An organic electron transport material containing naphthalene and benzonitrile groups and use thereof

Abstract

This invention relates to an organic electron transport material containing naphthalene and benzyl nitrile groups and its applications. By introducing benzyl and triazine groups at the 1,4 positions of naphthalene, this invention improves the material's thermal stability and film-forming properties, and increases its electron mobility. The organic electroluminescent compound provided by this invention exhibits high thermal stability and film-forming properties, as well as strong electron mobility. Organic electroluminescent devices fabricated using this compound demonstrate excellent luminous efficiency and longer device lifetime.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, specifically to an organic electronic material containing naphthalene and benzyl nitrile groups, its preparation method, and its applications. Background Technology

[0002] Organic light-emitting diodes (OLEDs), as a novel display technology, and related research began as early as 1963 when Pope et al. first discovered the electroluminescence phenomenon of single-crystal anthracene, an organic compound. In 1987, Dr. Ching W. Tang of Kodak reported on OLED devices prepared using diaromatic diamine as hole transport material and lithium 8-hydroxyquinoline as both the light-emitting and electron transport materials. Since then, OLEDs have developed rapidly and become a mainstream display technology.

[0003] Typical organic light-emitting diodes (OLEDs) employ a sandwich structure, where an organic layer is sandwiched between an anode and a cathode. Driven by an external voltage, holes and electrons overcome energy barriers and are injected into the hole transport layer and electron transport layer through the anode and cathode, respectively. They then recombine in the light-emitting layer, releasing energy and transferring it to the organic light-emitting material. This energy allows the light-emitting material to transition from its ground state to an excited state. When the excited molecules return to the ground state, light emission occurs.

[0004] Electron transport materials are materials that transport electrons from the cathode to the light-emitting layer. They are an important component of organic electroluminescent devices and help to reduce the electron injection energy barrier. Some commonly used electron transport materials contain organic compounds such as imidazole, thiazolyl, phenanthroline and thiazole. These compounds generally require good thermal stability and photoelectric properties.

[0005] Although organic electroluminescent devices have been gradually improved recently, materials with better performance in terms of luminous efficiency, driving voltage, and lifetime are still required. Therefore, it is necessary to develop electron transport materials with good thermal stability and excellent performance. Summary of the Invention

[0006] The purpose of this invention is to provide an organic electron transport material containing naphthalene and benzyl nitrile groups and its application in organic electroluminescent devices, overcoming the technical problem of poor stability in existing organic electron transport materials. This invention improves the thermal stability and film-forming properties of the material and increases its electron mobility by introducing benzyl and triazine groups at the 1,4 positions of naphthalene. The organic electron transport material containing naphthalene and benzyl nitrile groups provided by this invention also exhibits strong electron mobility, and organic electroluminescent devices made from it have excellent luminous efficiency and longer device lifetime.

[0007] An organic electron transport material containing naphthalene and benzyl nitrile groups according to the present invention comprises a compound of structural formula I:

[0008]

[0009] Where Ar1 is represented as C1-C 30 The substituted benzyl nitrile is C1-C 30 The substitution is a substituted pyridinyl group;

[0010] Ar2-Ar3 are independently represented as C6-C 30 The unsubstituted aryl group is replaced, C3-C 30 Substituted or unsubstituted heteroaryl groups;

[0011] L is a single bond, C6-C 30 Substituted or unsubstituted aryl group, C3-C 30 One of the substituted or unsubstituted heteroaryl groups;

[0012] One or more of Z1-Z3 are N, and the rest are CH.

[0013] Preferably, Ar1 is represented as benzyl nitrile, methylbenzyl nitrile, dimethylbenzyl nitrile, pyridyl, methylpyridyl, dimethylpyridyl or phenylpyridyl.

[0014] Preferably, Ar2 is phenyl, deuterated phenyl, or tolyl.

[0015] Preferably, Ar1 and Ar3 are one of phenyl, tolyl, biphenyl, naphthyl, phenanthryl, anthracene, perylene, fluoranthyl, pyrene, phenylnaphthyl, naphthylphenyl, diphenylphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-spirodifluorenyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, spiro[fluoren-9,9'-oxazanthyl], pyridyl, benzylphenyl, pyridylphenyl, indolyl, carbazoleindolyl, fluorencarbazole, imidazolyl, oxazolyl, thiazolyl, thiadiazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, azadibenzofuranyl, azadibenzothiopheneyl, and the above aryl and heteroaryl groups may further be C1-C 12 Alkyl substitution.

[0016] Preferably, L is phenyl, biphenyl, naphthyl, phenylnaphthyl, 9,9-dialkylfluorenyl, arylphenyl, or anthracene.

[0017] The so-called hydrogen atom in this invention includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0018] More preferably, the organic electronic material includes, but is not limited to, any one of the following compounds 1-48:

[0019]

[0020]

[0021]

[0022]

[0023]

[0024] The aforementioned organic electronic materials can be used to prepare organic electroluminescent devices, which include an anode, a cathode, and an organic layer.

[0025] The organic layer comprises one or more of the following: a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and an electron transport layer.

[0026] At least one of the organic layers contains an organic electronic material of the above-described structural formula I.

[0027] Preferably, the electron transport layer or electron injection layer in the organic layer contains an organic electronic material of the above-described structural formula I.

[0028] Preferably, the hole-blocking layer in the organic layer contains the aforementioned organic electronic material.

[0029] When the aforementioned organic electronic materials are used as electron transport materials, they can be doped with organometallic complexes, such as lithium 8-hydroxyquinoline, wherein the doping mass content of the metal complex is 20-70 wt%.

[0030] The total thickness of the organic layer is 1-1000 nm; more preferably, the total thickness of the organic layer is 50-500 nm.

[0031] Each organic layer in the organic electroluminescent device of the present invention can be prepared by vacuum evaporation, molecular beam evaporation, solvent-based dip coating, spin coating, bar coating or inkjet printing. Metal electrodes can be prepared by evaporation or sputtering.

[0032] The aforementioned organic electronic materials can also be applied to organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, and organic photosensors.

[0033] The beneficial effects of this invention are as follows:

[0034] 1. An organic electron transport material containing naphthalene and benzyl nitrile groups according to the present invention, with naphthalene as the bridging chain, has a better conjugated system, which can increase the stability of the material.

[0035] 2. An organic electron transport material containing naphthalene and benzyl nitrile groups according to the present invention, wherein a 3-phenyl-4-benzyl-phenyl group is introduced at the 1-position of naphthalene and a substituted triazine group is introduced at the 4-position of naphthalene. The synergistic effect of the two increases the electronegativity of the material, improves the electron transport performance of the material, and can reduce the operating voltage of the device.

[0036] 3. An organic electron transport material containing naphthalene and benzyl nitrile groups according to the present invention, wherein the introduction of a 3-phenyl-4-benzyl-phenyl group at the 1-position of naphthalene can increase the stability of the material, and the glass transition temperature of the prepared electron transport material is greater than 135 degrees, which can meet the temperature requirements for its use as an electron transport material.

[0037] 4. An organic electron transport material containing naphthalene and benzyl nitrile groups according to the present invention can be used as an electron transport material in organic electroluminescent devices to improve the high luminous efficiency of the devices and extend their service life. Attached Figure Description

[0038] Figure 1 This is a differential scanning calorimeter of compound 3.

[0039] Figure 2 This is a differential scanning calorimeter of compound 9.

[0040] Figure 3 Differential scanning calorimetry (DSC) of compound 25.

[0041] Figure 4 This is a differential scanning calorimeter of compound 43.

[0042] Figure 5 This is a schematic diagram of an organic electroluminescent device. Detailed Implementation

[0043] The present invention will now be further described with reference to the accompanying drawings and specific embodiments. However, the following embodiments are merely preferred embodiments of the present invention and not all embodiments. Other embodiments obtained by those skilled in the art based on the embodiments described herein without inventive effort are all within the protection scope of the present invention.

[0044] Examples 1 to 6 below describe in detail the synthesis process of some intermediates and / or compounds of the present invention. The synthesized intermediates or products were separated by column chromatography, followed by nuclear magnetic resonance mass spectrometry (NMR mass spectrometry). 1 H NMR), high-resolution mass spectrometry (H NMR), 1 Molecular structure characterization was performed using HRMS.

[0045] Example 1

[0046] Synthesis of intermediate 3-1

[0047]

[0048] 4'-chloro-[1,1':2',1”-terphenyl]-4-carboxynitrile (5.0 g, 17.26 mmol), 1-naphthoboric acid (3.1 g, 18.02 mmol), and potassium carbonate (3.6 g, 26.05 mmol) were added, followed by toluene (30 mL), ethanol (15 mL), and deionized water (15 mL). Under nitrogen protection, ditriphenylphosphine palladium chloride (0.1 g, 0.14 mmol) was added, and the mixture was refluxed for 10 h. The mixture was separated into liquid and liquid phases, the organic phase was concentrated to dryness, and the crude product was separated by column chromatography to give 4.6 g of white solid, with a yield of 70%.

[0049] Hydrogen nuclear magnetic resonance (HMR) spectroscopy (also known as protium spectroscopy) is an application of nuclear magnetic resonance spectroscopy that utilizes the nuclear magnetic resonance effect of H-1 (H-1 atom, i.e., protium) atoms in molecules. When a sample contains hydrogen, especially the isotope hydrogen-1, HMR spectroscopy can be used to determine the molecular structure. Currently, 1 ¹H NMR has become the primary technique for determining the structure of organic compounds. Its basic principle is that, due to the shielding effect of electrons, even within the same molecule, hydrogen nuclei in different environments (different functional groups) still possess different magnetic fields and absorb energy at different frequencies. Therefore, magnetic resonance occurs at different frequencies. Through this method, hydrogen nuclei in different environments can be identified, and chemical shifts (denoted by the symbol δ, in ppm) serve as important reference data, applied to the structural analysis and configuration determination of reactants or products in organic compounds. The ¹H NMR data for intermediate 3-1 are as follows: 1 H NMR (400MHz, CDCl3) δ:7.98-8.01(m,1H),7.87-7.91(m,3H),7.58-7.71(m,7H),7.46-7.55(m,7H),7.38-7.42(m,1H).

[0050] Synthesis of intermediate 3-2

[0051]

[0052] Intermediate 3-1 (4.0 g, 10.49 mmol) and dichloromethane (40 mL) were added to a single-necked flask. Liquid bromine (2.2 g, 13.77 mmol) was dispersed in dichloromethane (10 mL) and added dropwise to the intermediate 3-1 solution. The mixture was stirred at room temperature for 3 h. The reaction was quenched with sodium hydroxide / sodium sulfite aqueous solution until neutral. The mixture was separated, and the organic phase was concentrated to approximately 10 mL. After stirring for 1 h, a solid precipitated. 10 mL of ethanol was added and the mixture was stirred for 0.5 h. The mixture was filtered, washed with ethanol, and the filter cake was dried to obtain 3.8 g of white solid, with a yield of 79%. The proton NMR spectrophotometer data of intermediate 3-2 are as follows: 1H NMR (400MHz, CDCl3) δ: 8.03-8.06 (m, 1H), 7.74-7.89 (m, 3H), 7.63-7.67 (m, 3H), 7.53-7.60 (m, 6H), 7.45-7.50 (m, 3H), 7.39-7.44 (m, 2H).

[0053] Synthesis of Compound 3

[0054]

[0055] Intermediate 3-2 (1.0 g, 2.17 mmol), 2,4-diphenyl-6-(4-phenylboronic acid ester)-1,3,5-triazine (1.0 g, 2.30 mmol), and potassium carbonate (0.45 g, 3.26 mmol) were added to a three-necked flask, followed by toluene (6 mL), tetrahydrofuran (3 mL), and deionized water (3 mL). Under nitrogen protection, ditriphenylphosphine palladium chloride (0.01 g, 0.014 mmol) was added, and the mixture was refluxed for 8 h. A solid precipitated, was filtered, washed with ethanol, and separated by column chromatography with a PE / DCM ratio of 4 / 1-2 / 1. The solution was concentrated to dryness and dried to give 0.98 g of a white solid, with a yield of 65%. The proton NMR spectrophotometer data for compound 3 are as follows: 1 H NMR (400MHz, CDCl3)δ:8.18-8.21(m,4H),7.96-8.00(m,2H),7.75-7.85(m,5H),7.54-7.67(m,8H),7.47-7.51(m,2H),7.34-7.44(m,11H).

[0056] High-resolution mass spectrometry (HRMS) can provide the precise mass of ions or fragment ions in organic compound molecules, and based on this precise mass information, the molecular formula of the compound can be determined. The HRMS characterization results of compound 3 are as follows: HRMS (ESI, m / z): [M+H] + calcd for:C 50 H 33 N4,689.2700,found,689.2697.Anal.:calcd:C,87.18;H,4.68;N,8.13;found:C,87.13;H,4.65;N,8.18.

[0057] Example 2

[0058] Synthesis of Compound 9

[0059]

[0060] The synthesis method and reaction conditions were the same as those for compound 3 in Example 1, and the yield of compound 9 was 67%. The proton NMR spectroscopy data for compound 9 are as follows: 1 ¹H NMR (400MHz, CDCl₃) δ: 8.12–8.22 (m, 4H), 7.98–8.03 (m, 4H), 7.83–7.87 (m, 3H), 7.76–7.79 (m, 2H), 7.62–7.68 (m, 3H), 7.55–7.61 (m, 5H), 7.33–7.54 (m, 13H). The HRMS characterization results of compound 9 are as follows: HRMS (ESI, m / z): [M+H] + calcd for:C 56 H 35 N4O,779.2805,found,779.2802.Anal.:calcd:C,86.35;H,4.40;N,7.19;O,2.05.found:C,86.31;H,4.45;N,7.23;O,2.01.

[0061] Example 3

[0062] Synthesis of Compound 18

[0063]

[0064] The synthesis method and reaction conditions were the same as those for compound 3 in Example 1, and the yield of compound 18 was 63%. The proton NMR spectrophotometer data for compound 18 are as follows: 1 ¹H NMR (400MHz, CDCl₃) δ: 8.19–8.23 (m, 3H), 7.98–8.08 (m, 3H), 7.83–7.87 (m, 3H), 7.76–7.79 (m, 2H), 7.46–7.68 (m, 14H), 7.31–7.44 (m, 11H). The HRMS characterization results of compound 18 are as follows: HRMS (ESI, m / z): [M+H] + calcd for:C 56 H 37 N4,765.3013,found,765.3012.Anal.:calcd:C,87.93;H,4.74;N,7.32.found:C,87.88;H,4.78;N,7.30.

[0065] Example 4

[0066] Synthesis of Compound 25

[0067]

[0068] The synthesis method and reaction conditions were the same as those for compound 3 in Example 1, and the yield of compound 26 was 68%. The proton NMR spectrophotometer data for compound 25 are as follows: 1 ¹H NMR (400MHz, CDCl₃) δ: 8.23–8.26 (m, 1H), 8.16–8.21 (m, 5H), 7.82–7.88 (m, 3H), 7.69–7.78 (m, 3H), 7.57–7.67 (m, 6H), 7.47–7.51 (m, 2H), 7.34–7.44 (m, 12H). HRMS characterization of compound 25 is as follows: HRMS (ESI, m / z): [M+H] + calcd for:C 50 H 33 N4,689.2700,found,689.2703.Anal.:calcd:C,87.18;H,4.68;N,8.13;found:C,87.21;H,4.60;N,8.14.

[0069] Example 5

[0070] Synthesis of intermediate 43-1

[0071]

[0072] The synthesis method was the same as that for intermediate 3-1 in Example 1, and the yield of intermediate 43-1 was 70%. The proton NMR spectrometry data for intermediate 43-1 are as follows: 1 HNMR(400MHz, CDCl3)δ:7.93-7.95(m,1H),7.86-7.90(m,2H),7.72-7.76(m,2H),7.67-7.70(m,2H),7.59-7.65(m,4H),7.46-7.53(m,3H).

[0073] Synthesis of intermediate 43-2

[0074]

[0075] The synthesis method was the same as that for intermediate 3-2, with a yield of 79%. The proton NMR spectrometry data for intermediate 43-2 are as follows: 1 H NMR (400MHz, CDCl3)δ:7.98-8.00(m,1H),7.88-7.90(m,1H),7.72-7.74(m,2H),7.62-7.69(m,2H),7.54-7.59(m,3H),7.39-7.49(m,2H).

[0076] Synthesis of Compound 43

[0077]

[0078] The synthesis method was the same as that for compound 3 in Example 1, and the yield of compound 43 was 68%. The proton NMR spectrophotometer data for compound 43 are as follows: 1 ¹H NMR (400MHz, CDCl₃) δ: 8.18–8.22 (m, 4H), 7.96–8.00 (m, 2H), 7.83–7.88 (m, 2H), 7.75–7.78 (m, 2H), 7.56–7.67 (m, 9H), 7.36–7.44 (m, 8H). The HRMS characterization results of compound 43 are as follows: HRMS (ESI, m / z): [M+H] + calcd for:C 50 H 28 D5N4,694.3014,found,694.3011.Anal.:calcd:C,86.55;H,5.37;N,8.07;found:C,86.58;H,5.33;N,8.09.

[0079] Example 6

[0080] Synthesis of intermediate 46-1

[0081]

[0082] The synthesis method was the same as for intermediate 3-1, with a yield of 71%. The proton NMR spectrometry data for intermediate 46-1 are as follows: 1 H NMR (400MHz, CDCl3) δ:7.98-8.01(m,1H),7.87-7.94(m,4H),7.65-7.71(m,3H),7.46-7.62(m,10H),7.37-7.42(m,1H).

[0083] Synthesis of intermediate 46-2

[0084]

[0085] The synthesis method was the same as for intermediate 3-2, with a yield of 74%. The proton NMR spectrometry data for intermediate 46-2 are as follows: 1 H NMR(400MHz, CDCl3)δ:8.03-8.06(m,1H),7.83-7.89(m,3H),7.74-7.77(m,1H ),7.62-7.68(m,4H),7.53-7.59(m,4H),7.45-7.50(m,3H),7.39-7.44(m,2H).

[0086] Synthesis of Compound 46

[0087]

[0088] The synthesis method was the same as for compound 3, with a yield of 63%. The proton NMR spectrophotometer data for compound 46 are as follows: 1 ¹H NMR (400MHz, CDCl₃) δ: 8.16–8.26 (m, 6H), 7.83–7.92 (m, 4H), 7.63–7.73 (m, 5H), 7.47–7.59 (m, 5H), 7.34–7.44 (m, 12H). HRMS characterization of compound 46 is as follows: HRMS (ESI, m / z): [M+H] + calcd for:C 50 H 33 N4,689.2700,found,689.2705.Anal.:calcd:C,87.18;H,4.68;N,8.13;found:C,87.22;H,4.63;N,8.15.

[0089] The glass transition temperature (Tg) is the temperature at which a material transitions from a glassy state to a rubbery state. At the glass transition temperature, organic compound materials undergo changes in deformation and modulus, and many physical properties, such as volume, coefficient of thermal expansion, specific heat, thermal conductivity, and dielectric constant, also change significantly. Therefore, the glass transition temperature affects the material's performance in use and processing. The glass transition temperatures of the compounds prepared in Examples 1 to 6 of this invention were tested using a SHIMADZU DSC-60Plus differential scanning calorimeter. The test conditions were: under a nitrogen atmosphere, heating and cooling at a rate of 20°C / min from 30°C to 300°C, and the glass transition temperatures (Tg) were measured. The test results are shown in Table 1. Figures 1 to 4 Differential scanning calorimetry (DSC) images of compounds 3, 9, 25, and 43 from the aforementioned embodiments are shown. In the comparative example, the electron transport material used is ET1, whose structural formula is:

[0090]

[0091] Table 1 Physical properties of the compounds

[0092] Example compound <![CDATA[Glass transition temperature T g (°C)]]> 7 3 138.76 8 9 163.87 9 18 145.18 10 25 136.63 11 43 138.59 12 46 135.53 Comparative Example 1 ET1 119.83

[0093] From Table 1 and Figures 1-4Experimental data show that the present invention, represented by chemical formula I, has a high glass transition temperature, increasing from 119.83°C to 135.53-163.87°C compared to other compounds. The addition of a benzene ring significantly improves the glass transition temperature, indicating excellent thermal stability. Good thermal stability enhances the film-forming properties of the material, thereby improving the lifespan of devices fabricated from the material.

[0094] The effects of the compounds of the present invention will be further described in detail below through examples.

[0095] Examples 13 to 18 illustrate the fabrication of organic electroluminescent devices using the aforementioned compounds; detailed structural diagrams are shown below. Figure 5 . Figure 5 In the diagram: 110 represents the glass substrate, 120 represents the anode, 130 represents the hole injection layer, 140 represents the hole transport layer, 150 represents the blocking layer, 160 represents the light-emitting layer, 170 represents the electron transport layer, 180 represents the electron injection layer, and 190 represents the cathode. The specific structure of the organic electroluminescent device of this invention is: glass / anode (ITO) / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / light-emitting layer (EML, main material BH: blue light-emitting material BD) / electron transport layer (ETL, electron transport material: 8-hydroxyquinoline lithium) / electron injection layer (EIL) / cathode (Mg:Ag, 10:1).

[0096] Example 13

[0097] Device fabrication: OLEDs were fabricated using compound 3 prepared in Example 1, and the fabrication method is as follows:

[0098] The transparent conductive ITO glass substrate 110 (with an anode 120) (China Southern Glass Group Co., Ltd.) was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, and then washed in sequence with ethanol, acetone and deionized water. It was baked in a clean environment until all moisture was removed, cleaned with ultraviolet photosynthetic ozone, and then treated with oxygen plasma for 30 seconds.

[0099] The glass substrate with the anode was placed in a vacuum chamber, a vacuum was drawn, and HIL (5nm) was deposited on the ITO as a hole injection layer 130 at a deposition rate of 0.1nm / s.

[0100] Compound HT was deposited on the hole injection layer to form an 80 nm thick hole transport layer 140, with a deposition rate of 0.1 nm / s.

[0101] Electron barrier layer 150 (EB) was deposited on the void transport layer to form a 10 nm thick electron blocking layer. The deposition rate was 0.1 nm / s.

[0102] A 30 nm thick light-emitting layer 160 was deposited on a hole blocking layer, wherein BH was the host light-emitting material and BD was used as the dopant guest material at a weight ratio of 2%, and the deposition rate was 0.1 nm / s.

[0103] A 30 nm thick layer of compound 3 (50% by weight) and LiQ (50% by weight) was deposited on the luminescent layer as an electron transport layer 170. The deposition rate was 0.1 nm / s.

[0104] A 1 nm thick LiQ layer was deposited on the electron transport layer as an electron injection layer 180.

[0105] A 100 nm thick layer of magnesium silver with a doping ratio of 10:1 was deposited in the electron injection layer as the device cathode 190.

[0106] Examples 14-18

[0107] The device was prepared using the same method as in Example 13, except that the electron transport material was replaced with other compounds from Examples 1 to 12 instead of compound 3. The specific electronic materials used in each example are shown in Table 2.

[0108] Comparative Example 1

[0109] The only difference from Example 13 is that compound 3 is replaced with compound ET1 as the electron transport material.

[0110] The structural formula described in the device is as follows:

[0111]

[0112]

[0113] The organic materials mentioned above are all existing, known materials, obtained through market procurement.

[0114] Table 2 Device Structure

[0115]

[0116] The following examples demonstrate the performance testing of the devices prepared according to the present invention, further illustrating the beneficial technical effects of the compound containing general formula I as an organic electronic material.

[0117] Device performance was tested using a Photo Research PR655 spectrometer, and measurements were taken at 10 mA / cm². 2 Operating voltage, efficiency, emission wavelength at current density, and measurements at 30 mA / cm². 2 The time (T90) for the brightness to become 90% of the initial brightness under current density, device performance parameters and test results are shown in Table 3.

[0118] Table 3 Device Performance Parameters

[0119]

[0120] As shown in Table 3, the organic electroluminescent device prepared using the electron transport material of this invention, compared with ET1, exhibits a higher efficiency at 10 mA / cm². 2 The operating voltage for current density is reduced by 0.1-0.5V, current efficiency increases from 7.44cd / A to 8.19-9.21cd / A, and external quantum efficiency increases from 8.8% to 9.5-10.2%. Furthermore, at 30mA / cm... 2 At current densities, the T90 lifespan increased from 116 hours to 151-183 hours, resulting in a significant improvement in lifespan.

[0121] The preferred embodiments of the present invention have been described in detail above. It should be understood that those skilled in the art can make numerous modifications and variations based on the concept of the present invention without creative effort. Therefore, all technical solutions that can be obtained by those skilled in the art based on the concept of the present invention through logical analysis, reasoning, or limited experimentation on the basis of existing technology should be within the scope of protection defined by the claims.

Claims

1. An organic electronic material containing naphthyl and benzyl nitrile groups in its structure, characterized in that, The organic electronic material is any one of the following compounds: 3-22 and 25-48.

2. An organic electron transport material, characterized in that, It is made by doping 20-70 wt% of an organometallic complex with any one of the structures of compounds 3-22 and 25-48 in claim 1.

3. The application of the organic electron transport material of claim 2 in organic electroluminescent devices, organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, and organic photosensors.

4. An organic electroluminescent device prepared using the organic electron transport material of claim 2, comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises one or more of a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and an electron transport layer, and at least one of the organic layers contains the organic electron transport material.

5. The organic electroluminescent device as described in claim 4, characterized in that, The organic layer, including the electron transport layer, electron injection layer, or hole blocking layer, contains the organic electron transport material.

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