Organic light-emitting device

Abstract

The invention discloses an organic light-emitting device which comprises a first electrode, a second electrode and an organic layer between the first electrode and the second electrode. The organic layer comprises a light-emitting layer, the light-emitting layer comprises a P-type main body material, an N-type main body material, a first doping material and a second doping material, the P-type main body material is shown as a formula 1-1 or a formula 1-2, and the N-type main body material is selected from a triazine compound; the first doping material is selected from a platinum complex or a platinum complex; and the second doping material is a B / N type MR-TADF material. The luminous layer of the device improves chemical stability, photoelectric stability and thermal stability of a compound through deuteration at active sites of a GH-P material, improves stability of the device, further prolongs service life, combines GH-N to form a double-main-body material, and is matched with a small amount of precious metal first doping material and second doping material, so that the luminous efficiency of the device is improved. Therefore, better efficiency and longer service life are realized.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more specifically, to an organic electroluminescent device. Background Technology

[0002] Organic electroluminescence, generally speaking, refers to organic light-emitting diodes (OLEDs) that emit light by driving an organic semiconductor thin film with an electric current, thereby achieving the purpose of display.

[0003] Organic light-emitting diodes (OLEDs) consist of a cathode, an anode, and an organic layer sandwiched between them. Currently, industrially used OLED devices typically have a multi-layered organic structure, including layers such as a hole injection layer, a hole transport layer / electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. In OLED devices containing these layers, applying a voltage between the two electrodes causes holes to be injected into the organic layer from the anode and electrons to be injected from the cathode. When holes and electrons meet, excitons are formed. These excitons transfer energy to the doped material, and light is emitted through radiative transitions within the doped material.

[0004] Traditional fluorescent doped materials, limited by early technologies, can only utilize 25% of singlet excitons generated by electrical excitation for luminescence. This results in low internal quantum efficiency (maximum 25%) and external quantum efficiency generally below 5%, significantly lagging behind phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling at the heavy atom centers, enhance intersystem crossing and can effectively utilize singlet and triplet excitons generated by electrical excitation for luminescence, achieving an internal quantum efficiency of 100%. With advancements in technology, higher demands are being placed on color rendering standards. Besides high efficiency and stability, luminescent materials also require narrower half-widths (HWHMs) to improve the purity of the emitted color. Fluorescent doped materials can achieve high fluorescence quantum density and narrow HWHM through molecular design engineering. Significant breakthroughs have been achieved in blue fluorescent doped materials, with the HWHM of boron-nitrogen materials reduced to below 30 nm. However, research on the green light region, which is more sensitive to the human eye, has primarily focused on phosphorescent doped materials. The peak shape of this region is difficult to narrow using simple methods. Therefore, researching efficient green fluorescent doped materials with narrow HWHMs is crucial to meeting higher color rendering standards. Currently, sensitization technology combines triplet exciton-sensitized materials with fluorescent doping materials. Utilizing triplet exciton-sensitized materials as exciton sensitization media, it fully leverages triplet excitons to transfer energy to the fluorescent doping material, achieving 100% in-device quantum efficiency. This technology compensates for the insufficient exciton utilization of fluorescent doping materials, effectively utilizing the high radiative rate, high fluorescence quantum yield, high device stability, and high color purity of fluorescent doping materials, while significantly reducing costs compared to precious metal phosphorescent materials. It holds great promise for OLED applications. Therefore, developing phosphorescent sensitized devices with good matching, high stability, and high performance based on sensitization technology has unique advantages and strong potential for meeting BT.2020 display specifications. The poor P / N stability of existing GH premix materials leads to reduced stability in evaporation production lines, resulting in lower yields, and also fails to form a good match with current B / N-type MR-TADF materials. Summary of the Invention

[0005] This invention provides an organic electroluminescent device based on existing technology, comprising: a first electrode, a second electrode, and an organic layer between the first and second electrodes; the organic layer includes a light-emitting layer, which comprises a P-type host material, an N-type host material, a first doped material, and a second doped material, wherein the P-type host material is shown in Formula 1-1 or Formula 1-2:

[0006]

[0007] Among them, AR1, AR2, AR3, and AR4 are each independently selected from substituted or unsubstituted C6-C30 aryl and C5-C20 heteroaryl groups, and their substituents are selected from hydrogen, deuterium, F, cyano, C6-C30 aryl, and C5-C20 heteroaryl groups; R1-R4 are each independently selected from hydrogen or deuterium.

[0008] The N-type main material is shown in Formula 2:

[0009]

[0010] Among them, AR5, AR6, and AR7 are each independently selected from substituted or unsubstituted C6-C30 aryl groups and C5-C20 heteroaryl groups, and their substituents are selected from hydrogen, deuterium, F, cyano, C6-C30 aryl groups, and C5-C20 heteroaryl groups; m, n, and o are each independently 0 or 1; L is selected from direct bond, deuterated or undeuterated phenylene; D is deuterium; when m is 0, x is selected from integers from 0 to 7; when m is 1, x is selected from integers from 0 to 6; when n is 0, y is selected from integers from 0 to 8; when n is 1, y is selected from integers from 0 to 7; when o is 0, z is selected from integers from 0 to 5; when o is 1, z is selected from integers from 0 to 4; the first dopant is selected from a monolithic complex or a platinum complex; the second dopant is a B / N type MR-TADF material.

[0011] As a preferred embodiment of the present invention, the first doped material is as shown in formulas 3-1, 3-2, 3-3, 3-4, and 3-5:

[0012]

[0013] Among them, R5-R 18 Each of the following is an independent group derived from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C20 aryl, wherein the substituent is selected from at least one of the following atoms or groups: deuterium, monodeuterylmethyl, dideuterylmethyl, trideuterylmethyl; R 19 R 20 Each is independently derived from hydrogen or deuterium, R 21 -R 24 Each aryl group, independently derived from hydrogen, deuterium, or substituted or unsubstituted C6-C20, R 21 -R 24 Two adjacent groups can join or fuse to form a phenyl or naphthyl group.

[0014] As a preferred embodiment of the present invention, the second doped material is as shown in formulas 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, and 4-7:

[0015]

[0016] Among them, R 25To R 37 Each is independently selected from H, D, F, Cl, Br, I, CN, Si(R) 38 )3, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, each of which may be atomized by one or more groups R 38 Substitution, wherein in each case one or more non-adjacent CH2 groups can be replaced by Si(R) 38 2. C = NR 38 P(=O)(R) 38 SO, SO2, NR 38 O, S or CONR 38 The substitution, and one or more H atoms may be replaced by D, F, Cl, Br or I, in an aromatic ring system having 6 to 60 C atoms, wherein in each case the ring system may be replaced by one or more R groups. 38 Substitution, heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which can be replaced by one or more R groups 38 The substitution, or the presence of an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, wherein in each case the group may be replaced by one or more groups R 38 Substitution, in which two or more adjacent substituents R 25 To R 37 Optionally, a monocyclic or polycyclic aliphatic ring system can be formed, said ring system being mediated by one or more groups R 38 replace;

[0017] R 38 Selected from H, D, F, aliphatic hydrocarbon groups having 1 to 20 carbon atoms, or aromatic or heteroaromatic ring systems having 5 to 30 carbon atoms, wherein one or more H atoms can be replaced by D or F, and wherein two or more adjacent substituents R 38 They can form monocyclic or polycyclic aliphatic ring systems with each other.

[0018] In a preferred embodiment of the present invention, AR1, AR2, AR3, and AR4 are each independently selected from the following groups:

[0019]

[0020] Where D is deuterium, a is an independent integer selected from 0 to 5, b is an independent integer selected from 0 to 4, c is an independent integer selected from 0 to 3, and d is an independent integer selected from 0 to 7.

[0021] As a preferred embodiment of the present invention, the P-type host material is at least one of the following compounds with structural formulas:

[0022]

[0023]

[0024]

[0025]

[0026] In a preferred embodiment of the present invention, AR5, AR6, and AR7 are each independently selected from the following groups:

[0027]

[0028] Where D is deuterium, e are each independently selected from integers from 0 to 5, and f are each independently selected from integers from 0 to 4. As a preferred embodiment of the present invention, the N-type host material is at least one of the following structural compounds:

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045] As a preferred embodiment of the present invention, the first doping material is at least one of the following compounds with the following structural formulas:

[0046]

[0047]

[0048]

[0049] As a preferred embodiment of the present invention, the second doping material is at least one of the following compounds:

[0050]

[0051]

[0052]

[0053]

[0054]

[0055] In a preferred embodiment of the present invention, the weight percentage of the first dopant material in the light-emitting layer is 2%-8%; and the weight percentage of the second dopant material is 0.3%-1%.

[0056] The beneficial effects of this invention are:

[0057] The light-emitting layer of this invention features deuteration at the GH-P active sites, enhancing the chemical, photoelectric, and thermal stability of the compound and improving device stability, thereby increasing lifetime. The combined GH-N and GH-P compounds form a good premix material, exhibiting excellent P / N stability and mass production stability during evaporation. Furthermore, the premix material possesses a more balanced carrier mobility, significantly improving device efficiency and lifetime. The addition of small amounts of noble metal first dopant (3%-5% of the total weight percentage of the light-emitting layer) and TADF material (0.5%-0.8% of the total weight percentage of the light-emitting layer) further achieves even better efficiency and longer lifetime. Attached Figure Description

[0058] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device provided by the present invention;

[0059] The numbers in the diagram represent: 1-anode, 2-hole injection layer, 3-hole transport layer, 4-electron blocking layer, 5-light emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, and 9-cathode.

[0060] Figure 2This is the HPLC chromatogram of compound P-66 of the present invention.

[0061] Figure 3 The DSC spectrum of compound P-66 of this invention is shown below. Figure 3 It can be seen that the Tm value of compound P-66 is 196.63℃.

[0062] Figure 4 The TGA spectrum of compound P-66 of this invention is shown below. Figure 4 It can be seen that the thermal weight loss temperature Td of compound P-66 is 495.32℃.

[0063] Figure 5 This is the HPLC chromatogram of compound N-80 of the present invention.

[0064] Figure 6 The DSC spectrum of compound N-80 of this invention is shown below. Figure 6 It can be seen that the Tm value of compound N-80 is 292.15℃.

[0065] Figure 7 The TGA spectrum of compound N-80 of this invention is shown below. Figure 7 It can be seen that the thermogravimetric temperature Td of compound N-80 is 488.82℃. Detailed Implementation

[0066] Embodiments of various aspects are further illustrated and described below. It should be understood that the description herein is not intended to limit the claims to the specific aspects described. Rather, it is intended to cover substitutions, modifications, and equivalents that may be included within the spirit and scope of this disclosure as defined by the appended claims.

[0067] As used herein, in the context of “substituted” or “unsubstituted”, the term “substituted” means that at least one hydrogen in the group is recoordinated with a deuterium, alkyl group, hydrocarbon derivative group, halogen, or cyano (-CN). The term “unsubstituted” means that at least one hydrogen in the group is not recoordinated with a deuterium, alkyl group, hydrocarbon derivative group, halogen, or cyano (-CN). Examples of alkyl or hydrocarbon derivative groups may include, but are not limited to, C1 to C30 alkyl, C2 to C30 alkenyl, C2 to C30 alkynyl, C6 to C30 aryl, C5 to C30 heteroaryl, C1 to C30 alkylamino, C6 to C30 aromaticamino, C6 to C30 heteroarylamino, C6 to C30 aryl heteroarylamino, etc.

[0068] In this invention, deuterium refers to a stable isotope of hydrogen, also known as heavy hydrogen, and its element symbol is D.

[0069] In this invention, an aromatic group refers to a monocyclic or fused polycyclic group with 6 to 30 carbon atoms, possessing a fully conjugated π-electron system. Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, benzo[1,12-bcd]furanyl, phenanthrene, etc.

[0070] Unless otherwise specified in the examples, the procedures should be performed under standard conditions or conditions recommended by the manufacturer. Reagents or instruments whose manufacturers are not specified are all commercially available products.

[0071] Synthesis example 1:

[0072]

[0073] Procedure: Under nitrogen protection, 66-SM1 (100g, 0.3952mol, 1eq), iodobenzene (104.8g, 0.514mol, 1.3eq), xylene (0.8L), tripotassium phosphate (252g, 1.186mol, 3eq), 1,10-phenanthroline (21.36g, 0.119mol, 30%eq), and cuprous iodide (11.28g, 0.0593mol, 15%eq) were added to the reaction flask. After the addition was complete, the reaction solution was heated to reflux and reacted for 12 hours. HPLC analysis showed that approximately 5% of the raw materials remained, and no further reaction occurred after the reaction time was extended.

[0074] Post-processing: The reaction solution was passed through silica gel, the filtrate was concentrated to dryness, and 101.44 g of product was obtained by PE column chromatography, with a yield of 77.9%.

[0075]

[0076] Procedure: Under nitrogen protection, 66-SM1 (120g, 0.474mol, 1eq), pinacol diboronate (156.4g, 0.6163mol, 1.3eq), 1,4-dioxane (0.96L), potassium acetate (116.2g, 1.185mol, 2.5eq), and Pd(dppf)cl2 (13.5g, 0.01846mol, 3.9%eq) were added to the reaction flask. After the addition was complete, the reaction solution was heated to reflux and reacted for 10h. The reaction was detected by HPLC.

[0077] Post-processing: The reaction solution was passed through silica gel, concentrated to dryness, and ethanol was frozen to -20°C with stirring to precipitate. The mixture was then filtered, and the filter cake was dried at 85°C with forced air to obtain 115.6 g of product, with a yield of 81.2%.

[0078]

[0079] Procedure: Under nitrogen protection, 66-ZJ1 (80g, 0.243mol, 1eq), 66-ZJ2 (73g, 0.243mol, 1eq), 800ml toluene, 400ml ethanol, potassium carbonate (100.8g, 0.729mol, 3eq), 240ml water, and tetraphenylphosphine palladium (4.21g, 3.645mmol, 1.5%eq) were added to the reaction flask. After the addition was complete, the reaction solution was heated to reflux and reacted overnight. The reaction was then sampled and analyzed by HPLC to confirm its completion.

[0080] Post-processing: The reaction solution was cooled and water was added, followed by filtration. The filter cake was washed with water and ethanol, dried by forced air, and then heated with twice the amount of toluene, cooled, and filtered again. The filter cake was dried by forced air at 85°C to obtain 54.3 g of product, with a yield of 52.9%.

[0081]

[0082] Procedure: Under nitrogen protection, 66-ZJ3 (54.3 g, 0.129 mol, 1 eq), halogenated compound (44.7 g, 0.139 mol, 1.08 eq), toluene (600 ml), sodium tert-butoxide (16.1 g, 0.168 mol, 1.3 eq), Pd2(dba)3 (1.77 g, 1.935 mmol, 1.5% eq), and tbu-xphos (1.64 g, 3.87 mmol, 3%) were added to the reaction flask. After the addition was complete, the reaction solution was heated to reflux and reacted overnight. The reaction was then sampled and analyzed by HPLC to confirm its completion.

[0083] Post-processing: The reaction solution was cooled and passed directly through silica gel. The filtrate was concentrated to dryness, toluene was added, and the solution was hot-filtered and concentrated to dryness. The solution was recrystallized using a toluene-ethanol 1:2:2 system. Then, it was heated with 2.5 times the amount of dichloromethane at 55°C. This process was repeated four times to obtain 42.8g of product, with a yield of 50%.

[0084] Synthesis example 2:

[0085]

[0086] Procedure: In a 2L three-necked flask, N-80-SM1 (100g, 0.395mol, 1eq), N-80-SM2 (50.6g, 0.415mol, 1.05eq), potassium carbonate (109.2g, 0.79mol, 2eq), and toluene / ethanol / water (1000ml + 500ml + 300ml) were added. Under N2 protection, tetrakis(triphenylphosphine)palladium (9.13g, 7.9mmol, 0.02eq) was added, and the mixture was heated to reflux with stirring. HPLC monitoring showed that SM1 ≤ 1%.

[0087] Post-processing: Stop the reaction, add water, stir and separate the liquids. Extract the aqueous phase with DCM, combine the organic phases, dry with anhydrous sodium sulfate, filter through silica gel, concentrate the filtrate to dryness, add 100 ml of ethanol, stir to precipitate crystals, filter, and dry the filter cake at 85°C with forced air to obtain 84.6 g of gray solid, yield 85.6%.

[0088]

[0089] Procedure: Under N2 protection, N-80-ZJ1 (84.6 g, 0.338 mol, 1 eq) and ultra-dry THF (800 ml) were added to a 2 L three-necked flask. The temperature was lowered to below -20 °C, and 1.6 M n-butyllithium (222 ml, 0.355 mol, 1.05 eq) was added dropwise. After the addition was complete, the mixture was kept warm and stirred for 1 h. Under N2 protection, N-80-SM3 (234.3 g, 1.014 mol, 3 eq) and ultra-dry THF (1200 ml) were added to a 3 L three-necked flask. The temperature was lowered to below -20 °C, and the lithium salt solution of ZJ1 was added dropwise. After the addition was complete, the mixture was moved to room temperature and stirred for 10–18 h.

[0090] Post-processing: Stop the reaction, cool to below 0℃, slowly add 50% ammonium chloride aqueous solution to quench, filter, wash the filter cake with ethanol 3-4 times, dry the filter cake and recrystallize it twice with o-dichlorobenzene, filter, wash the filter cake with ethanol, dry the filter cake at 85℃ with forced air to obtain 75.37g of off-white solid, yield 56%.

[0091]

[0092] Procedure: Under N2 protection, N-80-ZJ2 (75g, 0.188mol, 2eq), N-80-SM4 (11.93g, 0.094mol, 1eq), potassium carbonate (19.5g, 0.141mol, 1.5eq), and toluene / ethanol / water (750ml + 375ml + 225ml) were added to a 2L three-necked flask. Under N2 protection, tetrakis(triphenylphosphine)palladium (2.17g, 1.88mmol, 0.02eq) was added, and the mixture was heated to 70℃ and stirred for 8–12 h.

[0093] Post-processing: Stop the reaction, cool to room temperature, filter, wash the filter cake with water and ethanol, dry the filter cake and recrystallize it twice with o-dichlorobenzene, filter, wash the filter cake with ethanol, dry the filter cake at 85°C with forced air to obtain 21.4 g of off-white solid, yield 51.2%.

[0094]

[0095] Procedure: Under N2 protection, N-80-SM5 (45g, 0.159mol, 1eq), heavy water (63.6g, 3.18mol, 20eq), trifluoromethanesulfonic anhydride (224.2g, 0.795mol, 5eq) and 1,4-dioxane (270ml) were added to a 1L three-necked flask, and the mixture was heated to 110℃ and stirred for 24h.

[0096] Post-treatment: The reaction was stopped, cooled to room temperature, and 500 ml of water was added. The mixture was filtered, the filter cake was washed with ethanol, and dried to obtain 42 g of gray solid. Deuteration was performed again under the above conditions, followed by post-treatment, ultimately yielding 38 g of gray solid, with a yield of 82.6%.

[0097]

[0098] Procedure: In a 500 ml three-necked flask, N-80-ZJ4 (38 g, 0.131 mol, 1 eq), pinacol diboronate (43.3 g, 0.171 mol, 1.3 eq), potassium acetate (38.6 g, 0.394 mol, 3 eq), XPhos (3.75 g, 7.86 mmol, 0.06 eq), Pd2(dba)3 (3.6 g, 3.93 mmol, 0.03 eq), and 1,4-dioxane (400 ml) were added. Under N2 protection, the mixture was heated to 90–100 °C and stirred. The ZJ4 content was monitored by HPLC to be ≤0.5%.

[0099] Post-processing: Stop the reaction, filter the mixture through silica gel while hot, wash the filter cake with 300 ml of DCM, concentrate under reduced pressure to dryness, add 100 ml of ethanol to crystallize, filter, and dry the filter cake at 85°C with forced air to obtain 33.2 g of gray solid, yield 66.4%.

[0100] S6:

[0101]

[0102] Procedure: In a 1L three-necked flask, N-80-ZJ3 (21.4g, 48.1mmol, 1eq), N-80-ZJ5 (20.2g, 52.9mmol, 1.1eq), potassium carbonate (13.3g, 96.2mmol, 2eq), and THF / water (660ml + 110ml) were added. Under N2 protection, tetrakis(triphenylphosphine)palladium (1.11g, 0.962mmol, 0.02eq) were added. The mixture was heated to 75℃ and refluxed with stirring for 10–16 h. HPLC monitoring showed that ZJ3 ≤ 2%.

[0103] Post-processing: Stop the reaction, filter while hot, wash the filter cake with water and ethanol, dry the filter cake at 85°C with forced air, recrystallize the filter cake with o-dichlorobenzene 5 times, filter, wash the filter cake with ethanol, dry the filter cake at 85°C with forced air, and obtain 21 g of off-white solid, yield 65.8%.

[0104] Device performance testing

[0105] Application Example 1

[0106] ITO was used as the anode substrate material for the reflective layer, and its surface was treated sequentially with water, acetone, and N2 ions.

[0107] A 10 nm layer of HT-1 doped with 3% NDP-9 is deposited on top of the ITO anode substrate to form a hole injection layer (HIL).

[0108] A hole transport layer (HTL) is formed by depositing 100 nm of HT-1 above the hole injection layer (HIL);

[0109] GP-1 was vacuum-deposited above the hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 10 nm.

[0110] After GPL evaporation, the emissive layer (EML) of the OLED light-emitting device is fabricated. Compounds P-66 and N-80 of the present invention are used as the host materials, SP-49 is used as the first dopant material, and compound GD-1 is used as the second dopant material. The mass ratio of P-66, N-80, SP-49 and compound GD-1 is 66.5:30:3:0.5, and the thickness of the emissive layer is 30 nm.

[0111] HB-1 was deposited onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0112] ET-1 and LiQ were co-deposited onto the hole blocking layer (HBL) in a 5:5 ratio to obtain an electron transport layer (ETL) with a thickness of 30 nm.

[0113] Magnesium (Mg) and silver (Ag) are mixed in a 9:1 ratio and vapor-deposited onto the electron transport layer (ETL) to form an electron injection layer (EIL) with a thickness of 50 nm.

[0114] Subsequently, silver (Ag) is vapor-deposited onto the electron injection layer to form a cathode with a thickness of 100 nm. A 50 nm thick DNTPD is then deposited on the cathode sealing layer. Furthermore, the cathode surface is sealed with a UV-curable adhesive and a sealing cap containing a desiccant to protect the organic electroluminescent device from the influence of atmospheric oxygen or moisture. Thus, an organic electroluminescent device is prepared.

[0115]

[0116]

[0117] The P-type host material, N-type host material, first doped material, and second doped material in D1-D7 are shown in Table 1 below:

[0118] Table 1

[0119]

[0120]

[0121] Application Example 2-30

[0122] Compounds P-66 and GD-1 in Application Example 1 were replaced with compounds P-1, GD-13; P-18, GD-27; P-66, GD-49; P-72, GD-59; P-74, GD-76; P-78, GD-75 of the present invention, respectively, while the rest of the components were the same as in Application Example 1. Based on this, organic electroluminescent devices of Application Examples 2-7 were fabricated.

[0123] Compounds N-5, GD-1; N-12, GD-13; N-15, GD-27; N-21, GD-49; N-80, GD-59; N-250, GD-76; N-266, GD-75 of the present invention were used to replace compounds N-80 and GD-1 in Application Example 1, while the rest of the components were the same as in Application Example 1. Based on this, organic electroluminescent devices of Application Examples 8-14 were fabricated.

[0124] Compounds SP-49 and GD-1 in Application Example 1 were replaced with compounds SP-1, GD-1; SP-2, GD-13; SP-19, GD-27; SP-21, GD-49; SP-42, GD-59; SP-49, GD-76; SP-53, GD-75 of the present invention, respectively, while the rest of the components were the same as in Application Example 1. Based on this, organic electroluminescent devices of Application Examples 15-21 were fabricated.

[0125] Comparative Example 1

[0126] Using compound D1-P from example CN116178403A instead of P-66 in application example 1, and D1-N instead of N-80 in application example 1, with the other parts being the same as application example 1, an organic electroluminescent device was fabricated accordingly.

[0127] Comparative Example 2

[0128] Using compound D2-P from example CN118206574A to replace P-66 in application example 1, D2-N to replace N-80 in application example 1, and D2-GD to replace GD-1 in application example 1, with the other parts being the same as application example 1, an organic electroluminescent device was fabricated accordingly.

[0129] Comparative Example 3

[0130] Using compound D3-P from example CN111377957A to replace P-66 in application example 1, D3-N to replace N-80 in application example 1, D3-SP to replace SP-49 in application example 1, and D3-GD to replace GD-1 in application example 1, with the other parts being the same as application example 1, an organic electroluminescent device was fabricated accordingly.

[0131] Comparative Example 4

[0132] An organic electroluminescent device was fabricated by replacing P-66 in Application Example 1 with compound D4-P from the example in CN116925114A, replacing N-80 in Application Example 1 with D4-N, and replacing GD-1 in Application Example 1 with D4-GD.

[0133] Comparative Example 5

[0134] An organic electroluminescent device was fabricated by replacing P-66 in Application Example 1 with compound D5-P from the example in CN116396311A, replacing N-80 in Application Example 1 with D5-N, and replacing GD-1 in Application Example 1 with D5-GD.

[0135] Comparative Example 6

[0136] An organic electroluminescent device was fabricated by replacing P-66 in Application Example 1 with compound D6-P from the example in CN116655664A, replacing N-80 in Application Example 1 with D6-N, and replacing GD-1 in Application Example 1 with D6-GD.

[0137] Comparative Example 7

[0138] Organic electroluminescent devices were fabricated by replacing P-66 in Application Example 1 with compound D7-P from the example in CN118852220, replacing N-80 in Application Example 1 with D7-N, and replacing GD-1 in Application Example 1 with D7-GD.

[0139] Comparative Example 8

[0140] Using compounds P-11 and N-80 of the present invention as the main materials and compound SP-49 as the dopant material, the mass ratio of P-66, N-80 and compound SP-49 is 66.5:30:3.5, and the thickness of the light-emitting layer is 30 nm; the other parts are the same as in Application Example 1, and an organic electroluminescent device is fabricated accordingly.

[0141] Organic electroluminescent devices (OLEDs) prepared in Application Examples 1-21 and Control Examples 1-8 were tested separately. Voltage, luminous efficiency, lifetime, and luminous lifetime were measured for both. The luminous lifetime test yielded the luminous lifetime T97% data (the time it takes for the luminous brightness to decrease to 97% of its initial brightness). The testing equipment was a TEO OLED lifetime testing system. The test results are shown in Table 2.

[0142] Table 2

[0143]

[0144]

[0145] As shown in Table 2 above, compared to the dual host materials of TADF and the first dopant in Comparative Examples 1-7, the compounds with a host structure of deuterated biscarbazole or indolecarbazole used in Examples 1-21 of the present invention, with TADF and the first dopant combined with the deuterated biscarbazole or indolecarbazole as the P-type host and triazine compounds as the N-type host, are applied in organic electroluminescent devices, achieving high-performance, high-stability, and long-life OLED devices. Compared to Comparative Example 8, which used a compound with a deuterated biscarbazole host structure as the P-type host and triazine compounds as the N-type host, with a complex as the dopant, Examples 1-21 of the present invention use a complex as the first dopant and TADF as the second dopant, achieving better efficiency and longer lifespan, providing new possibilities for the development of display and lighting technologies.

Claims

1. An organic electroluminescent device, characterized in that, include: The first electrode, the second electrode, and the organic layer between the first electrode and the second electrode; the organic layer includes a light-emitting layer, which includes a P-type host material, an N-type host material, a first doped material, and a second doped material; The P-type host material is selected from the compounds shown in Formula 1-1 or Formula 1-2: Among them, AR1, AR2, AR3, and AR4 are each independently selected from substituted or unsubstituted C6-C30 aryl and C5-C20 heteroaryl groups, and their substituents are selected from hydrogen, deuterium, F, cyano, C6-C30 aryl, and C5-C20 heteroaryl groups; R1, R2, R3, and R4 are each independently selected from hydrogen or deuterium. The N-type host material is selected from the compound shown in Formula 2: Among them, AR5, AR6, and AR7 are each independently selected from substituted or unsubstituted C6-C30 aryl and C5-C20 heteroaryl groups, and their substituents are selected from hydrogen, deuterium, F, cyano, C6-C30 aryl, and C5-C20 heteroaryl groups; L is selected from direct bond, deuterated or undeuterated phenylene; m, n, and o are each independently 0 or 1; D is deuterium; when m is 0, x is selected from integers from 0 to 7; when m is 1, x is selected from integers from 0 to 6; when n is 0, y is selected from integers from 0 to 8; when n is 1, y is selected from integers from 0 to 7; when o is 0, z is selected from integers from 0 to 5; when o is 1, z is selected from integers from 0 to 4; the first dopant is selected from a monolithic complex or a platinum complex; the second dopant is a B / N type MR-TADF material.

2. The organic electroluminescent device as described in claim 1, characterized in that, The first doped material is selected from the compounds shown in formulas 3-1, 3-2, 3-3, 3-4, and 3-5: Among them, R5-R 18 Each of the following is an independent group derived from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C20 aryl, wherein the substituent is selected from at least one of the following atoms or groups: deuterium, monodeuterylmethyl, dideuterylmethyl, trideuterylmethyl; R 19 R 20 Each is independently derived from hydrogen or deuterium; R 21 -R 24 Each aryl R is independently derived from hydrogen, deuterium, or substituted or unsubstituted C6-C20. 21 -R 24 Two adjacent groups can join or fuse to form a phenyl or naphthyl group.

3. The organic electroluminescent device as described in claim 1, characterized in that, The second doped material is selected from the compounds shown in formulas 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, and 4-7: Among them, R 25 To R 37 Each is independently selected from H, D, F, Cl, Br, I, CN, Si(R) 38 )3, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, each of which may be atomized by one or more groups R 38 Substitution, wherein in each case one or more non-adjacent CH2 groups can be replaced by Si(R) 38 2. C = NR 38 P(=O)(R) 38 SO, SO2, NR 38 O, S or CONR 38 The substitution, and one or more H atoms may be replaced by D, F, Cl, Br or I, in an aromatic ring system having 6 to 60 C atoms, wherein in each case the ring system may be replaced by one or more R groups. 38 Substitution, heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which can be replaced by one or more R groups 38 The substitution, or the presence of an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, wherein in each case the group may be replaced by one or more groups R 38 Substitution, in which two or more adjacent substituents R 25 To R 37 Optionally, a monocyclic or polycyclic aliphatic ring system can be formed, said ring system being mediated by one or more groups R 38 replace; R 38 Selected from H, D, F, aliphatic hydrocarbon groups having 1 to 20 carbon atoms, or aromatic or heteroaromatic ring systems having 5 to 30 carbon atoms, wherein one or more H atoms can be replaced by D or F, and wherein two or more adjacent substituents R 38 They can form monocyclic or polycyclic aliphatic ring systems with each other.

4. An organic electroluminescent device as described in claim 1, characterized in that, AR1, AR2, AR3, and AR4 are each independently selected from the following groups: Where D is deuterium, a are integers independently selected from 0 to 5, b are integers independently selected from 0 to 4, c are integers independently selected from 0 to 3, and d are integers selected from 0 to 7.

5. An organic electroluminescent device as described in claim 1, characterized in that, The P-type host material is at least one of the following compounds with the following structural formulas:

6. An organic electroluminescent device as described in claim 1, characterized in that, AR5, AR6, and AR7 are each independently selected from the following groups: Where D is deuterium, e are integers independently selected from 0 to 5, and f are integers independently selected from 0 to 4.

7. An organic electroluminescent device as described in claim 1, characterized in that, The N-type host material is at least one of the following compounds with the following structural formulas:

8. An organic electroluminescent device as described in claim 1, characterized in that, The first doping material is at least one of the following compounds with the following structural formulas:

9. An organic electroluminescent device as described in claim 1, characterized in that, The second doping material is at least one of the following compounds:

10. An organic electroluminescent device as described in claim 1, characterized in that, The weight percentage of the first dopant material in the light-emitting layer is 2%-8%; the weight percentage of the second dopant material is 0.3%-1%.

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