Organic electroluminescent device and electronic device

Abstract

The present invention discloses an organic electroluminescent device and an electronic device, wherein the organic electroluminescent device comprises a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, and the light-emitting layer comprises at least a compound 1 and a compound 2, wherein the compound 1 is selected from the compound represented by formula A or formula B, and the compound 2 is selected from the compound represented by formula C. The organic electroluminescent device of the present application comprises a composition of the first compound and the second compound, and can ultimately adjust the electron and hole characteristics in the device stack to achieve an optimal balance.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and in particular to an organic electroluminescence device and an electronic device. Background Art

[0002] Generally speaking, an organic electronic device that uses electrical energy to make an organic material emit light usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is usually formed of a multilayer structure composed of different materials to improve the efficiency and stability of the organic electronic device, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] Research on improving the performance of organic electroluminescent devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device. In order to continuously improve the performance of organic electroluminescent devices, it is necessary not only to continuously research and innovate organic electrophotoelectric functional materials and create higher performance organic electrophotoelectric functional materials, but also to innovate the structure and manufacturing process of organic electroluminescent devices, and continuously require the development of new materials for organic light-emitting devices as described above.

[0004] In organic electroluminescent devices, the organic light-emitting layer is generally prepared by doping a dye with a single host material. The electrons and holes in the light-emitting layer do not recombine sufficiently, resulting in reduced energy utilization and affecting device performance. Taking green organic electroluminescent devices as an example, their organic light-emitting layer (EML) is usually prepared by doping a dye with a single N-type host material; a single N-type green light host material often has a low hole mobility or even a strong hole blocking effect, which leads to insufficient recombination of electrons and holes in the organic light-emitting layer, low energy utilization, and ultimately low current efficiency and serious impact on device life.

[0005] In organic electroluminescent devices, not all materials have a good match in energy levels, and the potential barriers between them seriously hinder the effective injection of holes and electrons. A reasonable energy level structure is conducive to the formation of step barriers in the energy levels of each layer of the device, which can reduce the barrier for hole injection and the driving voltage of the device, thereby improving the luminous efficiency and life of the device.

[0006] The compound disclosed in the patent with patent number "CN112225726A" adopts a triazine main structure, and the side chain of the triazine is arranged with an N-phenylcarbazolyl group and a dibenzofuranyl group substituted with a deuterated phenyl. The compound is used as an N-type green light main material, and its matching P-type green light main material discloses a compound of dicarbazole and tricarbazole; the patent with patent number "CN115368293A" discloses a compound with a tricarbazole structure, and two of the carbozolies are deuterated. The compound is used as a P-type green light main material, and its matching N-type green light main material discloses a triazine main structure, and the side chain of the triazine is arranged with a carbazole group. The invention patent with the patent number of "CN117800897A" discloses a tricarbazole compound, and two of the carbazoles are partially deuterated. At the same time, the patent uses a triazine main body, a compound modified by dibenzofuran, carbazole, and deuterated phenyl as an N-type green light main material. The compound after deuteration has better thermal stability, thereby improving the life of the device; the device verifies that the compound after hydrogen at some sites of the compound is replaced by deuterium has a better life and lower cost than other similar compounds; the deuterated GH material has better phase solubility with the deuterated GD material, which is more conducive to energy transfer, thereby improving the preparation yield, stability, efficiency and life of the device. It is necessary to conduct further research and development and exploration on this basis, and it is necessary to develop and combine different organic electroluminescent materials to develop organic electroluminescent devices with excellent luminous efficiency and life. The compounds and organic electroluminescent devices in the present invention can improve the green light luminous efficiency and life, and promote the localization of OLED materials. Summary of the invention

[0007] The object of the present invention is to provide an organic electroluminescent device and an electronic apparatus based on the prior art.

[0008] The purpose of the present invention can be achieved by the following measures:

[0009] An organic electroluminescent device comprises a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer; the light-emitting layer comprises at least a compound 1 and a compound 2, wherein the compound 1 is selected from the compounds represented by formula A or formula B:

[0010] ;

[0011] in,

[0012] D is deuterium,

[0013] n1, n2, n3 are each independently selected from integers of 0-7,

[0014] n4, n5, n9, n11 are each independently selected from an integer of 0-5;

[0015] n6 is an integer selected from 0 to 6,

[0016] n7, n8, n10 are each independently selected from integers of 0-4,

[0017] AR 1 is selected from hydrogen, deuterium, phenyl, deuterated phenyl;

[0018] Compound 2 is selected from the compound shown in formula C:

[0019] ;

[0020] in,

[0021] R 1 -R 24 are each independently selected from hydrogen, deuterium, phenyl, deuterated phenyl, biphenyl or deuterated biphenyl; and

[0022] The HOMO energy level range of compound 1 is: 5.6eV - 5.8 eV;

[0023] The LUMO energy level range of compound 2 is: 2.6eV - 2.9eV.

[0024] As a preferred embodiment of the present invention, the deuteration rate of the compound represented by formula A is 45%-68%; the deuteration rate of the compound represented by formula B is 18%-100%.

[0025] As a preferred solution of the present invention, the sum of n1, n2, n3, n4 and n5 is greater than or equal to 5, and the sum of n6, n7, n8, n9, n10 and n11 is greater than or equal to 4.

[0026] As a more preferred embodiment of the present invention, the sum of n1, n2, n3, n4 and n5 is greater than or equal to 13, and the sum of n6, n7, n8, n9, n10 and n11 is greater than or equal to 6.

[0027] As a more preferred embodiment of the present invention, 13≤n1+n2+n3+n4+n5≤21; 6≤n6+n7+n8+n9+n10+n11≤28.

[0028] As a preferred embodiment of the present invention, compound 1 is selected from one or more of the following structural formulas:

[0029] .

[0030] As a preferred embodiment of the present invention, compound 2 is selected from the compound represented by formula C-2:

[0031] ,

[0032] in,

[0033] D is deuterium,

[0034] m1, m2, m3, m4, m5, and m6 are each independently selected from 0 or 1,

[0035] n12 is selected from an integer of 0-48.

[0036] Preferably,

[0037] When m1, m2, m3, m4, m5, and m6 are all 0, n12 is selected from an integer of 0 to 23;

[0038] When one of m1, m2, m3, m4, m5, and m6 is 1, n12 is selected from an integer of 0 to 27;

[0039] When two of m1, m2, m3, m4, m5, and m6 are 1, n12 is selected from an integer between 0 and 31;

[0040] When three of m1, m2, m3, m4, m5, and m6 are 1, n12 is selected from an integer of 0 to 35;

[0041] When four of m1, m2, m3, m4, m5, and m6 are 1, n12 is selected from an integer of 0 to 39;

[0042] When five of m1, m2, m3, m4, m5, and m6 are 1, n12 is selected from an integer of 0 to 44;

[0043] When m1, m2, m3, m4, m5, and m6 are all 1, n12 is selected from an integer of 0-48.

[0044] As a preferred embodiment of the present invention, compound 2 is selected from one or more of the following structural formulas:

[0045] .

[0046] As a preferred embodiment of the present invention, the electron blocking layer is selected from the compounds represented by formula D-1 and D-2:

[0047] ,

[0048] in,

[0049] X and Y are O, S, single bond or non-bonding,

[0050] L is a single bond or a phenyl group,

[0051] Ar 2 Selected from dimethylpentyl, biphenyl, methyl-substituted biphenyl or deuterated methyl-substituted biphenyl;

[0052] Ar 3 ,Ar 4 Each independently selected from hydrogen or tert-butyl;

[0053] Ar 5 is a substituted or unsubstituted biphenyl group or a substituted or unsubstituted dibenzofuranyl group, wherein the substituent is selected from one or more of methyl, deuterated methyl, phenyl or deuterated phenyl;

[0054] Ar 6 ,Ar 9 Each is independently selected from methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, phenyl or deuterated phenyl;

[0055] Ar 7 ,Ar8 Each is independently selected from hydrogen, deuterium, phenyl or deuterated phenyl;

[0056] Ar 10 is hydrogen, deuterium, phenyl or deuterated phenyl.

[0057] As a preferred embodiment of the present invention, the electron blocking layer is selected from one of the following specific compounds:

[0058] .

[0059] The present invention provides an electronic device comprising any one of the organic electroluminescent devices of the present invention.

[0060] Beneficial effects of the present invention:

[0061] The main material of the light-emitting layer of the organic electroluminescent device of the present application is composed of compound one and compound two, wherein compound one adopts a compound of a tricarbazole structure, and two of the carbazoles are deuterated; compound two adopts a main structure of triazine, and a deuterated or undeuterated carbazole group, a deuterated or undeuterated dibenzofuran group, a deuterated or undeuterated phenyl group are arranged on the side chain of triazine. By controlling the deuteration rate of compound one of the present invention, when the device is formed by matching with compound two, due to the lower interface energy barrier between the functional layers, the device has a lower voltage, higher efficiency and smaller capacitance.

[0062] The GH-P material of the present invention introduces heavy hydrogen (deuterium), and selects GH-P materials with a HOMO energy level range of 5.6eV-5.8eV and GH-N materials with a LUMO energy level range of 2.6eV-2.9eV; the mixture formed by the GH-P material and the GH-N material has better compatibility with the GD material, improves the energy transfer efficiency between the main material and the doping material, and thus greatly improves the efficiency of the device.

[0063] When the GH-P material of the present invention selects the compound shown in formula A, the deuterium substitution rate is 45%-68%; when the GH-P material selects the compound shown in formula B, the deuterium substitution rate is 18%-100%; such selection and design improve the thermal stability and chemical stability of the material. At the same time, the mixture formed by the P-type GH material and the N-type GH material of the present invention has better film-forming properties, more suitable Tm temperature and Tg temperature, and better solubility, thereby significantly improving the life and temperature stability of the device, and solving the problems of hole plugging in the production line and cleaning of the mask. BRIEF DESCRIPTION OF THE DRAWINGS

[0064] Figure 1 A schematic diagram of the structure of an organic electroluminescent device provided by the present invention;

[0065] The numbers in the figure 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, 9-cathode. DETAILED DESCRIPTION

[0066] The following further illustrates and describes embodiments of various aspects. It should be understood that the description herein is not intended to limit the claims to the specific aspects described. On the contrary, it is intended to cover substitutions, modifications and equivalents that may be included in the spirit and scope of the present disclosure defined by the appended claims.

[0067] As used herein, in "substituted" or "unsubstituted", the term "substituted" means that at least one hydrogen in the group is re-coordinated with deuterium, a hydrocarbon group, a hydrocarbon derivative group, a halogen, or a cyano group (-CN). The term "unsubstituted" means that at least one hydrogen in the group is not re-coordinated with deuterium, a hydrocarbon group, a hydrocarbon derivative group, a halogen, or a cyano group (-CN). Examples of hydrocarbon groups or hydrocarbon derivative groups may include 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 arylamino, C6 to C30 heteroarylamino, C6 to C30 arylheteroarylamino, etc., but are not limited thereto.

[0068] Deuterium in the present invention refers to a stable isotope of hydrogen, also known as heavy hydrogen, and its element symbol is D.

[0069] The aromatic group in the present invention refers to an all-carbon monocyclic or condensed polycyclic group of 6 to 30 carbon atoms, having a completely conjugated π electron system. Non-limiting examples of aromatic groups include phenyl, naphthyl, anthracenyl, biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, triphenyl[1,12-bcd]furanyl, phenanthrenyl, and the like.

[0070] In the present invention, the integer of 0-7 specifically refers to 0 or 1 or 2 or 3 or 4 or 5 or 6 or 7; the integer of 0-5 specifically refers to 0 or 1 or 2 or 3 or 4 or 5; the integer of 0-6 specifically refers to 0 or 1 or 2 or 3 or 4 or 5 or 6; the integer of 0-4 specifically refers to 0 or 1 or 2 or 3 or 4; the integer of 0-5 specifically refers to 0 or 1 or 2 or 3 or 4 or 5; 13≤n1+n2+n3+n4+n5≤21 specifically refers to n1+n2+n3+n4+n5 taken from 13, 14, 15, 16, 17, 18, 19, 20, 21; 6≤n6+n7+n8+n9+n10+n11≤28 specifically refers to n6+n7+n8+n9 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, wherein the integers of 0-48 are 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48.

[0071] If the specific conditions are not specified in the examples, the experiments were carried out under conventional conditions or conditions recommended by the manufacturer. If the manufacturers of the reagents or instruments are not specified, they are all conventional products that can be purchased commercially.

[0072] Synthesis example 1:

[0073]

[0074] The synthesis method of compound P-1 is as follows:

[0075] S1:

[0076] S2:

[0077] S3:

[0078] Synthesis example 2:

[0079]

[0080] The synthesis method of compound P-2 is as follows:

[0081] S1:

[0082] S2:

[0083] S3:

[0084] S4: Synthesis example 3:

[0085]

[0086] The synthesis method of compound P-3 is as follows:

[0087] S1:

[0088] Process: Under nitrogen protection, add 3,6-dibromodeuterated carbazole (70g, 0.21mol, 1eq) and 500ml of ultra-dry THF into the reaction bottle, cool to -70°C, add n-butyl lithium (176ml, 0.441mol, 3.1eq) dropwise, and after the addition is completed, the reaction solution is reacted at -70°C for 1h.

[0089] Post-treatment: Add saturated aqueous ammonium chloride solution to the reaction solution, stir for 30 minutes, separate the liquids, and concentrate the organic phase to dryness to obtain about 32 g of product with a yield of 60%.

[0090] S2:

[0091] Process: Under nitrogen protection, intermediate 2 (45.7 g, 0.139 mol, 1 eq) and 500 ml of ultra-dry THF were added to the reaction flask, cooled to -70°C, and n-butyl lithium (58.4 ml, 0.146 mol, 1.06 eq) was added dropwise. After the addition was complete, the mixture was stirred for 1 h, and triisopropyl borate (39 g, 0.2085 mol, 1.5 eq) was added dropwise. After the addition was complete, the mixture was naturally warmed to room temperature and reacted overnight.

[0092] Post-treatment: Add saturated aqueous ammonium chloride solution to the reaction solution, separate the liquids, extract the aqueous phase once with EA, combine the organic phases, concentrate to dryness, and dry with air at 65°C to obtain about 32 g of the product with a yield of 78.3%.

[0093] S3:

[0094] Process: Under nitrogen protection, intermediate 2 (32 g, 0.109 mol, 1 eq), intermediate 1 (27.58 g, 0.109 mol, 1 eq), 300 ml of toluene, 150 ml of ethanol, potassium carbonate (37.95 g, 0.275 mol, 2.5 eq), 150 ml of water, and tetrakistriphenylphosphine palladium (1.27 g, 0.0011 mol, 1% eq) were added to the reaction flask. After the addition was completed, the reaction solution was heated to reflux and reacted overnight. The reaction was completed by sampling and HPLC detection.

[0095] Post-treatment: The reaction solution was cooled and water was added, filtered, the filter cake was washed with water and ethanol, and dried at 85°C to obtain about 33 g of product with a yield of 71.9%.

[0096] S4: Process: Under nitrogen protection, intermediate 3 (33 g, 0.078 mol, 1 eq), 3-bromo-N-phenylcarbazole (25.25 g, 0.078 mol, 1 eq), 600 ml of toluene, sodium tert-butoxide (9 g, 0.0936 mol, 1.2 eq), palladium acetate (0.35 g, 0.00156 mol, 2% eq), and X-phos (1.48 g, 0.00312 mol, 4%) were added to the reaction flask. After the addition was completed, the reaction solution was heated to reflux and reacted overnight. The reaction was completed by sampling and HPLC detection.

[0097] Post-treatment: The reaction solution was cooled, water was added, the solution was separated, filtered through silica gel, concentrated to dryness, and subjected to column chromatography to obtain about 20 g of the product with a yield of 38.7%.

[0098] Synthesis example 4:

[0099]

[0100] The synthesis method of compound P-9 is as follows:

[0101] Reaction equation:

[0102] Process: Under nitrogen protection, carbazole compounds (45g, 0.11mol, 1eq), halides (30g, 0.129mol, 1.17eq), 500ml toluene, sodium tert-butoxide (21g, 0.2184mol, 2eq), palladium acetate (0.7g, 0.003mol, 2.5%eq), and X-phos (2.1g, 0.0044mol, 4%) were added to the reaction bottle. After the addition was completed, the reaction solution was heated to reflux and reacted overnight. The reaction was completed by sampling and HPLC detection.

[0103] Post-treatment: cool the reaction solution, add water, filter with suction, wash the filter cake with water and ethanol, dry and then perform column chromatography.

[0104] Synthesis example 5:

[0105]

[0106] The synthesis method of compound P-10 is as follows:

[0107]

[0108] Synthesis example 6:

[0109]

[0110] The synthesis method of compound N-6 is as follows:

[0111] S1:

[0112] Procedure: Add CP7118-SM1 (100 g, 0.411 mol, 1 eq), CP7118-SM2 (139.4 g, 0.617 mol, 1.5 eq) and THF (1000 ml) into a 1 L single-necked flask, cool to below 0°C, add sodium tert-butoxide (59.3 g, 0.617 mol, 1.5 eq) in batches, and after the addition is complete, move to room temperature and stir to react overnight.

[0113] Post-treatment: stop the reaction, add 300 ml of water, stir and filter, rinse the filter cake with water and ethanol, add 500 ml of toluene to the filter cake and heat and slurry for 30 minutes, cool and stir to crystallize to room temperature, filter, heat the filter cake with 500 ml of toluene and reflux and slurry for 30 minutes, filter, and dry the filter cake at 85°C to obtain 112.66 g of light yellow solid with a yield of 63.3%.

[0114] S2: Procedure: CP7118-ZJ1 (112.66 g, 0.26 mol, 1 eq), CP7118-SM3 (117.2 g, 0.31 mol, 1.2 eq), potassium carbonate (90 g, 0.65 mol, 2.5 eq) and toluene / ethanol / water (1500 ml + 750 ml + 450 ml) were added into a 3 L three-necked flask. Under N2 protection, tetrakistriphenylphosphine palladium (6 g, 5.2 mmol, 0.02 eq) was added. The temperature was raised and the mixture was stirred under reflux to react. HPLC monitored CP7118-ZJ1 ≤ 2%.

[0115] Post-treatment: stop the reaction, filter while hot, rinse the filter cake with water and ethanol, add 1500ml of o-dichlorobenzene to the filter cake and heat to dissolve, filter through silica gel and activated carbon while hot, cool the filtrate to 60℃, stir and crystallize overnight, filter, heat the filter cake with o-dichlorobenzene (1L*2) to dissolve, cool to 90℃, stir and crystallize for 1~3h, filter, add toluene (1000ml*5) to the filter cake, stir and slurry at 120℃, filter while hot each time, dry the filter cake at 85℃, and obtain 72.23g of off-white solid with a yield of 43% and a HPLC purity of 99.98%.

[0116] Synthesis example 7:

[0117]

[0118] The synthesis method of compound N-2 is as follows:

[0119] S1:

[0120] S2: Synthesis example 8:

[0121]

[0122] The synthesis method of compound N-3 is as follows:

[0123] S1:

[0124] S2: Synthesis example 9:

[0125]

[0126] The synthesis method of compound N-14 is as follows:

[0127] S1:

[0128] S2: Synthesis example 10:

[0129]

[0130] The synthesis method of compound N-22 is as follows:

[0131] S1:

[0132] S2: Synthesis example 11:

[0133]

[0134] The synthesis method of compound N-39 is as follows:

[0135] S1:

[0136] S2:

[0137] Synthesis example 12:

[0138]

[0139] The synthesis method of compound N-54 is as follows:

[0140] S1:

[0141] S2: Synthesis example 13:

[0142]

[0143] The synthesis method of compound N-66 is as follows:

[0144] S1:

[0145] S2:

[0146] S3:

[0147] S4: Synthesis example 14:

[0148]

[0149] The synthesis method of compound N-67 is as follows:

[0150] S1:

[0151] Process: Under nitrogen protection, deuterated carbazole (27.5g, 0.157mol, 1eq), m-bromofluorobenzene (55g, 0.314mol, 2eq), and DMF 200ml were added to the reaction bottle, and cesium carbonate (102g, 0.314mol, 2eq) was added. After the addition was completed, the reaction solution was heated to 150℃ and stirred for 6h. The reaction was completed by HPLC sampling.

[0152] Post-treatment: After the reaction solution was cooled, it was added into water and filtered, the filter cake was washed with water and ethanol, and after drying, about 28.75 g of product was obtained, with a yield of 55%.

[0153] S2:

[0154] Process: Under nitrogen protection, intermediate 1 (28.75g, 0.087mol, 1eq), diboronic acid pinacol ester (27.6g, 0.10875mol, 1.25eq), 250ml of 1,4-dioxane, potassium acetate (21.35g, 0.2178mol, 2.5eq), dppf palladium dichloride (1.9g, 0.00261mol, 3%eq) were added to the reaction bottle. After the addition was completed, the reaction solution was heated to 100℃ for 6h, and the reaction was completed after sampling and HPLC detection.

[0155] Post-treatment: After the reaction solution was cooled, water was added to separate the liquid. The organic phase was concentrated to dryness after being filtered through silica gel. Ethanol was added, stirred, and then filtered to obtain about 26.7 g of the product with a yield of 81.4%.

[0156] S3: Process: Under nitrogen protection, borate compounds (36.6g, 0.0976mol, 1eq), triazine compounds (66.2g, 0.293mol, 3eq), 200ml of toluene, 40ml of ethanol, potassium carbonate (27g, 0.195mol, 2eq), Pd(PPh3)4 (1g, 0.00086mol, 0.9%eq) were added to the reaction bottle. After the addition, the mixture was reacted at 75℃ for 6h. The reaction was then completed after sampling and HPLC detection.

[0157] Post-treatment: add water to the reaction solution, cool and filter, wash the filter cake with ethanol, dry and recrystallize from toluene to obtain about 32g of product with a yield of 74%.

[0158] S4: Process: Under nitrogen protection, intermediate 2 (24 g, 0.0548 mol, 1 eq), intermediate 3 (21.7 g, 0.0575 mol, 1.05 eq), 240 ml of toluene, 60 ml of ethanol, potassium carbonate (18.9 g, 0.137 mol, 2.5 eq), 60 ml of water, and tetrakistriphenylphosphine palladium (0.64 g, 0.00055 mol, 1% eq) were added to the reaction bottle. After the addition was completed, the reaction solution was heated to 82°C for 5 hours, and the reaction was completed by HPLC sampling.

[0159] Post-treatment: add water to the reaction solution, filter with suction, wash the filter cake with water and ethanol, dry it at 85°C, and purify it by recrystallization from toluene to obtain about 17.75g of product with a yield of 49.6%.

[0160] The synthesis and identification results of the compounds prepared above are shown in Tables 1-1, 1-2, 1-3, 1-4 and 1-5 below:

[0161] Table 1-1

[0162]

[0163] Table 1-2

[0164] Table 1-3

[0165] Table 1-4

[0166] Table 1-5

[0167] The compounds of the above-listed synthesis examples 1-14 were subjected to energy level testing using an IPS-3 device, and the test results are shown in Table 2 below:

[0168] Table 2:

[0169] Synthesis example HOMO level (eV) LUMO level (eV) Synthesis example HOMO level (eV) LUMO level (eV) 1 5.68 - 8 - 2.63 2 5.71 - 9 - 2.84 3 5.69 - 10 - 2.79 4 5.74 - 11 - 2.63 5 5.76 - 12 - 2.88 6 - 2.74 13 - 2.87 7 - 2.71 14 - 2.71

[0170] As shown in Table 2 above, the HOMO energy level range of compound 1 of the present invention is 5.6eV-5.8eV; the LUMO energy level range of compound 2 is 2.6eV-2.9eV. Reasonable energy level structure is conducive to the formation of step barriers in the energy levels of each layer of the device, which can reduce the barrier for hole injection and the driving voltage of the device, thereby improving the luminous efficiency and life of the device.

[0171] Device performance test:

[0172] Application Example 1:

[0173] ITO was used as the reflective layer anode substrate material, and water, acetone, N 2 Surface treatment thereof;

[0174] On top of the ITO anode substrate, 10 nm of HT-1 containing 3 wt% NDP-9 was deposited to form a hole injection layer (HIL);

[0175] A hole transport layer (HTL) was formed by evaporating 100 nm of HT-1 on the hole injection layer (HIL);

[0176] Vacuum evaporation of the compound GP-2 of the present invention on the hole transport layer (HTL) to form an electron blocking layer with a thickness of 30 nm;

[0177] Compound P-1 of the present invention and compound N-6 were co-evaporated as luminescent host materials in a mass ratio of 6:4, and GD-1 was evaporated as a doping material (the amount of GD-1 was 8% of the total weight of compound 1 and G15) on the electron blocking layer to form a luminescent layer with a thickness of 30 nm;

[0178] NB-1 was evaporated onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0179] ET-1 and LiQ were co-evaporated onto the hole blocking layer (HBL) in a mass ratio of 5:5 to obtain an electron transport layer (ETL) with a thickness of 50 nm;

[0180] Magnesium (Mg) and silver (Ag) were mixed and evaporated on the electron transport layer (ETL) in a mass ratio of 9:1 to form an electron injection layer (EIL) with a thickness of 50 nm;

[0181] Thereafter, silver (Ag) is evaporated onto the electron injection layer to form a cathode with a thickness of 100 nm, and a DNTPD with a thickness of 50 nm is deposited on the cathode sealing layer. In addition, the cathode surface is sealed with a UV curable adhesive and a packaging film (seal cap) containing a dehumidifier to protect the organic electroluminescent device from being affected by oxygen or moisture in the atmosphere. Thus, an organic electroluminescent device is prepared.

[0182]

[0183] Application Example 2-13

[0184] The compound P-2, P-3, P-9 and P-10 of the present invention were used to replace the compound P-1 in Application Example 1, respectively, and the other parts were consistent with Application Example 1, and Application Examples 2-5 were prepared accordingly; the compounds N-2, N-3, N-14, N-22, N-39, N-54, N-66 and N-67 of the present invention were used respectively, and the other parts were consistent with Application Example 1, and the organic electroluminescent devices of Application Examples 6-13 were prepared accordingly.

[0185] Comparative Examples 1-3

[0186] D1-N, D1-P, and GD used in the embodiment of CN112225726A were used to replace the corresponding layers in Example 1 to prepare Control Example 1; D2-N, D2-P, and GD-0 used in the embodiment of CN115368293A were used to replace the corresponding layers in Example 1 to prepare Control Example 2; D3-N, D3-P, and GD used in the embodiment of CN117800897A were used to replace the corresponding layers in Example 1 to prepare Control Example 3.

[0187] The organic electroluminescent devices prepared in application examples 1-13 and control examples 1-3 were tested respectively. The voltage, luminous efficiency, life, and luminous life tests were performed on the organic electroluminescent devices prepared in control examples 1-3 and application examples 1-13. The luminous life test obtained the luminous life T97% data (the time when the luminous brightness is reduced to 97% of the initial brightness). The test equipment was a TEO luminescent device life test system. The test results are shown in Table 3.

[0188] Table 3

[0189] Experimental Group N-type body P-type body GD Voltage (V) Luminous efficiency (Cd / A) life Emitting color Comparative Example 1 D1-N D1-P GD 3.65 142 517 green Comparative Example 2 D2-N D2-P GD-0 3.56 157 594 green Comparative Example 3 D3-N D3-P GD 3.43 168 608 green Application Example 1 P-1 N-6 GD-1 3.20 198 729 green Application Example 2 P-2 N-6 GD-1 3.32 171 684 green Application Example 3 P-3 N-6 GD-1 3.26 194 723 green Application Example 4 P-9 N-6 GD-1 3.37 176 691 green Application Example 5 P-10 N-6 GD-1 3.34 184 668 green Application Example 6 P-1 N-2 GD-1 3.29 185 724 green Application Example 7 P-1 N-3 GD-1 3.21 187 728 green Application Example 8 P-1 N-14 GD-1 3.28 183 719 green Application Example 9 P-1 N-22 GD-1 3.24 182 705 green Application Example 10 P-1 N-39 GD-1 3.27 189 704 green Application Example 11 P-1 N-54 GD-1 3.23 186 709 green Application Example 12 P-1 N-66 GD-1 3.26 183 719 green Application Example 13 P-1 N-67 GD-1 3.25 188 703 green

[0190] As can be seen from Table 3 above, the combination of Compound 1 and Compound 2 of the present invention and their application in organic electroluminescent devices as luminescent main materials can achieve the adjustment of the electron and hole characteristics within the device stack to achieve the best balance so that the luminous efficiency of the organic electroluminescent device is improved to a certain extent, and the starting voltage is reduced, the power consumption is relatively reduced, and the efficiency and life are improved.

Claims

1. An organic electroluminescent device, comprising a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer; the light-emitting layer comprises at least a compound 1 and a compound 2, wherein the compound 1 is selected from the compounds represented by formula A or formula B: ； wherein D is deuterium, n1 and n2 are each independently 6 or 7, n3 is 0 or 7, n4 and n5 are 0, n6 is 6, n7 is 0 or 4, n8-n11 are 0, and AR1 is selected from hydrogen, deuterium, phenyl, and deuterated phenyl; Compound 2 is selected from the compound shown in formula C: ； Wherein R1-R8, R10-R16, R20-R22, R24 are hydrogen or deuterium, R9, R17-R19, R23 are hydrogen or deuterium or phenyl; L1 is a single bond or phenyl, and the HOMO energy level range of compound one is: 5.6eV - 5.8 eV; the LUMO energy level range of compound two is: 2.6eV - 2.9eV, the deuteration rate of the compound represented by formula A is 45%-68%; the deuteration rate of the compound represented by formula B is 18%-100%.

2. An organic electroluminescent device according to claim 1, characterized in that: Compound 1 is selected from one or more of the following structural formulas: 。 3. The organic electroluminescent device according to claim 1, characterized in that: Compound 2 is selected from one or more of the following structural formulas: 。 4. The organic electroluminescent device according to claim 1, characterized in that: The electron blocking layer is selected from the compounds shown in formula D-1 and D-2 , wherein X and Y are O, S, a single bond or no bond, L is a single bond or a phenyl group, Ar2 is selected from dimethylpentyl, biphenyl, methyl-substituted biphenyl, and deuterated methyl-substituted biphenyl; Ar3 and Ar4 are each independently selected from hydrogen and tert-butyl; Ar5 is substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl; Ar6 and Ar9 are each independently selected from methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, phenyl, and deuterated phenyl; Ar7 and Ar8 are each independently selected from hydrogen, deuterium, phenyl, or deuterated phenyl; Ar10 is hydrogen, deuterium, phenyl, or deuterated phenyl.

5. An organic electroluminescent device according to claim 4, characterized in that: The electron blocking layer is selected from one of the following specific compounds: 。 6. An electronic device, characterized in that: An organic electroluminescent device comprising any one of claims 1 to 5.

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