An organic electronic material containing triazine group and benzonitrile group and its application

Abstract

The present invention relates to an organic electronic material containing triazine and benzonitrile groups in its structure, and a preparation method and application thereof. In the preparation process of the organic electronic material containing triazine and benzonitrile groups in its structure, the electron transport performance and stability of the material can be increased by introducing triazine and benzonitrile groups into the structure, and the operating voltage of the device can also be reduced. The organic electron transport material containing triazine and benzonitrile groups in the present invention is applied as an electron transport material to an organic electroluminescent device, which can improve the high luminous efficiency of the device and extend the service life of the device.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescence, and in particular to a triazine-based and benzonitrile-based organic electronic material and a preparation method and application thereof. Background Art

[0002] In 1963, Pope and his colleagues published an article on electroluminescence from anthracene single crystals. This was the first attempt to perform a photoelectric conversion process on a device based on organic materials. In 1987, Tang et al. from Kodak reported a double-layer organic electroluminescent device (OLED), which greatly reduced the driving voltage of the device (less than 10V) and the brightness exceeded 10 3 cd / m 2 , the efficiency is about 1%, this breakthrough research has triggered a milestone development of OLED. Organic electroluminescent devices (OLEDs) actively emit light, have short response time, high color contrast, and low energy consumption, and are widely used in mobile phones, flat panel displays, televisions, lighting, and car displays.

[0003] General organic electroluminescent devices adopt a sandwich structure, that is, the organic layer is sandwiched between the anode and cathode on both sides. Under the action of external bias, holes (electrons) are injected from the anode (cathode) and migrate to the light-emitting layer (EML) through the hole (electron) transport layer. The light-emitting layer material obtains energy and transitions from the ground state to the excited state. When the excited molecules transition to the ground state again, luminescence occurs.

[0004] Electron transport materials are materials that transfer electrons from the cathode to the light-emitting layer. They are an important component of organic electroluminescent devices and are beneficial for reducing the electron injection barrier. They can also prevent the cathode from contacting the light-emitting layer, which would lead to luminescence quenching. Electron transport materials generally require good thermal stability and film-forming properties, high electron mobility, high electron affinity, and high excited state energy levels.

[0005] In the production process of organic electroluminescent devices, multiple processes such as photolithography, evaporation, and packaging are required. They need to be treated at high temperatures, and Joule heat is also generated when the device is working. These high temperature factors will damage the OLED device, reduce the device efficiency and shorten the life of the device. Therefore, the glass transition temperature of the material can be increased to improve the impact of high temperature on the material and device. Benzonitrile is a commonly used electron acceptor group. The difference between benzonitrile and general electron acceptor groups is that it can expand the conjugation of the benzene ring, promote the construction of the charge transfer state within the molecule, and increase the conjugation, which can effectively balance the LE state and CT state within the molecule. The introduction of benzonitrile as an electron transport material can increase the stability of the compound and improve the electron transport ability of the compound.

[0006] Therefore, in order to overcome the above-mentioned problems of the prior art and further improve the characteristics of the organic electroluminescent device, it is necessary to develop an electron transport material with good thermal stability and excellent performance. Summary of the invention

[0007] In order to overcome the above technical problems existing in the prior art, the object of the present invention is to provide a triazine-based and benzonitrile-based organic electronic material and its application in an organic electroluminescent device.

[0008] The organic electronic material provided by the present invention is a compound having the following structural formula I:

[0009]

[0010] Where R represents C 1 -C 30 a substituted or unsubstituted benzonitrile group;

[0011] Ar 1 -Ar 4 Independently denoted as C 6 -C 30 Substituted or unsubstituted aryl, C 3 -C 30 a substituted or unsubstituted heteroaryl group;

[0012] Z 1 -Z 6 In the formula, any 4 or 5 of them are represented by N, and the rest are CH.

[0013] The organic electronic material of the present invention introduces triazine groups, benzonitrile groups, and pyridine / pyrimidine groups at the 1, 3, and 5 positions of benzene, thereby overcoming the technical problem that the existing organic electron transport materials have poor thermal stability, resulting in a low life span of the organic electroluminescent device prepared using the materials. At the same time, the film-forming property of the material is improved, and the electron mobility of the material is increased. Therefore, the organic electroluminescent device prepared using the organic electronic material of the present invention has excellent luminous efficiency and a longer device life span.

[0014] Furthermore, the structural formula I is preferably the following structural formula:

[0015]

[0016] Preferably, R represents benzonitrile, methylbenzonitrile or dimethylbenzonitrile.

[0017] Preferably, Ar 1 -Ar 4The phenyl group is independently represented by phenyl, tolyl, biphenyl, naphthyl, phenanthryl, anthracenyl, peryl, fluoranthenyl, pyrenyl, phenylnaphthyl, naphthylphenyl, diphenylphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-spirobifluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, triphenylenyl, spiro[fluorene-9,9'-xanthene], pyridyl, benzylphenyl, pyridylphenyl, indolyl, carbazole indolyl, fluorene carbazolyl, imidazolyl, oxazolyl, thiazolyl, thiadiazolyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, azadibenzofuranyl, azadibenzothienyl, the above aryl and heteroaryl groups can further be C 1 -C 12 of alkyl substitution.

[0018] More preferably, the organic electronic material includes but is not limited to any one of the following compounds 1-30:

[0019]

[0020]

[0021]

[0022] The above-mentioned organic electronic material can be used to prepare an organic electroluminescent device, which includes an anode, a cathode and an organic layer; the organic layer includes 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 layer of the organic layer contains the organic electronic material of the above-mentioned structural formula I.

[0023] Preferably, the electron transport layer or the electron injection layer in the organic layer contains the organic electronic material of the above structural formula I.

[0024] Preferably, the hole blocking layer in the organic layer contains the above-mentioned organic electronic material.

[0025] When the above organic electronic material is used as an electron transport material, it can be doped with an organic metal complex, such as 8-hydroxyquinoline lithium, wherein the doping mass content of the metal complex is 20-70 wt %.

[0026] The total thickness of the organic layer is 1-1000 nm; more preferably, the total thickness of the organic layer is 50-500 nm.

[0027] Each organic layer in the organic electroluminescent device of the present invention can be prepared by vacuum evaporation, molecular beam evaporation, solvent-dissolved dip coating, spin coating, rod coating or inkjet printing. The metal electrode can be prepared by evaporation or sputtering.

[0028] The above-mentioned 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 photoreceptors.

[0029] The beneficial effects of the present invention are as follows:

[0030] 1. In the structure of an organic electronic material containing a triazine group and a benzonitrile group of the present invention, a benzonitrile group is introduced. Since benzonitrile has a strong electronegativity, the electron transport performance of the target compound can be increased. In addition, the benzonitrile group can form an intermolecular hydrogen bond with the hydrogen atoms on the aromatic ring, which can increase the glass transition temperature of the compound, thereby making the glass transition temperature of the compound of the present invention higher than 120 degrees, thereby increasing the stability of the material, and at the same time, it is also beneficial to reduce the distance between molecules, easily forming a stable film, and facilitating the charge transport of the material.

[0031] 2. In the structure of an organic electron transport material containing a triazine group and a benzonitrile group of the present invention, an aromatic group-substituted triazine group is introduced. Since triphenyl-s-triazine has a higher LUMO (2.71 eV), the injection energy barrier between the cathode and the device can be reduced, thereby reducing the operating voltage of the device.

[0032] 3. In the structure of an organic electron transport material containing a triazine group and a benzonitrile group of the present invention, a pyridyl group or a pyrimidine group is introduced. Pyridine and pyrimidine are 6-membered heterocyclic groups with electron-deficient properties, which can reduce the HOMO and LUMO energy levels of the material, enhance the injection and transport of electrons, and block holes.

[0033] 4. The organic electron transport material containing triazine and benzonitrile groups of the present invention is used as an electron transport material in an organic electroluminescent device to improve the luminous efficiency of the device and extend the service life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 The differential scanning calorimetry diagram of compound 1.

[0035] Figure 2 The differential scanning calorimetry diagram of compound 19.

[0036] Figure 3 is the differential scanning calorimetry diagram of compound 20.

[0037] Figure 4 is the differential scanning calorimetry diagram of compound 21.

[0038] Figure 5 Schematic diagram of the structure of an organic electroluminescent device.

[0039] Figure 6 This is a graph showing the relationship between the device's operating voltage and luminous brightness.

[0040] Figure 7 This is the relationship between the device's operating voltage and current efficiency.

[0041] Figure 8 This is the device life graph. DETAILED DESCRIPTION

[0042] The present invention is further described below in conjunction with the accompanying drawings and specific embodiments, but the following embodiments are only preferred embodiments of the present invention, not all. Based on the embodiments in the implementation mode, other embodiments obtained by those skilled in the art without creative work all belong to the protection scope of the present invention.

[0043] The following examples 1 to 9 are the synthesis methods of some intermediates and / or compounds of the present invention. The synthesized intermediates or products are separated by column chromatography and then analyzed by nuclear magnetic resonance hydrogen mass spectrometry ( 1 H NMR and high-resolution mass spectrometry (HRMS) were used to characterize the molecular structure.

[0044] Example 1

[0045] Synthesis of intermediate 1-1

[0046]

[0047] 2-(3-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (5.0 g, 11.83 mmol), 3-cyanophenylboronic acid (3.1 g, 12.93 mmol) and potassium carbonate (2.5 g, 18.09 mmol) were added with toluene (30 mL), ethanol (15 mL) and deionized water (15 mL), and ditriphenylphosphine palladium chloride (0.1 g, 0.14 mmol) was added under nitrogen protection, and the mixture was refluxed for 8 h. The organic phase was concentrated to dryness, and the crude product was separated by column chromatography to obtain 4.1 g of a white solid with a yield of 78%.

[0048] High-resolution mass spectrometry (HRMS) can provide the accurate mass of ions or fragment ions of organic compound molecules. Based on this accurate mass information, the molecular formula of the compound can be determined. The HRMS characterization results of intermediate 1-1 are as follows: HRMS (ESI, m / z): [M+H] + calcdfor:C 28 H 18 C1N 4 ,445.1214,found,445.1217.

[0049] Synthesis of compound 1

[0050]

[0051] The intermediate 1-1 (1.0 g, 2.17 mmol), 2,4-diphenyl-6-(3-phenylboronic acid pinacol ester) pyridine (1.02 g, 2.35 mmol) and potassium carbonate (0.47 g, 3.40 mmol) were added to a three-necked flask, and then toluene (6 mL), ethanol (3 mL) and deionized water (3 mL) were added. Palladium acetate (0.01 g, 0.014 mmol) and x-phos (0.02 g, 0.04 mmol) were added under nitrogen protection. After reflux reaction for 10 hours, a solid precipitated, filtered, washed with ethanol, and the crude product was separated by column chromatography, eluted with PE / EA=5 / 1-2 / 1, concentrated to dryness, and dried to obtain 1.13 g of a white solid with a yield of 70%.

[0052] 1 H NMR has become the main technology for determining the structure of organic compounds. It uses chemical shift (expressed by the symbol δ, unit ppm) as an important reference data to analyze the structure and determine the configuration of organic compound reactants or products.

[0053] Compound 1 1 The HNMR and HRMS characterization results are as follows:

[0054] 1 H NMR (400 MHz, CDCl 3 )δ:8.17-8.24(m,6H),8.11-8.14(m,2H),7.99-8.06(m,3H),7.89-7.93(m,2H),7.82-7.85(m,2H),7.45-7.66(m,8H),7.35-7.44(m,10H).

[0055] HRMS(ESI,m / z):[M+H] + Calculate for:C 51 H 34 N 5 ,716.2809,found,716.2806.Anal.:calcd:C,85.57;H,4.65;N,9.78;found:C,85.64;H,4.62;N,9.74.

[0056] Example 2

[0057] Synthesis of compound 19

[0058]

[0059] The synthesis method is the same as compound 1, with a yield of 68%. 1 The H NMR and HRMS characterization results are as follows:

[0060] 1 H NMR (400 MHz, CDCl 3 )δ:8.18-8.24(m,6H),8.10-8.14(m,4H),8.00-8.02(m,2H),7.86-7.94(m,4H),7.63-7.73(m,3H),7.47-7.55(m,6H),7.35-7.45(m,8H).

[0061] HRMS(ESI,m / z):[M+H] + Calculate for:C 51 H 34 N 5 ,716.2809,found,716.2812.Anal.:calcd:C,85.57;H,4.65;N,9.78;found:C,85.51;H,4.68;N,9.76.

[0062] Example 3

[0063] Synthesis of Intermediate 20-1

[0064]

[0065] The synthesis method is the same as that of intermediate 1-1, with a yield of 74%. The HRMS characterization results of intermediate 20-1 are as follows: HRMS (ESI, m / z): [M+H] + Calculate for:C 28 H 18 C1N 4 ,445.1214,found,445.1215.

[0066] Synthesis of compound 20

[0067]

[0068] The synthesis method is the same as compound 1, with a yield of 64%. 1 The H NMR and HRMS characterization results are as follows:

[0069] 1 H NMR (400 MHz, CDCl 3)δ:8.24(t,J=1.6Hz,1H),8.18-8.22(m,5H),8.10-8.14(m,4H),7.99(t,J=1.6Hz ,1H),7.89(s,2H),7.87(t,J=1.6Hz,1H),7.68-7.76(m,6H),7.35-7.53(m,13H).

[0070] HRMS(ESI,m / z):[M+H] + Calculate for:C 51 H 34 N 5 ,716.2809,found,716.2810.Anal.:calcd:C,85.57;H,4.65;N,9.78;found:C,85.55;H,4.71;N,9.73.

[0071] Example 4

[0072] Synthesis of compound 21

[0073]

[0074] The synthesis method is the same as compound 1, with a yield of 81%. 1 The H NMR and HRMS characterization results are as follows:

[0075] 1 H NMR (400 MHz, CDCl 3 )δ:8.15-8.24(m,11H),8.00-8.06(m,3H),7.91-7.94(m,1H),7.80-7.83(m,1H),7.59-7.66(m,3H),7.49-7.55(m,3H),7.34-7.47(m,10H).

[0076] HRMS(ESI,m / z):[M+H] + Calculate for:C 50 H 33 N 6 ,717.2761,found,717.2765.Anal.:calcd:C,83.78;H,4.50;N,11.72;found:C,83.72;H,4.57;N,11.70.

[0077] Example 5

[0078] Synthesis of compound 22

[0079]

[0080] The synthesis method is the same as compound 1, with a yield of 73%. 1 The H NMR and HRMS characterization results are as follows:

[0081] 1 H NMR (400 MHz, CDCl 3 )δ:8.15-8.24(m,11H),8.03-8.05(m,2H),7.80-7.83(m,1H),7.69-7.75(m,4H),7.59-7.66(m,2H),7.49-7.53(m,2H),7.34-7.47(m,10H).

[0082] HRMS(ESI,m / z):[M+H] + Calculate for:C 50 H 33 N 6 ,717.2761,found,717.2758.Anal.:calcd:C,83.78;H,4.50;N,11.72;found:C,83.81;H,4.48;N,11.69.

[0083] Example 6

[0084] Synthesis of Intermediate 23-1

[0085]

[0086] The synthesis method is the same as that of intermediate 1-1, with a yield of 69%. The HRMS characterization results of intermediate 23-1 are as follows: HRMS (ESI, m / z): [M+H] + Calculate for:C 30 H 20 C1N 2 ,443.1310,found,443.1313.

[0087] Synthesis of compound 23

[0088]

[0089] The synthesis method is the same as compound 1, with a yield of 62%. 1 The H NMR and HRMS characterization results are as follows:

[0090] 1 H NMR (400 MHz, CDCl 3)δ:8.19-8.25(m,6H),8.10-8.14(m,4H),7.90-7.97(m,6H),7.76-7.79(m,2H),7.60-7.66(m,2H),7.48-7.58(m,5H),7.35-7.45(m,8H).

[0091] HRMS(ESI,m / z):[M+H] + Calculate for:C 51 H 34 N 5 ,716.2809,found,716.2804.Anal.:calcd:C,85.57;H,4.65;N,9.78;found:C,85.52;H,4.68;N,9.81.

[0092] Example 7

[0093] Synthesis of Intermediate 24-1

[0094]

[0095] The synthesis method is the same as that of intermediate 1-1, with a yield of 77%. The HRMS characterization results of intermediate 24-1 are as follows: HRMS (ESI, m / z): [M+H] + Calculate for:C 29 H 19 C1N 3 ,444.1262,found,444.1259.

[0096] Synthesis of compound 24

[0097]

[0098] The synthesis method is the same as compound 1, with a yield of 72%. 1 The H NMR and HRMS characterization results are as follows:

[0099] 1 H NMR (400 MHz, CDCl 3 )δ:8.15-8.25(m,11H),8.13-8.14(m,1H),8.02-8.06(m,2H),7.95-7.97(m,1H),7.83-7.86(m,2H),7.60-7.66(m,2H),7.34-7.55(m,13H).

[0100] HRMS(ESI,m / z):[M+H] + Calculate for:C50 H 33 N 6 ,717.2761,found,717.2760.Anal.:calcd:C,83.78;H,4.50;N,11.72;found:C,83.85;H,4.44;N,11.67.

[0101] Example 8

[0102] Synthesis of Intermediate 25-1

[0103]

[0104] The synthesis method is the same as that of intermediate 1-1, with a yield of 75%. The HRMS characterization results of intermediate 25-1 are as follows: HRMS (ESI, m / z): [M+H] + Calculate for:C 30 H 20 C1N 2 ,443.1310,found,443.1307.

[0105] Synthesis of compound 25

[0106]

[0107] The synthesis method is the same as compound 1, with a yield of 68%. 1 The H NMR and HRMS characterization results are as follows:

[0108] 1 H NMR (400 MHz, CDCl 3 )δ:8.19-8.25(m,6H),8.10-8.14(m,4H),7.88-7.95(m,5H),7.73-7.79(m,3H ),7.65-7.69(m,2H),7.59-7.63(m,1H),7.48-7.53(m,4H),7.35-7.45(m,8H).

[0109] HRMS(ESI,m / z):[M+H] + Calculate for:C 51 H 34 N 5 ,716.2809,found,716.2807.Anal.:calcd:C,85.57;H,4.65;N,9.78;found:C,85.62;H,4.60;N,9.77.

[0110] Example 9

[0111] Synthesis of Intermediate 26-1

[0112]

[0113] The synthesis method is the same as that of intermediate 1-1, with a yield of 70%. The HRMS characterization results of intermediate 26-1 are as follows: HRMS (ESI, m / z): [M+H] + Calculate for:C 29 H 19 C1N 3 ,444.1262,found,444.1267.

[0114] Synthesis of compound 26

[0115]

[0116] The synthesis method is the same as compound 1, with a yield of 66%. 1 The H NMR and HRMS characterization results are as follows:

[0117] 1 H NMR (400 MHz, CDCl 3 )δ:8.11-8.25(m,12H),8.00-8.03(m,2H),7.83-7.86(m,1H),7.73-7.77(m,2H ),7.67-7.70(m,2H),7.60-7.65(m,1H),7.49-7.53(m,2H),7.34-7.47(m,10H).

[0118] HRMS(ESI,m / z):[M+H] + Calculate for:C 50 H 33 N 6 ,717.2761,found,717.2763.Anal.:calcd:C,83.78;H,4.50;N,11.72;found:C,83.82;H,4.52;N,11.65.

[0119] Differential scanning calorimeter (DSC) is widely used in many fields such as inorganic materials, metal materials, composite materials, etc., and is used to study the melting and crystallization process, glass transition, phase transition, liquid crystal transition, curing, oxidation stability, reaction temperature and reaction enthalpy of materials. The following uses SHIMADZU DSC-60Plus differential scanning calorimeter to test and characterize the glass transition temperature of the compounds prepared in Examples 1 to 9. Test conditions: Under a nitrogen inert atmosphere, the glass transition temperature Tg of the compounds prepared in Examples 1 to 9 was tested at a heating and cooling rate of 20°C / min from 30°C to 350°C. The test results are shown in Table 1, where the corresponding differential scanning calorimeter diagrams of compounds 1, 19, 20, and 21 are shown in Table 1, respectively. Figure 1-4 .

[0120] Table 1 Glass transition temperature of the compounds

[0121] Example Compound <![CDATA[Glass transition temperature T g (°C) <!-- 12 -->]]> 1 1 131.17 2 19 135.98 3 20 125.68 4 21 132.05 5 22 137.54 6 23 128.23 7 24 133.74 8 25 129.18 9 26 134.06

[0122] It can be seen from the experimental data in Table 1 that the compound represented by the chemical formula I claimed in the present invention has a high glass transition temperature, and the glass transition temperature of the compounds prepared in all embodiments is higher than 120°, which can meet the requirements of being used as an electron transport material. This is mainly due to the fact that the structure of the compound of the present invention contains a benzonitrile group. Due to the introduction of the benzonitrile group, the interaction between molecules is increased, the glass transition temperature of the material is increased, and the thermal stability of the material of the present invention is increased, and the electron transport performance of the compound represented by the chemical formula I of the present invention as an organic electronic material is improved.

[0123] The uses and effects of the compounds of the present invention are further described in detail below through examples.

[0124] In the following embodiments 10 to 18, the structure of the organic electroluminescent device includes: glass / anode (ITO) / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / luminescent 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). See the schematic diagram of the specific device structure. Figure 5 , Figure 5 In the figure: 110 represents a glass substrate, 120 represents an anode, 130 represents a hole injection layer, 140 represents a hole transport layer, 150 represents a blocking layer, 160 represents a light emitting layer, 170 represents an electron transport layer, 180 represents an electron injection layer, and 190 represents a cathode.

[0125] Example 10

[0126] Preparation of organic electroluminescent device: OLED was prepared using compound 1 prepared in Example 1. The preparation method is as follows:

[0127] A transparent conductive ITO glass substrate 110 (with an anode 120 thereon) (China Southern Glass Group Co., Ltd.) was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, and then washed in ethanol, acetone and deionized water in sequence, baked in a clean environment to completely remove moisture, cleaned with ultraviolet photosynthetic ozone, and then treated with oxygen plasma for 30 seconds.

[0128] The glass substrate with the anode is placed in a vacuum chamber, evacuated, and HIL (5 nm) is evaporated on the ITO as a hole injection layer 130 at a rate of 0.1 nm / s.

[0129] Compound HT is evaporated on the hole injection layer to form a hole transport layer 140 with a thickness of 80 nm. The evaporation rate is 0.1 nm / s.

[0130] EB is evaporated on the void transport layer to form a 10 nm thick electron blocking layer 150. The evaporation rate is 0.1 nm / s.

[0131] A 30 nm thick light emitting layer 160 is evaporated on the hole blocking layer, wherein BH is the main light emitting material and 2% by weight of BD is used as the doping guest material, and the evaporation rate is 0.1 nm / s.

[0132] On the light-emitting layer, 50% by weight of compound 1 and 50% by weight of LiQ were evaporated to form an electron transport layer 170 with a thickness of 30 nm. The evaporation rate was 0.1 nm / s.

[0133] LiQ was evaporated to a thickness of 1 nm on the electron transport layer to serve as the electron injection layer 180 .

[0134] A 100 nm thick magnesium-silver layer with a doping ratio of 10:1 is evaporated on the electron injection layer as the device cathode 190.

[0135] Examples 11-18

[0136] The only difference from Example 10 is that Compound 1 is replaced with other compounds of the present invention as the electron transport material. The specific electronic materials used in each example are shown in Table 2.

[0137] Comparative Example 1-2

[0138] The only difference from Example 10 is that Compound 1 is replaced by Compounds ET1 and ET2 as the electron transport material.

[0139] The structural formula of the device is as follows:

[0140]

[0141] The above organic materials are all existing known materials and are purchased from the market.

[0142] Table 2 Device structure

[0143]

[0144]

[0145] The beneficial technical effects of the compounds containing the structural formula I of the present invention as organic electronic materials are described in detail below through further performance tests on the devices prepared in Examples 10 to 18.

[0146] Photo Research PR655 spectrometer at 1000cd / m 2 Under the brightness, the device's operating voltage, efficiency, emission wavelength, and measurement at 12mA / cm 2 The time (T97) when the brightness becomes 97% of the initial brightness under the current density is shown in Table 3 and Figure 6 , Figure 7 In addition, the service life of the devices prepared by using compound 1 prepared in Example 1 and compound 19 prepared in Example 2 as electron transport materials was also tested. The results are shown in FIG. Figure 8 .

[0147] Table 3 Device performance parameters

[0148]

[0149]

[0150] It can be seen from Table 3 that the organic electroluminescent device prepared by using the electron transport material of the present invention has a higher emission than ET1 at 1000 cd / m 2 The operating voltage under brightness is reduced by 0.1-0.5V, and the current efficiency is increased from 6.81-7.88cd / A to 9.05-10.21cd / A. 2 Under the current density of 1.54 W, T97 is increased from 125 hours to 191-226 hours, and the life span is greatly improved. The introduction of benzonitrile group is beneficial to improve the electron transmission capacity, reduce the operating voltage and extend the service life of the device.

[0151] from Figure 6 It can be seen that the device prepared by the compound of the present invention has a relatively low operating voltage, and the starting voltage is basically around 2.8V. As the voltage increases, the brightness also increases. At 1000cd / m 2 The voltage at the working voltage under brightness is basically between 3.4-3.6V.

[0152] from Figure 7 It can be seen that the device prepared by the compound of the present invention has a higher efficiency and a lower roll-off, and the efficiency is basically 8 cd / A at an operating voltage of 5 V.

[0153] from Figure 8 It can be seen that the device prepared by the compound of the present invention is at 12mA / cm 2 The brightness decay curve at a current density of 2.5 % and a slow roll-off is shown, indicating that the compound has good stability.

[0154] The preferred specific embodiments of the present invention are described in detail above. It should be understood that a person skilled in the art can make many modifications and changes based on the concept of the present invention without creative work. Therefore, any technical solution that can be obtained by a person skilled in the art through logical analysis, reasoning or limited experiments based on the concept of the present invention on the basis of the prior art should be within the scope of protection determined by the claims.

Claims

1. An organic electronic material containing a triazine group and a benzonitrile group, characterized in that: The organic electronic material contains any one of the following compounds:

2. Use of the organic electronic material containing triazine groups and benzonitrile groups according to claim 1 in organic electroluminescent devices, organic solar cells, organic thin film transistors, organic photodetectors, organic field effect transistors, organic integrated circuits and organic photoreceptors.

3. An organic electroluminescent device, 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, characterized in that: At least one of the organic layers contains the organic electronic material containing triazine groups and benzonitrile groups as claimed in claim 1.

4. The organic electroluminescent device according to claim 3, characterized in that: The electron transport layer or the electron injection layer in the organic layer contains the organic electronic material containing triazine groups and benzonitrile groups as claimed in claim 1.

5. The organic electroluminescent device according to claim 4, characterized in that: At least one layer of the electron transport material in the organic layer is doped with 20-70 wt% of an organic metal complex.

6. The organic electroluminescent device according to claim 4, characterized in that: The hole blocking layer in the organic layer contains the organic electronic material containing triazine groups and benzonitrile groups as claimed in claim 1.

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