Aryl tri-substituted benzanthracene-based organic electroluminescent compound and a double-emitting-layer organic electroluminescent device thereof

Abstract

The application relates to the technical field of organic photoelectric materials, and particularly discloses an aryl-trisubstituted benzanthracene organic electroluminescent compound and a double-emitting-layer organic electroluminescent device thereof. The structural general formula of the aryl-trisubstituted benzanthracene organic electroluminescent compound is shown as formula I, Ar1 and Ar3 each independently represent any one or a combination of any two of deuterated or non-deuterated aryl with 6-30 carbon atoms, deuterated or non-deuterated condensed ring aryl with 10-30 carbon atoms; Ar2 represents deuterated or non-deuterated phenyl or naphthyl; any hydrogen in formula I can be independently substituted by deuterium. By introducing the substituent defined in the application to the 4th, 7th and 12th positions of benzanthracene, the thermal stability of the compound can be improved, the molecular orientation can be improved, the PL spectrum peak of the compound provided by the application can be well overlapped with the absorption spectrum of a BD material, and energy transmission is more favorable.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic materials technology, and in particular to an aryl trisubstituted benzanthracene organic electroluminescent compound and its dual-emitting-layer organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs), as a new generation of display and lighting technology, have been widely used in consumer electronics products such as smartphones, smartwatches, tablets, and televisions due to their outstanding advantages such as self-illumination, high contrast, wide viewing angle, fast response speed, flexibility and foldability, and low-voltage DC drive.

[0003] In recent years, in order to improve the device performance of blue OLEDs, a dual-emitting-layer device architecture has been proposed. This architecture uses two adjacent emitting layers with different host triplet energy levels. By using the dexter energy transfer method, the "carrier recombination process" and "triplet-triplet fusion process" that traditionally occur in a single emitting layer are separated into two adjacent emitting layers, thereby significantly reducing the quenching of carriers and excitons, and singlet excitons and triplet excitons, and achieving a significant efficiency improvement. However, in existing dual-emitting-layer devices, the benzene-anthracene-based blue light materials, which are usually used as the host material of the first emitting layer, still have the following problems: (1) Unlike anthracene, benzene-anthracene has poor stability due to its special angular fusion method. (2) As the first emitting layer that acts as a carrier recombination layer, the 25% singlet excitons formed by recombination will directly transfer energy to the BD material (guest material or dopant material) doped in it, and then emit light through the BD material. The light extraction efficiency of the first emitting layer in this process will directly affect the device efficiency performance. The molecular orientation of the host and guest in the existing first emitting layer needs to be further improved. (3) The singlet exciton energy of benzene is too high, and the emission is biased towards the ultraviolet, which is not conducive to the energy transfer process between the host and guest.

[0004] Based on this, the development of a novel type of benzene-anthracene organic electroluminescent compound, through the rational design of the type and mode of substituents, optimizes the photoelectric properties and physicochemical properties of the molecule, significantly improving the overall performance of blue OLED devices and meeting the application needs of high-end display and lighting fields, has become an urgent technical problem to be solved in the field of organic optoelectronic materials. Summary of the Invention

[0005] To address the aforementioned problems, this invention provides an aryl trisubstituted benzanthracene organic electroluminescent compound and its dual-emitting-layer organic electroluminescent device. By rationally designing the substituent type, substituent connection sites, and number of substituents in the benzanthracene material, the electron cloud distribution, frontier orbital energy level, photophysical properties, and charge transport performance of its π-conjugated system are optimized, significantly improving the overall performance of the blue OLED device.

[0006] To solve the above-mentioned technical problems, the technical solution provided by the present invention is as follows:

[0007] In a first aspect, the present invention provides an aryl trisubstituted benzanthracene-based organic electroluminescent compound, the general structural formula of which is shown in Formula I.

[0008] I

[0009] In formula I,

[0010] Ar1 and Ar3 each independently represent any one or any combination of two of the following: aryl groups with 6 to 30 deuterated or non-deuterated carbon atoms, and fused-ring aryl groups with 10 to 30 deuterated or non-deuterated carbon atoms.

[0011] Ar2 represents a deuterated or non-deuterated phenyl or naphthyl group;

[0012] In Formula I, any hydrogen atom can be independently replaced by deuterium.

[0013] Compared with the prior art, the aryl trisubstituted benzanthracene organic electroluminescent compounds provided by the present invention, by simultaneously introducing substituents defined in the present invention at positions 4, 7 and 12 of benzanthracene, can not only improve the thermal stability of the compound, but also improve the molecular orientation. By specifically defining the substituent types at positions 4, 7 and 12 of benzanthracene, the present invention enables the PL (photoluminescence) spectral peak of the compound provided by the present invention to be located at 425nm~435nm, which can produce good overlap with the absorption spectrum of BD materials, and is more conducive to energy transfer.

[0014] Preferably, the aryl group is selected from phenyl or biphenyl.

[0015] In this invention, "any combination of two" refers to a combination in which Ar1 and Ar3 independently represent any one of the aryl groups and any one of the fused-ring aryl groups connected by a single bond.

[0016] Preferably, the number of carbon atoms in the fused-ring aryl group is 10 to 20.

[0017] More preferably, the fused aryl group shown is selected from naphthyl, phenanthryl, anthraceneyl, hydroxyl, pyrene, or benzophenanthryl.

[0018] More preferably, Ar1 and Ar3 are each independently selected from phenyl, biphenyl, naphthyl, anthraceneyl, phenanthryl, hydroxyl, pyrene, or benzophenanthryl.

[0019] More preferably, Ar1 and Ar3 are each independently selected from phenyl, biphenyl, naphthyl, ... , , , , , , or .

[0020] More preferably, Ar3 is selected from deuterated or non-deuterated phenyl, biphenyl, naphthyl or pyrene.

[0021] Preferably, Ar1 and Ar3 contain one and only one steric hindrance group. Specifically, the steric hindrance group can be... , , , , , or .

[0022] Further preferred, Ar1 contains sterically hindered groups, while Ar3 does not contain sterically hindered groups.

[0023] Most preferably, the structure of the aryl trisubstituted benzanthracene organoelectroluminescent compound is selected from any one of the following structural formulas.

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053] .

[0054] In a second aspect, the present invention provides a dual-emitting-layer organic electroluminescent device, comprising the aforementioned aryl trisubstituted benzanthracene organic electroluminescent compound.

[0055] Preferably, the structure of the dual-emitting-layer organic electroluminescent device includes an anode, a hole transport region, an electron blocking layer, a first emitting layer, a second emitting layer, a hole blocking layer, an electron transport region, and a cathode sequentially disposed on a substrate; wherein, the first emitting layer includes a first host material and a first guest material, and the first host material includes one or more of the aryl trisubstituted benzanthracene organic electroluminescent compounds.

[0056] More preferably, the hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer.

[0057] More preferably, the electron transport region includes an electron transport layer and an electron injection layer.

[0058] More preferably, the mass ratio of the first main material to the first object material is 90:10 to 99.5:0.5.

[0059] The present invention has the following beneficial effects:

[0060] The aryl trisubstituted benzanthracene organic electroluminescent compounds provided by this invention improve the thermal stability of benzanthracene organic electroluminescent compound materials by simultaneously introducing substituents defined in this invention at positions 4, 7, and 12 of benzanthracene, and avoid the introduction of too many sterically hindered substituents, thereby improving the molecular orientation of the compound materials. By specifically defining the substituent types at positions 4, 7, and 12 of benzanthracene, this invention enables the PL spectrum peak of the compounds provided by this invention to be located in the range of 425 nm to 435 nm, which can produce good overlap with the absorption spectrum of BD materials, thus facilitating energy transfer.

[0061] Using the aryl trisubstituted benzanthracene organic electroluminescent compounds provided by this invention as the main material in the first light-emitting layer of a dual-emitting-layer organic electroluminescent device, the compounds provided by this invention not only have high thermal stability but also improve molecular orientation. At the same time, they can have good overlap with the absorption spectrum of BD materials, which is more conducive to energy transfer. Therefore, the compounds provided by this invention can improve the luminous efficiency of the device and extend its lifespan, overcoming the defects of the prior art. Attached Figure Description

[0062] Figure 1 This is a schematic diagram of the structure of a dual-emitting-layer organic electroluminescent device in an embodiment of the present invention.

[0063] In the figure, 1 represents the substrate, 2 represents the anode, 3 represents the hole injection layer, 4 represents the hole transport layer, 5 represents the electron blocking layer, 6 represents the first light-emitting layer, 7 represents the second light-emitting layer, 8 represents the hole blocking layer, 9 represents the electron transport layer, 10 represents the electron injection layer, 11 represents the cathode, and 12 represents the capping layer. Detailed Implementation

[0064] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to embodiments. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the invention.

[0065] Terms and Definitions

[0066] The terms "preferred," "further preferred," and "more preferred" used in this invention refer to embodiments of the invention that provide certain beneficial effects under certain circumstances. However, other embodiments may also be preferred under the same or other circumstances. Furthermore, the description of one or more preferred embodiments does not imply that other embodiments are unavailable, nor is it intended to exclude other embodiments from the scope of this invention.

[0067] "Deuterium" refers to the hydrogen isotope deuterium.

[0068] "Deuteration" refers to the substitution of one or more hydrogen atoms in a group by deuterium.

[0069] “ "" indicates the connection site with other atoms.

[0070] "The same substituents but different connection sites" means that the substituents have the same structure. For example, when Ar1, Ar2 and Ar3 are all naphthyl groups, the parent nucleus structure can be connected to the 1st (α-position) and 2nd (β-position) positions of the naphthyl group respectively by single bonds.

[0071] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0072] The following are specific examples. Unless otherwise specified, the solvents and reagents used in the examples can be purchased from conventional reagent suppliers, and the relevant compounds can be prepared by existing processes or conventional processes in the art.

[0073] In this embodiment of the invention, the anode uses a commonly used anode material in the art, such as ITO, Ag, or their multilayer structures. The hole injection layer uses a commonly used hole injection material in the art, and is doped with F4TCNQ, HATCN, NDP-9, etc. The hole transport layer uses a commonly used hole transport material in the art. The light-emitting layer uses the host and guest material composition provided by this invention. The electron transport layer uses a commonly used electron transport material in the art. The electron injection layer uses a commonly used electron injection material in the art, such as LiQ, LiF, Yb, etc. The cathode uses a commonly used material in the art, such as metallic Al, Ag, or metal mixtures (Ag-doped Mg, Ag-doped Ca, etc.). The electrode preparation method and the deposition method of each functional layer in this invention are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, etc., and will not be described in detail here.

[0074] The general formula for the synthesis of aryl trisubstituted benzanthracene organoelectroluminescent compounds is shown in Formula 1:

[0075]

[0076] Formula 1

[0077] Synthesis example 1

[0078] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-1), with chemical equations shown in Formulas 2 and 3.

[0079]

[0080] Formula 2

[0081]

[0082] Formula 3

[0083] S1. In a three-necked flask, under nitrogen protection, 200 mL of toluene, 100 mL of ethanol, and 100 mL of water were added. Then, compound A (12.28 g, 40 mmol), compound B (6.88 g, 40 mmol), potassium carbonate (16.60 g, 120 mmol), and tetraphenylphosphine palladium (1.4 g, 1.2 mmol) were added. The mixture was heated to 80 °C and reacted for 12 h. After the reaction was completed, the mixture was cooled to room temperature and filtered. The filter cake was dissolved in toluene and then filtered to remove the solid insoluble matter. The mixture was then recrystallized to give compound C1: 12.74 g, yield: 90%, MS (m / z) (M+): 354.

[0084] S2. In a three-necked flask, compound C1 (10.62 g, 30 mmol) was stirred with 200 mL of N,N-dimethylformamide. N-bromosuccinimide (6.42 g, 36 mmol) was added at room temperature, and the mixture was stirred for 8 h. Methanol was added to the reaction solution and the resulting yellow solid was filtered. The solid was recrystallized from toluene and dried under vacuum to give compound D1: 11.04 g, yield: 85%, MS (m / z) (M+): 433.

[0085] S3. In a three-necked flask, under nitrogen protection, add 125 mL of toluene, 80 mL of ethanol, and 80 mL of water. Then add compound D1 (10.83 g, 25 mmol), compound E (4.30 g, 25 mmol), potassium carbonate (10.375 g, 75 mmol), and tetraphenylphosphine palladium (0.88 g, 0.75 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insoluble matter, and then recrystallize to obtain compound F1: 9.98 g, yield: 83%, MS (m / z) (M+): 481.

[0086] S4. In a three-necked flask, compound F1 (9.62 g, 20 mmol) was stirred with 200 mL of N,N-dimethylformamide. N-bromosuccinimide (4.28 g, 24 mmol) was added at room temperature, and the mixture was stirred for 8 h. Methanol was added to the reaction solution and the resulting yellow solid was filtered. The solid was recrystallized from toluene and dried under vacuum to give compound G1: 7.84 g, yield: 70%, MS (m / z) (M+): 560.

[0087] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G1 (5.60 g; 10 mmol), compound B (1.72 g; 10 mmol), potassium carbonate (4.15 g; 30 mmol), and tetraphenylphosphine palladium (0.35 g; 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-1: 5.16 g, yield: 85%, MS (m / z) (M+): 607. 1 H NMR(500 MHz, DMSO-d6) δ 8.42 – 8.35 (m, 2H), 8.30 – 8.18 (m, 5H), 8.16 – 8.12(m, 1H), 8.07 (d, J = 8.1 Hz, 1H), 8.05 – 7.97 (m, 5H), 7.95 – 7.91 (m, 3H), 7.84 (d, J = 7.1 Hz, 1H), 7.77 – 7.73 (m, 1H), 7.69 – 7.62 (m, 2H), 7.59 –7.46 (m, 9H).

[0088] Synthesis example 2

[0089] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-2), the chemical equation of which is shown in Formula 4.

[0090]

[0091] Formula 4

[0092] Compound G2 was prepared using a synthetic method similar to that of Synthesis Example 1, except that in S1, compound B was replaced with an equimolar amount of compound E. The remaining conditions were the same as S1-S4 of Synthesis Example 1 and will not be repeated here.

[0093] S5. Under nitrogen protection, 50 mL of toluene, 25 mL of ethanol, and 25 mL of water were added to a three-necked flask. Then, compound G2 (5.60 g; 10 mmol), compound B (1.72 g; 10 mmol), potassium carbonate (4.15 g; 30 mmol), and tetraphenylphosphine palladium (0.35 g; 0.3 mmol) were added. The mixture was heated to 80 °C and reacted for 12 h. After the reaction was completed, the mixture was cooled to room temperature and filtered. The filter cake was dissolved in toluene and then filtered to remove the solid insoluble matter. The product I-2 was then recrystallized to give 5.28 g, yield: 87%, MS (m / z) (M+): 607. 1 H NMR(500 MHz, DMSO-d6) δ 8.45 – 8.38 (m, 2H), 8.33 – 8.20 (m, 6H), 8.10 (d, J =8.0 Hz, 1H), 8.08 – 7.99 (m, 4H), 7.98 – 7.90 (m, 4H), 7.85 – 7.80 (m, 2H), 7.79 – 7.73 (m, 1H), 7.67 (t, J = 7.4 Hz, 1H), 7.61 – 7.46 (m, 9H).

[0094] Synthesis example 3

[0095] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-3), the chemical equation of which is shown in Formula 5.

[0096]

[0097] Formula 5

[0098] Compound G3 was prepared using a synthetic method similar to that used in Synthesis Example 1, except that in S1, compound B was replaced with an equimolar amount. (Dedicated to compound Q), in S3, compound E is replaced with an equal molar amount. (Referring to compound O). The remaining conditions are the same as S1~S4 of synthesis example 1, and will not be repeated.

[0099] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G3 (4.64 g; 10 mmol), compound H (2.22 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-3: 4.89 g, yield: 87%, MS (m / z) (M+): 562.

[0100] Synthesis example 4

[0101] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-4), the chemical equation of which is shown in Formula 6.

[0102]

[0103] Formula 6

[0104] Compound G4 was prepared using a synthetic method similar to that of Synthesis Example 1, except that in S1, compound B was replaced with an equimolar amount of compound Q. The remaining conditions were the same as S1-S4 of Synthesis Example 1 and will not be repeated here.

[0105] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G4 (5.09 g; 10 mmol), compound J (2.72 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-4: 5.52 g, yield: 84%, MS (m / z) (M+): 657. 1 H NMR(500 MHz, DMSO-d6) δ 9.63 (s, 1H), 8.61 (d, J = 9.1 Hz, 1H), 8.55 – 8.50 (m,1H), 8.38 (d, J = 8.4 Hz, 1H), 8.31 – 8.16 (m, 7H), 8.07 (d, J = 8.1 Hz, 1H), 8.06 – 7.91 (m, 5H), 7.84 – 7.78 (m, 1H), 7.78 – 7.73 (m, 1H), 7.63 – 7.43(m, 12H), 7.43 – 7.35 (m, 1H).

[0106] Synthesis example 5

[0107] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-5).

[0108] I-5

[0109] Compound G4 was prepared using the same synthetic method as in Synthesis Example 4, and will not be described again.

[0110] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G4 (5.09 g; 10 mmol), compound H (2.22 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-5: 5.46 g, yield: 90%, MS (m / z) (M+): 607. 1 H NMR(500 MHz, DMSO-d6) δ 8.49 – 8.45 (m, 1H), 8.40 – 8.36 (m, 2H), 8.30 – 8.16(m, 7H), 8.12 – 8.06 (m, 2H), 8.06 – 8.01 (m, 2H), 7.94 – 7.90 (m, 1H), 7.83 – 7.79 (m, 1H), 7.76 – 7.72 (m, 1H), 7.63 – 7.43 (m, 12H), 7.42 – 7.36 (m,1H).

[0111] Synthesis example 6

[0112] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-6), the chemical equation of which is shown in Formula 7.

[0113]

[0114] Formula 7

[0115] Compound G6 was prepared using a synthetic method similar to that of Synthesis Example 1, with the only differences being that in S1, compound B was replaced with an equimolar amount of compound O, and in S3, compound E was replaced with an equimolar amount of compound Q. The remaining conditions were the same as S1-S4 of Synthesis Example 1, and will not be repeated here.

[0116] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G6 (4.64 g; 10 mmol), compound K (2.72 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-6: 5.45 g, yield: 89%, MS (m / z) (M+): 612.

[0117] Synthesis Example 7

[0118] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-7), the chemical equation of which is shown in Formula 8.

[0119]

[0120] Formula 8

[0121] Compound G3 was prepared using the same synthetic method as in Synthesis Example 3, and will not be described again.

[0122] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G3 (4.64 g; 10 mmol), compound L (2.46 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-7: 4.92 g, yield: 84%, MS (m / z) (M+): 586.

[0123] Synthesis example 8

[0124] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-8), the chemical equation of which is shown in Formula 9.

[0125]

[0126] Formula 9

[0127] Compound G8 was prepared using a synthetic method similar to that of Synthesis Example 1, with the only difference being that in S1, compound B was replaced with an equimolar amount of compound E, and in S3, compound E was replaced with an equimolar amount of compound Q. The remaining conditions were the same as S1-S4 of Synthesis Example 1, and will not be repeated here.

[0128] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G8 (5.09 g; 10 mmol), compound B (1.72 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, and dissolve the filter cake in toluene by heating and then filter to remove the solid insoluble matter. Then recrystallize to give product I-8: 4.73 g, yield: 85%, MS (m / z) (M+): 557. 1H NMR(500 MHz, DMSO-d6) δ 8.41 – 8.35 (m, 2H), 8.28 – 8.16 (m, 5H), 8.05 – 7.99(m, 3H), 7.96 – 7.90 (m, 3H), 7.86 – 7.80 (m, 2H), 7.69 – 7.64 (m, 1H), 7.61 – 7.45 (m, 11H), 7.40 (d, J = 7.3 Hz, 1H).

[0129] Synthesis example 9

[0130] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-9), the chemical equation of which is shown in Formula 10.

[0131]

[0132] Formula 10

[0133] Compound G9 was prepared using a synthetic method similar to that of Synthesis Example 4, except that hydrogen was replaced with deuterium in all the starting compounds in S1-S4, and the molar amounts of all the starting compounds were the same as in Synthesis Example 4. All other conditions were the same as for S1-S4 in Synthesis Example 4 and will not be repeated here.

[0134] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G9 (5.31 g; 10 mmol), compound M (1.79 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-9: 4.74 g, yield: 81%, MS (m / z) (M+): 585.

[0135] Synthesis example 10

[0136] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-10), the chemical equation of which is shown in Formula 11.

[0137]

[0138] Formula 11

[0139] Compound G10 was prepared using a synthetic method similar to that of Synthesis Example 1, with the only differences being that in S1, compound B was replaced with an equimolar amount of compound Q, and in S3, compound E was replaced with an equimolar amount of compound Q. The remaining conditions were the same as S1-S4 of Synthesis Example 1, and will not be repeated here.

[0140] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G10 (4.59 g; 10 mmol), compound B (1.72 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-10: 4.61 g, yield: 91%, MS (m / z) (M+): 507. 1 HNMR (500 MHz, DMSO-d6) δ 8.40 – 8.34 (m, 2H), 8.29 – 8.12 (m, 4H), 8.07 –8.00 (m, 2H), 7.96 – 7.92 (m, 1H), 7.85 – 7.78 (m, 2H), 7.65 – 7.60 (m, 1H), 7.55 – 7.44 (m, 12H), 7.42 – 7.37 (m, 2H).

[0141] Synthesis example 11

[0142] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-11), the chemical equation of which is shown in Formula 12.

[0143]

[0144] Formula 12

[0145] Compound G11 was prepared using a synthetic method similar to that of Synthesis Example 1, except that in S3, compound E was replaced with an equimolar amount of compound Q. The remaining conditions were the same as S1-S4 of Synthesis Example 1 and will not be repeated here.

[0146] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G11 (5.09 g; 10 mmol), compound L (2.46 g; 10 mmol), potassium carbonate (4.15 g; 30 mmol), and tetraphenylphosphine palladium (0.35 g; 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-11: 5.62 g, yield: 89%, MS (m / z) (M+): 631. 1 HNMR (500 MHz, DMSO-d6) δ 8.63 (d, J = 8.0 Hz, 1H), 8.41 – 8.32 (m, 2H), 8.28– 8.11 (m, 8H), 8.04 – 7.92 (m, 6H), 7.87 (t, J = 7.5 Hz, 1H), 7.68 – 7.63(m, 1H), 7.59 – 7.46 (m, 10H), 7.42 – 7.37 (m, 1H).

[0147] Synthesis example 12

[0148] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-12), the chemical equation of which is shown in Formula 13.

[0149]

[0150] Formula 13

[0151] Compound G10 was prepared using the same synthetic method as in Synthesis Example 10, and will not be described again.

[0152] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G10 (4.59 g; 10 mmol), compound N (1.98 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-12: 4.80 g, yield: 90%, MS (m / z) (M+): 533. 1HNMR (500 MHz, DMSO-d6) δ 8.38 – 8.32 (m, 1H), 8.26 (d, J = 6.9 Hz, 1H), 8.24– 8.16 (m, 3H), 8.02 (d, J = 7.7 Hz, 1H), 7.83 – 7.79 (m, 1H), 7.72 – 7.68(m, 1H), 7.64 – 7.59 (m, 1H), 7.58 – 7.44 (m, 16H), 7.39 – 7.32 (m, 3H).

[0153] Synthesis example 13

[0154] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-13), the chemical equation of which is shown in Formula 14.

[0155]

[0156] Formula 14

[0157] Compound G13 was prepared using a synthetic method similar to that used in Synthesis Example 1, except that in S1, compound B was replaced with an equimolar amount of compound Q, and in S3, compound E was replaced with an equimolar amount of compound Q. (Referring to compound P). The remaining conditions are the same as S1~S4 of synthesis example 1, and will not be repeated.

[0158] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G13 (5.16 g; 10 mmol), compound L (2.46 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-13: 5.17 g, yield: 81%, MS (m / z) (M+): 638.

[0159] Synthesis example 14

[0160] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-14).

[0161] I-14

[0162] Compound G10 was prepared using the same synthetic method as in Synthesis Example 10, and will not be described again.

[0163] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G10 (4.59 g; 10 mmol), compound J (2.72 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-14: 5.28 g, yield: 87%, MS (m / z) (M+): 607. 1 HNMR (500 MHz, DMSO-d6) δ 9.64(s, 1H), 8.62 (d, J = 9.1 Hz, 1H), 8.56 – 8.51(m, 1H), 8.40 – 8.34 (m, 1H), 8.28 – 8.15 (m, 6H), 8.02 (d, J = 7.8 Hz, 1H), 8.00 – 7.96 (m, 1H), 7.95 – 7.88 (m, 1H), 7.84 – 7.78 (m, 1H), 7.63 – 7.44(m, 14H), 7.42 – 7.30 (m, 2H).

[0164] Synthesis Example 15

[0165] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-15).

[0166] I-15

[0167] Compound G2 was prepared using the same synthetic method as in Synthesis Example 2, and will not be described again.

[0168] S5. Under nitrogen protection, 50 mL of toluene, 25 mL of ethanol, and 25 mL of water were added to a three-necked flask. Then, compound G2 (5.60 g; 10 mmol), compound J (2.72 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol) were added. The mixture was heated to 80 °C and reacted for 12 h. After the reaction was completed, the mixture was cooled to room temperature and filtered. The filter cake was dissolved in toluene and then filtered to remove the solid insoluble matter. The product I-15 was then recrystallized to give 5.87 g, yield: 83%, MS (m / z) (M+): 707. 1HNMR (500 MHz, DMSO-d6) δ 9.65 (s, 1H), 8.60 (d, J = 9.1 Hz, 1H), 8.54 – 8.49 (m, 1H), 8.40 (d, J = 8.2 Hz, 1H), 8.31 – 8.16 (m, 8H), 8.07 (d, J = 8.0 Hz,1H), 8.04 – 8.00 (m, 3H), 7.99 – 7.95 (m, 1H), 7.94– 7.90 (m, 4H), 7.85 –7.80 (m, 1H), 7.77 – 7.73 (m, 1H), 7.63 – 7.47 (m, 11H).

[0169] Synthesis example 16

[0170] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-16), the chemical equation of which is shown in Formula 15.

[0171]

[0172] Formula 15

[0173] Compound G16 was prepared using a synthetic method similar to that used in Synthesis Example 1, except that in S1, compound B was replaced with an equimolar amount. (Denotes it as compound R). In S3, replace compound E with an equal molar amount of compound B. The remaining conditions are the same as S1~S4 of synthesis example 1, and will not be repeated.

[0174] S5. Under nitrogen protection, 50 mL of toluene, 25 mL of ethanol, and 25 mL of water were added to a three-necked flask. Then, compound G16 (5.67 g; 10 mmol), compound Q (1.22 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol) were added. The mixture was heated to 80 °C and reacted for 12 h. After the reaction was completed, the mixture was cooled to room temperature and filtered. The filter cake was dissolved in toluene and then filtered to remove the solid insoluble matter. The product I-16 was then recrystallized to give 5.13 g, yield: 91%, MS (m / z) (M+): 564.

[0175] Synthesis Example 17

[0176] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-17), the chemical equation of which is shown in Formula 16.

[0177]

[0178] Formula 16

[0179] Compound G17 was prepared using a synthetic method similar to that of Synthesis Example 1, with the only differences being that in S1, compound B was replaced with an equimolar amount of compound Q, and in S3, compound E was replaced with an equimolar amount of compound L. The remaining conditions were the same as S1-S4 of Synthesis Example 1, and will not be repeated here.

[0180] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G17 (5.82 g; 10 mmol), compound Q (1.22 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-17: 5.29 g, yield: 91%, MS (m / z) (M+): 581. 1 HNMR (500 MHz, DMSO-d6) δ 8.62 (d, J = 8.3 Hz, 1H), 8.40 – 8.24 (m, 5H), 8.21– 8.11 (m, 4H), 8.05 – 7.96 (m, 3H), 7.90 – 7.84 (m, 1H), 7.83 – 7.77 (m,1H), 7.58 – 7.43 (m, 11H), 7.42 – 7.30 (m, 2H).

[0181] Synthesis Example 18

[0182] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-18), the chemical equation of which is shown in Formula 17.

[0183]

[0184] Formula 17

[0185] Compound G1 was prepared using the same synthetic method as in Synthesis Example 1, and will not be described again.

[0186] S5. Under nitrogen protection, 50 mL of toluene, 25 mL of ethanol, and 25 mL of water were added to a three-necked flask. Then, compound G1 (5.60 g; 10 mmol), compound S (1.98 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol) were added. The mixture was heated to 80 °C and reacted for 12 h. After the reaction was completed, the mixture was cooled to room temperature and filtered. The filter cake was dissolved in toluene and then filtered to remove the solid insoluble matter. The product I-18 was then recrystallized to give 5.25 g, yield: 83%, MS (m / z) (M+): 633. 1 HNMR (500 MHz, DMSO-d6) δ 8.38 (d, J = 8.2 Hz, 1H), 8.31 – 8.25 (m, 3H), 8.22– 8.18 (m, 2H), 8.16 – 8.12 (m, 1H), 8.07 (d, J = 8.1 Hz, 1H), 8.05 – 7.97(m, 4H), 7.95 – 7.91 (m, 2H), 7.77 – 7.72 (m, 5H), 7.69– 7.63 (m, 3H), 7.59 –7.44 (m, 9H), 7.41 – 7.37 (m, 1H).

[0187] Synthesis example 19

[0188] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-19).

[0189] I-19

[0190] Compound G11 was prepared using the same synthetic method as in Synthesis Example 11, and will not be described again.

[0191] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G11 (5.09 g; 10 mmol), compound S (1.98 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, and dissolve the filter cake in toluene by heating and then filter to remove the solid insoluble matter. Then recrystallize to give product I-19: 4.72 g, yield: 81%, MS (m / z) (M+): 583. 1HNMR (500 MHz, DMSO-d6) δ 8.39 (d, J = 8.0 Hz, 1H), 8.30 – 8.24 (m, 2H), 8.22– 8.17 (m, 2H), 8.15 – 8.12 (m, 1H), 8.03 – 7.97 (m, 3H), 7.94 (dd, J = 7.5,1.6 Hz, 1H), 7.75 (d, J = 1.4 Hz, 4H), 7.67 – 7.63 (m, 3H), 7.58 – 7.44 (m,11H), 7.39 – 7.35 (m, 2H).

[0192] Synthesis example 20

[0193] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-20).

[0194] I-20

[0195] Compound G4 was prepared using the same synthetic method as in Synthesis Example 4, and will not be described again.

[0196] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G4 (5.09 g; 10 mmol), compound Q (1.22 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-20: 4.61 g, yield: 91%, MS (m / z) (M+): 507. 1 HNMR (500 MHz, DMSO-d6) δ 8.37 (d, J = 8.5 Hz, 1H), 8.29 – 8.23 ​​(m, 3H), 8.20– 8.15 (m, 2H), 8.07 (d, J = 8.1 Hz, 1H), 8.05 – 8.01 (m, 2H), 7.95 – 7.90(m, 1H), 7.82 – 7.78 (m, 1H), 7.77 – 7.74 (m, 1H), 7.59 – 7.44 (m, 12H), 7.43– 7.36 (m, 2H).

[0197] Synthesis Example 21

[0198] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-21), the chemical equation of which is shown in Formula 18.

[0199]

[0200] Formula 18

[0201] Compound G21 was prepared using a synthetic method similar to that of Synthesis Example 1, with the only differences being that in S1, compound B was replaced with an equimolar amount of compound Q, and in S3, compound E was replaced with an equimolar amount of compound S. The remaining conditions were the same as S1-S4 of Synthesis Example 1, and will not be repeated here.

[0202] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G21 (5.35 g; 10 mmol), compound Q (1.22 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-21: 4.74 g, yield: 89%, MS (m / z) (M+): 533. 1 HNMR (500 MHz, DMSO-d6) δ 8.36 (d, J = 8.2 Hz, 1H), 8.29 – 8.24 (m, 2H), 8.22– 8.16 (m, 2H), 8.02 (d, J = 7.7 Hz, 1H), 7.83 – 7.78 (m, 1H), 7.75 (s, 4H), 7.67 – 7.63 (m, 2H), 7.57 – 7.43 (m, 12H), 7.40 – 7.36 (m, 3H).

[0203] Synthesis Example 22

[0204] This synthetic example provides a method for synthesizing an aryl trisubstituted benzanthracene organic electroluminescent compound (denoted as I-22).

[0205] I-22

[0206] Compound G10 was prepared using the same synthetic method as in Synthesis Example 10, and will not be described again.

[0207] S5. In a three-necked flask, under nitrogen protection, add 50 mL of toluene, 25 mL of ethanol, and 25 mL of water. Then add compound G10 (4.59 g; 10 mmol), compound E (1.72 g; 10 mmol), potassium carbonate (4.15 g, 30 mmol), and tetraphenylphosphine palladium (0.35 g, 0.3 mmol). Heat to 80 °C and react for 12 h. After the reaction is complete, cool to room temperature, filter, dissolve the filter cake in toluene, filter to remove solid insolubles, and then recrystallize to give product I-22: 4.16 g, yield: 82%, MS (m / z) (M+): 507. 1 HNMR (500 MHz, DMSO-d6) δ 8.42 – 8.34 (m, 1H), 8.33 – 8.23 ​​(m, 3H), 8.23 ​​–8.15 (m, 2H), 8.07 (d, J = 8.1 Hz, 1H), 8.03 (dd, J = 7.7, 2.9 Hz, 2H), 7.94– 7.89 (m, 1H), 7.83 – 7.78 (m, 1H), 7.74 (dd, J = 8.1, 1.9 Hz, 1H), 7.60 –7.43 (m, 12H), 7.43 – 7.36 (m, 2H).

[0208] Example 1

[0209] This embodiment provides a dual-emitting-layer organic electroluminescent device, the structure of which is as follows: Figure 1 As shown, it includes an anode, a hole transport region, an electron blocking layer, a first light-emitting layer, a second light-emitting layer, a hole blocking layer, an electron transport region, and a cathode, which are sequentially disposed on a substrate; wherein, the first light-emitting layer includes a first host material and a first guest material, and the second light-emitting layer includes a second host material and a second guest material.

[0210] The fabrication method of the above-mentioned double-emitting-layer organic electroluminescent device includes the following steps:

[0211] S100. After patterning the ITO substrate to achieve a light-emitting area of ​​3mm × 3mm, perform ultrasonic treatment with water / isopropanol, UV / ozone irradiation, and drying at 100℃. Then, mount the ITO substrate on the substrate support of the vacuum deposition apparatus and adjust the pressure to achieve a vacuum rate of 1 × 10⁻⁶. -7 torr.

[0212] S200. On the ITO layer (anode) formed on the substrate, a hole injection layer is formed by vacuum depositing compound HT01 and compound PD01 (mass ratio of compound HT01 to compound PD01 is 97:3) with a thickness of 10 nm.

[0213] S300. On the hole injection layer, a hole transport layer is formed by vacuum deposition of compound HT01 with a thickness of 100 nm.

[0214] S400. On the hole transport layer, an electron blocking layer is formed by vacuum deposition of compound BP01 with a thickness of 5 nm.

[0215] S500, a first host material I-1 and a dopant material BD01 (i.e., a first guest material) are co-deposited on an electron blocking layer, with the mass ratio of compound I-1 to compound BD01 being 97:3, to form a first light-emitting layer with a film thickness of 5 nm.

[0216] S600, a second host material BH2-01 and a dopant material BD01 (i.e., a second guest material) are co-deposited on the first light-emitting layer, with the mass ratio of compound BH2-01 to compound BD01 being 98:2, to form a second light-emitting layer with a film thickness of 15nm.

[0217] S700, HB01 compound is deposited on the second light-emitting layer to form a hole blocking layer with a thickness of 5 nm.

[0218] S800, on the hole blocking layer, a 30 nm thick compound ET01 and compound LiQ (the mass ratio of compound ET01 to compound LiQ is 1:1) are vacuum deposited to form an electron transport layer.

[0219] S900, on the electron transport layer, a 1 nm thick Yb layer is vacuum deposited to form an electron injection layer.

[0220] S1000, on the electron injection layer, Mg and Ag (Mg to Ag mass ratio of 1:9) are deposited to form a cathode with a thickness of 15 nm.

[0221] S1100: On the cathode, a 50nm thick compound CP01 is deposited to form a capping layer. Then, the substrate after evaporation is encapsulated. A UV adhesive coating process is used to coat the cleaned cover plate with adhesive. The coated cover plate is then moved to the lamination section. The evaporated substrate is placed on the top of the cover plate. Finally, the substrate and cover plate are laminated under the action of a lamination device. At the same time, the UV adhesive is photocured to prepare a top-emitting double-emitting organic electroluminescent device (i.e., blue OLED device).

[0222] The molecular structural formulas of the compound materials used in each layer of this embodiment are as follows:

[0223]

[0224]

[0225]

[0226] Examples 2-22

[0227] Examples 2-22 provide a dual-emitting-layer organic electroluminescent device, the structure and preparation method of which are similar to those of Example 1, except that the first host material is replaced with compounds I-2 to I-22 respectively. Other conditions and parameter settings are the same as those in Example 1, and will not be repeated here.

[0228] Comparative Examples 1-6

[0229] Comparative Examples 1-6 provide a dual-emitting-layer organic electroluminescent device, the structure and preparation method of which are similar to those of Example 1, except that the first host material is replaced with compounds DB01-DB06 respectively. Other conditions and parameter settings are the same as those of Example 1, and will not be repeated here.

[0230] The molecular structural formulas of compounds DB01~DB06 are as follows:

[0231]

[0232] Verification test

[0233] 1. Performance testing of the first main material

[0234] (1) In order to demonstrate the improvement in thermal stability after introducing stable aryl substituents at three key sites, thermal stability tests were conducted to verify the present invention.

[0235] The aryl trisubstituted benzanthracene organoluminescent compounds provided in Examples 1-22 of this invention and the comparative compounds DB01-DB06 were subjected to a thermal stability test at 265°C for 240 h. The purity changes of each benzanthracene organoluminescent compound before and after the thermal stability test were measured by high performance liquid chromatography. The evaluation results are shown in Table 1 below. A purity change of <0.01% was rated as excellent, a purity change of 0.01%~0.1% was rated as good, and a purity change of >0.1% was rated as poor.

[0236] (2) In order to investigate the reason why the aryl trisubstituted benzanthracene organic electroluminescent compound provided by the present invention exhibits an efficiency advantage in the device compared with existing compounds, the present invention conducted tests such as spectral peak and molecular orientation, and the results are shown in Table 1.

[0237] Spectral peak measurement method: The aryl trisubstituted benzene-anthracene organic electroluminescent compounds provided in Examples 1-22 of this invention and the comparative compounds DB01-DB06 were respectively deposited on high-transparency quartz glass sheets to form films with a thickness of 60 nm. The luminescence intensity in the range of 400 nm to 620 nm was measured using a Horiba Fluorolog-3 series fluorescence spectrometer. After normalizing the luminescence intensity, the wavelength corresponding to an intensity value of 1 is the spectral peak (PL peak). The larger the peak value and the closer it is to the absorption spectral range of the doped material (typically 440 nm to 450 nm), the greater the spectral overlap between the host and guest components, which is more conducive to energy transfer.

[0238] Molecular orientation testing method: The transition dipole moment orientation of molecules in the first luminescent layer was measured using angle-dependent fluorescence spectroscopy, employing a molecular orientation testing system manufactured by Hamamatsu Corporation, Japan. Testing method: The aryl trisubstituted benzene-anthracene organic electroluminescent compounds provided in Synthetic Examples 1-22 and the comparative compounds DB01-DB06 were deposited onto high-transmittance quartz glass slides to form organic films. The samples were then excited with 365 nm ultraviolet light, emitting emission light. The p-polarized light in the emitted light was detected by a polarizer and received by a detector. The fluorescence intensity distribution of the organic film with respect to the test angle was measured, and its anisotropy factor Θ (dimensionless) was determined using optical fitting software: Θ = ∑p z 2 / ∑p 2 In the formula, p z Let p represent the vertical dipole electrode moment, and ∑p represent the dipole electrode moment. z 2 ∑p represents the total vertical dipole emission power. 2 This represents the total emission power of all dipoles. The smaller the value of Θ, the higher the probability that the molecules are arranged in a horizontal orientation, indicating that the compound material has a better molecular orientation.

[0239] Table 1 Performance test results of the first main material

[0240]

[0241] As can be seen from Table 1, compared with the comparative compounds, the aryl trisubstituted benzanthracene organic electroluminescent compounds provided by the present invention have better thermal stability, better molecular orientation, and emission wavelengths that are closer to the maximum absorption wavelength of the doped material.

[0242] Specifically, compared to the comparative compound DB01, compound I-16 provided by this invention significantly improves thermal stability and also improves the molecular orientation of BH (i.e., the host material) in the film. Similarly, compared to the comparative compound DB02, compound I-17 provided by this invention shows significant improvements in both thermal stability and orientation, and its spectrum also exhibits a significant red shift, meaning the emission spectrum of the host material is close to the absorption spectrum of the guest material, which is beneficial for energy transfer between the host and guest materials. Comparative compound DB03 has a certain orientation advantage due to its longer molecular structure, but compared to compound I-18 provided by this invention, its thermal stability is poorer. This is presumably because the present invention reduces the reactivity of the CH bond by introducing a naphthyl group at the 4 position of benzenexanthracene, thereby enhancing the compound's stability. Compared to the comparative compound DB04, compound I-21 provided by this invention shows significantly enhanced thermal stability. This is presumably because comparative compound DB04 introduces an oxygen-containing substituent into benzenexanthracene, but since CO and CN bonds are less stable than CC bonds, comparative compound DB04 exhibits poor thermal stability. Compared with the compounds provided in this invention, the comparative compounds DB05 and DB06 exhibit poor thermal stability. Furthermore, the comparative compound DB05 uses sterically hindered structures at all three sites, which not only leads to the existence of isomers but also severely disrupts the orientation advantage of the molecule. The comparative compound DB06 introduces an electron-donating carbazole structure at the 4th position, causing a blue shift in the molecular spectrum, i.e., the emission spectrum of the host material is far away from the absorption spectrum of the guest material, which is not conducive to energy transfer between the host and guest materials.

[0243] 2. Performance Testing of Double-Emitting-Layer Organic Electroluminescent Devices

[0244] At J = 10 mA / cm 2 At a current density of J=20mA / cm², the driving voltage and luminous efficiency of the dual-emitting-layer organic electroluminescent devices provided in Examples 1-22 and Comparative Examples 1-6 were tested respectively, and the results are shown in Table 2. LT97 refers to the blue OLED device at J=20mA / cm². 2 When operating, the luminous intensity drops to 97% of its initial value L0 after time LT97.

[0245] The testing instruments and methods used for the above performance tests are as follows:

[0246] Luminous efficacy (CE) (cd / A) and chromaticity coordinates (CIEy) were measured using a PhotoResearch PR-635 spectral scanner.

[0247] Current density and turn-on voltage were tested using a Keithley 2400 digital source meter.

[0248] The luminous efficiency of blue OLED devices is greatly affected by color coordinates, and the industry generally uses the BI value as a basis for the efficiency of blue OLED devices. BI (Blue index) is obtained by dividing the luminous efficiency CE (cd / A) by the color coordinates (CIEy).

[0249] The lifetime testing uses a silicon optoelectronic OLED device lifetime testing system.

[0250] The transient electroluminescence spectrum was obtained by collecting signals using an FLS980 spectrometer manufactured by Edinburgh Instruments.

[0251] Table 2 Performance test results of double-emitting-layer organic electroluminescent devices

[0252]

[0253] As can be seen from Table 2, compared with the device comparative examples 1 to 6, the device embodiments provided by the present invention have higher luminous efficiency and longer lifetime.

[0254] Because this invention simultaneously introduces the substituents specified in this invention at positions 4, 7, and 12 of benzenexane, it not only improves the thermal stability of benzenexane-based organic electroluminescent compound materials but also avoids the introduction of too many sterically hindered substituents, thereby improving molecular orientation. This results in the blue OLED device provided by this invention exhibiting relatively good lifetime and efficiency. Compared with devices in Comparative Examples 1-3, the lifetime of the device embodiments provided by this invention is significantly increased. Compared with devices in Comparative Examples 4-6, this invention avoids the introduction of unstable heteroaryl groups and obtains a more suitable BH emission spectrum through reasonable control of the molecular structure, which is beneficial for energy transfer between materials, thereby significantly improving device efficiency.

[0255] In summary, although the aryl trisubstituted benzanthracene organic electroluminescent compounds provided by this invention have only minor structural differences compared to the comparative compounds, significant performance differences still exist. The compounds of this invention significantly improve the evaluation performance of blue OLED devices by enhancing thermal stability, regulating molecular orientation, and adjusting the host emission spectrum.

[0256] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions or improvements made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. An aryl trisubstituted benzanthracene-based organoelectroluminescent compound, characterized in that, Its general structural formula is shown in Formula I. I In formula I, Ar1 and Ar3 each independently represent deuterated or non-deuterated phenyl, biphenyl, naphthyl, phenanthryl, anthracene, hydroxyl, pyrene, or benzo[a]phenanthryl; Ar2 represents a deuterated or non-deuterated phenyl or naphthyl group; In Formula I, any hydrogen atom can be independently replaced by deuterium.

2. The aryl trisubstituted benzanthracene organoelectroluminescent compound as described in claim 1, characterized in that, Ar1 and Ar3 are each independently selected from phenyl, biphenyl, naphthyl, ... , , , , or .

3. The aryl trisubstituted benzanthracene organoelectroluminescent compound as described in claim 1, characterized in that, Ar3 is selected from deuterated or non-deuterated phenyl, biphenyl, naphthyl, or pyrene.

4. An aryl trisubstituted benzanthracene-based organoelectroluminescent compound, characterized in that, The structure of the aryl trisubstituted benzanthracene organic electroluminescent compound is selected from any one of the following structural formulas. 。 5. A dual-emitting-layer organic electroluminescent device, characterized in that, The first luminescent layer comprises a first host material and a first guest material, wherein the first host material comprises one or more aryl trisubstituted benzanthracene organic electroluminescent compounds as described in any one of claims 1 to 4.

6. The dual-emitting-layer organic electroluminescent device as described in claim 5, characterized in that, The structure of the dual-emitting-layer organic electroluminescent device includes an anode, a hole transport region, an electron blocking layer, a first emitting layer, a second emitting layer, a hole blocking layer, an electron transport region, and a cathode, which are sequentially disposed on a substrate.

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