Pyrene-containing compound and application thereof in organic electroluminescent device

Abstract

The invention belongs to the technical field of organic electroluminescent materials, and relates to a pyrene-containing compound and application thereof in an organic electroluminescent device. According to the pyrene-containing compound, fluorene adamantane and pyrene are combined to serve as a mother nucleus, the mother nucleus and pyrene, benzophenanthrene, phenanthrene and other fused ring molecules form a fused ring structure with certain rigidity and molecular distortion at a specific position, and the pyrene-containing compound has proper HOMO, LUMO and T1 values and is suitable for being used as a blue light host material. The pyrene-containing compound is used as a blue light host material for an organic electroluminescent device, and plays a key role in improving the brightness efficiency, the service life and the like of the device, the brightness efficiency of the device is improved by 9.4-38.5%, and the service life of the device is prolonged by 22.8-68.7%.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of organic electroluminescent materials, and relates to a pyrene-containing compound and application thereof in an organic electroluminescent device. BACKGROUND

[0002] An organic electroluminescent device (OLED) is a current-driven device with an organic semiconductor thin film as a light-emitting layer, and light radiation is generated by recombination of electrons and holes in the light-emitting layer through voltage driving. The OLED has the characteristics of self-luminescence, wide viewing angle, high contrast, low energy consumption and flexible design. As a core sub-class of OLEDs, blue organic electroluminescent diodes have irreplaceability in full-color display and white light illumination. The blue light device needs to meet the requirements of high color purity and stability, and especially needs to meet the BT.2020 ultra-high-definition color gamut standard. Exciton quenching is a core challenge that restricts the performance of blue organic electroluminescent diodes, which reduces the efficiency and stability of the device through non-radiative energy dissipation.

[0003] In order to reduce exciton quenching, researchers use the method of solid-state dilution. By doping the light-emitting material in a suitable host material, the quenching effect can be effectively reduced, thereby improving the overall performance of the device. The host material needs to meet the following conditions: first, the host material must have a wider energy gap than the guest material, so that the energy generated by the recombination of carriers can be effectively transferred to the guest material for light emission. At the same time, the host material with a wider energy gap is also conducive to limiting excitons within the light-emitting layer; second, the host material must have good carrier transport performance, which can effectively reduce the driving voltage of the device; finally, the host material needs to have good thermal stability and morphological stability, which is conducive to the improvement of the stability of the device.

[0004] Therefore, the design and optimization of blue light host materials are very important. How to develop high-quality host materials that meet the basic requirements of energy level matching, carrier transport performance and thermal stability, and have good stability is a difficult and hot issue in the field of OLED technology. SUMMARY

[0005] To solve the above technical problems, the application provides a pyrene-containing compound and application thereof in an organic electroluminescent device. The pyrene-containing compound has a certain rigidity and molecular twist, and is suitable for use as a blue light host material due to the appropriate HOMO, LUMO and T1 values. The pyrene-containing compound is used as a blue light host material in an organic electroluminescent device, which plays a key role in improving the luminance efficiency, service life and other performances of the device. The luminance efficiency of the device is improved by 9.4-38.5%, and the service life of the device is prolonged by 22.8-68.7%.

[0006] To achieve the technical purpose of the present application, in one aspect, the present application provides a pyrene-containing compound having a structure as shown in formula (I), Ar1 and Ar2 in the formula (I) are independently selected from one of substituted or unsubstituted C6-30 aryl and substituted or unsubstituted heteroaryl. L in the formula (I) is selected from one of single bond, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.

[0007] Further, the C6-30 aryl in the substituted or unsubstituted C6-30 aryl is selected from one of phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, benzophenanthryl and chrysenyl.

[0008] Further, when Ar1 and Ar2 are independently selected from substituted or unsubstituted heteroaryl, the heteroaryl is selected from one of dibenzofuranyl, naphthofuranyl, dibenzothiophenyl, benzonaphthofuranyl and benzocarbazolyl.

[0009] Further, the aryl in the substituted or unsubstituted aryl is selected from one of phenyl, naphthyl, anthryl, benzanthryl, pyrenyl and fluorenyl.

[0010] Further, when L is selected from substituted or unsubstituted heteroaryl, the heteroaryl is selected from one of furanyl, carbazolyl and thiophenyl.

[0011] The substitution includes substitution by deuterium atom, substitution by methyl and substitution by phenyl.

[0012] Further, the pyrene-containing compound of the present application has a structure as shown below,

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[0051] In another aspect, the application claims the use of the pyrene-containing compound as described above as a blue light host material in a light-emitting layer of an organic electroluminescent device.

[0052] Specifically, the application applies the pyrene-containing compound as described above as a blue light host material to an OLED device, which can significantly improve the performance of the device, and the luminance efficiency and lifetime performance of the device are greatly improved, compared with the existing OLED device, the luminance efficiency of the device is increased by 9.4~38.5%, and the lifetime of the device is extended by 22.8~68.7%.

[0053] In another aspect, the application claims an organic electroluminescent device containing a light-emitting layer, wherein the host material of the light-emitting layer uses the pyrene-containing compound as described above.

[0054] In addition, the application claims a display assembly comprising the organic electroluminescent device as described above.

[0055] Compared with the prior art, the technical scheme provided by the application has at least the following beneficial effects or advantages: (1) The application provides a fused ring compound with fluorene-adamantane combined with pyrene as the core, which fully utilizes the stability of adamantane and the rigidity of pyrene to improve the thermal stability and carrier migration ability of the material, and further modified by fused ring molecules such as pyrene, benzophenanthrene, chrysene, and phenanthrene or heteroaryl groups, which can optimize the front orbital energy level and triplet state energy of the compound. The pyrene-containing compound has suitable HOMO, LUMO, and T1 values, and is suitable for use as a blue light host material.

[0056] (2) The pyrene-containing compound provided by the application is applied to an OLED device as a blue light host material, which can significantly improve the performance of the device, and the luminance efficiency and lifetime of the device are greatly improved, compared with the existing OLED device, the luminance efficiency of the device is increased by 9.4~38.5%, and the lifetime of the device is extended by 22.8~68.7%. For example, if compound 5 is used as a blue light host material, the luminance efficiency is increased by 35.2% compared with BH1 as a blue light host material, and the device lifetime is increased by 36.6%; compared with BH1 as a blue light host material, the luminance efficiency of the device is increased by 38.5% when the deuterated host material compound 108 is used as a blue light host material, and the device lifetime is increased by 68.7%. It can be seen that the pyrene-containing compound of the application has great application value in OLED devices and has good industrialization prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0057] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the following briefly introduces the drawings required for use in the embodiments or the description of the prior art. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying any creative work.

[0058] Figure 1 Schematic diagram of the structure of an organic electroluminescent device. 1 is the substrate, 2 is the anode layer, 3 is the hole injection layer, 4 is the first hole transport layer, 5 is the second hole transport layer, 6 is the light-emitting layer, 7 is the hole blocking layer, 8 is the electron transport layer, 9 is the electron injection layer, and 10 is the cathode layer. DETAILED DESCRIPTION

[0059] The technical solutions of the present invention are described below with reference to the following examples. However, the present invention is not limited to the following examples. The experimental methods and detection methods described in each example are conventional methods unless otherwise specified. The reagents and materials described are commercially available unless otherwise specified. The percentages in the following examples are percentages by mass unless otherwise specified.

[0060] Example 1 This example provides the synthesis of intermediate compounds.

[0061] 1. Synthesis of Intermediate 1: The synthetic route is as follows, specifically comprising the following steps:

[0062] S1: Under nitrogen, add intermediate 1-1 (82.2 g, 261.32 mmol) and tetrahydrofuran (650 mL) to a three-necked round-bottom flask. After cooling to -78°C, add a 2.5 M solution of n-butyllithium in tetrahydrofuran (125.4 mL, 313.59 mmol) dropwise with stirring. Maintain stirring at -78°C for 1 hour. Then, add a solution of adamantanone (43.2 g, 287.46 mmol) in tetrahydrofuran (170 mL) dropwise. Maintain the temperature for 1 hour, then allow the mixture to warm to room temperature and continue stirring for 12 hours. To the reaction solution was added a solution of hydrochloric acid (12 M) (39.2 mL, 470.4 mmol) in water (200 mL), and the mixture was stirred for 0.5 h. The organic phase was separated, and the organic phase was washed with water until neutral, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using ethyl acetate / n-heptane (volume ratio 1:2) to obtain intermediate 1-3 (55.5 g, yield 62.7%).

[0063] S2: Under nitrogen protection, intermediate 1-3 (51.6 g, 152.27 mmol), glacial acetic acid (550 mL) were added into a three-necked round-bottom flask, and a solution of concentrated sulfuric acid (98%) (3.1 mL, 30.4 mmol) in acetic acid (60 mL) was slowly added dropwise under stirring at room temperature. After the addition was completed, the temperature was raised to 80°C, and stirring was performed for 2 h. After the reaction was completed, the temperature was lowered to room temperature, and the mixture was filtered. The filter cake was washed with water until neutral, dissolved in dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-hexane system (1:2) to obtain intermediate 1-4 (40.6 g, yield 83.1%).

[0064] S3: Under nitrogen protection, intermediate 1-4 (37.6 g, 117.18 mmol), N,N- dimethylformamide (380 mL), potassium carbonate (24.3 g, 175.78 mmol) were added into a three-necked round-bottom flask, and N-bromosuccinimide (21.3 g, 119.5 mmol) was further added after complete dissolution under stirring at room temperature. The temperature was raised to 80°C, and stirring was performed for 4 h. After the reaction was completed, the temperature was lowered to room temperature, and the reaction solution was poured into 1 L of water under stirring. The mixture was filtered, the filter cake was washed with water until neutral, dissolved in dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The product was purified by silica gel column chromatography using a dichloromethane / n-hexane system (1:2) to obtain intermediate 1-5 (39.9 g, yield 85.3%).

[0065] S4: Under nitrogen protection, intermediate 1-5 (30.8 g, 77.0 mmol), intermediate 1-6 (25.3 g, 78.6 mmol), potassium carbonate (21.3 g, 154.1 mmol), tetrabutylammonium bromide (2.5 g, 7.7 mmol), toluene (450 mL), ethanol (150 mL), water (70 mL) were added into a three-necked round-bottom flask, and tetrakis(triphenylphosphine)palladium (1.78 g, 1.54 mmol) was added after complete dissolution under stirring at room temperature. The temperature was raised to 80°C, and stirring was performed for 8 h. After the reaction was completed, the temperature was lowered to room temperature, and the reaction solution was washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The product was purified by silica gel column chromatography using a dichloromethane / n-hexane system (1:2) to obtain intermediate 1 (33.5 g, yield 72.9%).

[0066] 2, Synthesis of intermediate 2, the synthesis route is shown below, which specifically comprises the following steps:

[0067] S1: Refer to the synthesis of intermediate 1-3, and replace intermediate 1-3 with intermediate 2-1 to obtain a yield of 66.3%.

[0068] S2: Refer to the synthesis of intermediate 1-4, replace intermediate 1-3 with intermediate 2-2, yield 76.4%.

[0069] S3: Under nitrogen protection, add intermediate 2-3 (27.6 g, 96.4 mmol), potassium carbonate (39.9 g, 289.1 mmol), N,N-dimethylformamide (280 mL) into a three-necked round-bottom flask, stir to dissolve completely at room temperature, then add N-bromosuccinimide (34.6 g, 194.6 mmol), and warm to 80°C, and keep stirring for 4 h. After the reaction is completed, cool to room temperature, pour the reaction solution into 1 L of water under stirring, filter, dissolve the filter cake in dichloromethane after washing to neutral, dry over anhydrous sodium sulfate, remove the solvent under reduced pressure, and purify by silica gel column chromatography using a dichloromethane / n-heptane system (1:2) to obtain intermediate 2 (33.5 g, yield 78.2%).

[0070] 3, Synthesis of intermediate 3, the synthesis route is shown below, which specifically includes the following steps:

[0071] Refer to the synthesis of intermediate 1, except that intermediate 1-6 is replaced with intermediate 3-1, yield 71.6%.

[0072] 4, Synthesis of intermediate 4, the synthesis route is shown below, which specifically includes the following steps:

[0073] Refer to the synthesis of intermediate 1, except that intermediate 1-6 is replaced with intermediate 4-1, yield 75.1%.

[0074] Example 2 This example provides the synthesis of a pyrene-containing compound.

[0075] 1, Synthesis of compound 1 (having a structure as shown in formula (I), wherein Ar1 is phenyl, L is a single bond, and Ar2 is a pyrene group), the synthesis route is shown below, which specifically includes the following steps:

[0076] In a three-necked round bottom flask was added intermediate 1 (4.0 g, 6.7 mmol), compound 1-1 (1.8 g, 7.4 mmol), palladium acetate (0.02 g, 0.1 mmol), potassium carbonate (1.8 g, 13.4 mmol), X-phos (0.1 g, 0.2 mmol), toluene (60 mL), ethanol (20 mL), water (10 mL), and the mixture was stirred at 80 °C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, washed with water until neutral, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane / n-hexane (1:2) as the eluent to give compound 1 (3.4 g, yield 67.3%).

[0077] The mass spectrum of the obtained sample was detected as follows: HR-MS (APCI): m / z 763.3253 [M+H] + ; C 60 H 42 Calculated: C, 94.4513; H, 5.5487; Found: C, 94.4519; H, 5.5481.

[0078] 2, Synthesis of compound 2 (having a structure as shown in formula (I), wherein Ar1 is phenyl, L is anthracenyl, and Ar2 is phenyl), the synthesis route is shown below, and the synthesis method is similar to that of compound 1, except that compound 1-1 is replaced by compound 2-1, and the yield is 72.2%.

[0079] The mass spectrum of the obtained sample was detected as follows: HR-MS (APCI): m / z 815.3577 [M+H] + ; C 64 H 46 Calculated: C, 94.3112; H, 5.6888; Found: C, 94.3121; H, 5.6879.

[0080]

[0081] 3, Synthesis of compound 2 (having a structure as shown in formula (I), wherein Ar1 is phenyl, L is pyrenyl, and Ar2 is phenyl), the synthesis route is shown below, and the synthesis method comprises the following steps:

[0082] Into a three-necked round bottom flask, was added intermediate 2 (4.0 g, 9.0 mmol), intermediate 1-6 (3.0 g, 9.2 mmol), potassium carbonate (2.5 g, 18.4 mmol), tetrabutylammonium bromide (0.3 g, 0.9 mmol), toluene (60 mL), ethanol (20 mL), water (10 mL), stirred and dissolved at room temperature, then added tetrakis(triphenylphosphine)palladium (0.2 g, 0.18 mmol), heated to 80 °C, kept the temperature and stirred for 8 hours. The reaction was completed and cooled to room temperature, the reaction liquid was washed with water until neutral, the organic phase was dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the silica gel column chromatography was performed using dichloromethane / n-heptane system (1:2) to purify, to obtain compound 5 (5.2 g, yield 68.5%).

[0083] The mass spectrum detection result of the obtained sample was: HR-MS (APCI): m / z 839.3629 [M+H] + ; C 66 H 46 Calculated: C, 94.4740; H, 5.5260; Found: C, 94.4753; H, 5.5247.

[0084] 4, Synthesis of compound 11 (having a structure as shown in formula (I), wherein Ar1 is phenyl, L is anthracenyl, and Ar2 is dibenzofuranyl), the synthesis route is shown below, and the synthesis method refers to the synthesis of compound 1, except that compound 1-1 is replaced by compound 11-1, and the yield is 72.7%.

[0085] The mass spectrum detection result of the obtained sample was: HR-MS (APCI): m / z 905.3687 [M+H] + ; C 70 H 48 Calculated: C, 92.8871; H, 5.3454; O, 1.7675; Found: C, 92.8889; H, 5.3449; O, 1.7662.

[0086]

[0087] 5, Synthesis of compound 40 (having a structure as shown in formula (I), wherein Ar1 is dibenzofuranyl, L is a single bond, and Ar2 is dibenzofuranyl), the synthesis route is shown below, and the synthesis method refers to the synthesis of compound 1, except that intermediate 1 is replaced by intermediate 3, and compound 1-1 is replaced by compound 40-1, and the yield is 63.9%.

[0088] The mass spectrum detection result of the obtained sample was: HR-MS (APCI): m / z 819.3176 [M+H]+ ; C 62 H 42 O2 (%) calcd: C, 90.9240; H, 5.1691; O, 3.9069; found: C, 90.9262; H, 5.1683; O, 3.9055.

[0089]

[0090] 6, Synthesis of compound 41 (having a structure as shown in formula (I) wherein Ar1 is phenyl, L is phenyl, and Ar2 is pyrenyl), the synthetic route is shown below, the synthetic method refers to the synthesis of compound 1, the difference is that compound 1-1 is replaced by compound 41-1, the yield is 75.5%.

[0091] The mass spectrum detection result of the obtained sample is: HR-MS (APCI): m / z 839.3621 [M+H] + ; C 66 H 46 (%) calcd: C, 94.4740; H, 5.5260; found: C, 94.4751; H, 5.5249.

[0092]

[0093] 7, Synthesis of compound 43 (having a structure as shown in formula (I) wherein Ar1 is phenyl, L is anthryl, and Ar2 is pyrenyl), the synthetic route is shown below, the synthetic method refers to the synthesis of compound 1, the difference is that compound 1-1 is replaced by compound 43-1, the yield is 72.0%.

[0094] The mass spectrum detection result of the obtained sample is: HR-MS (APCI): m / z 939.3926 [M+H] + ; C 74 H 50 (%) calcd: C, 94.6338; H, 5.3662; found: C, 94.6349; H, 5.3651.

[0095]

[0096] 8, Synthesis of compound 44 (having a structure as shown in formula (I) wherein Ar1 is phenyl, L is naphthyl, and Ar2 is pyrenyl), the synthetic route is shown below, the synthetic method refers to the synthesis of compound 1, the difference is that compound 1-1 is replaced by compound 44-1, the yield is 68.2%.

[0097] The mass spectrum detection result of the obtained sample is: HR-MS (APCI): m / z 736.2609 [M+H] + ; C 70 H 48 Calcd: C, 94.5584; H, 5.4416; Found: C, 94.5592; H, 5.4408.

[0098]

[0099] 9. Synthesis of compound 108 (having a structure as shown in formula (I), wherein Ar1 is phenyl, L is a single bond, and Ar2 is dibenzofuranyl substituted by deuterium atom), synthesis route is shown below, synthesis method refers to synthesis of compound 1, the difference is that intermediate 1 is replaced by intermediate 4, compound 1-1 is replaced by compound 108-1, yield is 61.7%.

[0100] The mass spectrum detection result of the obtained sample is: HR-MS (APCI): m / z 736.2609 [M+H] + ; C 56 H 33 OD7 (%) Calcd: C, 93.1757; H, 4.6080; O, 2.2163; Found: C, 91.4006; H, 6.4254; O, 2.1741.

[0101]

[0102] 10. Synthesis of compound 113 (having a structure as shown in formula (I), wherein Ar1 is phenyl, L is dibenzofuran, and Ar2 is phenyl), synthesis route is shown below, synthesis method refers to synthesis of compound 1, the difference is that compound 1-1 is replaced by compound 113-1, yield is 65.6%.

[0103] The mass spectrum detection result of the obtained sample is: HR-MS (APCI): m / z 736.2609 [M+H] + ; C 62 H 44 O (%) Calcd: C, 92.5036; H, 5.5135; O, 1.9907; Found: C, 92.5827; H, 5.5181; O, 1.9963.

[0104]

[0105] The other compounds except compound 1, compound 2, compound 3, compound 5, compound 11, compound 22, compound 32, compound 40, compound 41, compound 43, compound 44, compound 108, and compound 113 can be prepared by referring to the preparation method described above.

[0106] Example 3 This example provides the photoelectric performance parameters of the pyrene-containing compounds, and the HOMO and LUMO are data obtained by simulation calculation, the calculation method adopts B3LYP hybrid functional, and the base group is 6-31g (d, P), and the results are shown in Table 1.

[0107] Table 1 T1 energy level and HOMO and LUMO simulation calculation results of pyrene-containing compounds

[0108] As shown in Table 1, the pyrene-containing compounds with fluorene adamantane and pyrene combination as the mother nucleus have suitable HOMO, LUMO and T1 values, and these compounds are suitable for use as blue light host materials.

[0109] Example 4 This example determines the performance of an organic electroluminescent device with a pyrene-containing compound as a light-emitting layer host material.

[0110] 1. Functional layer of organic electroluminescent device The structure of the organic electroluminescent device is shown in Figure 1 The organic electroluminescent device includes a substrate 1, an anode layer 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9 and a cathode layer 10 which are sequentially stacked.

[0111] The material of the anode layer 2 is selected to be indium tin oxide (ITO) with a high work function, the material of the hole injection layer 3 is selected to be HAT-CN, and the thickness is 5 nm; the material of the first hole transport layer 4 is selected to be HT1, and the thickness is 60 nm; the material of the second hole transport layer 5 is selected to be HT2, and the thickness is 15 nm; the light-emitting layer 6 uses a pyrene-containing compound or BH1 as a host material, and BD01 as a light-emitting material, and the doping mass ratio is 3%, and the thickness is 30 nm; the material of the hole blocking layer 7 is selected to be HB, and the thickness is 10 nm; the material of the electron transport layer 8 is selected to be ET-1, and the thickness is 30 nm; the material of the electron injection layer 9 is selected to be Liq, and the thickness is 2 nm; and the material of the cathode layer 10 is selected to be Al, and the thickness is 100 nm.

[0112] The basic material structure used in each functional layer of the organic electroluminescent device is as follows:

[0113]

[0114] 2. Preparation of organic electroluminescent device 1) Clean the ITO anode on transparent glass or plastic substrate, respectively, with deionized water, acetone, ethanol, each for 20 minutes of ultrasonic cleaning, and then perform plasma treatment in oxygen atmosphere for 5 minutes; 2) On the ITO anode layer, evaporate the hole injection layer material HAT-CN by vacuum evaporation method, with a thickness of 5 nm, which serves as a hole injection layer; 3) On the hole injection layer, evaporate the hole transport material HT1 by vacuum evaporation method, with a thickness of 60 nm, which serves as the first hole transport layer; 4) On the first hole transport layer HT1, evaporate the hole transport material HT2 by vacuum evaporation method, with a thickness of 15 nm, which serves as the second hole transport layer; 5) On the second hole transport layer, co-evaporate the light-emitting layer by vacuum evaporation method, using a pyrene compound or BH1 as the host material and BD01 as the light-emitting material, with a doping mass ratio of 3%, and a thickness of 30 nm; 6) On the light-emitting layer, evaporate the hole blocking material HB by vacuum evaporation method, with a thickness of 10 nm, which serves as a hole blocking layer; 7) On the hole blocking layer, evaporate the electron transport material ET-1 by vacuum evaporation method, with a thickness of 30 nm, which serves as an electron transport layer; 8) On the electron transport layer, evaporate the electron injection material Liq by vacuum evaporation method, with a thickness of 2 nm, which serves as an electron injection layer; 9) On the electron injection layer, evaporate the cathode Al by vacuum evaporation method, with a thickness of 100 nm, which serves as a cathode conductive electrode.

[0115] Connect the cathode and anode of each group of organic electroluminescent devices with a known driving circuit, and test the voltage-efficiency-current density relationship of the OLED device by standard method using Keithley 2400 power supply combined with PR670 luminometer. The lifetime of the blue light device is tested by constant current method, and the test conditions are as follows: under the application of 20 mA / cm 2 current density, the initial brightness of the device is 100%, and the time required when the brightness decays to 90% of the initial brightness is the LT 90 lifetime of the device, and the test results are shown in Table 2.

[0116] Table 2 Performance parameters of organic electroluminescent device

[0117] As can be seen from Table 2, the pyrene-containing compound provided by the present application applied to an OLED device as a blue light host material can significantly improve the performance of the device, and the luminous efficiency and service life performance of the device are greatly improved. Compared with the existing OLED device, the luminous efficiency of the OLED device with the pyrene-containing compound as a blue light host material in the light-emitting layer is improved by 9.4~38.5%, and the service life of the device is prolonged by 22.8~68.7%. For example, the compound 5 in the blue light device embodiment 3 as a blue light host material compared with BH1 in the comparative example 1, the luminous efficiency is improved by 35.2%, and the service life of the device is improved by 36.6%; the deuterated host material compound 108 compared with the comparative material BH1, the luminous efficiency of the device is improved by 38.5%, and the service life of the device is improved by 68.7%. It can be seen that the pyrene-containing compound of the present application has great application value in the OLED device and has good industrialization prospect.

[0118] As described above, the basic principles, main features and advantages of the present application are better described. The above examples and descriptions are only to describe the preferred embodiments of the present application, and the present application is not limited by the above examples. Without departing from the spirit and scope of the present application, various changes and improvements to the technical solutions of the present application made by those skilled in the art shall fall within the scope of protection of the present application.

Claims

1. A pyrene-containing compound, characterized in that: Having a structure as shown in formula (I), ； Ar1 and Ar2 in the formula (I) are independently selected from a substituted or unsubstituted C6-30 aryl group, or a substituted or unsubstituted heteroaryl group; L in the formula (I) is selected from a single bond, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

2. The pyrene-containing compound according to claim 1, characterized in that The C6-30 aryl group in the substituted or unsubstituted C6-30 aryl group is selected from one of phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, triphenylenyl and chrysyl.

3. The pyrene-containing compound according to claim 1, wherein When Ar1 and Ar2 are independently selected from substituted or unsubstituted heteroaryl groups, the heteroaryl group is selected from one of dibenzofuranyl, naphthofuranyl, dibenzothiophenyl, benzonaphthofuranyl and benzocarbazolyl.

4. The pyrene-containing compound according to claim 1, characterized in that The aryl group in the substituted or unsubstituted aryl group is selected from one of phenyl, naphthyl, anthracenyl, benzanthryl, pyrenyl and fluorenyl.

5. The pyrene-containing compound according to claim 1, characterized in that When L is selected from a substituted or unsubstituted heteroaryl group, the heteroaryl group is selected from one of furyl, carbazolyl and thienyl.

6. The pyrene-containing compound according to claim 1, characterized in that Has the structure shown below, 。 7. Use of the pyrene-containing compound according to any one of claims 1 to 6 in an organic electroluminescent device, characterized in that: The pyrene-containing compound is used as a blue light host material in a light-emitting layer of an organic electroluminescent device.

8. An organic electroluminescent device comprising a light-emitting layer, characterized in that: The host material of the light-emitting layer uses the pyrene-containing compound according to any one of claims 1 to 6.

9. A display component, characterized in that: The organic electroluminescent device according to claim 8 is included.

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