A pyrene-containing compound and its use in organic electroluminescent devices

Abstract

The present application belongs to the technical field of organic electroluminescent material, and relates to a pyrene-containing compound and application thereof in an organic electroluminescent device. The pyrene-containing compound of the present application takes a combination of fluorene and adamantane and pyrene as a mother nucleus, and is combined with pyrene, triphenylene, chrysene, phenanthrene and other fused ring molecules at specific positions to form a fused ring structure with certain rigidity and molecular twist. The compound has suitable HOMO, LUMO and T1 values, and is suitable for use as a blue light host material. The pyrene-containing compound of the present application is used as a blue light host material in an organic electroluminescent device, plays a key role in improving the luminance efficiency, service life and other performances of the device, and improves the luminance efficiency of the device by 9.4-38.5% and prolongs the service life of the device 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),

[0007] ;

[0008] Ar1 and Ar2 in the formula (I) are independently selected from one of substituted or unsubstituted C6-30 aryl and substituted or unsubstituted heteroaryl;

[0009] L in the formula (I) is selected from one of a single bond, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.

[0010] 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.

[0011] 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.

[0012] Further, the aryl in the substituted or unsubstituted aryl is selected from one of phenyl, naphthyl, anthryl, benzanthryl, pyrenyl and fluorenyl.

[0013] Further, when L is selected from substituted or unsubstituted heteroaryl, the heteroaryl is selected from one of furanyl, carbazolyl and thiophenyl.

[0014] The substitution includes substitution by a deuterium atom, substitution by a methyl group and substitution by a phenyl group.

[0015] Further, the pyrene-containing compound of the present application has a structure as shown below,

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[0054] .

[0055] In another aspect, the application claims the use of the pyrene-containing compound as described above in an organic electroluminescent device as a blue light host material in the light-emitting layer of the organic electroluminescent device.

[0056] 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 luminous efficiency and the life performance of the device are greatly improved, compared with the existing OLED device, the luminous efficiency of the device is increased by 9.4~38.5%, and the life of the device is extended by 22.8~68.7%.

[0057] 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.

[0058] In addition, the application claims a display assembly comprising the organic electroluminescent device as described above.

[0059] Compared with the prior art, the technical solution provided by the application at least has the following beneficial effects or advantages:

[0060] (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 on this basis, further modified by fused ring molecules such as pyrene, triphenylene, chrysene, and phenanthrene or heteroaryl groups, the front orbital energy level and triplet state energy of the compound can be optimized. The pyrene-containing compound has a suitable HOMO, LUMO, and T1 value, and is suitable for use as a blue light host material.

[0061] (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 luminous efficiency and service life of the device are greatly improved, compared with the existing OLED device, the luminous efficiency of the device is increased by 9.4-38.5%, and the service life of the device is prolonged by 22.8-68.7%. If compound 5 is used as a blue light host material, compared with BH1 as a blue light host material, the luminous efficiency is increased by 35.2%, and the service life of the device is increased by 36.6%; compared with BH1 as a blue light host material, the luminous efficiency of the device is increased by 38.5%, and the service life of the device is increased by 68.7%. It can be seen that the pyrene-containing compound has great application value in the OLED device and has good industrialization prospect. BRIEF DESCRIPTION OF DRAWINGS

[0062] In order to more clearly illustrate the technical solutions in the embodiments of the application or the prior art, the following will briefly introduce the drawings needed to be used in the embodiments or the prior art description. Obviously, the drawings in the following description are only some embodiments of the application, and for those skilled in the art, other drawings can also be obtained without creative labor on the basis of these drawings.

[0063] Figure 1 The structure of the organic electroluminescent device is shown in the figure. Wherein, 1 is a substrate, 2 is an anode layer, 3 is a hole injection layer, 4 is a first hole transport layer, 5 is a second hole transport layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. DETAILED DESCRIPTION

[0064] The technical solutions of the application will be described below in combination with the embodiments. However, the application is not limited to the following embodiments. The experimental methods and detection methods described in each embodiment are conventional methods unless otherwise specified. The reagents and materials described are commercially available unless otherwise specified. The % in the following examples is the mass percentage unless otherwise specified.

[0065] Example 1

[0066] This embodiment provides the synthesis of intermediate compounds.

[0067] 1. Synthesis of intermediate 1, the synthesis route is shown below, which specifically includes the following steps:

[0068]

[0069] S1: Under nitrogen protection, intermediate 1-1 (82.2 g, 261.32 mmol) and tetrahydrofuran (650 mL) were added into a three-necked round-bottom flask. After cooling to -78 °C, n-butyllithium tetrahydrofuran solution (2.5 M) (125.4 mL, 313.59 mmol) was added dropwise under stirring. After the dropwise addition was completed, the mixture was stirred at -78 °C for 1 h. Then, adamantane ketone (43.2 g, 287.46 mmol) was dissolved in tetrahydrofuran (170 mL) and the solution was added dropwise. After the dropwise addition was completed, the mixture was kept at -78 °C for 1 h and then naturally warmed to room temperature. The mixture was continuously stirred for 12 h. Hydrochloric acid (12 M) (39.2 mL, 470.4 mmol) was added to the reaction solution. After stirring for 0.5 h, the organic phase was washed with water until neutral. Anhydrous sodium sulfate was added for drying. 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 (1:2, by volume) as the eluent to obtain intermediate 1-3 (55.5 g, yield 62.7%).

[0070] S2: Under nitrogen protection, intermediate 1-3 (51.6 g, 152.27 mmol) and glacial acetic acid (550 mL) were added into a three-necked round-bottom flask. Concentrated sulfuric acid (98%) (3.1 mL, 30.4 mmol) was slowly added dropwise to the acetic acid (60 mL) under stirring at room temperature. After the dropwise addition was completed, the mixture was warmed to 80 °C and stirred for 2 h. After the reaction was completed, the mixture was cooled to room temperature. 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 dichloromethane / n-heptane (1:2) as the eluent to obtain intermediate 1-4 (40.6 g, yield 83.1%).

[0071] S3: Under nitrogen protection, intermediate 1-4 (37.6 g, 117.18 mmol), N,N- dimethylformamide (380 mL), and potassium carbonate (24.3 g, 175.78 mmol) were added into a three-necked round-bottom flask. After complete dissolution under stirring at room temperature, N-bromosuccinimide (21.3 g, 119.5 mmol) was further added. The mixture was warmed to 80 °C and stirred for 4 h. After the reaction was completed, the mixture was cooled to room temperature. The mixture 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 crude product was purified by silica gel column chromatography using dichloromethane / n-heptane (1:2) as the eluent to obtain intermediate 1-5 (39.9 g, yield 85.3%).

[0072] 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, stirred and dissolved at room temperature, then tetrakis(triphenylphosphine)palladium (1.78 g, 1.54 mmol) was added, the temperature was raised to 80°C, and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, washed with water until neutral, the organic phase was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and silica gel column chromatography was performed using a dichloromethane / n-heptane system (1:2) to purify the product, thereby obtaining intermediate 1 (33.5 g, yield 72.9%).

[0073] 2. Synthesis of intermediate 2, the synthesis route is shown below, which specifically includes the following steps:

[0074]

[0075] S1: Refer to the synthesis of intermediate 1-3, replace intermediate 1-1 with intermediate 2-1, and the yield is 66.3%.

[0076] S2: Refer to the synthesis of intermediate 1-4, replace intermediate 1-3 with intermediate 2-2, and the yield is 76.4%.

[0077] S3: Under nitrogen protection, intermediate 2-3 (27.6 g, 96.4 mmol), potassium carbonate (39.9 g, 289.1 mmol), and N,N-dimethylformamide (280 mL) were added into a three-necked round-bottom flask, stirred and completely dissolved at room temperature, then N-bromosuccinimide (34.6 g, 194.6 mmol) was added, the temperature was raised to 80°C, and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, the reaction solution was poured into 1 L of water under stirring, filtered, the filter cake was washed with water until neutral, then dissolved in dichloromethane, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and silica gel column chromatography was performed using a dichloromethane / n-heptane system (1:2) to purify the product, thereby obtaining intermediate 2 (33.5 g, yield 78.2%).

[0078] 3. Synthesis of intermediate 3, the synthesis route is shown below, which specifically includes the following steps:

[0079]

[0080] Refer to the synthesis of intermediate 1, except that intermediate 1-6 is replaced by intermediate 3-1, and the yield is 71.6%.

[0081] 4. Synthesis of intermediate 4, the synthesis route is shown below, which specifically includes the following steps:

[0082]

[0083] Referring to the synthesis of intermediate 1, the difference is that intermediate 1-6 is replaced by intermediate 4-1, and the yield is 75.1%.

[0084] Example 2

[0085] This example provides the synthesis of a pyrene-containing compound.

[0086] 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 pyrenyl), the synthesis route is as shown below, which specifically comprises the following steps:

[0087]

[0088] In a three-necked round-bottom flask, 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) were added, and the mixture was stirred at 80°C for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was washed with water until it was neutral. The organic phase was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography using a dichloromethane / n-heptane system (1:2) to obtain compound 1 (3.4 g, yield 67.3%).

[0089] 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 value: C, 94.4513; H, 5.5487; measured value: C, 94.4519; H, 5.5481.

[0090] 2. Synthesis of compound 2 (having a structure as shown in formula (I), wherein Ar1 is phenyl, L is anthryl, and Ar2 is phenyl), the synthesis route is as shown below, and the synthesis method refers to the synthesis of compound 1, the difference being that compound 1-1 is replaced by compound 2-1, and the yield is 72.2%.

[0091] 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, 94.4740; H, 5.5260; found: C, 94.4753; H, 5.5247.

[0092]

[0093] 3. Synthesis of compound 2 (having a structure as shown in formula (I) wherein Ar1is phenyl, L is pyrenyl, and Ar2is phenyl), the synthesis route is shown below, which specifically comprises the following steps:

[0094]

[0095] Under nitrogen protection, a three-necked round-bottom flask was added with 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), and water (10 mL), and after stirring and dissolving at room temperature, tetrakis(triphenylphosphine)palladium (0.2 g, 0.18 mmol) was added, and the temperature was increased to 80°C, and the temperature was kept for 8 hours of stirring. After the reaction was completed and the temperature was cooled to room temperature, the reaction liquid was washed with water until it was neutral, the organic phase was dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and silica gel column chromatography was performed using a dichloromethane / n-heptane system (1:2) to purify, to obtain compound 5 (5.2 g, yield 68.5%).

[0096] 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.

[0097] 4. Synthesis of compound 11 (having a structure as shown in formula (I) wherein Ar1is phenyl, L is anthryl, and Ar2is 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%.

[0098] The mass spectrum detection result of the obtained sample was: HR-MS (APCI): m / z 905.3687 [M+H] + ; C 70 H 48 O(%) calculated: C, 92.8871; H, 5.3454; O, 1.7675; found: C, 92.8889; H, 5.3449; O, 1.7662.

[0099]

[0100] 5. Synthesis of compound 40 (having the structure as shown in formula (I) wherein Ar1is dibenzofuranyl, L is single bond, Ar2is dibenzofuranyl), the synthetic route is shown below, the synthetic method refers to the synthesis of compound 1, the difference is that intermediate 1 is replaced by intermediate 3, compound 1-1 is replaced by compound 40-1, the yield is 63.9%.

[0101] The mass spectrum detection result of the obtained sample is: HR-MS (APCI): m / z 819.3176 [M+H] + ; C 62 H 42 O2 (%) calculated: C, 90.9240; H, 5.1691; O, 3.9069; found: C, 90.9262; H, 5.1683; O, 3.9055.

[0102]

[0103] 6. Synthesis of compound 41 (having the structure as shown in formula (I) wherein Ar1is phenyl, L is phenyl, Ar2is 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%.

[0104] The mass spectrum detection result of the obtained sample is: HR-MS (APCI): m / z 839.3621 [M+H] + ; C 66 H 46 (%) calculated: C, 94.4740; H, 5.5260; found: C, 94.4751; H, 5.5249.

[0105]

[0106] 7. Synthesis of compound 43 (having the structure as shown in formula (I) wherein Ar1is phenyl, L is anthryl, Ar2is 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%.

[0107] The mass spectrum detection result of the obtained sample is: HR-MS (APCI): m / z 939.3926 [M+H] + ; C 74 H 50Calculated: C, 94.5584; H, 5.4416; Found: C, 94.5592; H, 5.4408.

[0108]

[0109] 8. Synthesis of compound 44 (having the structure as shown in formula (I) wherein Ar1is phenyl, L is naphthyl, and Ar2is pyrenyl), the synthetic route is shown below, the synthetic method is referred to the synthesis of compound 1, except that compound 1-1 is replaced by compound 44-1, the yield is 68.2%.

[0110] The mass spectrum of the obtained sample is detected as follows: HR-MS (APCI): m / z 889.3763 [M+H] + ; C 70 H 48 Calculated: C, 94.5584; H, 5.4416; Found: C, 94.5592; H, 5.4408.

[0111]

[0112] 9. Synthesis of compound 108 (having the structure as shown in formula (I) wherein Ar1is phenyl, L is single bond, and Ar2is dibenzofuranyl substituted by deuterium atom), the synthetic route is shown below, the synthetic method is referred to the synthesis of compound 1, except that intermediate 1 is replaced by intermediate 4, and compound 1-1 is replaced by compound 108-1, the yield is 61.7%.

[0113] The mass spectrum of the obtained sample is detected as follows: HR-MS (APCI): m / z 736.2609 [M+H] + ; C 56 H 33 OD7 (%) Calculated: C, 93.1757; H, 4.6080; O, 2.2163; Found: C, 91.4006; H, 6.4254; O, 2.1741.

[0114]

[0115] 10. Synthesis of compound 113 (having the structure as shown in formula (I) wherein Ar1is phenyl, L is dibenzofuran, and Ar2is phenyl), the synthetic route is shown below, the synthetic method is referred to the synthesis of compound 1, except that compound 1-1 is replaced by compound 113-1, the yield is 65.6%.

[0116] The mass spectrometry results of the obtained sample are as follows: HR-MS (APCI): m / z 806.0385 [M+H] + C 62 H 44 Calculated values ​​of O (%): C, 92.5036; H, 5.5135; O, 1.9907; Measured values: C, 92.5827; H, 5.5181; O, 1.9963.

[0117]

[0118] All compounds disclosed in this invention, except for compounds 1, 2, 3, 5, 11, 22, 32, 40, 41, 43, 44, 108, and 113, can be prepared by referring to the above preparation method.

[0119] Example 3

[0120] This embodiment provides photoelectric performance parameters of pyrene-containing compounds. HOMO and LUMO are data obtained from simulation calculations. The calculation method uses B3LYP hybrid functionals with a basis set of 6-31g(d,P). The results are shown in Table 1.

[0121] Table 1. T1 energy levels of pyrene-containing compounds and HOMO and LUMO simulation results.

[0122]

[0123] As shown in Table 1, the pyrene-containing compounds of the present invention, which use a combination of fluorenyramane and pyrene as the parent core, have suitable HOMO, LUMO, and T1 values, and these compounds are suitable for use as blue light host materials.

[0124] Example 4

[0125] This embodiment measures the performance of an organic electroluminescent device using a pyrene-containing compound as the host material for the light-emitting layer.

[0126] 1. Functional layer of organic electroluminescent devices

[0127] The structure of organic electroluminescent devices is as follows Figure 1 As shown, it 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 stacked in sequence.

[0128] The anode layer 2 is made of indium tin oxide (ITO) with high work function, the hole injection layer 3 is made of HAT-CN with a thickness of 5 nm, the first hole transport layer 4 is made of HT1 with a thickness of 60 nm, the second hole transport layer 5 is made of HT2 with a thickness of 15 nm, the light-emitting layer 6 is made of a pyrene-containing compound or BH1 as a host material and BD01 as a light-emitting material with a doping mass ratio of 3% and a thickness of 30 nm, the hole blocking layer 7 is made of HB with a thickness of 10 nm, the electron transport layer 8 is made of ET-1 with a thickness of 30 nm, the electron injection layer 9 is made of Liq with a thickness of 2 nm, and the cathode layer 10 is made of Al with a thickness of 100 nm.

[0129] The basic material structures used in the functional layers of the organic electroluminescent device are as follows:

[0130]

[0131]

[0132] 2. Preparation of the organic electroluminescent device

[0133] 1) Clean the ITO anode on the transparent glass or plastic substrate, and ultrasonically clean with deionized water, acetone and ethanol for 20 minutes respectively, and then perform plasma treatment in an oxygen atmosphere for 5 minutes;

[0134] 2) On the ITO anode layer, vacuum evaporate the hole injection layer material HAT-CN with a thickness of 5 nm, which serves as the hole injection layer;

[0135] 3) On the hole injection layer, vacuum evaporate the hole transport material HT1 with a thickness of 60 nm, which serves as the first hole transport layer;

[0136] 4) On the first hole transport layer HT1, vacuum evaporate the hole transport material HT2 with a thickness of 15 nm, which serves as the second hole transport layer;

[0137] 5) On the second hole transport layer, co-evaporate the light-emitting layer by vacuum evaporation, using a pyrene-containing compound or BH1 as a host material and BD01 as a light-emitting material with a doping mass ratio of 3% and a thickness of 30 nm;

[0138] 6) On the light-emitting layer, vacuum evaporate the hole blocking material HB with a thickness of 10 nm, which serves as the hole blocking layer;

[0139] 7) On the hole blocking layer, vacuum evaporate the electron transport material ET-1 with a thickness of 30 nm, which serves as the electron transport layer;

[0140] 8) On the electron transport layer, electron injection material Liq was evaporated by vacuum evaporation, with a thickness of 2 nm, which served as an electron injection layer;

[0141] 9) On the electron injection layer, cathode Al was evaporated by vacuum evaporation, with a thickness of 100 nm, which served as a cathode conductive electrode.

[0142] Each group of organic electroluminescent devices was connected to the cathode and anode by a known driving circuit, and the voltage-efficiency-current density relationship of the OLED device was tested by a standard method using a Keithley 2400 power supply combined with a PR670 luminometer. The lifetime of the blue light device was tested by a constant current method, and the test conditions were that the initial brightness of the device was 100% under the application of 20 mA / cm 2 , and the time required when the brightness decayed to 90% of the initial brightness was the LT 90 of the device. The test results are shown in Table 2.

[0143] Table 2 Performance parameters of organic electroluminescent devices

[0144]

[0145] As can be seen from Table 2, the pyrene-containing compound provided by the present application applied to the OLED device as a blue light host material can significantly improve the performance of the device, and the brightness efficiency and lifetime performance of the device are greatly improved. Compared with the existing OLED device, the brightness efficiency of the OLED device with the pyrene-containing compound provided by the present application as a blue light host material in the light-emitting layer is increased by 9.4~38.5%, and the device lifetime is extended by 22.8~68.7%. For example, in the blue light device embodiment 3, the brightness efficiency of the compound 5 as a blue light host material is increased by 35.2% compared with BH1 in the comparative example 1, and the device lifetime is increased by 36.6%; the brightness efficiency of the deuterated host material compound 108 is increased by 38.5% compared with the comparative material BH1, and the device lifetime is increased by 68.7%. It can be seen that the pyrene-containing compound provided by the present application has great application value in the OLED device and has good industrialization prospects.

[0146] As described above, the basic principles, main features and advantages of the present application are better described. The above examples and descriptions only 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, It has a structure as shown in equation (I), ； In formula (I), Ar1 and Ar2 are each independently selected from one of the aryl and heteroaryl groups of C6 to 30. In the formula (I), L is selected from one of single bond, aryl, and heteroaryl; The aryl group of C6-30 is selected from one of phenyl, naphthyl, phenanthryl, pyrene, benzo[a]phenanthryl, and alkyl. When Ar1 and Ar2 are independently selected from heteroaryl groups, the heteroaryl group is selected from one of dibenzofuranyl, naphthofuranyl, dibenzothiophenyl, benzonaphthofuranyl, and benzocarbazoyl. When L is selected from aryl, aryl is selected from one of phenyl, naphthyl, benzanthyl, pyrene, and fluorenyl. When L is selected from a heteroaryl group, the heteroaryl group is selected from one of furanyl, carbazoyl, and thiophenyl.

2. A pyrene-containing compound, characterized in that, It has the structure shown below. 。 3. The application of the pyrene-containing compound according to any one of claims 1 to 2 in organic electroluminescent devices, characterized in that, The pyrene-containing compound serves as the main blue light source material in the emitting layer of the organic electroluminescent device.

4. An organic electroluminescent device comprising a light-emitting layer, characterized in that, The main material of the light-emitting layer is the pyrene-containing compound as described in any one of claims 1 to 2.

5. A display component, characterized in that, It includes the organic electroluminescent device as described in claim 4.

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