An organic electroluminescent material and an organic electroluminescent device, display component comprising the same
Patent Information
- Application Number
- CN202611265811.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2026-08-20
- Publication Date
- 2026-09-25
AI Technical Summary
[0003]然而，深的LUMO材料因具有强拉电子性取代基而不易合成，且难以同时拥有深LUMO、高稳定性等特质
本发明提供一种有机电致发光材料及包含其的有机电致发光器件、显示组件。本发明提供的有机电致发光材料具有嘧啶并嘧啶结构，并且采用对称设计的四个氰基和双取代芳基，化合物的结构稳定，升华后纯度高，同时升华产率高，并且具有较优异的掺杂能力。将本发明提供的有机电致发光材料用于制备有机电致发光器件，不仅能提高空穴注入层的空穴注入能力，降低器件的电压，还能够显著提高器件的热稳定性，延长器件的使用寿命。
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Figure CN122810122A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of organic electroluminescent materials technology, and more particularly to an organic electroluminescent material and an organic electroluminescent device or display component comprising the same. Background Technology
[0002] p-type doped materials (PD materials) are crucial in OLED (Organic Light Emitting Diode) devices, primarily used in conjunction with hole transport materials to form hole injection layers or p-type charge generation layers. When fabricating OLED display panels using PD materials, the PD material and hole transport material are typically deposited onto the substrate surface via co-evaporation and thermal sublimation to form a thin film, followed by the gradual deposition of other functional layers and the light-emitting layer. Therefore, excellent PD materials require good thermal stability to withstand the prolonged high-temperature environment of the evaporation process, ensuring the performance of the deposited device. Good device performance also requires excellent hole injection capability; specifically, the PD material needs a low LUMO (Low Unoccupied Molecular Orbit) energy level to effectively match the HOMO (Highest Occupied Molecular Orbit) energy level of the hole transport material, thereby enhancing hole injection capability.
[0003] However, deep LUMO materials are difficult to synthesize due to their strong electron-withdrawing substituents, and it is also difficult to simultaneously possess the characteristics of deep LUMO and high stability. For example, although the p-type hole-implanting material F4-TCNQ (2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone) has a very deep LUMO, its evaporation temperature is too low, the deposition is difficult to control, the production performance is poorly reproducible, and the device has poor thermal stability. HATCN (1,4,5,8,9,11-hexaazatriphenylhexanitrile) has poor film formation in devices due to its strong crystallinity, and its LUMO is not deep enough, resulting in poor doping ability.
[0004] Furthermore, commonly used PD materials, due to their extreme lack of electrons and strong oxidizing properties, may have low sublimation yields. However, for organic small-molecule materials used in OLEDs, sublimation is an essential process before device fabrication, and the evaporation process for OLED devices using organic small-molecule materials is also a sublimation process. Therefore, the sublimation yield of organic small-molecule materials directly affects the cost of production and application.
[0005] Given that the hole injection layer has a significant impact on the voltage, efficiency, and lifespan of OLED devices, the development of materials with deep LUMO, high stability, and high sublimation yield is of great importance and urgency in the industry. Summary of the Invention
[0006] To address the aforementioned problems, this invention provides an organic electroluminescent material and organic electroluminescent devices and display components comprising the same. By rationally designing the unique structure of the organic electroluminescent material, it possesses excellent hole injection capability, high thermal stability, and high sublimation yield, thereby providing excellent overall performance for organic electroluminescent devices.
[0007] To solve the above-mentioned technical problems, the technical solution provided by the present invention is as follows: In a first aspect, the present invention provides an organic electroluminescent material, the general structural formula of which is shown in Formula I. I In formula I, L 1 L 2 Each is independently selected from any one or any combination of two of the following: single bond, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene ring group having 3 to 30 carbon atoms; R 1 R 2 Each is independently selected from any one or any combination of two of the following: substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; R 1 R 2 At least one of them has an electron-withdrawing group; When L 1 L 2 R 1 R 2 When substituents are present, there are one or more substituents, each of which is independently selected from any one of deuterium, halogen, haloalkyl, haloalkoxy, nitroso, nitro, carbonyl, carboxylic acid, ester, cyano, isocyano, -SCN, -OCN, -SF5, cycloalkyl, boranyl, silyl, sulfinyl, sulfonyl, phosphoxy, or azirrocycloalkyl. In Formula I, any hydrogen atom can be independently replaced by deuterium.
[0008] In this invention, "any combination of two" refers to L 1 L 2 Each independently represents a combination of any one of the aryl groups and any one of the heterocyclic aryl groups linked by a single bond, or R 1 R 2 Each can independently represent any combination of aryl and heterocyclic aryl groups connected by a single bond.
[0009] Preferably, L 1 L 2Each is independently selected from any one or any combination of two of the following: single bond, substituted or unsubstituted arylene group having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene ring group having 3 to 20 carbon atoms; R 1 R 2 Each is independently selected from any one or any combination of two of the following: substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms; In Formula I, any hydrogen atom can be independently replaced by deuterium.
[0010] Preferably, the arylene group is selected from fused arylene groups or non-fused arylene groups.
[0011] More preferably, the fused arylene is selected from naphthylene, anthracene, or phenanthrene.
[0012] More preferably, the non-fused arylene group is selected from phenylene or biphenylene.
[0013] Preferably, the aryl group is selected from fused aryl or non-fused aryl.
[0014] More preferably, the fused aryl group is selected from naphthyl, anthracene, or phenanthrene.
[0015] More preferably, the non-fused aryl group is selected from phenyl or biphenyl.
[0016] Preferably, the heterocyclic group is selected from fused heterocyclic groups or non-fused heterocyclic groups, and the heteroatom in the heterocyclic group is selected from any one or any combination of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom or boron atom.
[0017] More preferably, the fused heterocyclic cyclohexane is selected from benzofuranyl, benzoimidazolyl, indoleyl, quinolinyl, diazanaphthyl, dibenzofuranyl, or phenanthrolineyl.
[0018] More preferably, the non-fused heterocyclic cycloalkanes are selected from pyridinyl, pyrimidinyl, triazineyl, furanyl, thiopheneyl, pyrrolyl, oxazolyl, or thiazolyl.
[0019] Preferably, the heteroaromatic group is selected from fused heteroaromatic groups or non-fused heteroaromatic groups, and the heteroatom in the heteroaromatic group is selected from any one or any combination of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom or boron atom.
[0020] More preferably, the fused heterocyclic group is selected from benzofuranyl, benzimidazolyl, indolyl, quinolinyl, diazanaphthyl, dibenzofuranyl, or o-phenanthrolineyl.
[0021] More preferably, the non-fused heterocyclic aromatic group is selected from pyridinyl, pyrimidinyl, triazine, furanyl, thiophene, pyrrole, oxazolyl, or thiazolyl.
[0022] Preferably, L 1 L 2 Each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted pyridinylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted triazineylene, substituted or unsubstituted furanylene, substituted or unsubstituted pyrroloylene, substituted or unsubstituted oxazolylene, substituted or unsubstituted benzofuranylene, substituted or unsubstituted benzimidazolylene, substituted or unsubstituted indoleylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted diazonylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted o-phenanthrolineylene.
[0023] Preferably, when L 1 L 2 When substituents are present, there are one or more substituents, each independently selected from -D, -F, -CF3, -OCF3, -CN, -NO2, -t-Bu, -OCN, -SCN, -NO, -CH3, -SF5, -CD3, , , , , , , , , , , , , Or substituted phenyl.
[0024] Further preferred, when L 1 or L 2 When the substituent is a substituted phenyl group, the substituted phenyl group may have one or more substituents, and the substituents in the substituted phenyl group may be -D, -F, -OCF3, -CN, or -CF3.
[0025] Preferred, R 1 R 2Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted quinolinyl, or substituted or unsubstituted benzimidazolyl.
[0026] Preferably, when R 1 R 2 When substituents are present, there are one or more substituents, each independently selected from -D, -F, -CF3, -OCF3, -CN, -NO2, -t-Bu, -SCF3, -SF5, and -C6F. 13 -OC3F7, -OC2F5 , , Or substituted phenyl.
[0027] Further preferred, when R 1 Or R 2 When the substituent is a substituted phenyl group, the substituted phenyl group may have one or more substituents, and the substituents in the substituted phenyl group are selected from -D, -CN, -F, -CF3 or -OCF3.
[0028] More preferably, L 1 L 2 Each is independently selected from a single bond or the structure shown in formulas L1 to L172. In formulas L1 to L172, any one hydrogen atom can be independently replaced by deuterium; “ " indicates L 1 L 2 Connection sites with the parent structure of Formula I, " indicates L 1 L 2 With R 1 R 2 The connection site.
[0029] Further optimized, L 1 With L 2 They have the same structure.
[0030] More preferably, R 1 R 2 Each is independently selected from the structures shown in formulas B1 to B160. Any hydrogen atom in formulas B1 to B160 can be independently replaced by deuterium; “ " indicates R 1 R 2 With L 1L 2 The connection site.
[0031] It should be noted that -nC3F7 in B37 represents straight-chain propane.
[0032] Further optimized, R 1 With R 2 They have the same structure.
[0033] More preferably, the organic electroluminescent material is selected from compounds with structures shown as P1~P1422. In compounds numbered P1 to P1422, any one hydrogen atom can be independently replaced by deuterium.
[0034] More preferably, the organic electroluminescent material is selected from compounds with the following structures. In the above compounds, any one hydrogen atom can be independently replaced by deuterium.
[0035] In a second aspect, the present invention provides an organic electroluminescent device, comprising: anode, cathode, And an organic layer disposed between the anode and the cathode; The organic layer comprises the organic electroluminescent material.
[0036] Preferably, the organic layer includes a hole injection layer or a hole transport layer; the hole injection layer or the hole transport layer is formed independently of the organic electroluminescent material alone, or is formed by a combination of the organic electroluminescent material and the hole transport material.
[0037] Preferably, the organic electroluminescent device comprises at least two light-emitting units, and the organic layer includes a charge generation layer disposed between the light-emitting units; the charge generation layer includes a p-type charge generation layer and an n-type charge generation layer; The p-type charge generation layer comprises the organic electroluminescent material and the hole transport material.
[0038] It should be noted that the charge generation layer is located between the light-emitting units. That is, if there are three light-emitting units, there will be two charge generation layers, and so on.
[0039] More preferably, the mass doping ratio of the organic electroluminescent material to the hole transport material is 1000:1 to 1:1000.
[0040] More preferably, the mass doping ratio of the organic electroluminescent material to the hole transport material is 10:1 to 1:100.
[0041] More preferably, the hole transport material includes at least one of triarylamine compounds, spirodifluorene compounds, pentanebenzene compounds, oligothiophene compounds, oligophenyl compounds, oligophenylenevinyl compounds, oligofluorene compounds, porphyrin complexes, or metal phthalocyanine complexes.
[0042] More preferably, the charge generation layer further includes a buffer layer disposed between the p-type charge generation layer and the n-type charge generation layer, the buffer layer comprising the organic electroluminescent material.
[0043] Thirdly, the present invention provides a display component including the aforementioned organic electroluminescent device.
[0044] The present invention has the following beneficial effects: This invention provides an organic electroluminescent material and an organic electroluminescent device and display component comprising the same. The organic electroluminescent material provided by this invention has a pyrimidine-pyrimidine structure and employs a symmetrically designed four cyano groups and disubstituted aryl groups. The compound exhibits structural stability, high purity after sublimation, high sublimation yield, and excellent doping ability. Using the organic electroluminescent material provided by this invention to fabricate organic electroluminescent devices not only improves the hole injection capability of the hole injection layer and reduces the device voltage, but also significantly improves the thermal stability of the device and extends its lifespan. Attached Figure Description
[0045] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device 100 in one embodiment of the present invention; wherein, the organic electroluminescent device 100 includes a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Figure 2 This is a schematic diagram of the structure of an organic electroluminescent device 200 according to an embodiment of the present invention; wherein, the organic electroluminescent device 200 includes a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, a cathode 190, and an encapsulation layer 102; Figure 3 This is a schematic diagram of the structure of an organic electroluminescent device 300 according to an embodiment of the present invention; wherein, the organic electroluminescent device 300 includes a substrate 101, an anode 110, a first hole injection layer 311, a first hole transport layer 312, a first electron blocking layer 313, a first light-emitting layer 314, a first hole blocking layer 315, a first electron transport layer 316, an n-type charge generation layer 320, a p-type charge generation layer 321, a second hole injection layer 330, a second hole transport layer 331, a second electron blocking layer 332, a second light-emitting layer 333, a second hole blocking layer 334, a second electron transport layer 335, a second electron injection layer 336, a cathode 190, and an encapsulation layer 102. Detailed Implementation
[0046] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to embodiments. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the invention.
[0047] Terms and Definitions In this invention, the terms "preferred," "further preferred," "more preferred," and "even more preferred" refer to embodiments of the invention that provide certain beneficial effects under certain circumstances. However, other embodiments may also be preferred under the same or other circumstances. Furthermore, the description of one or more preferred embodiments does not imply that other embodiments are unavailable, nor is it intended to exclude other embodiments from the scope of this invention.
[0048] "Deuterium" refers to the hydrogen isotope deuterium.
[0049] "Deuteration" refers to the substitution of one or more hydrogen atoms in a group by deuterium.
[0050] “ " "" represents the connection site with other atoms. In formulas L1~L172, " " indicates L 1 L 2 Connection sites with the parent structure of Formula I, " indicates L 1 L 2 With R 1 R 2 The connection sites. In formulas B1~B160, " " indicates R 1 R 2 With L 1 L 2 The connection site.
[0051] "Identical substituents but different connection sites" refers to substituents having the same structure, such as R 1 When it is naphthyl, L 1 It can be connected to the 1-position (α-position) and 2-position (β-position) of the naphthyl group via single bonds.
[0052] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.
[0053] The organic compounds for organic electroluminescence provided by this invention are suitable for preparing electronic devices such as light-emitting elements and display panels, and are particularly suitable for preparing organic electroluminescent devices. The electronic devices of this invention are devices comprising a layer of at least one organic electroluminescent material; these devices may also comprise inorganic materials or layers formed entirely of inorganic materials. Preferred electronic devices include organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic dye-sensitized solar cells (O-DSSCs), organic optical detectors, organic photosensors, organic field quenching devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), or organic plasma emitting devices. Organic electroluminescent devices are preferred.
[0054] This invention does not impose any special limitations on the fabrication method of organic electroluminescent devices. The fabrication methods in the following embodiments are merely examples and should not be construed as limitations. Those skilled in the art can reasonably improve the fabrication methods in the following embodiments based on existing technology. For example, the proportions of various materials in each organic layer are not particularly limited, and those skilled in the art can reasonably select them within a certain range based on existing technology.
[0055] In the device embodiments, the device characteristics are tested using equipment conventional in the art and methods well known to those skilled in the art. Since those skilled in the art are familiar with the aforementioned equipment usage, testing methods, and other related matters, and can reliably and unaffectedly obtain the inherent data of the sample, these related matters will not be elaborated upon further in this invention.
[0056] The following are specific examples. Unless otherwise specified, the solvents and reagents used in the examples can be purchased from conventional reagent suppliers, and the relevant compounds can be prepared by existing processes or conventional processes in the art.
[0057] Furthermore, the present invention does not limit the synthesis method of organic electroluminescent materials, but typically, but not limitedly, uses compound P25 as an example.
[0058] Synthesis example 1 This synthetic example provides a method for synthesizing an organic electroluminescent material (numbered P25), with chemical equations shown in Formulas 1 to 3.
[0059] Formula 1 S1. As shown in Formula 1, compound SMO (6.5 g, 24.1 mmol), compound P25-SM1 (9.15 g, 48.0 mmol), sodium carbonate (5.62 g, 53.0 mmol), and Pd(PPh3)4 (1.39 g, 1.23 mmol) were added sequentially to a two-necked flask. Nitrogen gas was purged three times. Under nitrogen protection, 600 mL of toluene, 200 mL of ethanol, and 200 mL of water were added, and the mixture was heated to 100 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to give a white solid intermediate P25-A (5.68 g, yield 43%).
[0060] Formula 2 S2. As shown in Formula 2, intermediate P25-A (5.68 g, 11.6 mmol), malononitrile (3.97 g, 60.2 mmol), potassium carbonate (6.41 g, 46.4 mmol), and Pd(PPh3)4 (1.21 g, 1.05 mmol) were added sequentially to a two-necked flask. Under nitrogen protection, 350 mL of DMF was added, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3M hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. This was filtered to obtain the crude product. Crystallization then yielded a white solid intermediate P25-B (5.41 g, 85% yield).
[0061] Formula 3 S3. As shown in Formula 3, under a nitrogen atmosphere, intermediate P25-B (5.41 g, 9.86 mmol) and 1000 mL of DCM were added to a single-necked flask. Bis(trifluoroacetoxy)iodobenzene (PIFA, 6.36 g, 14.8 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction solution was concentrated to an appropriate volume and filtered to obtain a black solid compound P25 (3.77 g, 70% yield). The product was identified as the target product with a molecular weight of 546.0.
[0062] The method used is similar to that used to synthesize compound P25 (i.e., replacing compound P25-SM1 with the corresponding structure). Compounds P36 (molecular weight 614.0), P41 (molecular weight 682.0), P44 (molecular weight 682.0), P115 (molecular weight 766.1), P119 (molecular weight 834.1), P122 (molecular weight 834.1), P355 (molecular weight 802.1), P359 (molecular weight 870.1), P539 (molecular weight 970.1), and P599 (molecular weight 1106.1) were prepared.
[0063] Comparative compounds The present invention selects the following compounds PD-1, PD-2, and PD-3 as comparative compounds to demonstrate the advantages of the organic electroluminescent materials with specific structures of the present invention.
[0064] Verification Example 1: Sublimation thermal stability of the compound The organic electroluminescent material provided by this invention and the comparative compounds PD-1 to PD-3 were uniformly spread in a vacuum sublimation apparatus, and the pressure was adjusted to achieve a vacuum rate of 1×10⁻⁶. -5 Below torr; a programmed temperature rise method was used, gradually increasing the temperature at a rate of 5℃ / min until material was deposited in the collection zone of the vacuum sublimation apparatus, at which point the temperature rise was stopped and maintained constant; once it was confirmed that the material in the collection zone of the vacuum sublimation apparatus had stopped increasing, heating was stopped, the temperature was slowly lowered, and the sublimed material in the collection zone of the vacuum sublimation apparatus was collected. The purity, purity change, and sublimation yield of each compound before and after sublimation were tested, and the results are shown in Table 1.
[0065] Table 1. Results of sublimation thermal stability tests for each compound. As shown in Table 1, the purity change of the organic electroluminescent material provided by this invention before and after sublimation is ±0.4%, with the purity increasing to varying degrees after sublimation. In contrast, the purity of the comparative compounds PD-1 to PD-3 decreased to varying degrees after sublimation, and the significant decrease in purity rendered the materials unsuitable for device evaluation. This indicates that the organic electroluminescent material provided by this invention has a more stable structure and better heat resistance. Furthermore, the sublimation yield of the organic electroluminescent material provided by this invention is 75% to 83%, exhibiting excellent sublimation yield; the significantly reduced sublimation yield of the comparative compounds PD-1 to PD-3 (especially PD-1) will adversely affect the stability of subsequent devices.
[0066] Example 1 This embodiment provides an organic electroluminescent device (i.e., a blue OLED device), the structure of which is as follows: Figure 1 As shown (for example, if an encapsulation layer 102 is added, please refer to...) Figure 2 The organic electroluminescent device 100 includes an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190, which are sequentially disposed on a substrate 101. The hole injection layer 120 contains compound P25.
[0067] The above-mentioned method for fabricating organic electroluminescent devices includes the following steps: S100. After patterning the ITO substrate to achieve a light-emitting area of 2mm × 2mm, it undergoes isopropanol washing and UV / ozone irradiation. The ITO substrate is then mounted on the substrate support of the vacuum deposition apparatus, and the pressure is adjusted to achieve a vacuum rate of 1 × 10⁻⁶. -7 torr.
[0068] S200. A hole injection layer is formed on the ITO layer (anode) formed on the substrate by vacuum deposition of a mixture of compound P25 and compound HT-1 (mass ratio of compound P25 to compound HT-1 is 2:98) with a thickness of 10 nm.
[0069] S300. On the hole injection layer, a hole transport layer is formed by vacuum deposition of compound HT-1 with a thickness of 110 nm.
[0070] S400, On the hole transport layer, an electron blocking layer is formed by vacuum deposition of compound EB-1 with a thickness of 10 nm.
[0071] S500, On the electron blocking layer, a mixture of compound BD-1 and compound BH (mass ratio of compound BD-1 to compound BH is 2:98) is vacuum deposited to a thickness of 20 nm to form a light-emitting layer.
[0072] S600. On the light-emitting layer, a hole-blocking layer is formed by vacuum depositing compound HB-1 with a thickness of 5 nm.
[0073] S700, On the hole blocking layer, a mixture of compound ET-1 and compound Liq (mass ratio of compound ET-1 to compound Liq is 1:1) is vacuum deposited to a thickness of 30 nm to form an electron transport layer.
[0074] S800: On the electron transport layer, an electron injection layer is formed by vacuum deposition of LiF with a thickness of 1 nm.
[0075] S900: An organic electroluminescent device is fabricated by depositing Al with a thickness of 150 nm on the electron injection layer to form a cathode.
[0076] The molecular structural formulas of the compound materials used in each layer of this embodiment are as follows: Examples 2-11 Examples 2-11 each provide an organic electroluminescent device, the structure and preparation method of which are similar to those of Example 1, except that the compound P25 in the hole injection layer is replaced with equal masses of compounds P36, P41, P44, P115, P119, P122, P355, P359, P539, and P599, respectively. Other conditions and parameter settings are the same as in Example 1 and will not be repeated.
[0077] Comparative Examples 1-3 Comparative Examples 1-3 each provide an organic electroluminescent device, the structure and preparation method of which are similar to those of Example 1, except that the compound P25 in the hole injection layer is replaced with an equal mass of compounds PD-1 to PD-3. Other conditions and parameter settings are the same as in Example 1, and will not be repeated here.
[0078] Verification Example 2: Performance of Blue OLED Devices At J = 10 mA / cm 2 At a current density of 1000 m / s, the driving voltage (Volt) and current efficiency (CE) of the organic electroluminescent devices provided in Examples 1-11 and Comparative Examples 1-3 were tested respectively, and the results are shown in Table 2. LT95 refers to the blue OLED device at J=25mA / cm². 2 When operating, the luminous intensity drops to 95% of its initial value L0 after time LT95.
[0079] The testing instruments and methods used for the above performance tests are as follows: Brightness was tested using a PhotoResearch PR-635 spectral scanner.
[0080] Current density and turn-on voltage were tested using a Keithley 2400 digital source meter.
[0081] The lifetime testing uses a silicon optoelectronic OLED device lifetime testing system.
[0082] Table 2 Performance test results of organic electroluminescent devices As shown in Table 2, the organic electroluminescent devices (Examples 1-11) fabricated using the organic electroluminescent materials provided by this invention have lower driving voltages and longer lifetimes than those in comparative examples 1-3. This indicates that the organic electroluminescent materials of this invention have excellent hole injection capabilities as hole injection layer doping materials. Furthermore, due to the good stability of the organic electroluminescent materials provided by this invention, they have higher purity and better sublimation yield after sublimation, which is more conducive to extending the device lifetime.
[0083] In summary, the organic electroluminescent material provided by this invention has excellent hole injection layer doping capability, and the organic electroluminescent device made using this organic electroluminescent material has excellent device performance and wide application value.
[0084] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions or improvements made within the spirit and principles of the present invention should be included within the protection scope of the present invention.
Claims
1. An organic electroluminescent material, characterized in that, Its general structural formula is shown in Formula I. I In formula I, L 1 L 2 Each is independently selected from any one or any combination of two of the following: single bond, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene ring group having 3 to 30 carbon atoms; R 1 R 2 Each is independently selected from any one or any combination of two of the following: substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; R 1 R 2 At least one of them has an electron-withdrawing group; When L 1 L 2 R 1 R 2 When substituents are present, there are one or more substituents, each of which is independently selected from any one of deuterium, halogen, haloalkyl, haloalkoxy, nitroso, nitro, carbonyl, carboxylic acid, ester, cyano, isocyano, -SCN, -OCN, -SF5, cycloalkyl, boranyl, silyl, sulfinyl, sulfonyl, phosphoxy, or azirrocycloyl. In Formula I, any hydrogen atom can be independently replaced by deuterium.
2. The organic electroluminescent material as described in claim 1, characterized in that, The arylene group is selected from fused arylene groups or non-fused arylene groups; The aryl group is selected from fused aryl or non-fused aryl; The heterocyclic ring group is selected from fused heterocyclic ring groups or non-fused heterocyclic ring groups, and the heteroatom in the heterocyclic ring group is selected from any one or any combination of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom or boron atom; The heteroaromatic ring group is selected from fused heteroaromatic ring groups or non-fused heteroaromatic ring groups, and the heteroatom in the heteroaromatic ring group is selected from any one or any combination of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom or boron atom.
3. The organic electroluminescent material as described in claim 2, characterized in that, The fused arylene group is selected from naphthylene, anthracene, or phenanthrene; the non-fused arylene group is selected from phenylene or biphenylene. The fused aryl group is selected from naphthyl, anthracel, or phenanthryl; the non-fused aryl group is selected from phenyl or biphenyl. The fused heterocyclic cyclohexane group is selected from benzofuranyl, benzimidazolyl, indoleyl, quinolinyl, diazonyl, dibenzofuranyl, or o-phenanthrolineyl; the non-fused heterocyclic cyclohexane group is selected from pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrrolyl, oxazolyl, or thiazolyl. The fused heterocyclic group is selected from benzofuranyl, benzimidazolyl, indolyl, quinolinyl, diazanaphthyl, dibenzofuranyl, or o-phenanthrolineyl; the non-fused heterocyclic group is selected from pyridyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, or thiazolyl.
4. The organic electroluminescent material as described in claim 2, characterized in that, L 1 L 2 Each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted pyridinylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted triazineylene, substituted or unsubstituted furanylene, substituted or unsubstituted pyrroloylene, substituted or unsubstituted oxazolylene, substituted or unsubstituted benzofuranylene, substituted or unsubstituted benzimidazolylene, substituted or unsubstituted indoleylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted diazonaphthylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted o-phenanthrolineylene; When L 1 L 2 When substituents are present, there are one or more substituents, each independently selected from -D, -F, -CF3, -OCF3, -CN, -NO2, -t-Bu, -OCN, -SCN, -NO, -CH3, -SF5, -CD3, , , , , , , , , , , , , Or substituted phenyl; when L 1 or L 2 When the substituent is a substituted phenyl group, the substituted phenyl group may have one or more substituents, and the substituted phenyl group may be -D, -F, -OCF3, -CN, or -CF3.
5. The organic electroluminescent material as described in claim 2, characterized in that, R 1 R 2 Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted quinolinyl, or substituted or unsubstituted benzimidazolyl. When R 1 R 2 When substituents are present, there are one or more substituents, each independently selected from -D, -F, -CF3, -OCF3, -CN, -NO2, -t-Bu, -SCF3, -SF5, and -C6F. 13 -OC3F7, -OC2F5 , , Or substituted phenyl; when R 1 or R 2 When the substituent is a substituted phenyl group, the substituted phenyl group may have one or more substituents, and the substituents in the substituted phenyl group are selected from -D, -CN, -F, -CF3 or -OCF3.
6. The organic electroluminescent material according to any one of claims 1 to 5, characterized in that, L 1 L 2 Each is independently selected from a single bond or the structure shown in formulas L1 to L172. In formulas L1 to L172, any one hydrogen atom can be independently replaced by deuterium; " " indicates L 1 L 2 The connection site with the parent structure of Formula I, " indicates L 1 L 2 With R 1 R 2 Connection sites; R 1 R 2 Each is independently selected from the structures shown in formulas B1 to B160. Any hydrogen atom in formulas B1 to B160 can be independently replaced by deuterium; " " indicates R 1 R 2 With L 1 L 2 The connection site.
7. The organic electroluminescent material according to any one of claims 1 to 5, characterized in that, The organic electroluminescent material is selected from compounds with the following structures. In the above compounds, any one hydrogen atom can be independently replaced by deuterium.
8. An organic electroluminescent device, characterized in that, include: anode, cathode, And an organic layer disposed between the anode and the cathode; The organic layer comprises the organic electroluminescent material according to any one of claims 1 to 7.
9. The organic electroluminescent device as described in claim 8, characterized in that, The organic layer includes a hole injection layer or a hole transport layer; the hole injection layer or the hole transport layer is formed independently of the organic electroluminescent material alone, or is formed by a combination of the organic electroluminescent material and the hole transport material. or The organic electroluminescent device includes at least two light-emitting units, and the organic layer includes a charge generation layer disposed between the light-emitting units; the charge generation layer includes a p-type charge generation layer and an n-type charge generation layer. The p-type charge generation layer comprises the organic electroluminescent material and the hole transport material.
10. A display component, characterized in that, Including the organic electroluminescent device as described in claim 8 or 9.