OLED with deuterated boron-nitrogen compound, and organic electroluminescent device

Abstract

The present invention relates to the technical field of the preparation of organic photoelectric materials, and particularly relates to an OLED with a deuterated boron-nitrogen compound, and an organic electroluminescent device. In the organic electroluminescent device of the present invention, the deuterated boron-nitrogen compound is used, and the light-emitting characteristic of the compound can be improved by means of the combination of deuterated phenyl of a defined site in a parent nucleus and a defined group. The boron-nitrogen compound provided in the present invention is used as a light-emitting layer material, such that the organic electroluminescent device can effectively have a lower driving voltage and maintain the stability of the voltage, and the light-emitting efficiency is improved.

Description

An OLED and organic light-emitting device with deuterated boron nitride compounds Technical Field

[0001] This invention relates to the field of organic optoelectronic material preparation technology, specifically to an OLED and organic light-emitting device having a deuterated boron nitride compound. Background Technology

[0002] With the development of multimedia technology and the increasing demands for information technology, the requirements for panel display performance are becoming increasingly stringent. Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, are a technology that converts electrical energy into light energy through organic light-emitting materials. This technology involves applying voltage to organic electroluminescent elements to inject holes from the anode and electrons from the cathode into the light-emitting layer. The injected holes and electrons then recombine to form excitons, causing light to be emitted.

[0003] Most OLED devices use a host-guest light-emitting system in their emissive layers, where a guest material is doped into the host material. In the field of OLED materials, scholars and researchers have actively studied organic materials with light-emitting properties such as blue (one of the three primary colors of light) and organic materials with charge transport capabilities such as holes and electrons (potentially becoming semiconductors or superconductors). Currently, boron-nitrogen heterocyclic fused ring molecules are a hot research topic for blue light-doping materials, but the variety and quantity of existing materials are still relatively small, making structure-property relationship studies difficult. Furthermore, in applications, display technology still suffers from high driving voltage and short display lifetime, severely hindering the further practical application of this technology.

[0004] Therefore, continuous efforts are needed to develop organic light-emitting devices with low voltage drive, high brightness and long lifespan, and to find suitable OLED optoelectronic functional materials for OLED devices to solve the above problems is a long-term need in this field. Summary of the Invention

[0005] To address the aforementioned technical problems, this invention provides an OLED and a display or lighting device incorporating a deuterated boron nitride compound. The boron nitride compound used in the organic light-emitting device provided by this invention, through the combination of a deuterated phenyl group at a defined site in the core and a defined functional group, serves as the light-emitting layer material. This effectively enables the organic light-emitting device to have a lower driving voltage while maintaining voltage stability, and also improves luminous efficiency.

[0006] The organic electroluminescent device with deuterated boron nitride compound provided by the present invention is achieved through the following technical solution:

[0007] An organic electroluminescent device having a deuterated boron nitride compound, comprising:

[0008] Substrate layer;

[0009] A first electrode is located on the substrate;

[0010] An organic light-emitting functional layer is disposed on the first electrode;

[0011] The second electrode is located on the organic light-emitting functional layer;

[0012] The organic light-emitting functional layer includes a light-emitting layer; the light-emitting layer includes a host material and a dopant material, wherein the highest occupied molecular orbital (HOMO) energy level of the host material is in the range of -5.5 to -5.8 eV.

[0013] The doped material includes compounds having the structure shown in formula (I):

[0014] In formula (I), Ar1 is selected from in, Let n1 and n2 represent the contiguous edges, D represent deuterium, and n1 and n2 are each selected from integers between 0 and 12.

[0015] L1-L2 are each independently selected from single bonds, C6-C12 aryl groups substituted or unsubstituted with C1-C4 alkyl groups, and C4-C30 heteroaryl groups; R1 and R3 are each independently selected from C1-C10 alkyl groups, C3-C24 cycloalkyl groups substituted or unsubstituted with C3-C24 cycloalkyl groups, C6-C30 aryl groups substituted or unsubstituted with C6-C30 heteroaryl groups.

[0016] R2 and R4 can be unsubstituted, monosubstituted, polysubstituted, or substituted with the maximum number of substitutions. R2 and R4 are each independently selected from hydrogen, deuterium, C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C4-C30 heteroaryl, and substituted or unsubstituted C6-C30 aromatic amino.

[0017] The heteroatoms of the heteroaryl groups in L1-L2 and R1-R4 are selected from N, O or S atoms; the substituted groups in L1-L2 and R1-R4 are selected from one or more of deuterium, C1-C10 alkyl, and C6-C18 aryl; the compound of formula (I) may be fully or partially deuterated.

[0018] Preferably, the structure shown in formula (I) is selected from any one of the following formulas I-1 to I-5:

[0019] The substitution restrictions for Ar1, L1-L2, R1, and R3 are the same as those defined above.

[0020] More preferably, each of L1-L2 is independently selected from single-bonded, C1-C10 alkyl-substituted or unsubstituted phenyl, biphenyl, or dibenzofuranyl; and each of R1 and R3 is independently selected from tert-butyl, phenyl, tert-butylphenyl, di-tert-butylphenyl, methyl-substituted tetrahydronaphthyl, methyl-substituted or unsubstituted dibenzofuranyl, or methyl-substituted or unsubstituted dibenzothiophene.

[0021] Preferably, the Ar1 is selected from in, Let D represent the contiguous edge, and let n1 be 0, 3, or 9.

[0022] According to one or more embodiments, the present invention provides an organic electroluminescent device having a deuterated boron nitride compound, wherein the doping material is selected from any one or more combinations of the following chemical structures:

[0023] Preferably, the organic light-emitting functional layer further includes an auxiliary light-emitting material layer, wherein the HOMO energy level of the auxiliary light-emitting material layer is in the range of -5.20 to -5.50 eV.

[0024] Preferably, the weight percentage of the host material to the dopant material in the light-emitting layer is 1-99:99-1.

[0025] Preferably, the difference between the HOMO energy level of the host material and the HOMO energy level of the doped material is less than 0.8 eV.

[0026] The organic electroluminescent device of the present invention can be used in OLED lighting or display devices. Preferably, the organic electroluminescent device prepared by the present invention is used in smartphones, tablets, smart wearable devices, televisions, VR, microdisplays, and automotive center console screens or taillights.

[0027] The present invention also provides a display or lighting device comprising one or more of the organic electroluminescent devices described above.

[0028] In summary, compared with the prior art, the present invention has the following beneficial effects:

[0029] The organic electroluminescent device of the present invention uses a deuterated boron nitride compound. Through the combination of the deuterated phenyl group at a defined site in the core and the defined group, the structure has good stability and film-forming properties. After the boron nitride compound provided by the present invention is used to prepare an organic light-emitting device, it can effectively enable the organic light-emitting device to have a lower driving voltage while maintaining voltage stability, and improve luminous efficiency and achieve better working life. Detailed Implementation

[0030] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of the present invention.

[0031] The term "alkyl" refers to and includes both straight-chain and branched alkyl groups. Preferred alkyl groups are those containing 1 to 4 carbon atoms, including methyl, ethyl, propyl, and tert-butyl. Additionally, alkyl groups may optionally be substituted.

[0032] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 20 ring carbon atoms, more preferably those containing 3 to 12 ring carbon atoms, and particularly preferably those containing 3 to 6 ring carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. Additionally, the cycloalkyl group may optionally be substituted.

[0033] The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. Preferred aryl groups are those containing six to twelve carbon atoms. Particularly preferred are aryl groups having six, ten, or twelve carbon atoms. Phenyl, biphenyl, terphenyl, naphthalene, etc., are preferred. Furthermore, the aryl group may optionally be substituted.

[0034] The term "heteroaryl" refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. These heteroatoms include, but are not limited to, oxygen, sulfur, silicon, or nitrogen atoms. The heteroaryl group can be a monocyclic or fused-ring heteroaryl group, and can have 4 to 30 carbon atoms, preferably 6 to 20 carbon atoms. Examples include pyridyl, pyrrole, pyridinyl, thiophene, furanyl, indolyl, quinolinyl, isoquinolinyl, benzothiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, etc., but are not limited to these.

[0035] Throughout this specification, unless explicitly stated otherwise, the term "including" any component will be understood to imply the inclusion of other components, not to exclude any other components. Furthermore, it should be understood that throughout this specification, when an element such as a layer, film, region, or substrate is referred to as being "on" or "above" another element, it may be "directly on" the other element, or there may be intermediate elements present. Additionally, "on" or "above" means located above the target portion, and not necessarily above it in the direction of gravity.

[0036] One object of the present invention is to provide an electroluminescent device, the organic electroluminescent device comprising: a substrate layer; a first electrode on the substrate; an organic light-emitting functional layer on the first electrode; and a second electrode on the organic light-emitting functional layer; the organic light-emitting functional layer includes a light-emitting layer comprising a host material and a dopant material, wherein the HOMO energy level of the host material is in the range of -5.5 to -5.8 eV, and the dopant material comprises materials having... Boron-nitrogen compounds with a specific structure.

[0037] In one embodiment of the present invention, the light-emitting layer of the organic electroluminescent (OLED) device comprises one or more compounds as light-emitting dopant materials as shown in the above general formula (I).

[0038] In a preferred embodiment of the present invention, an OLED is provided, comprising a substrate, an anode, a cathode, and an organic light-emitting functional layer, wherein the organic light-emitting functional layer may include a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, etc., or may only include a light-emitting layer and one or more other layers; wherein the light-emitting layer comprises a light-emitting dopant material composed of one or more compounds represented by the above general formula (I). Optionally, a capping layer, a protective layer, and / or an encapsulation layer are further provided above the organic light-emitting functional layer.

[0039] The substrate described in this invention can be any substrate typically used in organic light-emitting devices. It can be a glass or transparent plastic substrate, an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance, and their applications vary depending on their properties.

[0040] As for the materials used in the hole injection layer, hole transport layer, and electron injection layer, any material can be selected from known materials used in OLED devices.

[0041] As a host material capable of producing blue, green, and blue-green fluorescence, it not only needs to have extremely high fluorescence quantum luminescence efficiency, but also needs to have an appropriate energy level that can effectively cooperate with the excitation energy of the guest material to emit light.

[0042] The present invention will now be described in detail with reference to specific embodiments. Unless otherwise specified, all raw materials and solvents used in the synthesis embodiments are commercially available, and the solvents were used directly without further processing.

[0043] Example

[0044] Example 1: Synthesis of Compound 001

[0045] Synthesis route:

[0046] 1) Compounds 001-1 (1 mmol) and 001-2 (1 mmol) were dissolved in 50 mL of toluene solution. Under a nitrogen atmosphere, sodium tert-butoxide (2 mmol), palladium acetate (0.05 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmol) were added. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3 × 100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was purified by silica gel column chromatography with an eluent (dichloromethane: petroleum ether) of 1:4. The intermediate product was 001-3.

[0047] 2) Dissolve intermediate 001-3 (1 mmol) and compound 001-4 (1 mmol) in 50 mL of toluene solution. Under a nitrogen atmosphere, add sodium tert-butoxide (2 mmol), palladium acetate (0.05 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmol). Reflux the reaction system for 72 hours and then cool to room temperature. Remove the solvent by rotary evaporation, and extract the residue with dichloromethane (3 × 100 mL). Wash the organic phase with water and dry with sodium sulfate. Remove the solvent by vacuum distillation, and purify the crude product by silica gel column chromatography with eluent (dichloromethane: petroleum ether) = 1:4. Intermediate product 001-5.

[0048] 3) Dissolve intermediate 001-5 (1 mmol) and compound 001-6 (1 mmol) in 50 mL of toluene solution. Under a nitrogen atmosphere, add sodium tert-butoxide (2 mmol), palladium acetate (0.05 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmol). Reflux the reaction system for 72 hours and then cool to room temperature. Remove the solvent by rotary evaporation, and extract the residue with dichloromethane (3 × 100 mL). Wash the organic phase with water and dry with sodium sulfate. Remove the solvent by vacuum distillation, and purify the crude product by silica gel column chromatography with eluent (dichloromethane: petroleum ether) = 1:4. Intermediate product 001-7.

[0049] 4) Dissolve intermediate 001-7 (1 mmol) and compound 001-8 (1 mmol) in 50 mL of toluene solution. Under a nitrogen atmosphere, add sodium tert-butoxide (2 mmol), palladium acetate (0.05 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmol). Reflux the reaction system for 72 hours and then cool to room temperature. Remove the solvent by rotary evaporation, and extract the residue with dichloromethane (3 × 100 mL). Wash the organic phase with water and dry with sodium sulfate. Remove the solvent by vacuum distillation, and purify the crude product by silica gel column chromatography with eluent (dichloromethane: petroleum ether) = 1:4. Intermediate product 001-9.

[0050] 5) Dissolve intermediate 001-9 (1 mmol) in 60 mL of anhydrous tert-butylbenzene. Cool the reaction system to -78 °C and slowly add BuLi (1 mL, 2 mmol, 2 M in hexane). After reacting at -78 °C for 4 hours, slowly add BBr (3247 mg, 1 mmol). After reacting at -50 °C for 1 hour, raise the temperature to room temperature, then add N,N-diisopropylethylamine (387 mg, 3 mmol), and then heat to 120 °C for 12 hours. After cooling to room temperature, add 5 mL of sodium acetate aqueous solution (1 M). Remove the solvent by rotary evaporation, and extract the residue with dichloromethane (3 × 100 mL). Wash the organic phase with water and dry with sodium sulfate. Remove the solvent by vacuum distillation, and purify the crude product by silica gel column chromatography with eluent (dichloromethane: petroleum ether) = 1:8 to obtain the final product 001. The structure of the target product 001 was tested: the theoretical value was 835.51 and the measured value was 835.93, obtained by liquid chromatography-mass spectrometry (LC-MS) analysis.

[0051] Example 2: Synthesis of Compound 016

[0052] Following the synthesis steps and reaction conditions of Example 1, compound 016 was synthesized. Analysis by liquid chromatography-mass spectrometry yielded the following LC-MS (m / z)(M+): theoretical value 931.51, measured value 931.97.

[0053] Example 3: Synthesis of Compound 033

[0054] Following the synthesis steps and reaction conditions of Example 1, compound 033 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 929.66 and a measured value of 930.18.

[0055] Example 4: Synthesis of Compound 047

[0056] Following the synthesis steps and reaction conditions of Example 1, compound 047 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1020.67 and a measured value of 1021.19.

[0057] Example 5: Synthesis of Compound 052

[0058] Following the synthesis steps and reaction conditions of Example 1, compound 052 was synthesized. Analysis by liquid chromatography-mass spectrometry yielded the following LC-MS (m / z)(M+): theoretical value 1095.66, measured value 1096.28.

[0059] Example 6: Synthesis of Compound 053

[0060] Following the synthesis steps and reaction conditions of Example 1, compound 053 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1065.67 and a measured value of 1066.25.

[0061] Example 7: Synthesis of Compound 055

[0062] Following the synthesis steps and reaction conditions of Example 1, compound 055 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1100.76 and a measured value of 1101.34 (m / z)(M+).

[0063] Example 8: Synthesis of Compound 059

[0064] Following the synthesis steps and reaction conditions of Example 1, compound 059 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1079.73 and a measured value of 1080.31.

[0065] Example 9: Synthesis of Compound 060

[0066] Following the synthesis steps and reaction conditions of Example 1, compound 060 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1155.76 and a measured value of 1156.38.

[0067] Example 10: Synthesis of Compound 065

[0068] Following the synthesis steps and reaction conditions of Example 1, compound 065 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1013.55 and a measured value of 1014.15.

[0069] Example 11: Synthesis of Compound 075

[0070] Following the synthesis steps and reaction conditions of Example 1, compound 075 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1096.70 and a measured value of 1097.42.

[0071] Example 12: Synthesis of Compound 078

[0072] Following the synthesis steps and reaction conditions of Example 1, compound 078 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1025.63 and a measured value of 1026.27.

[0073] Example 13: Synthesis of Compound 092

[0074] Following the synthesis steps and reaction conditions of Example 1, compound 092 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1110.68 and a measured value of 1110.26.

[0075] Example 14: Synthesis of Compound 104

[0076] Following the synthesis steps and reaction conditions of Example 1, compound 104 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1024.65 and a measured value of 1025.27.

[0077] Example 15: Synthesis of Compound 108

[0078] Following the synthesis steps and reaction conditions of Example 1, compound 108 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1134.55 and a measured value of 1135.13.

[0079] Example 16: Synthesis of Compound 115

[0080] Following the synthesis steps and reaction conditions of Example 1, compound 115 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1024.57 and a measured value of 1025.15.

[0081] Example 17: Synthesis of Compound 124

[0082] Following the synthesis steps and reaction conditions of Example 1, compound 124 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1026.58 and a measured value of 1027.14.

[0083] Example 18: Synthesis of Compound 128

[0084] Following the synthesis steps and reaction conditions of Example 1, compound 128 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1100.60 and a measured value of 1101.20.

[0085] Example 19: Synthesis of Compound 130

[0086] Following the synthesis steps and reaction conditions of Example 1, compound 130 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1117.63 and a measured value of 1118.31.

[0087] Example 20: Synthesis of Compound 136

[0088] Following the synthesis steps and reaction conditions of Example 1, compound 136 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1160.56 and a measured value of 1161.28.

[0089] Example 21: Synthesis of Compound 142

[0090] Following the synthesis steps and reaction conditions of Example 1, compound 142 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1266.77 and a measured value of 1267.41.

[0091] Example 22: Synthesis of Compound 147

[0092] Following the synthesis steps and reaction conditions of Example 1, compound 147 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1286.74 and a measured value of 1287.46.

[0093] Example 23: Synthesis of Compound 161

[0094] Following the synthesis steps and reaction conditions of Example 1, compound 161 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1116.59 and a measured value of 1117.25.

[0095] Example 24: Synthesis of Compound 165

[0096] Following the synthesis steps and reaction conditions of Example 1, compound 165 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1139.58 and a measured value of 1140.22.

[0097] Example 25: Synthesis of Compound 174

[0098] Following the synthesis steps and reaction conditions of Example 1, compound 174 was synthesized. LC-MS (m / z)(M+) analysis yielded a theoretical value of 1197.65 and a measured value of 1198.33.

[0099] The following are several examples of applications of the boron nitride compounds described in this invention in OLED devices to further illustrate the beneficial effects of the compounds. The materials used in the examples were either commercially available or synthesized in-house.

[0100] Manufacturing of OLED devices:

[0101] As a reference fabrication method for one embodiment of the device, the present invention involves depositing a 50-500 nm ITO / Ag / ITO layer as the anode on an alkali-free glass substrate. Then, a hole injection layer (5 nm-20 nm), a hole transport layer (50-150 nm), a light-emitting auxiliary layer (5-120 nm), a light-emitting layer (20-50 nm), a hole blocking layer (5-20 nm), an electron transport layer (20-80 nm), and an electron injection layer (1-10 nm) are deposited on the anode. Next, Mg and Ag (weight ratio 1:9, 100-150 nm) are co-deposited to form a semi-transparent cathode, followed by the deposition of a capping compound. Finally, the light-emitting device is encapsulated using epoxy resin adhesive under a nitrogen atmosphere.

[0102] In a preferred embodiment, the OLED device provided by the present invention has the following structure: First, an alkali-free glass substrate is washed with isopropanol for 15 minutes using an ultrasonic cleaner, followed by a 30-minute UV ozone cleaning treatment in air. The treated substrate is then vacuum-deposited with ITO / Ag / ITO 100nm as the anode. Next, a hole injection layer (HT:PD, 10nm, 2%), a hole transport layer (HT, 130nm), a light-emitting auxiliary layer (BP, 5nm), a blue light-emitting layer (body material: dopant material = BH: compound 001 (weight ratio 98:2, 30nm)), a hole blocking layer (HBL, 5nm), an electron transport layer (ET:Liq = 1:1, 30nm), and an electron injection layer (Yb, 1nm) are sequentially deposited. Finally, Mg and Ag (weight ratio 1:9, 130nm) are co-deposited to form a semi-transparent cathode. Finally, compound CPL (65nm) is deposited as a capping layer. Finally, the light-emitting device was encapsulated using epoxy resin adhesive under a nitrogen atmosphere, referred to as Application Example 1. The molecular structural formulas of the relevant materials are shown below (particularly preferably selected from the following structures, but this does not mean that the invention is limited to the following structures):

[0103] Application Examples 2-25 and Comparative Example 1 were prepared using the method described in Application Example 1 above, the only difference being that compounds listed in Table 1 were used as dopant materials to replace compound 001 in Application Example 1. The dopant material in Comparative Example 1 is as follows:

[0104] Performance evaluation of OLED devices:

[0105] The current of the OLED device at different voltages was measured using a Keithley 2365A digital nanovoltmeter, and then the current density of the OLED device at different voltages was obtained by dividing the current by the emitting area. The brightness and radiant energy flux density of the OLED device at different voltages were measured using a Konicaminolta CS-2000 spectroradiometer. Based on the current density and brightness of the OLED device at different voltages, the current density (10 mA / cm²) at the same voltage was obtained. 2 The operating voltage (Volt) and current efficiency (cd / A) are given by BI = E / CIEy, which refers to the Blue Index in blue light and is also a parameter measuring the luminous efficiency of blue light. E refers to the current efficiency, and CIEy refers to the ordinate color point obtained by substituting the wavelength of the device's emission half-width into the CIE1930 software. The test data are shown in Table 1.

[0106] Table 1 Organic Electroluminescent Devices and Electroluminescence Characteristics

[0107] As shown in Table 1, compared with Comparative Example 1, Application Examples 1 to 25 exhibit lower operating voltage, higher BI luminous efficiency, and longer lifespan. The performance improvements in each application example are based on the introduction of deuterated phenyl groups and defining groups into the boron-nitrogen core structure, which enhances the luminous efficiency of the boron-nitrogen compound material. Furthermore, the excellent compatibility of the doped materials in this invention enables the blue light-emitting layer to achieve better balance in electron and hole transport and exciton conversion efficiency, thereby reducing device power consumption and extending lifespan.

[0108] This specific embodiment is merely an explanation of the present invention and is not intended to limit the invention. After reading this specification, those skilled in the art can make modifications to this embodiment without contributing any inventive step, but such modifications are protected by patent law as long as they are within the scope of the claims of the present invention.

Claims

1. An organic electroluminescent device having a deuterated boron nitride compound, characterized in that, The organic electroluminescent device includes: Substrate layer; A first electrode is located on the substrate; An organic light-emitting functional layer is disposed on the first electrode; The second electrode is located on the organic light-emitting functional layer; The organic light-emitting functional layer includes a light-emitting layer; the light-emitting layer includes a host material and a dopant material, wherein the HOMO energy level of the host material is between -5.5 and -5.8 eV. The doped material includes compounds having the structure shown in formula (I): In formula (I), Ar1 is selected from in, Let n1 and n2 represent the contiguous edges, D represent deuterium, and n1 and n2 are each selected from integers between 0 and 12. L1-L2 are each independently selected from single bonds, C6-C12 aryl groups substituted or unsubstituted with C1-C4 alkyl groups, and C4-C30 heteroaryl groups; R1 and R3 are each independently selected from C1-C10 alkyl groups, C3-C24 cycloalkyl groups substituted or unsubstituted with C6-C30 aryl groups, and C6-C30 heteroaryl groups substituted or unsubstituted with C1-C10 alkyl groups. R2 and R4 can be unsubstituted, monosubstituted, polysubstituted, or substituted with the maximum number of substitutions. R2 and R4 are each independently selected from hydrogen, deuterium, C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C4-C30 heteroaryl, and substituted or unsubstituted C6-C30 aromatic amino. The heteroatoms of the heteroaryl groups in L1-L2 and R1-R4 are selected from N, O or S atoms; the substitutions in the substituted groups in L1-L2 and R1-R4 are selected from one or more of deuterium, C1-C10 alkyl, and C6-C18 aryl; the compound of formula (I) may be fully or partially deuterated.

2. The organic electroluminescent device with deuterated boron nitride compound according to claim 1, characterized in that, The structure shown in equation (I) is selected from any of the following equations I-1 to I-5: The substitution restrictions for Ar1, L1-L2, R1, and R3 are the same as those defined in claim 1.

3. The organic electroluminescent device with deuterated boron nitride compound according to claim 1, characterized in that, Each of L1-L2 is independently selected from single-bonded, C1-C10 alkyl-substituted or unsubstituted phenyl, biphenyl, or dibenzofuranyl; each of R1 and R3 is independently selected from tert-butyl, phenyl, tert-butylphenyl, di-tert-butylphenyl, methyl-substituted tetrahydronaphthyl, methyl-substituted or unsubstituted dibenzofuranyl, or methyl-substituted or unsubstituted dibenzothiophene.

4. The organic electroluminescent device with deuterated boron nitride compound according to claim 1, characterized in that, Ar1 is selected from in, Let D represent the contiguous edge, and let n1 be 0, 3, or 9.

5. The organic electroluminescent device with deuterated boron nitride compound according to claim 1, characterized in that, The doped material is selected from any one or more combinations of the chemical structures shown below:

6. The organic electroluminescent device with deuterated boron nitride compound according to claim 1, characterized in that, The organic light-emitting functional layer also includes an auxiliary light-emitting material layer, wherein the HOMO energy level of the auxiliary light-emitting material layer is between -5.20 and -5.50 eV.

7. The organic electroluminescent device with deuterated boron nitride compound according to claim 1, characterized in that, The weight percentage of the host material to the doped material in the light-emitting layer is 1-99:99-1.

8. The organic electroluminescent device with deuterated boron nitride compound according to claim 1, characterized in that, The difference between the HOMO energy level of the host material and the HOMO energy level of the doped material is less than 0.8 eV.

9. The use of the organic electroluminescent device having a deuterated boron nitride compound as described in any one of claims 1-8 in a display or lighting device.

10. A display or lighting device, characterized in that, The device comprises an organic electroluminescent device having a deuterated boron nitride compound as described in any one of claims 1-8.

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