OLED and organic light-emitting device having deuterated boron nitrogen compound

Abstract

The present invention relates to the technical field of organic photoelectric material preparation, in particular to an OLED and an organic light-emitting device having a deuterated boron nitrogen compound. The organic electroluminescent device of the present invention adopts a deuterated boron nitrogen compound, and the luminescent properties of the compound can be improved by matching the deuterated phenyl group at a defined site in the parent nucleus with a defined group; the boron nitrogen compound provided by the present invention is used as a light-emitting layer material, which can effectively make the organic light-emitting device have a lower driving voltage and maintain voltage stability, and the luminous efficiency is improved.

Description

Technical Field

[0001] The invention relates to the technical field of preparation of organic photoelectric materials, and in particular to an OLED and an organic light-emitting device having deuterated boron nitrogen compounds. Background Art

[0002] With the development of multimedia technology and the improvement of information requirements, the requirements for panel display performance are getting higher and higher. Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, are technologies that apply voltage to organic electroluminescent elements to inject holes from the anode and electrons from the cathode into the light-emitting layer, and the injected holes and electrons recombine to form excitons to cause light emission. It can convert electrical energy into light energy through organic light-emitting materials.

[0003] The light-emitting layer in OLED devices mostly uses a host-guest light-emitting system, that is, a guest material is doped in the host material. In the field of OLED materials, scholars and technology developers from all walks of life have actively studied organic materials with luminescent properties such as blue, one of the three primary colors of light, and organic materials with charge transport capabilities such as holes and electrons (with the possibility of becoming semiconductors and superconductors). At present, the research hotspot of blue light doping materials is mostly boron nitrogen fused ring molecules, but the types and quantities of existing materials are still relatively small, which makes the study of structure-activity relationship more difficult; and in its application, the display technology still has the problems of high driving voltage and short display life, which seriously affects 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 life. Finding suitable OLED optoelectronic functional materials for OLED devices to solve the above problems is a long-term need in the field. Summary of the invention

[0005] In order to solve the above technical problems, the present invention provides an OLED and a display or lighting device having a deuterated boron nitrogen compound. The boron nitrogen compound used in the organic electroluminescent device provided by the present invention, through the combination of the deuterated phenyl group at a defined site in the parent core and the defined group, as the light-emitting layer material, can effectively make the organic light-emitting device have a lower driving voltage and maintain voltage stability, and improve the luminous efficiency.

[0006] The present invention provides an organic electroluminescent device having a deuterated boron nitrogen compound, which is realized by the following technical scheme:

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

[0008] substrate layer;

[0009] a first electrode, the first electrode being on the substrate;

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

[0011] A second electrode, the second electrode being on the organic light-emitting functional layer;

[0012] The organic light-emitting functional layer comprises a light-emitting layer; the light-emitting layer comprises a main material and a doping material, wherein the highest occupied molecular orbital (HOMO) energy level of the main material is between -5.5 and -5.8 eV,

[0013] The doping material includes a compound having a structure shown in the following formula (I):

[0014] ;

[0015] In formula (I), Ar 1 Selected from ,in, represents the fused edge, D represents deuterium, n 1 、n 2 Each is selected from an integer between 0 and 12;

[0016] L 1 -L 2 Each is independently selected from a single bond, a C6-C12 aryl group which may be substituted by a C1-C4 alkyl group, a C4-C30 heteroaryl group, R 1 , R 3 Each is independently selected from C1-C10 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl;

[0017] R 2 , R 4 It can be unsubstituted, singly substituted, polysubstituted or substituted in the maximum number of terms, R 2 , R 4 Each is independently selected from hydrogen, deuterium, C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino;

[0018] The above L 1 -L 2 , R 1 -R 4 The heteroatom of the heteroaryl group is selected from N, O or S atoms; 1 -L 2 , R 1 -R 4The substitution in the substituted group is selected from one or more of deuterium, C1-C10 alkyl, C6-C18 aryl; the compound described in formula (I) may be fully or partially deuterated.

[0019] Preferably, the structure represented by formula (I) is selected from any one of the following formulas I-1 to I-5:

[0020] ;

[0021] Among them, Ar 1 , L 1 -L 2 , R 1 , R 3 The substitution limitations are the same as defined above.

[0022] More preferably, the L 1 -L 2 Each is independently selected from a single bond, a phenyl group, a biphenyl group, and a dibenzofuranyl group substituted or unsubstituted by a C1-C10 alkyl group; 1 , R 3 Each is independently selected from tert-butyl, phenyl, tert-butylphenyl, di-tert-butylphenyl, methyl-substituted tetrahydronaphthyl, methyl-substituted or unsubstituted dibenzofuranyl, methyl-substituted or unsubstituted dibenzothienyl.

[0023] Preferably, the Ar 1 Selected from ,in, represents the fused edge, D represents deuterium, n 1 It is 0, 3, and 9.

[0024] According to one or more embodiments, the present invention provides an organic electroluminescent device having a deuterated boron nitrogen compound, wherein the doping material is selected from any one or more combinations of the chemical structures shown below:

[0025]

[0026] Preferably, the organic light-emitting functional layer further comprises an auxiliary light-emitting material layer, and the HOMO energy level of the auxiliary light-emitting material layer is between -5.20 and -5.50 eV.

[0027] Preferably, the weight percentage of the main material to the doping material in the light-emitting layer is 1-99:99-1.

[0028] Preferably, the difference between the HOMO energy level of the host material and the HOMO energy level of the doping material is less than 0.8 eV.

[0029] 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 smart phones, tablet computers, smart wearable devices, televisions, VR, micro-display fields, and automobile central control screens or automobile taillights.

[0030] The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

[0031] In summary, compared with the prior art, the present invention has the following beneficial effects:

[0032] The organic electroluminescent device of the present invention adopts a deuterated boron nitrogen compound, and the structure has good stability and film-forming performance through the combination of the deuterated phenyl group at the defined site in the mother nucleus and the defined group; after the boron nitrogen compound provided by the present invention is prepared into an organic light-emitting device, the organic light-emitting device can effectively have a lower driving voltage and maintain voltage stability, and the luminous efficiency is improved, and the working life of the device can also be better. DETAILED DESCRIPTION

[0033] The following will be described clearly and completely in conjunction with the technical solutions of the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention.

[0034] The term "alkyl" refers to and includes straight and branched chain alkyl groups. Preferred alkyl groups are those containing 1 to 4 carbon atoms, including methyl, ethyl, propyl, tert-butyl. In addition, the alkyl group may be optionally substituted.

[0035] 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 preferred cycloalkyl groups are those containing 3 to 12 ring carbon atoms, and particularly preferred are those containing 3 to 6 ring carbon atoms, and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. In addition, the cycloalkyl group may be optionally substituted.

[0036] 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 carbons, ten carbons, or twelve carbons. Phenyl, biphenyl, terphenyl, naphthalene, etc. are preferred. In addition, aryl groups may be optionally substituted.

[0037] The heteroaryl group refers to a general term for a group obtained by replacing one or more aromatic carbon atoms in an aromatic group with a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, silicon or nitrogen atoms, and the heteroaryl group may be a monocyclic heteroaryl group or a condensed ring heteroaryl group, and may be a heteroaryl group having 4 to 30 carbon atoms, preferably a heteroaryl group having 6 to 20 carbon atoms. Examples may include pyridyl, pyrrolyl, pyridyl, thienyl, furanyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

[0038] Throughout the specification, unless explicitly described to the contrary, "comprising" any component will be understood to imply the inclusion of other elements, rather than excluding any other elements. In addition, it should be understood that throughout the specification, when an element such as a layer, film, region or substrate is referred to as being "on" or "above" another element, it can be "directly on" another element, or there may be intervening elements. In addition, "on..." or "above..." means being located above the target portion, and does not necessarily mean being located above according to the direction of gravity.

[0039] One object of the present invention is to provide an organic electroluminescent device, the organic electroluminescent device comprising: a substrate layer; a first electrode, the first electrode is on the substrate; an organic light-emitting functional layer, the organic light-emitting functional layer is on the first electrode; a second electrode, the second electrode is on the organic light-emitting functional layer; the organic light-emitting functional layer comprises a light-emitting layer, the light-emitting layer comprises a main material and a doping material, wherein the HOMO energy level of the main material is between -5.5 and -5.8 eV, and the doping material comprises a Structure of boron-nitrogen compounds.

[0040] In one embodiment of the present invention, the light-emitting layer in the organic electroluminescent (OLED) device comprises one or more of the compounds represented by the above general formula (I) as light-emitting doping materials.

[0041] In a preferred embodiment of the present invention, an OLED is provided, which includes 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 includes a light-emitting doping material composed of one or more of the compounds represented by the above general formula (I). Optionally, there is also a covering layer, a protective layer and / or an encapsulation layer on the organic light-emitting functional layer.

[0042] The substrate of the present invention can be any substrate used in a typical organic light-emitting device. It can be a glass or transparent plastic substrate, or a substrate of 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 waterproofness. Depending on the properties of the substrate, the use direction is different.

[0043] As materials for the hole injection layer, the hole transport layer, and the electron injection layer, any material can be selected from known related materials used for OLED devices.

[0044] As a host material capable of producing blue fluorescence, green fluorescence 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 to effectively cooperate with the guest material to excite and emit light.

[0045] The present invention is described in detail below in conjunction with specific examples. Synthesis Examples All raw materials and solvents are commercially available unless otherwise specified, and the solvents are used directly without further treatment.

[0046] Example

[0047] Example 1: Synthesis of Compound 001

[0048] Synthesis route:

[0049] ;

[0050] 1) Compound 001-1 (1 mmoL) and compound 001-2 (1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added. After the reaction system was refluxed for 72 hours, it was 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 with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent (dichloromethane: petroleum ether) = 1:4, and the intermediate product 001-3;

[0051] 2) Dissolve the intermediate product 001-3 (1 mmoL) and compound 001-4 (1 mmoL) in 50 mL toluene solution. Under nitrogen atmosphere, add sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL). After reflux for 72 hours, the reaction system is cooled to room temperature. The solvent is removed by rotary evaporation, and the residue is extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried with sodium sulfate. The solvent is removed by vacuum distillation, and the resulting crude product is separated and purified by silica gel chromatography, with the eluent (dichloromethane: petroleum ether) = 1:4, intermediate product 001-5;

[0052] 3) Dissolve the intermediate product 001-5 (1 mmoL) and compound 001-6 (1 mmoL) in 50 mL toluene solution. Under nitrogen atmosphere, add sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL). After reflux for 72 hours, the reaction system is cooled to room temperature. The solvent is removed by rotary evaporation, and the residue is extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried with sodium sulfate. The solvent is removed by vacuum distillation, and the resulting crude product is separated and purified by silica gel chromatography, with the eluent (dichloromethane: petroleum ether) = 1:4, intermediate product 001-7;

[0053] 4) Dissolve the intermediate product 001-7 (1 mmoL) and compound 001-8 (1 mmoL) in 50 mL toluene solution. Under nitrogen atmosphere, add sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL). After reflux for 72 hours, the reaction system is cooled to room temperature. The solvent is removed by rotary evaporation, and the residue is extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried with sodium sulfate. The solvent is removed by vacuum distillation, and the resulting crude product is separated and purified by silica gel chromatography, with the eluent (dichloromethane: petroleum ether) = 1:4, and the intermediate product 001-9;

[0054] 5) The intermediate product 001-9 (1 mmoL) was dissolved in 60 mL of anhydrous tert-butylbenzene. The reaction system was cooled to -78°C, and BuLi (1 mL, 2 mmoL, 2M in hexane) was slowly added. After reacting at -78°C for 4 hours, BBr (3247 mg, 1 mmoL) was slowly added. After reacting at -50°C for 1 hour, the mixture was warmed to room temperature, and then N,N-diisopropylethylamine (387 mg, 3 mmoL) was added. The mixture was then heated to 120°C for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. 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 distillation under reduced pressure, and the resulting crude product was separated and purified by silica gel chromatography with an eluent of (dichloromethane: petroleum ether) = 1:8 to obtain the final product 001. The structure of the test target product 001 was obtained by liquid chromatography-mass spectrometry analysis: LC-MS (m / z) (Μ+): the theoretical value was 835.51, and the test value was 835.93.

[0055] Example 2: Synthesis of Compound 016

[0056] Referring to the synthesis steps and reaction conditions of Example 1, compound 016 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 931.51 and the test value was 931.97.

[0057] Example 3: Synthesis of Compound 033

[0058] With reference to the synthesis steps and reaction conditions of Example 1, compound 033 was synthesized, and the LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 929.66, and the test value was 930.18.

[0059] Example 4: Synthesis of Compound 047

[0060] Compound 047 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) (Μ+) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1020.67 and the test value was 1021.19.

[0061] Example 5: Synthesis of Compound 052

[0062] Referring to the synthesis steps and reaction conditions of Example 1, compound 052 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1095.66 and the test value was 1096.28.

[0063] Example 6: Synthesis of Compound 053

[0064] Compound 053 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 1065.67 and the test value was 1066.25.

[0065] Example 7: Synthesis of Compound 055

[0066] Compound 055 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) (Μ+) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1100.76 and the test value was 1101.34.

[0067] Example 8: Synthesis of Compound 059

[0068] Referring to the synthesis steps and reaction conditions of Example 1, compound 059 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1079.73 and the test value was 1080.31.

[0069] Example 9: Synthesis of Compound 060

[0070] Referring to the synthesis steps and reaction conditions of Example 1, compound 060 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1155.76 and the test value was 1156.38.

[0071] Example 10: Synthesis of Compound 065

[0072] Compound 065 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) (M+) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1013.55 and the test value was 1014.15.

[0073] Example 11: Synthesis of Compound 075

[0074] Compound 075 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) (M+) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1096.70 and the test value was 1097.42.

[0075] Example 12: Synthesis of Compound 078

[0076] Referring to the synthesis steps and reaction conditions of Example 1, compound 078 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1025.63 and the test value was 1026.27.

[0077] Example 13: Synthesis of Compound 092

[0078] Referring to the synthesis steps and reaction conditions of Example 1, compound 092 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1110.68 and the test value was 1110.26.

[0079] Example 14: Synthesis of Compound 104

[0080] Compound 104 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) (Μ+) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1024.65 and the test value was 1025.27.

[0081] Example 15: Synthesis of Compound 108

[0082] Compound 108 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) (Μ+) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1134.55 and the test value was 1135.13.

[0083] Example 16: Synthesis of Compound 115

[0084] Referring to the synthesis steps and reaction conditions of Example 1, compound 115 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1024.57 and the test value was 1025.15.

[0085] Example 17: Synthesis of Compound 124

[0086] Referring to the synthesis steps and reaction conditions of Example 1, compound 124 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1026.58 and the test value was 1027.14.

[0087] Example 18: Synthesis of Compound 128

[0088] Referring to the synthesis steps and reaction conditions of Example 1, compound 128 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1100.60 and the test value was 1101.20.

[0089] Example 19: Synthesis of Compound 130

[0090] Referring to the synthesis steps and reaction conditions of Example 1, compound 130 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1117.63 and the test value was 1118.31.

[0091] Example 20: Synthesis of Compound 136

[0092] Referring to the synthesis steps and reaction conditions of Example 1, compound 136 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1160.56 and the test value was 1161.28.

[0093] Example 21: Synthesis of Compound 142

[0094] Referring to the synthesis steps and reaction conditions of Example 1, compound 142 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1266.77 and the test value was 1267.41.

[0095] Example 22: Synthesis of Compound 147

[0096] Referring to the synthesis steps and reaction conditions of Example 1, compound 147 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1286.74 and the test value was 1287.46.

[0097] Example 23: Synthesis of Compound 161

[0098] Referring to the synthesis steps and reaction conditions of Example 1, compound 161 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1116.59 and the test value was 1117.25.

[0099] Example 24: Synthesis of Compound 165

[0100] Referring to the synthesis steps and reaction conditions of Example 1, compound 165 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (Μ+): the theoretical value was 1139.58 and the test value was 1140.22.

[0101] Example 25: Synthesis of Compound 174

[0102] Compound 174 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) (Μ+) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1197.65 and the test value was 1198.33.

[0103] Several examples of the boron nitrogen compounds of the present invention being applied to OLED devices are listed below to further illustrate the beneficial effects of the compounds of the present invention. The materials used in the examples are purchased commercially or synthesized by themselves.

[0104] Fabrication of OLED devices:

[0105] As a reference preparation method for a device embodiment, the present invention evaporates 50-500nm ITO / Ag / ITO on an alkali-free glass substrate as an anode, evaporates a hole injection layer (5nm-20nm), a hole transport layer (50-150nm), a light-emitting auxiliary layer (5-120nm), a light-emitting layer (20-50nm), a hole blocking layer (5-20nm), an electron transport layer (20-80nm), and an electron injection layer (1-10nm) on the anode, and then co-evaporates Mg and Ag (weight ratio 1:9, 100-150nm) to make a semi-transparent cathode, and then evaporates a cover layer compound. Finally, the light-emitting device is encapsulated using an epoxy resin adhesive in a nitrogen atmosphere.

[0106] In a preferred embodiment, the structure of the OLED device provided by the present invention is as follows: first, an alkali-free glass substrate is washed with isopropyl alcohol for 15 minutes using an ultrasonic cleaner, and then a UV ozone cleaning treatment is performed in air for 30 minutes. The treated substrate is subjected to vacuum evaporation to deposit ITO / Ag / ITO 100nm as an anode, and then 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 (main material: doping 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 stacked and evaporated, and then Mg and Ag (weight ratio 1:9, 130nm) are co-evaporated to make a semi-transparent cathode, and then a compound CPL (65nm) is evaporated as a covering layer. Finally, the light emitting device is encapsulated with epoxy resin adhesive in a nitrogen atmosphere, which is recorded as Application Example 1. The molecular structure formula of the relevant material is as follows (particularly preferably selected from the following structure, but it does not mean that the present invention is limited to the following structure):

[0107] .

[0108] Application Examples 2 to Application 25 and Comparative Example 1 were prepared by referring to the method provided in Application Example 1, except that the compounds listed in Table 1 were used as doping materials to replace Compound 001 in Application Example 1. The doping materials in Comparative Example 1 are as follows: .

[0109] Performance evaluation of OLED devices:

[0110] The current of the OLED device at different voltages was tested using a Keithley 2365A digital nanovoltmeter, and the current was then divided by the luminous area to obtain the current density of the OLED device at different voltages. The brightness and radiant energy flux density of the OLED device at different voltages were tested 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 / cm 2 ) working voltage Volt and current efficiency (cd / A), BI=E / CIEy, refers to the Blue Index in blue light, and is also a parameter for measuring the luminous efficiency of blue light. E refers to the current efficiency, and CIEy refers to the vertical coordinate color point obtained by bringing the wavelength of the device's luminous half-peak width into the CIE1930 software. The test data is shown in Table 1.

[0111] As can be seen from Table 1, compared with Comparative Example 1, Application Examples 1 to 25 have lower operating voltage, higher BI luminous efficiency and longer service life. The performance improvement of each application example is based on the introduction of deuterated phenyl, limiting groups and boron nitrogen core structure in the present invention, so that the boron nitrogen compound material has better luminous efficiency, and the doping material in the present invention has good compatibility, which can make the blue light emitting layer better realize the balance of electron and hole transmission and exciton conversion rate, reduce the power consumption of the device, and improve the service life.

[0112] This specific embodiment is merely an explanation of the present invention and is not a limitation of the present invention. After reading this specification, those skilled in the art may make non-creative modifications to the present embodiment as needed. However, as long as they are within the scope of the claims of the present invention, they are protected by the patent law.

Claims

1. An organic electroluminescent device having a deuterated boron nitrogen compound, characterized in that: The organic electroluminescent device comprises: substrate layer; a first electrode, the first electrode being on the substrate; An organic light-emitting functional layer, the organic light-emitting functional layer is on the first electrode; A second electrode, the second electrode being on the organic light-emitting functional layer; The organic light-emitting functional layer comprises a light-emitting layer; the light-emitting layer comprises a main material and a doping material, wherein the HOMO energy level of the main material is between -5.5 and -5.8 eV; The doping material includes any one of the following formulas I-1 to I-5: Wherein Ar1 is selected from in, represents a fused edge, D represents deuterium, and n1 and n2 are each selected from integers of 0-12; The L1-L2 are each independently selected from a single bond, a phenyl group substituted or unsubstituted by a C1-C10 alkyl group, a biphenyl group, and a dibenzofuranyl group; the R1 and R3 are each independently selected from a tert-butyl group, a phenyl group, a tert-butylphenyl group, a di-tert-butylphenyl group, a methyl-substituted tetrahydronaphthyl group, a methyl-substituted or unsubstituted dibenzofuranyl group, and a methyl-substituted or unsubstituted dibenzothienyl group; R4 may be unsubstituted, singly substituted, polysubstituted or substituted in the maximum number, and each R4 is independently selected from hydrogen, deuterium, C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino; the heteroatom of the heteroaryl in R4 is selected from N, O or S atoms; the substitution in the group substituted by R4 is selected from one or more of deuterium, C1-C10 alkyl, C6-C18 aryl; the compound described in formula (I) may be fully or partially deuterated.

2. The organic electroluminescent device having a deuterated boron nitrogen compound according to claim 1, characterized in that: Ar1 is selected from in, represents a fused edge, D represents deuterium, and n1 is 0, 3, or 9.

3. The organic electroluminescent device having a deuterated boron nitrogen compound according to claim 1, characterized in that: The doping material is selected from any one or more combinations of the following chemical structures:

4. The organic electroluminescent device having a deuterated boron nitrogen compound according to claim 1, characterized in that: The organic light-emitting functional layer further comprises an auxiliary light-emitting material layer, and the HOMO energy level of the auxiliary light-emitting material layer is between -5.20 and -5.50 eV.

5. The organic electroluminescent device having a deuterated boron nitrogen compound according to claim 1, characterized in that: The weight percentage of the main material and the doping material in the light-emitting layer is 1-99:99-1.

6. The organic electroluminescent device having a deuterated boron nitrogen 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 dopant material is less than 0.8 eV.

7. Use of the organic electroluminescent device having a deuterated boron nitrogen compound according to any one of claims 1 to 6 in a display or lighting device.

8. A display or lighting device, characterized in that: The device comprises an organic electroluminescent device having a deuterated boron nitrogen compound as claimed in any one of claims 1 to 6.

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