An organic electroluminescence device, a display or illumination device comprising the same
By employing fluorenyl structures with phenyl and alkyl fixed substitutions and benzene rings with benzo5-membered ring substitutions as hole transport layer materials in OLEDs, combined with light-emitting auxiliary layer materials, the problems of thermal stability and luminous efficiency in OLEDs have been solved, resulting in high-efficiency and long-life OLED devices.
Patent Information
- Application Number
- CN202511544336.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2025-10-28
- Publication Date
- 2026-02-24
- Estimated Expiration
- 2045-10-28
AI Technical Summary
In existing organic light-emitting diodes (OLEDs), aromatic amine compounds used as hole transport layer materials suffer from poor thermal stability, low HOMO values, and low triplet energy levels, resulting in high driving voltage, low luminous efficiency, and short operating life of the devices.
A fluorenyl structure with fixed substitution of phenyl and alkyl groups is used as the core segment of the hole transport layer, and combined with a benzo5-membered ring and a limited substituted benzene ring as an amino side chain. With the help of a limited material for the light-emitting auxiliary layer, an OLED device with excellent light-emitting performance is formed.
It improves the luminous efficiency and lifespan of OLED devices, reduces device power consumption, enhances the balance of electron and hole transport, and extends device lifespan.
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Abstract
Description
Technical Field
[0001] This invention relates to the field of organic optoelectronic material preparation technology, specifically to an organic electroluminescent device and a display or lighting device containing the device. Background Technology
[0002] Organic light-emitting diodes (OLEDs), also known as organic light-emitting devices, are a technology that converts electrical energy into light energy through organic light-emitting materials. This technology involves applying voltage to an organic light-emitting element 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] Typically, organic material layers have multilayer structures composed of different materials to improve the efficiency and stability of organic light-emitting devices (OLEDs). For example, an organic material layer can include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. Currently, aromatic amine compounds are used as hole transport layer materials, but they suffer from poor thermal stability, low HOMO values, and low triplet energy levels. Their application in OLEDs still presents challenges in improving the device's driving voltage, luminous efficiency, and lifetime.
[0004] Therefore, it is necessary to develop organic optoelectronic materials with good stability and excellent luminescence performance, and to find suitable OLED optoelectronic functional materials for OLED devices to solve the above problems. Summary of the Invention
[0005] The purpose of this invention is to provide one or more organic electroluminescent devices with good lifespan and excellent light-emitting performance. To solve the above-mentioned technical problems, the hole transport layer compound of the device provided by this invention uses a fluorenyl structure with fixed substitution of phenyl and alkyl groups as the core segment, and a benzo5-membered ring and a defined substituted benzene ring as the other two amine side chains. It is then combined with a defined material of the light-emitting auxiliary layer to fabricate OLED elements, enabling the device to have both high efficiency and long operating life.
[0006] The organic electroluminescent device provided by this invention is achieved through the following technical solution:
[0007] An organic electroluminescent device, the organic electroluminescent device 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] A capping layer is placed over the second electrode;
[0013] The organic light-emitting functional layer includes a hole transport layer, and the hole transport layer comprises a compound with the structure shown in Formula I:
[0014] ;
[0015] In Formula I, Z is selected from C(CH3)2, O, or S atoms;
[0016] R represents monosubstituted or polysubstituted, and R is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, and substituted or unsubstituted C6-C30 aryl.
[0017] The substitutions in "substituted or unsubstituted" above are selected from hydrogen, deuterium, C1-C12 alkyl, and C6-C30 aryl;
[0018] The organic light-emitting functional layer further includes a light-emitting auxiliary layer, wherein the light-emitting auxiliary layer is a material with a structure of Formula II:
[0019] ;
[0020] Wherein, L, L1, and L2 are each independently selected from single bonds and C6-C30 arylene groups, and X is selected from O or S atoms; Ar1 and Ar2 are each independently selected from deuterated or undeuterated C6-C30 aryl groups and deuterated or undeuterated C5-C36 heteroaryl groups; Ra and Rb are each independently selected from hydrogen, deuterium, and phenyl groups, wherein the phenyl groups can be connected by fusion, and at least one of Ra and Rb is selected from phenyl groups; n1 is selected from integers from 0 to 3, and n2 is selected from integers from 0 to 4.
[0021] Preferably, R is a polysubstituted compound, and each occurrence is independently selected from any one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, methyl-substituted or unsubstituted cyclopentyl, methyl-substituted or unsubstituted cyclohexyl, 1-adamantyl, and phenyl.
[0022] According to one or more embodiments, the present invention provides an organic electroluminescent device, wherein the compound of the hole transport layer is selected from any of the chemical structures shown below, wherein "Ad" represents... “D” represents deuterium, “tBu” represents tert-butyl, and * indicates a linker site.
[0023] .
[0024] The organic light-emitting functional layer further includes a light-emitting auxiliary layer, wherein the light-emitting auxiliary layer is a material with a structure of Formula II:
[0025] ;
[0026] Wherein, L, L1, and L2 are each independently selected from single bonds and C6-C30 arylene groups, and X is selected from O or S atoms; Ar1 and Ar2 are each independently selected from deuterated or undeuterated C6-C30 aryl groups and deuterated or undeuterated C5-C36 heteroaryl groups; Ra and Rb are each independently selected from hydrogen, deuterium, and phenyl groups, wherein the phenyl groups can be connected by fusion, and at least one of Ra and Rb is selected from phenyl groups; n1 is selected from integers from 0 to 3, and n2 is selected from integers from 0 to 4; the hydrogen atoms in Formula II may be partially or completely deuterated.
[0027] Preferably, in Formula II, L1 and L2 are each independently selected from single bonds, phenyl, and naphthyl; Ar1 and Ar2 are each independently selected from the following groups, whether deuterated or undeuterated: phenyl, naphthyl, phenyl-substituted naphthyl, and dibenzofuranyl.
[0028] Preferably, in Formula II, L is selected from phenyl or biphenyl.
[0029] According to one or more embodiments, in the organic electroluminescent device provided in this application, the compound of the light-emitting auxiliary layer is selected from any one or more of the following, wherein D represents deuterium:
[0030] .
[0031] The organic electroluminescent device of the present invention can be used in OLED lighting or display devices.
[0032] The present invention also provides a display or lighting device comprising one or more of the organic electroluminescent devices described above.
[0033] The present invention also provides a composition comprising a compound having the structure shown in Formula I:
[0034] ;
[0035] In Formula I, Z is selected from C(CH3)2, O, or S atoms;
[0036] R represents monosubstituted or polysubstituted, and R is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, and substituted or unsubstituted C6-C30 aryl.
[0037] The substitutions in "substituted or unsubstituted" above are selected from hydrogen, deuterium, C1-C12 alkyl, and C6-C30 aryl;
[0038] And the structure described in Formula II:
[0039] ;
[0040] In this formula, L, L1, and L2 are each independently selected from single bonds and C6-C30 aryl groups, and X is selected from O or S atoms; Ar1 and Ar2 are each independently selected from deuterated or undeuterated C6-C30 aryl groups and deuterated or undeuterated C5-C36 heteroaryl groups; Ra and Rb are each independently selected from hydrogen, deuterium, and phenyl groups, wherein the phenyl groups can be connected by fusion, and at least one of Ra and Rb is selected from phenyl groups; n1 is selected from integers from 0 to 3, and n2 is selected from integers from 0 to 4. The hydrogen atoms in Formula I and Formula II may be partially or completely deuterated.
[0041] In summary, compared with the prior art, the present invention has the following beneficial effects:
[0042] The hole transport layer compound of the device provided by the present invention uses a fluorenyl structure with fixed substitution of phenyl and alkyl groups as the core segment, and a benzo5-membered ring and a limited substituted benzene ring as the other two side chains of the amine group. When combined with the limited material of the light-emitting auxiliary layer, it can be used to make OLED elements, which can effectively improve the luminous efficiency and working life of organic light-emitting devices. Detailed Implementation
[0043] 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.
[0044] The aryl group referred to in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic aryl or a fused-ring aryl. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples may include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthracene, phenanthryl, or pyrene, but are not limited thereto. Aryl or aromatic group – as used herein, considers both non-fused and fused systems. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fen, fluorene, pyrene, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylyl, 3,4-dimethylyl, 2,5-dimethylyl, mestriylyl, and m-tetraphenyl.
[0045] The alkyl groups described in this invention include straight-chain and branched alkyl groups. They can be alkyl groups having 1 to 24 carbon atoms, with preferred alkyl groups containing 1 to 10 carbon atoms, including methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, etc. Furthermore, the alkyl groups may optionally be substituted.
[0046] The cycloalkyl group described in this invention represents any functional group or substituent derived from an alicyclic ring. It is a saturated cycloalkyl group with 3 or more but less than 20 carbon atoms in the ring. The cycloalkyl group can be monocyclic, bicyclic, bridged, spirocyclic, or fused ring, for example, it can be cyclohexane, dihexane, 1-adamantane, bicyclo[2.2.2]octane, norbornyl alkyl, etc., but is not limited thereto.
[0047] 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.
[0048] 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; a second electrode on the organic light-emitting functional layer; the organic light-emitting functional layer comprising a hole transport layer; the hole transport layer comprising an aromatic amine compound as described in Formula I. The organic light-emitting functional layer further comprises a light-emitting auxiliary layer having an aromatic amine material with the structure of Formula II.
[0049] In one embodiment of the present invention, the hole transport layer in the organic electroluminescent (OLED) device comprises one or more components of the compounds represented by the above general formula I as an aromatic amine compound.
[0050] In one embodiment of the present invention, the light-emitting auxiliary layer in the organic electroluminescent (OLED) device comprises one or more components of the compounds represented by the above general formula Ⅲ as an aromatic amine compound.
[0051] In a preferred embodiment of the present invention, an OLED is provided, comprising a substrate, an anode, a cathode, an organic light-emitting functional layer, and a capping layer. The organic light-emitting functional layer may include a light-emitting layer, a light-emitting auxiliary 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. The hole transport layer comprises one or more components of the compounds shown in General Formula I above. The light-emitting auxiliary layer comprises one or more components of the compounds shown in General Formula II above. Optionally, a protective layer and / or an encapsulation layer are further provided above the capping layer.
[0052] 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.
[0053] As for the materials used in the hole injection layer, electron transport layer, electron injection layer, and light-emitting layer, any material can be selected from known materials used in OLED devices.
[0054] As a host-guest material capable of generating blue, green, and blue-green fluorescence, it not only needs to possess extremely high fluorescence quantum luminescence efficiency but also needs to have an appropriate energy level.
[0055] 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 are used directly without further processing. The intermediate MA-MC used below was custom-purchased from Shanghai Beixin Technology Development Co., Ltd.
[0056] .
[0057] Preparation Example 1
[0058] ;
[0059] Synthesis method:
[0060] 1) Dissolve SO (10 mmol) in 20 mL of dry THF (tetrahydrofuran). Under nitrogen protection, add n-butyllithium solution (15 mmol, 2.5 M) dropwise at -20 °C and stir for 1 h. Then raise the temperature to room temperature and stir for 1 h. Return to -20 °C, add triisopropyl borate (15 mmol), stir at -20 °C for 2 h, stir at room temperature for 6 h, then stop the reaction. Cool to room temperature (25 °C), add sodium carbonate solution to neutralize the pH to neutral, extract three times with dichloromethane, collect the organic phase, evaporate the solvent, and separate by silica gel column chromatography to obtain the target product -SM1.
[0061] 2) Add SM1 (10 mmol), SM2 (11 mmol), sodium carbonate (30 mmol), THF 30 mL, and water 10 mL to the reaction flask. After purging with nitrogen, add tetrakis(triphenylphosphine)palladium (5 × 10⁻⁶ mmol). -2 (mmoL), heat to 60℃, react for 3 hours, stop the reaction, cool to 25℃, add 50mL of water, extract 3 times with dichloromethane, concentrate under reduced pressure to dryness, and then column chromatography to obtain intermediate product S1.
[0062] 3) Add S1 (10 mmol), benzophenone imine (16 mmol), sodium tert-butoxide (15 mmol), and xylene (30 mL) to the reaction flask.
[0063] After nitrogen purging, Pd(dppf)Cl2 was added (5×10) -2The mixture was heated to 138°C and refluxed for 12 hours, then the reaction was stopped. The mixture was cooled to 25°C, 50 mL of water was added, and after filtration, column chromatography was used to obtain intermediate product S2.
[0064] Preparation Example 2
[0065] The preparation method is the same as that in Preparation Example 1, except that SM2 is changed to .
[0066] Example
[0067] Example 1: Synthesis of Compound 33
[0068] Synthesis route:
[0069] ;
[0070] Synthesis method:
[0071] 1) A-1 (10 mmol), A-2 (10.5 mmol), pd2(dba)3 (3 mmol), X-Phos (2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl, 6 mmol), and sodium tert-butoxide (13 mmol) were sequentially added to 50 mL of toluene solution. The mixture was stirred thoroughly at room temperature, and nitrogen gas was purged five times. The reaction was then carried out at 80 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, washed with water, and separated. The organic phase was concentrated and separated by column chromatography to obtain product A-S1.
[0072] 2) The products A-S1 (10 mmol), MA (11 mmol), pd2(dba)3 (3 mmol), X-Phos (6 mmol), and sodium tert-butoxide (13 mmol) were sequentially added to 50 mL of xylene solution. The mixture was stirred thoroughly at room temperature, and nitrogen gas was purged five times. The mixture was then refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, washed with water, and separated. The organic phase was concentrated and separated by column chromatography to obtain the target product, compound 33. The LC-MS (m / z) analysis showed a theoretical value of 851.45 and a measured value of 851.07.
[0073] Example 2: Synthesis of Compound 1
[0074] Following the synthesis steps and reaction conditions of Example 1, compound 1 was synthesized. The difference from Example 1 is that the starting material A-1 was replaced with... The theoretical value was 971.54 and the measured value was 972.08, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0075] Example 3: Synthesis of Compound 2
[0076] Following the synthesis steps and reaction conditions of Example 1, compound 2 was synthesized. The difference from Example 1 is that the starting material A-1 was replaced with... The theoretical value was 1047.57 and the measured value was 1048.15, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0077] Example 4: Synthesis of Compound 3
[0078] Following the synthesis steps and reaction conditions of Example 1, compound 315 was synthesized. The difference from Example 1 is that the starting material A-1 was replaced with... The theoretical value was 947.54 and the measured value was 948.10, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0079] Example 5: Synthesis of Compound 5
[0080] Following the synthesis steps and reaction conditions of Example 1, compound 5 was synthesized. The difference from Example 1 is that MA was replaced with MC, and starting material A-1 was replaced with... The theoretical value was 865.46 and the measured value was 865.98, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0081] Example 6: Synthesis of Compound 8
[0082] Following the synthesis steps and reaction conditions of Example 1, compound 8 was synthesized. The difference from Example 1 is that MA was replaced with MB, and starting material A-1 was replaced with... The theoretical value was 989.50 and the measured value was 990.18, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0083] Example 7: Synthesis of Compound 9
[0084] Following the synthesis steps and reaction conditions of Example 1, compound 9 was synthesized. The difference from Example 1 is that the starting material A-1 was replaced with... The theoretical value was 893.50 and the measured value was 894.16, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0085] Example 8: Synthesis of Compound 11
[0086] Following the synthesis steps and reaction conditions of Example 1, compound 11 was synthesized. The difference from Example 1 is that the starting material A-1 was replaced with... The theoretical value was 969.53 and the measured value was 970.15, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0087] Example 9: Synthesis of Compound 16
[0088] Following the synthesis steps and reaction conditions of Example 1, compound 16 was synthesized. The difference from Example 1 is that MA was replaced with MD, and starting material A-1 was replaced with... The theoretical value was 927.48 and the measured value was 928.12, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0089] Example 10: Synthesis of Compound 31
[0090] Following the synthesis steps and reaction conditions of Example 1, compound 31 was synthesized. The difference from Example 1 is that the starting material A-1 was replaced with... Replace 1-2 with The theoretical value was 901.43 and the measured value was 901.97, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0091] Example 11: Synthesis of Compound 47
[0092] Following the synthesis steps and reaction conditions of Example 1, compound 47 was synthesized. The difference from Example 1 is that MA was replaced with MF, and A-1 was replaced with... The theoretical value was 925.54 and the measured value was 926.12, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0093] Example 12: Synthesis of Compound 52
[0094] Following the synthesis steps and reaction conditions of Example 1, compound 52 was synthesized. The difference from Example 1 is that MA was replaced with ME, and A-1 was replaced with... The theoretical value was 866.54 and the measured value was 867.10, obtained by liquid chromatography-mass spectrometry (LC-MS).
[0095] The following are several examples of applications of the aromatic amine compounds described in this invention in OLED devices to further illustrate the beneficial effects of the compounds. The materials used were either commercially available or synthesized in-house. The BP materials combined in the following application examples are all commercially available.
[0096] Manufacturing of OLED devices:
[0097] As a reference fabrication method for one embodiment of the device, the present invention involves depositing a 50-500 nm layer of ITO / Ag / ITO (ITO / Ag / ITO weight ratio of 1:(10-20):1) as the anode on an alkali-free glass substrate. On the anode, a hole injection layer (5-20 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 (0.5-10 nm) are sequentially deposited. Then, Mg and Ag (weight ratio 1:9, 10-50 nm) are co-deposited to form a semi-transparent cathode, followed by the deposition of a capping compound (30-90 nm). Finally, the light-emitting device is encapsulated using epoxy resin adhesive under a nitrogen atmosphere.
[0098] 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, and then subjected to UV ozone washing treatment in the air for 30 minutes. The prepared substrate was deposited using a vacuum evaporation method. First, ITO / Ag / ITO (ITO / Ag / ITO weight ratio of 1:10:1, 100nm) was deposited as the anode. Then, a hole injection layer (compound 1:PD weight ratio of 97:3, 10nm), a hole transport layer (compound 1, 135nm), a light-emitting auxiliary layer (BP5, 5nm), a blue light-emitting layer (compound BH:compound BD weight ratio of 98:2, 20nm), a hole blocking layer (HBL, 5nm), an electron transport layer (compound ET: Liq=1:1, 30nm), and an electron injection layer (Yb, 10nm) were deposited sequentially. Then, Mg and Ag (weight ratio of 1:9, 14nm) were co-deposited to form a semi-transparent cathode. Finally, compound CPL (70nm) was deposited as a capping layer. This is referred to as Application Example 1. The molecular structure of the relevant materials is shown below (particularly preferred from the following structures, but this does not mean that the invention is limited to the following structures):
[0099] .
[0100] Application Examples 2-16 and Comparative Examples 1 and 2 were prepared using the method provided in Application Example 1 above, with the only difference being that the BP5 or compound 1 in the device of Application Example 1 was replaced with the compounds listed in Table 1.
[0101] The Ref-HT and Ref-BP structures used in Comparative Examples 1-2 are as follows:
[0102] .
[0103] Performance evaluation of OLED devices:
[0104] 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-peak into the CIE1930 software. The test data are shown in Table 1.
[0105] Table 1. Examples of Applications and Electroluminescence Properties of Composite Materials
[0106]
[0107] As can be seen from Table 1, the combination of the light-emitting auxiliary material and the hole transport material specified in this invention can better achieve the balance of electron and hole transport and exciton conversion rate, reduce the power consumption of the device, and improve the lifespan and light-emitting efficiency of the device.
[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, 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; A capping layer is placed over the second electrode; The organic light-emitting functional layer includes a hole transport layer, and the hole transport layer comprises a compound with the structure shown in Formula I: ; In Formula I, Z is selected from C(CH3)2, O, or S atoms; R represents monosubstituted or polysubstituted, and R is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, and phenyl; The substitutions in "substituted or unsubstituted" above are selected from hydrogen, deuterium, and C1-C12 alkyl groups; The organic light-emitting functional layer further includes a light-emitting auxiliary layer, wherein the light-emitting auxiliary layer is a material with a structure of Formula II: ; Wherein, X is selected from O or S atoms; L is selected from phenyl or biphenyl; L1 and L2 are each independently selected from single bonds, phenyl, and naphthyl; Ar1 and Ar2 are each independently selected from the following groups, either deuterated or undeuterated: phenyl, naphthyl, phenyl-substituted naphthyl, and dibenzofuranyl; Ra and Rb are each independently selected from hydrogen, deuterium, and phenyl, wherein the phenyl groups can be connected in a fused manner, and at least one of Ra and Rb is selected from phenyl; n1 is selected from integers from 0 to 3, and n2 is selected from integers from 0 to 4; the hydrogen atoms in Formula I and Formula II may be partially or completely deuterated.
2. The organic electroluminescent device according to claim 1, characterized in that, The R is a polysubstituted compound, and each time it appears, it is independently selected from any one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, methyl-substituted or unsubstituted cyclopentyl, methyl-substituted or unsubstituted cyclohexyl, 1-adamantyl, and phenyl.
3. The organic electroluminescent device according to claim 1, characterized in that, The compound of the hole transport layer is selected from any of the chemical structures shown below, where "Ad" represents... "D" represents deuterium, "tBu" represents tert-butyl, and * indicates a linker site. 。 4. The organic electroluminescent device according to claim 1, characterized in that, The compound of the light-emitting auxiliary layer is selected from any one or more of the following, where D represents deuterium: 。 5. The use of the organic electroluminescent device according to any one of claims 1-4 in the preparation of display or lighting devices.
6. A display or lighting device, characterized in that, The device comprises an organic electroluminescent device as described in any one of claims 1-4.
7. A composition, characterized in that, The composition comprises a compound with the structure shown in Formula I: ; In Formula I, Z is selected from C(CH3)2, O, or S atoms; R represents monosubstituted or polysubstituted, and R is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, and phenyl; The substitutions in "substituted or unsubstituted" above are selected from hydrogen, deuterium, and C1-C12 alkyl groups; And the structure described in Formula II: ; Wherein, X is selected from O or S atoms; L is selected from phenyl or biphenyl; L1 and L2 are each independently selected from single bonds, phenyl, and naphthyl; Ar1 and Ar2 are each independently selected from the following groups, either deuterated or undeuterated: phenyl, naphthyl, phenyl-substituted naphthyl, and dibenzofuranyl; Ra and Rb are each independently selected from hydrogen, deuterium, and phenyl, wherein the phenyl groups can be connected in a fused manner, and at least one of Ra and Rb is selected from phenyl; n1 is selected from integers from 0 to 3, and n2 is selected from integers from 0 to 4; The hydrogen atoms in Formula I and Formula II may be partially or completely deuterated.
Citation Information
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