5 to 8, characterized in that: The aromatic hydrocarbon and heteroaromatic hydrocarbon are independently substituted by any one or more of cyano, nitro and phenyl.

10. The method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 5 to 9, characterized in that: In step (1), the added amounts of substance 1, catalyst 1, and solvent 1 are: (5-15) g: (1-10) mg: 100 mL.

11. The method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 5 to 10, characterized in that: In step (2), the added amounts of substance 2, solvent 2, and substance 3 are: (1-10) g: (40-60) mL: (5-15) g.

12. The method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 5 to 11, characterized in that: In step (3), the added amounts of substance 4, borate ester, catalyst 2, alkaline substance, and solvent 3 are: (1-5) g: (1-5 g): (0.1-0.5) g: (1-5) g: 60 mL.

13. The method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 5 to 12, characterized in that: In step (4), the added amounts of substance 5, substance 6, catalyst 3, solvent 4, and alkaline solution are (0.5-2) g: (0.1-0.8) g: (15-25) mg: (15-25) mL: (1-5) mL.

14. The method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 5 to 13, characterized in that: In step (1), the reaction temperature is 20-50° C. and the reaction time is 40-60 h.

15. The method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 5 to 14, characterized in that: In step (2), the reaction conditions are: ice-water bath reaction for 20-28 hours.

16. The method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 5 to 15, characterized in that: In step (3), the reaction temperature is 70-90° C. and the reaction time is 40-55 h.

17. The method for preparing the oligoether and amide substituted aromatic derivatives according to any one of claims 5 to 16, characterized in that: In step (4), the reaction temperature is 70-95° C. and the reaction time is 20-30 h.

18. A QLED device, characterized in that: It includes a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and a second electrode which are sequentially stacked; Wherein, the electron transport layer includes functional materials; The functional material comprises zinc oxide nanoparticles and the oligoether and amide substituted aromatic derivatives according to any one of claims 1 to 4.

19. The QLED device according to claim 18, characterized in that: The QLED device also includes an electron injection layer; The electron injection layer is located between the second electrode and the electron transport layer.

20. The QLED device according to claim 18 or 19, characterized in that: The content of the oligoether and amide substituted aromatic derivatives in the zinc oxide nanoparticles is 0-10wt%, and the content does not include 0.

21. The QLED device according to any one of claims 18 to 20, characterized in that: The content of the oligoether and amide substituted aromatic derivatives in the zinc oxide nanoparticles is 0.5-5 wt %.

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