Polycyclic aromatic compound as well as organic light-emitting device and organic light-emitting device adopting same

Abstract

The invention provides a polycyclic aromatic compound as well as an organic light-emitting device and an organic light-emitting device adopting the polycyclic aromatic compound. The polycyclic aromatic compound has a structure as shown in a general formula I. According to the polycyclic aromatic compound, fluorene or carbazole is introduced on the basis of a parent nucleus; the stacking density and steric hindrance of the compound are increased due to excessive phenyl groups in the compound, the evaporation temperature of the compound is influenced, and the luminous efficiency and the service life are reduced. Fluorene or carbazole has a relatively large conjugation characteristic, so that on one hand, the stacking effect between molecules can be improved, and on the other hand, the horizontal arrangement degree of the molecules can be increased, so that the molecules are effectively and horizontally arranged, the luminous efficiency is effectively increased, and the service life of a device is also greatly prolonged. The service life and the efficiency of a device prepared from the doping material are obviously improved.

Description

Technical Field

[0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to a polycyclic aromatic compound and an organic light-emitting device and an organic light-emitting apparatus using the compound. Background Art

[0002] Organic light-emitting diodes (OLEDs) have been widely used in smart phones, smart watches, tablet computers, and televisions because of their high brightness and luminous efficiency, small size, wide viewing angle, fast response speed, application on flexible substrates, bendable devices, large-scale and large-area production, and high cost performance.

[0003] In the field of display and solid-state lighting, the development of blue light emitting materials is a key factor affecting the application scope of OLED in panel display. At the same time, blue light emission is also a key color component for achieving high-quality red, green, blue, yellow (RGBY) and RGB white display technology and solid-state light sources. At present, many red and green light emitters have been developed and are widely used in commercial OLED products. However, there is less development of blue light emitting materials, so the development of a blue light emitting material with narrow half-peak width and high color purity is the focus of the industry.

[0004] At present, polycyclic aromatic compounds formed by condensing multiple aromatic rings with boron atoms and heteroatoms such as nitrogen and oxygen have become mainstream because of their multiple vibration effects, high radiation transition rate, narrow half-peak width, high color purity and other characteristics. However, this material does not perform particularly well in terms of device service life and luminous efficiency, and the industrialization process of this technology still faces many key problems. Therefore, the development of a new material has always been an urgent problem to be solved by technical personnel in this field. Summary of the invention

[0005] In view of the shortcomings of the prior art, the purpose of the present invention is to provide a polycyclic aromatic compound and an organic light-emitting device and an organic light-emitting device using the same. The polycyclic aromatic compound of the novel structure provided by the present invention has the advantage that the polycyclic aromatic compound introduces fluorene or carbazole on the basis of the parent core because the two have greater conjugated properties, which can improve the stacking effect between molecules on the one hand, and increase the horizontal arrangement of molecules on the other hand, so that the molecules can be effectively arranged horizontally, thereby effectively increasing the luminous efficiency and greatly improving the device life. After being used in an organic light-emitting device, the efficiency of the device is improved and the service life is increased.

[0006] In order to achieve the purpose of the invention, the present invention adopts the following technical solutions:

[0007] In one aspect, the present invention provides a polycyclic aromatic compound having a structure shown in Formula I:

[0008]

[0009] In formula I, R1-R5 are substituted or unsubstituted C1-C30 alkyl groups or hydrogen atoms; R1-R5 are monosubstituted to maximally substituted;

[0010] X1 is selected from O or S;

[0011] X2 is selected from N, CR6, R6 is selected from substituted or unsubstituted C1-C30 alkyl or C6-C30 aryl;

[0012] In the present invention, the C1-C30 represents that the number of carbon atoms of the defined group can be any integer from 1 to 30, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 15, 18, 20, 22, 25, 28 or 30, and the C6-C30 represents that the number of carbon atoms of the defined group can be any integer from 6 to 30, for example, 6, 7, 8, 9, 10, 12, 15, 18, 20, 22, 25, 28 or 30.

[0013] The term "substituted" means substituted by one, two or more substituents selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a trifluoromethyl group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a butyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a 1-methylhexyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a thienyl group, a furanyl group, a pyrrolyl group, a benzothienyl group, a benzofuranyl group, a pyridyl group, an indolyl group, a cyclopentanyl group, a cyclohexanyl group, and an adamantane group, or substituted by two or more of the substituents shown above connected to each other, or having no substituents.

[0014] Preferably, R1-R5 are independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl or , where the wavy line represents the attachment site of the group.

[0015] Preferably, the polycyclic aromatic compound has a structure shown in Formula I-1 or I-2:

[0016]

[0017] Preferably, R6 is independently selected from methyl, ethyl or phenyl.

[0018] In the above formulae, all hydrogens are independently substituted with deuterium or not.

[0019] Preferably, the polycyclic aromatic compound is selected from any one of the following compounds:

[0020]

[0021]

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[0025]

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[0030]

[0031]

[0032]

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[0036]

[0037]

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[0039]

[0040]

[0041]

[0042]

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[0044]

[0045]

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[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058] .

[0059] The polycyclic aromatic compounds of the present invention can be prepared by a synthetic method known to those skilled in the art. For example, the following reaction scheme is preferred for preparation.

[0060]

[0061] wherein Hal1-Hal5 is selected from halogen (eg, F, Cl, Br or I).

[0062] Step 1 specifically includes the following steps: under nitrogen protection, raw material A (1.0 eq) and raw material B (1.0 eq) are dissolved in a toluene solution, sodium tert-butoxide (2.00 eq), tri(dibenzylideneacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) are added, stirred evenly, heated to 110° C., and refluxed for 6 hours; after the reaction is completed, the temperature is slightly lowered, diatomaceous earth is used for filtering to remove salt and catalyst, and the filtrate is cooled to room temperature and washed with water three times, the organic phase is retained, and then the aqueous phase is extracted with ethyl acetate; after the organic phases are combined, they are dried with anhydrous magnesium sulfate, and the solvent is removed with a rotary evaporator, and dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake is rinsed with petroleum ether for multiple times, and placed in a 60° C. oven for drying for 5 hours to obtain intermediate 1;

[0063] Step 2 specifically includes the following steps: under nitrogen protection, raw material C (1.0 eq) and raw material D (1.0 eq) are dissolved in a toluene solution, sodium tert-butoxide (2.00 eq), tri(dibenzylideneacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) are added, stirred evenly, heated to 110° C., and refluxed for 6 hours; after the reaction is completed, the temperature is slightly lowered, diatomaceous earth is used for filtering to remove salt and catalyst, and the filtrate is cooled to room temperature and washed three times with water, the organic phase is retained, and then the aqueous phase is extracted with ethyl acetate; after the organic phases are combined, they are dried with anhydrous magnesium sulfate, and the solvent is removed with a rotary evaporator, and dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake is rinsed with petroleum ether for multiple times, and placed in a 60° C. oven for drying for 5 hours to obtain intermediate 2;

[0064] Step 3 specifically includes the following steps:

[0065] Under nitrogen protection, raw material E (1.0 eq) and intermediate 1 (1.0 eq) were dissolved in toluene solution, sodium tert-butoxide (2.00 eq), tri(dibenzylideneacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) were added, stirred evenly, heated to 120°C, and refluxed for 12 h. After the reaction was completed, the temperature was slightly lowered, filtered using diatomaceous earth to remove salt and catalyst, and the filtrate was cooled to room temperature and washed three times with water, the organic phase was retained, and the aqueous phase was then extracted with ethyl acetate. After the organic phases were combined, they were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake was rinsed with petroleum ether several times and dried in a 60°C oven for 7 h to obtain intermediate 3.

[0066] Step 4 specifically includes the following steps:

[0067] Under nitrogen protection, intermediate 2 (1.0 eq) and intermediate 3 (1.0 eq) were dissolved in 1,4-dioxane solution, sodium tert-butoxide (2.00 eq), palladium acetate (0.05 eq), and X-Phos (2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl, 0.05 eq) were added and stirred evenly, and the temperature was raised to 100°C, and refluxed for 10 hours. After the reaction was completed, the temperature was slightly lowered, and diatomaceous earth was used for filtration to remove salt and catalyst. After the filtrate was cooled to room temperature, a rotary evaporator was used to remove the solvent. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=10:4) to obtain intermediate 4.

[0068] Step 5 specifically includes the following steps:

[0069] Under nitrogen atmosphere, intermediate 4 (1.0 eq) and anhydrous tert-butylbenzene were placed in a reaction bottle, nitrogen was replaced, and tert-butyl lithium pentane solution (5.0 eq) was added dropwise to the reaction system at -78 °C. After the addition was completed, the temperature was slowly raised to 65 °C and stirred for 3 h. The temperature was then lowered to -30 °C, and boron tribromide (5.0 eq) was added dropwise. The temperature was raised to room temperature, and stirring was continued for 1 h. N, N-diisopropylethylamine (10.0 eq) was added dropwise to the reaction system. The temperature was raised to 145 °C and the reaction was continued for 4 h. After monitoring the reaction, the reaction was cooled to room temperature, and a saturated sodium bicarbonate aqueous solution was added dropwise to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (eluent: V (ethyl acetate): V (petroleum ether) = 1:20) to obtain Formula I.

[0070] In another aspect, the present invention provides an organic light-emitting device, comprising an anode and a cathode and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin film layer comprises the polycyclic aromatic compound as described above.

[0071] Preferably, the organic thin film layer comprises a light-emitting layer, the light-emitting layer comprises a host material and a doping material, and the doping material comprises the polycyclic aromatic compound as described above.

[0072] Preferably, the organic thin film layer further includes at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer or an electron injection layer.

[0073] Compared with the prior art, the present invention has the following beneficial effects:

[0074] The polycyclic aromatic compound of the present invention introduces fluorene or carbazole on the basis of the parent core. The excessive number of phenyl groups in the compound will increase the packing density and steric hindrance of the compound, affect the evaporation temperature of the compound, and thus reduce the luminous efficiency and life. Fluorene or carbazole has a large conjugated property, which can improve the stacking effect between molecules on the one hand, and increase the horizontal arrangement of molecules on the other hand, so that the molecules are effectively arranged horizontally, thereby effectively increasing the luminous efficiency and greatly improving the device life. The device life and efficiency prepared by the doping material of the present invention are significantly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0075] Figure 1 is the H NMR spectrum of compound 48.

[0076] Figure 2 The H NMR spectrum of intermediate 4.

[0077] Figure 3 This is the hydrogen NMR spectrum of compound 177. DETAILED DESCRIPTION

[0078] The technical solution of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention and the related drawings. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0079] A series of palladium-catalyzed coupling reactions carried out in the present invention utilize the difference that the activity of Br is greater than that of Cl on the one hand, and on the other hand, the reaction site is controlled by controlling the reaction conditions, and the reaction is purified by column chromatography or silica gel funnel to remove by-products to obtain the target compound.

[0080] Reference to common knowledge is as follows:

[0081] "Transition Metal Organic Chemistry" (Original Sixth Edition), Robert H. Crabtree, Publisher: Shanghai East China University of Science and Technology Press, Publication Date: 2017-09-00, ISBN: 978-7-5628-5111-0, page 388.

[0082] "Organic Chemistry and Optoelectronic Materials Experimental Tutorial", Chen Runfeng, Publisher: Southeast University Press, Publication Date: 2019-11-00, ISBN: 9787564184230, Page 174.

[0083] Example 1

[0084]

[0085] Step 1 specifically includes the following steps: under nitrogen protection, raw material A (1.0 eq) and raw material B (1.0 eq) are dissolved in a toluene solution, sodium tert-butoxide (2.00 eq), tri(dibenzylideneacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) are added, stirred evenly, heated to 110° C., and refluxed for 6 hours; after the reaction is completed, the temperature is slightly lowered, diatomaceous earth is used for filtering to remove salt and catalyst, and the filtrate is cooled to room temperature and washed with water three times, the organic phase is retained, and then the aqueous phase is extracted with ethyl acetate; after the organic phases are combined, they are dried with anhydrous magnesium sulfate, and the solvent is removed with a rotary evaporator, and dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake is rinsed with petroleum ether for multiple times, and placed in a 60° C. oven for drying for 5 hours to obtain intermediate 1;

[0086] Step 2 specifically includes the following steps: under nitrogen protection, raw material C (1.0 eq) and raw material D (1.0 eq) are dissolved in a toluene solution, sodium tert-butoxide (2.00 eq), tri(dibenzylideneacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) are added, stirred evenly, heated to 110° C., and refluxed for 6 hours; after the reaction is completed, the temperature is slightly lowered, diatomaceous earth is used for filtering to remove salt and catalyst, and the filtrate is cooled to room temperature and washed three times with water, the organic phase is retained, and then the aqueous phase is extracted with ethyl acetate; after the organic phases are combined, they are dried with anhydrous magnesium sulfate, and the solvent is removed with a rotary evaporator, and dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake is rinsed with petroleum ether for multiple times, and placed in a 60° C. oven for drying for 5 hours to obtain intermediate 2;

[0087] Step 3 specifically includes the following steps:

[0088] Under nitrogen protection, raw material E (1.0 eq) and intermediate 1 (1.0 eq) were dissolved in toluene solution, sodium tert-butoxide (2.00 eq), tri(dibenzylideneacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) were added, stirred evenly, heated to 120°C, and refluxed for 12 h. After the reaction was completed, the temperature was slightly lowered, filtered using diatomaceous earth to remove salt and catalyst, and the filtrate was cooled to room temperature and washed three times with water, the organic phase was retained, and the aqueous phase was then extracted with ethyl acetate. After the organic phases were combined, they were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake was rinsed with petroleum ether several times and dried in a 60°C oven for 7 h to obtain intermediate 3.

[0089] Step 4 specifically includes the following steps:

[0090] Under nitrogen protection, intermediate 2 (1.0 eq) and intermediate 3 (1.0 eq) were dissolved in 1,4-dioxane solution, sodium tert-butoxide (2.00 eq), palladium acetate (0.05 eq), and X-Phos (0.05 eq) were added and stirred evenly, and the temperature was raised to 100°C, and the reaction was refluxed for 10 hours. After the reaction was completed, the temperature was slightly lowered, and diatomaceous earth was used for filtration to remove salt and catalyst. After the filtrate was cooled to room temperature, a rotary evaporator was used to remove the solvent. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=10:4) to obtain intermediate 4.

[0091] Step 5 specifically includes the following steps:

[0092] Under nitrogen atmosphere, intermediate 4 (1.0 eq) and anhydrous tert-butylbenzene were placed in a reaction bottle, nitrogen was replaced, and tert-butyl lithium pentane solution (5.0 eq) was added dropwise to the reaction system at -78 °C. After the addition was completed, the temperature was slowly raised to 65 °C and stirred for 3 h. The temperature was then lowered to -30 °C, and boron tribromide (5.0 eq) was added dropwise. The temperature was raised to room temperature, and stirring was continued for 1 h. N, N-diisopropylethylamine (10.0 eq) was added dropwise to the reaction system. The temperature was raised to 145 °C and the reaction was continued for 4 h. After monitoring the reaction, the reaction was cooled to room temperature, and a saturated sodium bicarbonate aqueous solution was added dropwise to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (eluent: V (ethyl acetate): V (petroleum ether) = 1:20) to obtain compound 48. (Yield: 35.8%, Mw: 919.68).

[0093] The obtained compound 48 was tested and analyzed, and the results were as follows:

[0094] HPLC purity: >99.95%.

[0095] Mass spectrometry test: theoretical value is 919.47; tested value is 919.68.

[0096] The H NMR spectrum of compound 48 is shown in Figure 1 shown.

[0097] Elemental Analysis:

[0098] Calculated values: C, 86.16; H, 6.35; B, 1.17; N, 4.57; O, 1.74.

[0099] The test values ​​are: C, 86.02; H, 6.44; B, 1.22; N, 4.65; O, 1.81.

[0100] Example 2

[0101]

[0102] Step 1 specifically includes the following steps: under nitrogen protection, raw material A (1.0 eq) and raw material B (1.0 eq) are dissolved in a toluene solution, sodium tert-butoxide (2.00 eq), tri(dibenzylideneacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) are added, stirred evenly, heated to 110° C., and refluxed for 6 hours; after the reaction is completed, the temperature is slightly lowered, diatomaceous earth is used for filtering to remove salt and catalyst, and the filtrate is cooled to room temperature and washed with water three times, the organic phase is retained, and then the aqueous phase is extracted with ethyl acetate; after the organic phases are combined, they are dried with anhydrous magnesium sulfate, and the solvent is removed with a rotary evaporator, and dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake is rinsed with petroleum ether for multiple times, and placed in a 60° C. oven for drying for 5 hours to obtain intermediate 1;

[0103] Step 2 specifically includes the following steps: under nitrogen protection, raw material C (1.0 eq) and raw material D (1.0 eq) are dissolved in a toluene solution, sodium tert-butoxide (2.00 eq), tri(dibenzylideneacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) are added, stirred evenly, heated to 110° C., and refluxed for 6 hours; after the reaction is completed, the temperature is slightly lowered, diatomaceous earth is used for filtering to remove salt and catalyst, and the filtrate is cooled to room temperature and washed three times with water, the organic phase is retained, and then the aqueous phase is extracted with ethyl acetate; after the organic phases are combined, they are dried with anhydrous magnesium sulfate, and the solvent is removed with a rotary evaporator, and dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake is rinsed with petroleum ether for multiple times, and placed in a 60° C. oven for drying for 5 hours to obtain intermediate 2;

[0104] Step 3 specifically includes the following steps:

[0105] Under nitrogen protection, raw material E (1.0 eq) and intermediate 1 (1.0 eq) were dissolved in toluene solution, sodium tert-butoxide (2.00 eq), tri(dibenzylideneacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) were added, stirred evenly, heated to 120°C, and refluxed for 12 h. After the reaction was completed, the temperature was slightly lowered, filtered using diatomaceous earth to remove salt and catalyst, and the filtrate was cooled to room temperature and washed three times with water, the organic phase was retained, and the aqueous phase was then extracted with ethyl acetate. After the organic phases were combined, they were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake was rinsed with petroleum ether several times and dried in a 60°C oven for 7 h to obtain intermediate 3.

[0106] Step 4 specifically includes the following steps:

[0107] Under nitrogen protection, intermediate 2 (1.0 eq) and intermediate 3 (1.0 eq) were dissolved in 1,4-dioxane solution, sodium tert-butoxide (2.00 eq), palladium acetate (0.05 eq), and X-Phos (0.05 eq) were added and stirred evenly, and the temperature was raised to 100°C, and the reaction was refluxed for 10 hours; after the reaction was completed, the temperature was slightly lowered, and diatomaceous earth was used for filtration to remove salt and catalyst. After the filtrate was cooled to room temperature, a rotary evaporator was used to remove the solvent; the remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=10:4) to obtain intermediate 4. The nuclear magnetic resonance hydrogen spectrum of intermediate 4 is shown as follows: Figure 2 shown.

[0108] Step 5 specifically includes the following steps:

[0109] Under nitrogen atmosphere, intermediate 4 (1.0 eq) and anhydrous tert-butylbenzene were placed in a reaction bottle, nitrogen was replaced, and tert-butyl lithium pentane solution (5.0 eq) was added dropwise to the reaction system at -78 °C. After the addition was completed, the temperature was slowly raised to 65 °C and stirred for 3 h. The temperature was then lowered to -30 °C, and boron tribromide (5.0 eq) was added dropwise. The temperature was raised to room temperature and stirred for 1 h. N, N-diisopropylethylamine (10.0 eq) was added dropwise to the reaction system. The temperature was raised to 145 °C and the reaction was continued for 4 h. After monitoring the reaction, the reaction was cooled to room temperature, and a saturated sodium bicarbonate aqueous solution was added dropwise to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (eluent: V (ethyl acetate): V (petroleum ether) = 1:20) to obtain compound 177. (Yield: 35.2%, Mw: 1061.73).

[0110] The obtained compound 177 was tested and analyzed, and the results were as follows:

[0111] HPLC purity: >99.95%.

[0112] Mass spectrometry test: theoretical value is 1061.59; tested value is 1061.73.

[0113] The H NMR spectrum of compound 177 is shown in Figure 3 shown.

[0114] Elemental Analysis:

[0115] Calculated values: C, 84.80; H, 7.21; B, 1.02; N, 3.96; S, 3.02.

[0116] The test values ​​are: C, 84.43; H, 7.34; B, 1.15; N, 4.07; S, 3.14.

[0117] The synthesis methods of other compounds are the same as those in the above examples, which are not described one by one here. The mass spectra, molecular formulas and yields of other synthesis examples are shown in Table 1 below:

[0118] Table 1 Mass spectrometry analysis and yield of the examples

[0119]

[0120]

[0121]

[0122] Device Example 1: Manufacturing an organic light-emitting device containing Compound 1, specifically comprising the following steps:

[0123] a. ITO anode: Wash the ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate with a coating thickness of 150nm in distilled water twice, ultrasonically wash for 30 minutes, and then repeatedly wash it with distilled water twice, ultrasonically wash for 10 minutes. After washing, transfer it to a spin dryer for drying, and finally bake it in a vacuum oven at 220℃ for 2 hours. After baking, cool it down and it can be used. Use this substrate as the anode, use an evaporation machine to carry out the evaporation device process, and evaporate other functional layers on it in sequence.

[0124] b. HIL (hole injection layer): vacuum evaporation of hole injection layer materials HT-1 and P-dopant at an evaporation rate of 1Å / s, with the evaporation rate ratio of HT-1 to P-dopant being 97:3 and the thickness being 10nm;

[0125] c. HTL (hole transport layer): 130nm of HT-1 was vacuum evaporated on the hole injection layer at a deposition rate of 1Å / s as the hole transport layer;

[0126] d. Light-emitting auxiliary layer: 10 nm EBL-1 was vacuum-deposited on the hole transport layer at a deposition rate of 0.5 Å / s as a light-emitting auxiliary layer;

[0127] e. EML (light-emitting layer): Then, on the above-mentioned light-emitting auxiliary layer, a host material (Host) with a thickness of 20 nm and the compound 48 provided in the above embodiment as a doping material (Dopant) were vacuum-deposited at a deposition rate of 1Å / s as a light-emitting layer, wherein the deposition rate ratio of Host to Dopant was 98:2.

[0128] f. HBL (hole blocking layer): 5 nm of HB-1 was vacuum-deposited on the light-emitting layer at a deposition rate of 0.5 Å / s as a hole blocking layer;

[0129] g. ETL (electron transport layer): 30 nm of ET-1 was vacuum-deposited on the hole blocking layer at a deposition rate of 1 Å / s as the electron transport layer;

[0130] h. EIL (electron injection layer): 1.0 nm Yb film was evaporated at a deposition rate of 0.5 Å / s to form an electron injection layer;

[0131] i. Cathode: evaporating magnesium and silver at a deposition rate ratio of 1Å / s to 18nm, with a deposition rate ratio of 1:9, to obtain an OLED device;

[0132] j. Light extraction layer: CPL-1 with a thickness of 70nm is vacuum evaporated on the cathode at an evaporation rate of 1Å / s as a light extraction layer. The evaporated substrate is then packaged. First, the cleaned cover is coated with UV glue using a glue coating device, and then the coated cover is moved to the pressing section, and the evaporated substrate is placed on the upper end of the cover. Finally, the substrate and the cover are bonded by the bonding equipment, and the UV glue is cured by light.

[0133] The required material structure is as follows:

[0134]

[0135] Device Example 2-Device Example 65 Referring to the above method, the compound 48 used in Device Example 1 was replaced by compounds 2, 10, 14, 19, 21, 24, 25, 29, 33, 27, 45, 55, 60, 66, 75, 102, 108, 117, 129, 130, 138, 143, 147, 165, 166, 177, 179, 183, 186, 210, 215, respectively. , 225, 234, 235, 237, 241, 245, 252, 259, 261, 270, 287, 293, 300, 306, 308, 311, 315, 319, 326, 333, 345, 353, 358, 369, 380, 389, 396, 400, 404, 414, 427, 435 and 449 are used as doping materials to prepare corresponding organic light-emitting devices.

[0136] Device Comparative Example 1: This comparative example provides an organic light-emitting device. The only difference between the preparation method of the organic light-emitting device and the device embodiment 1 is that the organic light-emitting device uses existing comparative compounds A, B, C, and D to replace the doping material in the device embodiment 1 for evaporation to prepare device comparative examples 1 to 4. The chemical structural formulas of comparative compounds A, B, C, and D are as follows:

[0137] .

[0138] The driving voltage, luminous efficiency, BI value and lifespan of the organic light-emitting devices obtained from the device embodiments 1 to 65 and the device comparative examples 1 to 4 were characterized at a brightness of 1000 (nits). The test results are shown in Table 2 below.

[0139] Table 2

[0140]

[0141]

[0142] According to the above table, the organic light-emitting device prepared by using the compound provided by the present invention as the doping material in the light-emitting layer has a slightly lower driving voltage, an improved luminous efficiency, and a lifespan increased by 25-90 hours compared with the organic light-emitting device prepared by using the comparative compounds A to D as the doping material.

[0143] The applicant declares that the present invention illustrates the compounds and applications of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned process steps to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of the raw materials selected by the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A polycyclic aromatic compound, characterized in that: The polycyclic aromatic compound has a structure shown in the general formula I: In formula I, R1-R5 are substituted or unsubstituted C1-C30 alkyl groups or hydrogen atoms; R1-R5 are monosubstituted to maximally substituted; X1 is selected from O or S; X2 is selected from N, CR6, R6 is selected from substituted or unsubstituted C1-C30 alkyl or C6-C30 aryl; All hydrogens in Formula I are independently substituted with deuterium or not.

2. The polycyclic aromatic compound according to claim 1, characterized in that The substituents in the substituted group are selected from one or a combination of at least two of the following groups: hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, 1-methylhexyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, thienyl, furanyl, pyrrolyl, benzothienyl, benzofuranyl, pyridyl, indolyl, cyclopentanyl, cyclohexanyl or adamantyl.

3. The polycyclic aromatic compound according to claim 1, characterized in that: R1-R5 are independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl or , where the wavy line represents the attachment site of the group.

4. The polycyclic aromatic compound according to claim 1, characterized in that The polycyclic aromatic compound has a structure shown in Formula I-1 or I-2: R6 is independently selected from methyl, ethyl or phenyl; all hydrogens in formulas I-1 and I-2 are independently substituted by deuterium or not.

5. The polycyclic aromatic compound according to claim 1, characterized in that: The polycyclic aromatic compound is selected from any one of the following compounds: 。 6. An organic light-emitting device, characterized in that: The organic light-emitting device comprises an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin film layer comprises the polycyclic aromatic compound according to any one of claims 1 to 5.

7. The organic light emitting device according to claim 6, characterized in that: The organic thin film layer includes a light-emitting layer, the light-emitting layer includes a host material and a doping material, and the doping material includes the polycyclic aromatic compound according to any one of claims 1 to 5.

8. The organic light emitting device according to claim 6, characterized in that: The organic thin film layer further includes at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer or an electron injection layer.

9. An organic light-emitting device, characterized in that: The organic light-emitting device comprises the organic light-emitting device according to any one of claims 6 to 8.

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