An organic electroluminescent compound and an organic light-emitting device

Abstract

This invention discloses an organic electroluminescent compound, characterized in that it is selected from compounds represented by Formula 1: wherein Y is selected from O or S; Ar1 ​​is selected from substituted or unsubstituted C5-C40 aromatic groups, substituted or unsubstituted C5-C40 heteroaryl groups, and the substituents are selected from at least one of the following atoms or groups: deuterium, hydroxyl, cyano, monodeuterylmethyl, dideuterylmethyl, trideuterylmethyl, C1-C4 straight-chain or branched alkyl, C6-C18 aromatic group, C5-C24 heteroaryl group; Ar2 is selected from hydrogen, deuterium, fluorine atom, C1-C4 straight-chain or branched alkyl, C6-C18 aromatic group, C5-C24 heteroaryl group. Based on the triazine linking group, this invention further links dibenzothiophene or dibenzofuran, expanding the conjugated structure of the organic light-emitting host compound, enhancing intramolecular electron transfer and exciton coupling effects, which is beneficial for improving luminescence efficiency, photoelectric conversion efficiency, and luminescence quantum yield; thus improving the material's performance and application potential.

Description

Technical Field

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

[0002] Organic light-emitting devices (OLEDs) are self-emissive light-emitting devices that utilize the following principle: when an electric field is applied, fluorescent material emits light through the recombination of holes injected at the positive electrode and electrons injected at the negative electrode. These self-emissive devices possess characteristics such as low voltage, high brightness, wide viewing angle, fast response, and good temperature adaptability. Furthermore, they are ultra-thin and can be fabricated on flexible panels, making them widely used in mobile phones, tablets, televisions, lighting, and other fields.

[0003] Organic electroluminescent devices (OLEDs) have a sandwich-like structure, consisting of electrode material layers and organic functional materials sandwiched between them. These various functional materials are stacked together according to their intended use to form the OLED. As a current-carrying device, when a voltage is applied to the two electrodes of the OLED, positive and negative charges are generated in the organic functional material layers through the action of an electric field. These positive and negative charges then recombine in the light-emitting layer, producing light; this process is called electroluminescence.

[0004] Research on improving the performance of organic electroluminescent devices includes reducing the driving voltage, increasing luminous efficiency, and extending lifespan. To continuously improve the performance of organic electroluminescent devices, innovation in their structure and fabrication processes is needed, along with ongoing research and innovation in organic electroluminescent functional materials to create higher-performance organic electroluminescent functional materials.

[0005] Invention patent CN116143795A discloses an organic electroluminescent compound with the following general formula: And the substituents therein are limited as follows (L is selected from the group consisting of: direct bond, aryl and heteroaryl; where G is selected from the group consisting of: triazine, pyrimidine, pyridine, pyrazine, benzofuran, aza-benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, aza-benzothiophene, dibenzothiophene, aza-dibenzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, indole, benzimidazole, indazole, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline, zoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, oxanthracene, phenothiazine, phenothiazine, benzofuran-pyridine, furan-dipyridine, benzothiophene-pyridine, thiophene-pyridine, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a] The patent discloses a scheme using the above materials as the main material for green light and achieving lower operating voltage and higher power efficiency. However, the compounds in this scheme are not suitable for red light devices, and the performance of the compounds needs to be further improved. The invention patent with patent number US20230292539A1 discloses a structure similar to that in CN116143795A. The specific compounds disclosed are deuterated improved compounds, but their performance and the effect of use in devices need to be further improved. Summary of the Invention

[0006] The purpose of this invention is to address the aforementioned technical problems. This invention provides an organic electroluminescent compound selected from compounds shown in Formula 1:

[0007] Where Y is selected from O or S;

[0008] Ar1 is selected from substituted or unsubstituted C5-C40 aromatic groups, substituted or unsubstituted C5-C40 heteroaryl groups, and the substituent is selected from at least one of the following atoms or groups: deuterium, hydroxyl, cyano, monodeuterium methyl, dideuterium methyl, trideuterium methyl, C1-C4 straight-chain or branched alkyl, C6-C18 aromatic group or C5-C24 heteroaryl group;

[0009] Ar2 is selected from hydrogen, deuterium, fluorine atoms, C1-C4 straight-chain or branched alkyl groups, C6-C18 aromatic groups, or C5-C24 heteroaryl groups.

[0010] As a preferred embodiment of the present invention, Ar1 is selected from one or more of substituted or unsubstituted phenyl, naphthalene, anthracene or phenanthrene; preferably, Ar1 is selected from one or more of substituted or unsubstituted phenyl, naphthalene or phenanthrene.

[0011] In a preferred embodiment, Ar2 is selected from one or more of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, anthracene, phenanthrene, or triphenylene. Preferably, Ar2 is selected from hydrogen or phenyl.

[0012] As a preferred embodiment of the present invention, the compounds are selected from those shown in Formulas 2-5:

[0013]

[0014] As a preferred embodiment of the present invention, the compounds are selected from those shown in Formulas 6-13:

[0015]

[0016] In a preferred embodiment of the present invention, Ar1 is selected from the following groups:

[0017] As a preferred embodiment of the present invention, the organic electroluminescent compound is one of the following structural formulas:

[0018]

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032] The present invention also provides 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 contains an organic electroluminescent compound as described above.

[0033] As a preferred embodiment of the present invention, the organic layer of the present invention comprises a hole injection layer, a hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; wherein, at least one of the hole injection layer, hole transport layer, second hole transport layer, light-emitting layer, hole blocking layer, electron transport layer, and electron injection layer contains an organic electroluminescent compound of any one of the above.

[0034] The present invention also provides an organic electroluminescent device, wherein the light-emitting layer contains any of the organic electroluminescent compounds described above.

[0035] The synthetic route for the compound of the present invention having the structure shown in Formula 1 is as follows:

[0036]

[0037]

[0038] Another synthetic route for the compound of the present invention having the structure shown in Formula 1 is as follows:

[0039]

[0040]

[0041] The beneficial effects of this invention are:

[0042] 1. The present invention relates to triazine linkage Based on the group, dibenzothiophene or dibenzofuran is also attached. The introduction of dibenzofuran or dibenzothiophene substituents expands the conjugated structure of the organic light-emitting host compound, enhances intramolecular electron transfer and exciton coupling effects, and improves luminescence efficiency.

[0043] 2. The introduction of new substituent structures can modulate the molecular energy level structure of organic light-emitting host compounds, optimize the generation and transport process of excitons, and help improve photoelectric conversion efficiency; dibenzofuran or dibenzothiophene structures can provide more π-π stacking and van der Waals interactions, enhance molecular stability, reduce the nonradiative lifetime of molecules in excited states, and help improve the luminescence quantum yield.

[0044] 3. The introduction of new substituent structures can modulate the photophysical properties of organic light-emitting host compounds, such as absorption and emission spectra, making them more suitable for the needs of specific application fields and improving the performance and application potential of materials. Attached Figure Description

[0045] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device provided by the present invention;

[0046] The numbers in the diagram represent: 1-anode, 2-hole injection layer, 3-hole transport layer, 4-second hole transport layer, 5-light-emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, and 9-cathode.

[0047] Figure 2 This is the HPLC chromatogram of compound 1 of the present invention.

[0048] Figure 3 The DSC spectrum of compound 1 of this invention is shown below. Figure 3 It can be seen that the Tg value of compound 4 is 132.16℃.

[0049] Figure 4 The TGA spectrum of compound 1 of this invention is shown below. Figure 4 It can be seen that the thermal weight loss temperature Td of compound 4 is 422.38℃. Detailed Implementation

[0050] 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.

[0051] As used herein, in the terms “deuterated” and “undeuterated,” the term “deuterated” means that at least one hydrogen in the group is recoordinated with deuterium. The term “undeuterated” means that none of the hydrogens in the group are recoordinated with deuterium.

[0052] In this document, "aromatic group," "aryl," or "aromatic group" refers to a group containing one or more aromatic rings, including but not limited to benzene, naphthalene, phenanthrene, fluorene, acenaphthene, pyridine, pyrrole, furan, and thiophene. In C5-C40 aromatic groups, C5-C40 means that the group contains 5-40 carbon atoms. Aromatic groups can be classified as monocyclic aryl and polycyclic aryl. Specific aromatic groups in this invention include, but are not limited to, phenyl, biphenyl, terphenyl, anthracene, naphthyl, phenanthrene, fluorene, dibenzofuranyl, dibenzothiophene, 9,9-spirodifluorenyl, 9,9-dimethylfluorenyl, or 9,9-diphenylfluorenyl. Aromatic groups can be substituted or unsubstituted.

[0053] As used herein, "cycloalkyl" refers to a monocyclic or fused ring group consisting entirely of carbon atoms (a "fused" ring means that each ring in the system shares an adjacent pair of carbon atoms with other rings in the system), wherein one or more rings are saturated alicyclic rings, generally having 3-20 carbon atoms, preferably 3-12 carbon atoms, and more preferably 3-10 carbon atoms. Cycloalkyl groups can be classified into monocyclic alkyl groups having only one ring and fused alkyl groups having multiple rings. Examples of monocyclic alkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and cycloheptane. Cycloalkyl groups can be substituted or unsubstituted.

[0054] As used herein, "cycloalkenyl" refers to a monocyclic or fused ring group consisting entirely of carbon (a "fused" ring means that each ring in the system shares a pair of adjacent carbon atoms with other rings in the system), wherein one or more rings do not have a fully connected π-electron system and contain at least one alkenyl group, which generally has 3-20 carbon atoms, preferably 3-12 carbon atoms, more preferably 3-10 carbon atoms. Examples of cycloalkenyl groups include, but are not limited to, cyclopentene, cyclohexene, cyclohexadiene, and cycloheptanetriene. The cycloalkenyl group can be substituted or unsubstituted.

[0055] In this article, "deuterated aromatic group" refers to an aromatic group in which one or more hydrogen atoms are replaced by deuterium.

[0056] In this article, "deuterated phenyl" refers to a group in which one or more hydrogen atoms in a phenyl group are replaced by deuterium.

[0057] In this article, "heteroaryl" refers to a heteroaryl group obtained by replacing one or more C atoms in the structure of "aryl" with one or more heteroatoms (such as N, O or S).

[0058] 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.

[0059] Example 1

[0060] Compound 1

[0061]

[0062] Compound 1 was prepared according to the following method:

[0063] Step S1: Procedure: In a 2L three-necked flask, add 1-SM1 (100g, 0.312mol, 1eq), pinacol diborate (103g, 0.41mol, 1.3eq), potassium acetate (91.86g, 0.936mol, 3eq), PdCl2 (dppf) (4.57g, 6.24mmol, 0.02eq), and 1,4-dioxane (1000ml). Under N2 protection, heat to 90-100℃ and stir the reaction. Monitor the concentration of 1-SM1 by HPLC.

[0064] Post-processing: Stop the reaction, filter the solution through silica gel while hot, wash the filter cake with 600 ml of DCM, concentrate the filtrate to dryness under reduced pressure, add 200 ml of ethanol, cool and stir to precipitate crystals, filter, and dry the filter cake at 85°C with forced air to obtain 98 g of gray solid, yield 86.3%.

[0065] Step S2: Procedure: In a 3L three-necked flask, add 1-ZJ1 (98g, 0.27mol, 1eq), 1-SM2 (80.7g, 0.27mol, 1eq), potassium carbonate (74.6g, 0.54mol, 2eq), Pd(PPd3)4 (6.24g, 5.4mmol, 0.02eq), and toluene / ethanol / water (1600ml + 800ml + 480ml). Under N2 protection, heat to reflux and react. Monitor with HPLC until 1-ZJ1 ≤ 1%.

[0066] Post-processing: Stop the reaction, add 300 ml of water, stir and separate the liquid. Extract the aqueous phase with DCM, combine the organic phases, dry the organic phase with anhydrous sodium sulfate, filter, concentrate the filtrate to dryness under reduced pressure, add 200 ml of PE, cool to 0℃ and stir to crystallize for 2 h, filter, dry the filter cake at 85℃ with forced air to obtain 93.1 g of gray solid, yield 83.6%.

[0067] Step S3: Procedure: Under N2 protection, 1-ZJ2 (93.1 g, 0.23 mol, 1 eq), 3-nitropyridine (2.85 g, 0.023 mol, 0.1 eq), palladium acetate (5.15 g, 0.023 mol, 0.1 eq), tert-butyl peroxide (89.34 g, 0.46 mol, 2 eq), 1,3-dimethyl-2-imidazolinone (230 ml), and hexafluorobenzene (345 ml) were added to a 1000 ml three-necked flask. The mixture was heated to 90 °C and stirred. HPLC monitoring showed that 1-ZJ2 ≤ 1%.

[0068] Post-processing: Stop the reaction, filter the solution while hot through silica gel, wash the filter cake with DCM, concentrate the filtrate to dryness under reduced pressure, add silica gel powder to make sand, perform column chromatography, wash with PE / DCM = 10 / 1~5 / 1~2 / 1, collect the product spot, concentrate to dryness under reduced pressure to give 63.2 g of off-white solid, yield 67%.

[0069] Step S4: Procedure: 1-ZJ3 (63.2 g, 0.154 mol, 1 eq), pinacol diborate (50.9 g, 0.2 mol, 1.3 eq), potassium acetate (45.34 g, 0.462 mol, 3 eq), PdCl2 (dppf) (2.25 g, 3.08 mmol, 0.02 eq), and 1,4-dioxane (600 ml) were added to a 1 L three-necked flask. Under N2 protection, the mixture was heated to 90–100 °C and stirred. The concentration of 1-ZJ3 was monitored by HPLC to be ≤0.5%.

[0070] Post-processing: Stop the reaction, filter the solution through silica gel while hot, wash the filter cake with 400 ml of DCM, concentrate the filtrate to dryness under reduced pressure, add 200 ml of ethanol, cool and stir to precipitate crystals, filter, and dry the filter cake at 85°C with forced air to obtain 57.5 g of gray solid, yield 82.3%.

[0071] Step S5:

[0072] Procedure: In a 2L three-necked flask, add 1-ZJ4 (40g, 88.2mmol, 1eq), 1-SM3 (31.56g, 88.2mmol, 1eq), potassium carbonate (24.38g, 0.1764mol, 2eq), Pd(PPd3)4 (2.04g, 1.764mmol, 0.02eq), and toluene / ethanol / water (800ml + 400ml + 240ml). Under N2 protection, heat to reflux and react. Monitor with HPLC until 1-ZJ4 ≤ 1%.

[0073] Post-processing: Stop the reaction, add water, cool and stir to crystallize to room temperature, filter, wash the filter cake with water and ethanol, dry the filter cake at 85°C with forced air to obtain 56g of gray solid. Dissolve the filter cake in 500ml of o-dichlorobenzene by heating, filter it while hot through silica gel and activated carbon, cool and stir to crystallize, filter, recrystallize the filter cake with o-dichlorobenzene 4 times, then hot beat it with toluene 3 times, filter while hot, dry the filter cake at 85°C with forced air to obtain 24.3g of off-white solid, yield 42.2%, HPLC purity.

[0074] Compounds 2, 5, 6, 7, 10, 13, 15, 16, 61, 62, 65, 66, 67, 70, 73, 74, and 76 were obtained using a similar method, as detailed in Table 1 below.

[0075] Table 1

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] Example 19

[0082] Compound 121

[0083]

[0084] Compound 121 was prepared according to the following method:

[0085] Step S1:

[0086] Procedure: In a 2L three-necked flask, add 121-SM1 (100g, 0.312mol, 1eq), pinacol diborate (103g, 0.41mol, 1.3eq), potassium acetate (91.86g, 0.936mol, 3eq), PdCl2 (dppf) (4.57g, 6.24mmol, 0.02eq), and 1,4-dioxane (1000ml). Under N2 protection, heat to 90-100℃ and stir the reaction. Monitor SM1 ≤ 0.5% using HPLC.

[0087] Post-processing: Stop the reaction, filter the solution through silica gel while hot, wash the filter cake with 600 ml of DCM, concentrate the filtrate to dryness under reduced pressure, add 200 ml of ethanol, cool and stir to precipitate crystals, filter, and dry the filter cake at 85°C with forced air to obtain 98 g of gray solid, yield 86.3%.

[0088] Step S2:

[0089] Procedure: In a 3L three-necked flask, add 121-ZJ1 (98g, 0.27mol, 1eq), 121-SM2 (80.7g, 0.27mol, 1eq), potassium carbonate (74.6g, 0.54mol, 2eq), Pd(PPd3)4 (6.24g, 5.4mmol, 0.02eq), and toluene / ethanol / water (1600ml + 800ml + 480ml). Under N2 protection, heat to reflux and react. Monitor with HPLC until 121-ZJ1 ≤ 1%.

[0090] Post-processing: Stop the reaction, add 300 ml of water, stir and separate the liquid. Extract the aqueous phase with DCM, combine the organic phases, dry the organic phase with anhydrous sodium sulfate, filter, concentrate the filtrate under reduced pressure to dryness, add 200 ml of PE, cool to 0℃ and stir to crystallize for 2 h, filter, dry the filter cake at 85℃ with forced air to obtain 91.9 g of gray solid, yield 81.1%.

[0091] Step S3:

[0092] Procedure: Under N2 protection, 121-ZJ2 (91.9 g, 0.223 mol, 1 eq), 3-nitropyridine (2.77 g, 0.0223 mol, 0.1 eq), palladium acetate (5 g, 0.0223 mol, 0.1 eq), tert-butyl peroxide (86.63 g, 0.446 mol, 2 eq), 1,3-dimethyl-2-imidazolinone (223 ml), and hexafluorobenzene (334.5 ml) were added to a 250 ml three-necked flask. The mixture was heated to 90 °C and stirred. HPLC monitoring showed that 121-ZJ2 ≤ 1%.

[0093] Post-processing: Stop the reaction, filter the solution while hot through silica gel, wash the filter cake with DCM, concentrate the filtrate to dryness under reduced pressure, add silica gel powder to make sand, perform column chromatography, wash with PE / DCM = 10 / 1~5 / 1~2 / 1, collect the product spot, concentrate to dryness under reduced pressure to give 60.1 g of off-white solid, yield 65.7%.

[0094] Step S4:

[0095] Procedure: 121-ZJ3 (60.1 g, 0.146 mol, 1 eq), pinacol diboronate (48.25 g, 0.19 mol, 1.3 eq), potassium acetate (43 g, 0.438 mol, 3 eq), PdCl2 (dppf) (2.14 g, 2.92 mmol, 0.02 eq), and 1,4-dioxane (600 ml) were added to a 1 L three-necked flask. Under N2 protection, the mixture was heated to 90–100 °C and stirred. The concentration of 121-ZJ3 was monitored by HPLC to be ≤0.5%.

[0096] Post-processing: Stop the reaction, filter the solution through silica gel while hot, wash the filter cake with 400 ml of DCM, concentrate the filtrate to dryness under reduced pressure, add 200 ml of ethanol, cool and stir to precipitate crystals, filter, and dry the filter cake at 85°C with forced air to obtain 55 g of gray solid, yield 82.8%.

[0097] Step S5:

[0098] Procedure: In a 2L three-necked flask, add 121-ZJ4 (40g, 88.2mmol, 1eq), 121-SM3 (31.56g, 88.2mmol, 1eq), potassium carbonate (24.38g, 0.1764mol, 2eq), Pd(PPd3)4 (2.04g, 1.764mmol, 0.02eq), and toluene / ethanol / water (800ml + 400ml + 240ml). Under N2 protection, heat to reflux and react. Monitor with HPLC until 121-ZJ4 ≤ 1%.

[0099] Post-processing: Stop the reaction, add water, cool and stir to crystallize to room temperature, filter, wash the filter cake with water and ethanol, dry the filter cake at 85°C with forced air to obtain 56g of gray solid. Dissolve the filter cake in 500ml of o-dichlorobenzene by heating, filter it while hot through silica gel and activated carbon, cool and stir to crystallize, filter, recrystallize the filter cake with o-dichlorobenzene 4 times, then hot beat it with toluene 3 times, filter while hot, dry the filter cake at 85°C with forced air to obtain 21.9g of off-white solid, yield 38%, HPLC purity.

[0100] Compounds 122, 125, 126, 128, 130, 133, 135, 136, 181, 182, 185, 186, 188, 190, 193, 195, and 196 were obtained using a similar method. See Table 2 below for details.

[0101] Table 2

[0102]

[0103]

[0104]

[0105]

[0106] The compounds prepared in Tables 1-2 above were synthesized and identified, and the results are shown in Table 3 below: Table 3

[0107]

[0108]

[0109] Basic performance tests were conducted on the above materials, including thermogravimetric temperature Td and melting point Tm. The test results are shown in Table 4 below.

[0110] Note: The thermogravimetric temperature Td is the temperature at which the mass loss is 5% in a nitrogen atmosphere, measured on a TGA N-1000 thermogravimetric analyzer at a nitrogen flow rate of 10 mL / min. Tg (glass transition temperature) is measured by differential scanning calorimetry (DSC, Shinco DSC N-650) at a heating rate of 10 °C / min.

[0111] Table 4

[0112]

[0113]

[0114] Based on the above data, it can be seen that the compounds synthesized in this invention have excellent thermal stability, indicating that compounds conforming to the general structural formula of this invention all have excellent thermal stability and can meet the requirements for use in organic electroluminescent materials.

[0115] Device performance testing:

[0116] Application Example 1:

[0117] ITO was used as the anode substrate material for the reflective layer, and its surface was treated sequentially with water, acetone, and N2 ions.

[0118] 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).

[0119] A first hole transport layer (HTL) is formed by depositing 100 nm of HT-1 above the hole injection layer (HIL);

[0120] RP is vacuum-deposited over the first hole transport layer (HTL) to form a second hole transport layer (RPL) with a thickness of 30 nm;

[0121] Compound 1 and P-10 designed in this invention were co-deposited as red host materials in a 5:5 mass ratio. RD was deposited as a dopant material (the amount of RD was 3% of the total mass of compound 1 and P-10) on the second hole transport layer (RPL) to form a light-emitting layer with a thickness of 30 nm.

[0122] HB-1 was deposited onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0123] 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.

[0124] 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.

[0125] 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.

[0126]

[0127]

[0128] Application Example 2-36

[0129] Compounds 1, 2, 5, 6, 7, 10, 13, 15, 16, 61, 62, 65, 66, 67, 70, 73, 74, 76, 121, 122, 125, 126, 128, 130, 133, 135, 136, 181, 182, 185, 186, 188, 190, 193, 195, 196 and P-10 were used as red base materials for co-evaporation deposition, with other parts being the same as in Application Example 1. Based on this, organic electroluminescent devices of Application Examples 2-36 were fabricated.

[0130] Compare with Example 1-11:

[0131] The difference from Application Example 1 is that compounds D1-D11 from US20230292539A1 and CN116143795A were used as red host materials for co-evaporation, while the rest is the same as Application Example 1.

[0132] The characteristics of the organic electroluminescent devices manufactured in the above application examples and the organic electroluminescent devices manufactured in the control examples were measured under a current density of 10 mA / cm2, and the results are shown in Table 5 below.

[0133] Table 5

[0134]

[0135]

[0136]

[0137] As shown in Table 5 above, when the compounds of the present invention are applied to organic electroluminescent devices, the luminous efficiency is significantly improved at the same current density, the device start-up voltage is reduced, the power consumption of the device is relatively reduced, and the lifespan of the device is correspondingly improved.

[0138] The organic electroluminescent devices prepared in Comparative Examples 1-11 and Application Examples 1-9 were subjected to luminescence lifetime tests to obtain the luminescence lifetime T97% data (the time for the luminous brightness to decrease to 97% of the initial brightness). The testing equipment was a TEO luminescent device lifetime testing system. The results are shown in Table 6.

[0139] Table 6:

[0140]

[0141]

[0142] As shown in Table 6 above, when the compounds of this invention are applied to organic electroluminescent devices, the service life is significantly improved at the same current density, indicating broad application prospects.

[0143] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit it. Although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art should understand that modifications or equivalent substitutions can be made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, and all such modifications or substitutions should be covered within the scope of the claims of the present invention.

Claims

1. An organic electroluminescent compound, characterized in that, Selected from the compounds shown in Formula 1: Y is selected from O or S; Ar1 ​​is selected from the following groups: ； Ar2 is selected from hydrogen and phenyl.

2. The organic electroluminescent compound as described in claim 1, characterized in that, Selected from compounds shown in Formula 2-5: 。 3. The organic electroluminescent compound as described in claim 1, characterized in that, Compounds selected from those shown in Formulas 6-13: 。 4. The organic electroluminescent compound as described in claim 1, characterized in that, The organic electroluminescent compound is one of the following structural formulas: 。 5. An organic electroluminescent device, characterized in that, The device includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode. The organic layer comprises a hole injection layer, a hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The light-emitting layer contains an organic electroluminescent compound as described in any one of claims 1-4.

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