Spirofluorene oxepin-based organic light-emitting device and panel
By introducing compounds with a spirofluoreneoxane structure into the functional layers on both sides of the emitting layer of an OLED device, the energy levels and carrier transport are modulated, solving the problem of unbalanced blue light transmission and improving the efficiency and lifespan of the device.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2022-12-09
- Publication Date
- 2026-03-17
AI Technical Summary
In existing OLED devices, the electron mobility of blue light materials is higher than that of holes, causing the exciton recombination region to be biased towards the electron blocking layer side, resulting in material degradation, affecting device lifetime and efficiency. Furthermore, the energy level mismatch between the functional layers on both sides of the light-emitting layer leads to transmission imbalance.
Compounds with spirofluoreneoxane structures are introduced into the functional layers on both sides of the luminescent layer. By adjusting the HOMO/LUMO energy levels of the material through different substituents, the carrier transport is balanced, the energy level difference is reduced, and the carrier injection barrier is improved.
It improves the luminous efficiency and lifetime of OLED devices, balances carrier transport, lowers the energy level barrier, and enhances the overall performance of the devices.
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Figure CN115884652B_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of organic electroluminescent device technology, and more particularly to an organic light-emitting device and panel based on spirofluoreneoxane. Background Technology
[0002] Currently, among the OLED devices on the market, red and green devices are based on phosphorescent materials, and their main light-emitting components are both dual-component materials. However, due to lagging technological development, blue light-emitting materials still use single-component fluorescent materials. The main body of the blue light-emitting layer generally uses anthracene-based materials. For the functional layers on both sides of the light-emitting layer, hole-type materials are mainly composed of aromatic amines, while electron-type materials are mainly composed of triazine derivatives.
[0003] Holes and electrons originate from the anode and cathode, respectively, and recombine in the emissive layer (EML) via the transport layer, forming 25% singlet excitons and 75% triplet excitons. Singlet excitons emit light, forming fluorescence. Because anthracene-based materials have a higher electron mobility than hole mobility, the exciton recombination region tends to shift towards the electron blocking layer. This makes the material in this layer vulnerable to exciton attack and degrades, leading to a decrease in device lifetime. Furthermore, energy level matching between the functional layers on both sides of the emissive layer is crucial for electron and hole transport. Energy level mismatch creates energy level barriers, hindering electron and hole transport and affecting device efficiency. Currently, hole-type materials are mainly composed of aromatic amines, while electron-type materials are mainly composed of triazine derivatives, leading to an imbalance in transport. Summary of the Invention
[0004] In view of this, the technical problem to be solved by the present invention is to provide an organic light-emitting device and panel based on spirofluoreneoxane, which improves the luminous efficiency, lifetime and other performance parameters of the device by adjusting the compounds of the functional layers on both sides of the light-emitting layer.
[0005] The present invention provides an organic light-emitting device based on spirofluoreneoxane, comprising a cathode, an anode, and a light-emitting layer located between the cathode and the anode, wherein a first stack is disposed between the anode and the light-emitting layer, and a second stack is disposed between the cathode and the light-emitting layer;
[0006] At least three layers in the first and second stacks contain compounds with the spirofluoroxanthracene structure shown in Formula I:
[0007]
[0008] Among them, L1, L2, L3, and L4 are independently selected from single bonds, N atoms, substituted or unsubstituted arylene or heteroarylene groups;
[0009] Ar1, Ar2, Ar3, and Ar4 are independently selected from deuterium, halogen, amino, cyano, nitro, and substituted or unsubstituted C1-30 alkyl, C2-30 alkenyl, C2-30 alkynyl, C1-30 alkoxy, C6-60 aryl, C6-60 aryl, C6-60 heteroaryl, and phosphoxy.
[0010] m, n, p, and q are independent integers selected from 0 to 4, and none of them are 0 at the same time.
[0011] The present invention provides a display panel including the above-mentioned organic light-emitting device based on spirofluoreneoxane.
[0012] This invention regulates compounds containing spirofluorenoxanthracene structures in at least three of the functional layers on both sides of the light-emitting layer. The spirofluorenoxanthracene group comprises an oxanthracene moiety and a fluorene moiety, both of which can be introduced with different substituents to adjust the HOMO / LUMO energy levels of the material, while also possessing excellent carrier transport capabilities. When the spirofluorenoxanthracene main structure is connected to a hole-transporting group, it can regulate hole transport; when it is connected to an electron-transporting group, it can regulate electron transport. When each functional layer of the light-emitting device contains a large number of spirofluorenoxanthracene structures, it can effectively regulate carrier transport. The fact that the materials on both sides of the light-emitting layer contain the same spirofluorenoxanthracene main structure reduces the energy level difference between different organic layers, lowers the injection barrier caused by the energy level difference, improves carrier transport, and thus enhances the device's efficiency and lifetime. Attached Figure Description
[0013] Figure 1 This is a schematic diagram of the structure of the organic light-emitting device provided by the present invention;
[0014] Among them, 110 is a glass substrate, 120 is an anode, 130 is a hole transport layer, 140 is an electron blocking layer, 150 is a light-emitting layer; 160 is a hole blocking layer, 170 is an electron transport layer, and 180 is a cathode. Detailed Implementation
[0015] The present invention provides an organic light-emitting device based on spirofluoreneoxane, comprising a cathode, an anode, and a light-emitting layer located between the cathode and the anode, wherein a first stack is disposed between the anode and the light-emitting layer, and a second stack is disposed between the cathode and the light-emitting layer;
[0016] At least three layers in the first and second stacks contain compounds with the spirofluoroxanthracene structure shown in Formula I:
[0017]
[0018] Among them, L1, L2, L3, and L4 are independently selected from single bonds, N atoms, substituted or unsubstituted arylene or heteroarylene groups;
[0019] Ar1, Ar2, Ar3, and Ar4 are independently selected from deuterium, halogen, amino, cyano, nitro, and substituted or unsubstituted C1-30 alkyl, C2-30 alkenyl, C2-30 alkynyl, C1-30 alkoxy, C6-60 aryl, C6-60 aryl, C6-60 heteroaryl, and phosphoxy.
[0020] m, n, p, and q are independent integers selected from 0 to 4, and none of them are 0 at the same time.
[0021] Optionally, three or four layers in the first and second stacks contain compounds with the spirofluorenexanthracene structure shown in Formula I.
[0022] Optionally, the first stack includes a hole transport layer and an electron blocking layer.
[0023] Optionally, the second stack includes a hole blocking layer and an electron transport layer.
[0024] Optionally, L1, L2, L3, and L4 are independently selected from single bonds, N atoms, substituted or unsubstituted phenylene or biphenylene.
[0025] Optionally, L1, L2, L3, and L4 can be independently selected from single bonds or N atoms.
[0026] In this invention, "single bond" refers to Ar1, Ar2, Ar3, or Ar4 being directly connected to the parent nucleus.
[0027] Optionally, Ar1, Ar2, Ar3, and Ar4 are independently selected from deuterium, halogen, amino, cyano, nitro, substituted or unsubstituted phenoxy, phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, fluorenyl, carbazoleyl, dibenzofuranyl, spirofluorenyl, or phosphoxy.
[0028] Optionally, Ar1, Ar2, Ar3, and Ar4 are independently selected from deuterium, halogen, amino, cyano, nitro, substituted or unsubstituted phenyl, triazinyl, carbazoyl, dibenzofuranyl, spirofluorenyl, and phosphooxy.
[0029] Optionally, the substituents in Ar1, Ar2, Ar3, and Ar4 are independently selected from one or more of deuterium, halogen, cyano, nitro, monocyclic aryl, monocyclic heteroaryl, and C1 to C10 alkyl groups.
[0030] Optionally, the substituents in Ar1, Ar2, Ar3, and Ar4 are independently selected from one or more of deuterium, halogen, cyano, phenyl, pyridyl, and C1-C5 alkyl groups.
[0031] The aforementioned phenyl, pyridyl, and C1-C5 alkyl groups can be further substituted with deuterium, cyano, phenyl, or pyridyl.
[0032] Optionally, the substituents in Ar1, Ar2, Ar3, and Ar4 are independently selected from one or more of deuterium, cyano, phenyl, pyridyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl, ethyl, n-propyl, and isopropyl.
[0033] Optionally, the compounds with the above-mentioned spirofluorenexanthracene structure have any of the following structures:
[0034]
[0035]
[0036] Optionally, the organic material in the n1 layer of the first stack is selected from compounds with the spirofluorenexanthracene structure shown in Formula I, where Ar1, Ar2, Ar3, and Ar4 in Formula I are independently selected from any of the following structures:
[0037]
[0038] Optionally, the organic material in the n2 layer of the second stack is selected from compounds with the spirofluorenexanthracene structure shown in Formula I, where Ar1, Ar2, Ar3, and Ar4 in Formula I are independently selected from any of the following structures:
[0039]
[0040] The curved line indicates the connection point;
[0041] n1 and n2 are independently chosen from 1 or 2, and the sum of n1 and n2 is greater than or equal to 3.
[0042] Optional, n1 is 1, n2 is 2.
[0043] Optional, n1 is 2, and n2 is 1 or 2.
[0044] Optionally, both n1 and n2 are 2.
[0045] Optionally, the organic material in the n1 layer of the first stack is selected from any of the following compounds:
[0046]
[0047] Optionally, the organic material in the n2 layer of the second stack is selected from any of the following compounds:
[0048]
[0049] Optionally, the first stack includes a hole transport layer and an electron blocking layer; the hole transport layer contains the following compounds:
[0050]
[0051] The electron blocking layer contains the following compounds:
[0052]
[0053] Optionally, the second stack includes a hole-blocking layer and an electron transport layer; the hole-blocking layer contains the following compounds:
[0054]
[0055] The electron transport layer contains the following compounds:
[0056]
[0057] The above combination, by introducing different substituents into the spirofluoreneoxane host core in different functional layers, can finely tune the HOMO and LUMO energy levels of each functional layer material, so that the molecular energy levels between the functional layer materials are matched with each other, which is conducive to the transport of charge carriers. At the same time, the introduction of different substituents can effectively tune the mobility of each functional layer material, thereby making the transport of holes and electrons more balanced, and thus enabling the device to obtain excellent performance.
[0058] Optionally, the host material of the light-emitting layer includes aromatic amine compounds represented by Formula II and anthracene compounds represented by Formula III;
[0059]
[0060] Among them, R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.
[0061] L5, L6, and L7 are independently selected from single-bonded, substituted, or unsubstituted C6-C60 aryl groups;
[0062] Ar5 and Ar6 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, C1-C40 silyl, C6-C60 aryl, and C3-C60 heteroaryl.
[0063] R3 is selected from substituted or unsubstituted phenyl, naphthyl, biphenyl, phenanthryl, carbazolyl, or dibenzofuranyl.
[0064] Optionally, the lowest unoccupied molecular orbital energy level of the aromatic amine compound represented by Formula II is greater than or equal to -2 eV and less than or equal to -2.7 eV.
[0065] Optionally, the lowest unoccupied molecular orbital energy level of the anthracene compounds represented by Formula III is greater than or equal to -2.7 eV and less than or equal to -3.2 eV.
[0066] Optionally, the highest unoccupied molecular orbital energy level of the aromatic amine compound represented by Formula II is greater than or equal to -5.4 eV and less than or equal to -6.0 eV.
[0067] Optionally, the highest unoccupied molecular orbital energy level of the anthracene compounds represented by Formula III is greater than or equal to -5.6 eV and less than or equal to -6.0 eV.
[0068] Optionally, R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1 to C5 alkyl groups.
[0069] Optionally, R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl.
[0070] Optionally, the substituents of the C1 to C5 alkyl groups are selected from deuterium, halogen, nitro or cyano.
[0071] Optionally, the substituents of R1 and R2 are selected from one or more of deuterium, halogen, cyano, and nitro.
[0072] Optionally, L5, L6, and L7 are independently selected from single-bonded, substituted, or unsubstituted phenylene compounds.
[0073] When L5 is selected as a single bond, it means that the fluorenyl group on the left side of L5 and the biphenyl group on the right side are directly connected.
[0074] When L6 and L7 are selected from single bonds, it means that Ar5 and Ar6 are directly connected to N atoms.
[0075] Optionally, Ar5 and Ar6 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted phenyl, biphenyl, carbazolyl, dibenzofuranyl, fluorenyl, and spirofluorenyl.
[0076] Optionally, the substituents in Ar5 and Ar6 are independently selected from one or more of deuterium, halogen, cyano, nitro, C1-C5 alkyl, and phenyl.
[0077] Optionally, the substituents in Ar5 and Ar6 are independently selected from one or more of deuterium, halogen, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and phenyl.
[0078] Optionally, the aromatic amine compounds represented by Formula II have any of the following structures:
[0079]
[0080]
[0081] Optionally, the anthracene compounds represented by Formula III have any of the following structures:
[0082]
[0083] Optionally, the host material of the luminescent layer includes compounds P-3 and N-2.
[0084] Optionally, the mass ratio of compound P-3 to compound N-2 is 5:5.
[0085] Optionally, the host material of the luminescent layer includes compounds P-2 and N-3.
[0086] Optionally, the mass ratio of compound P-2 to compound N-3 is 5:5.
[0087] This invention employs a dual-component blue light-emitting material, consisting of a P-type component and an N-type component. The P-type component is an aromatic amine material as shown in Formula II, and the N-type component is an anthracene material as shown in Formula III. The combination of the two has a small ΔEst, allowing triplet excitons to cross through the antigap to form singlet excitons, which are then transferred to the fluorescent doping material via Forster energy. This significantly improves exciton utilization. Because anthracene-based materials are electronic materials, when charge carriers recombine in the emitting layer to form excitons, the exciton recombination region tends to be biased towards the electron blocking layer, making the electron blocking layer vulnerable to exciton attacks, leading to material degradation and affecting device lifetime. Using the aforementioned composite material can significantly move the exciton recombination region away from the electron blocking layer, thereby further improving device efficiency and lifetime.
[0088] Experimental results show that the combination of the above-mentioned P-type and N-type components results in a spectral λ that is 20 nm or longer redshifted than that of the single-component spectral composition, making it more suitable as a blue light host material.
[0089] The organic electroluminescent device provided by the present invention can be an organic light-emitting device well known to those skilled in the art. Optionally, the organic light-emitting device includes: a substrate, an indium tin oxide (ITO) layer on a glass substrate as an anode, a hole injection layer HIL (optional, thickness of 5-30 nm), a hole transport layer HTL (optional, thickness of 100-2000 nm), an electron cathode layer EBL (optional, thickness of 5-100 nm), an emissive layer EML (optional, thickness of 20-100 nm), a hole blocking layer HBL (optional, thickness of 5-100 nm), an electron transport layer ETL (optional, thickness of 20-100 nm), an electron injection layer EIL (optional, thickness of 1-10 nm), and a cathode.
[0090] Optionally, the organic electroluminescent device structure is as follows:
[0091] ITO / HIL(10nm) / HTL(100nm) / EBL(10nm) / Host:Dopant(1:1,3wt%,20nm) / HBL(5nm) / ETL:LIQ(1:1,30nm) / EIL(1nm) / Cathode(100nm).
[0092] Optionally, the anode material of the organic electroluminescent device can be selected from metals such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and their alloys; metal oxides such as indium oxide, zinc oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); and conductive polymers such as polyaniline, polypyrrole, and poly(3-methylthiophene). In addition to the above-mentioned hole injection materials and combinations thereof, it also includes known materials suitable for anodes.
[0093] Optionally, the cathode material of the organic electroluminescent device can be selected from metals such as aluminum, magnesium, silver, indium, tin, titanium, and their alloys; such as multilayer metal materials such as LiF / Al, LiO2 / Al, BaF2 / Al, etc.; in addition to the above materials and combinations that facilitate electron injection, it also includes known materials suitable for use as cathodes.
[0094] Optionally, the organic thin film layer in the organic electroluminescent device has at least one light-emitting layer (EML) and an electron transport layer (ETL), and may also include other functional layers, including a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a hole blocking layer (HBL), and an electron injection layer (EIL).
[0095] Optional materials for each functional layer include, but are not limited to, the following:
[0096] 1. HIL: can be an inorganic oxide, such as MoO3, F4-TCNQ, HAT-CN, etc., but is not limited to these.
[0097] 2. HTL: Aromatic amine or carbazole materials with hole transport properties, such as NPB, m-MTDATA, TPD, etc., as well as the compounds provided in this invention, but not limited thereto.
[0098] 3. EBL: Aromatic amine or carbazole materials with hole transport properties, such as mCBP, Tris-PCz, etc., as well as compounds provided in this invention, but not limited thereto.
[0099] 4. Host: AND, TBADN, MADN, compounds of the present invention, etc., but not limited thereto.
[0100] 5. Dopant: Dpvbi, DPAVB, DSA-Ph, etc., but not limited to these.
[0101] 6. HBL: Hole blocking layer is generally an aromatic heterocyclic compound, such as BCP, Bphen, etc., as well as the compound provided in this invention, but is not limited thereto.
[0102] 7. ETL: The electron transport layer is generally an aromatic heterocyclic compound, such as TPBi, Bphen, etc., as well as the compounds provided in this invention, but is not limited thereto.
[0103] 8. EIL: Generally an alkali metal or a metal, such as LiF, Yb, or LIQ, but not limited to these.
[0104] Optionally, the organic light-emitting device of the present invention is prepared according to the following method:
[0105] An anode is formed on a smooth, transparent or opaque substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer.
[0106] Optionally, the organic thin layer can be formed using known film-forming methods such as vapor deposition, sputtering, spin coating, immersion, and ion plating.
[0107] Optionally, the above-mentioned organic electroluminescent device is a blue light device.
[0108] In this invention, the aforementioned organic electroluminescent device (OLED device) can be used in a display device, wherein the organic light-emitting display device can be a mobile phone display screen, a computer display screen, a television display screen, a smartwatch display screen, a smart car display panel, a VR or AR helmet display screen, a display screen of various smart devices, etc.
[0109] The present invention provides a display panel including the above-mentioned organic light-emitting device based on spirofluoreneoxane.
[0110] The present invention also provides a display device, including the above-described display panel.
[0111] 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 of ordinary skill in the art without creative effort are within the scope of protection of the present invention.
[0112] Examples 1-3
[0113] The fabrication process of organic electroluminescent devices is as follows:
[0114] (1) The glass plate with ITO was ultrasonically treated in a cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone-ethanol mixed solvent, and baked in a clean environment until all moisture was removed.
[0115] (2) Place the glass substrate with the anode into a vacuum chamber and evacuate to a vacuum level of 1x10 to 1x10. -5 Pa, a hole injection layer is vacuum-deposited on the above-mentioned anode layer film to form a hole injection material;
[0116] (3) Hole transport material is vapor-deposited on the hole injection layer to form a hole transport layer;
[0117] (4) Vacuum evaporation deposition of an electron blocking layer with hole transport capability on the hole transport layer;
[0118] (5) A light-emitting layer of a device is vacuum-deposited on an electron blocking layer. The light-emitting layer includes a host material and a guest material. The weight ratio of the host material to the guest material is 97:3 using a multi-source co-evaporation method.
[0119] (6) Vacuum evaporation of a hole blocking layer for the device on the light-emitting layer;
[0120] (7) Vacuum evaporation of an electron transport layer for a device on a hole blocking layer;
[0121] (8) A 0.5 nm thick LiF layer was vacuum-deposited on the electron transport layer (ETL) as an electron injection layer;
[0122] (9) An Al layer is deposited on the electron injection layer as the cathode of the device.
[0123] Comparative Examples 1-6
[0124] The preparation method is the same as in Examples 1-3.
[0125] The material structures of each functional layer in an OLED device are as follows:
[0126]
[0127] The material structures of each layer (HTL, EBL, HOST, HBL, ETL) in each embodiment and comparative example are shown in Table 1.
[0128] Table 1
[0129]
[0130] The performance results of the organic light-emitting diodes prepared in the above embodiments and comparative examples, tested at a fixed current density, are shown in Table 2 below.
[0131] Table 2
[0132] Example Voltage efficiency life CIEx CIEy Example 1 94.53% 110.67% 116.37% 0.134 0.121 Example 2 96.22% 103.41% 108.99% 0.134 0.125 Example 3 97.74% 103.12% 104.76% 0.133 0.122 Comparative Example 1 98.55% 101.98% 102.01% 0.135 0.121 Comparative Example 2 99.84% 99.01% 101.89% 0.135 0.123 Comparative Example 3 101.89% 102.63% 98.76% 0.134 0.119 Comparative Example 4 101.46% 99.68% 99.05% 0.134 0.123 Comparative Example 5 100.77% 101.33% 101.79% 0.134 0.121 Example 4 94.83% 112.86% 118.67% 0.134 0.121 Example 5 96.62% 103.41% 107.69% 0.134 0.125 Example 6 97.32% 106.12% 107.16% 0.133 0.122 Comparative Example 6 98.85% 101.18% 102.31% 0.135 0.121 Comparative Example 7 99.87% 99.62% 102.17% 0.135 0.123 Comparative Example 8 101.68% 102.13% 98.67% 0.134 0.120 Comparative Example 9 101.37% 99.28% 99.36% 0.134 0.123 Comparative Example 10 100.69% 101.53% 101.19% 0.134 0.121 Comparative Example 11 100% 100% 100% 0.134 0.121
[0133] As can be seen from Table 2 above, when three of the hole transport layer, electron blocking layer, hole blocking layer, and electron transport layer contain compounds with a spirofluorenoxanthracene structure, the device exhibits lower voltage and higher efficiency and lifetime. When all four layers contain compounds with a spirofluorenoxanthracene structure, the device's efficiency and lifetime are further improved, and the voltage is further reduced. When a specific PN material combination is used as the main body of the light-emitting layer and matched with the aforementioned hole transport layer, electron blocking layer, hole blocking layer, and electron transport layer, the device exhibits even better efficiency and lifetime, as well as lower voltage.
[0134] The above description of the embodiments is only for the purpose of helping to understand the method and core ideas of the present invention. It should be noted that those skilled in the art can make several improvements and modifications to the present invention without departing from the principles of the present invention, and these improvements and modifications also fall within the protection scope of the claims of the present invention.
Claims
1. An organic light emitting device based on spirofluorene xanthene, characterized in that, The organic light emitting device comprises a cathode, an anode, and a light emitting layer between the cathode and the anode, a first stack is arranged between the anode and the light emitting layer, and a second stack is arranged between the cathode and the light emitting layer. The n1 layers of organic matter in the first stack are selected from any one of the following compounds: 、 、 、 、 ; The n2 layers of organic matter in the second stack are selected from any one of the following compounds: 、 、 、 、 、 、 、 ; The n1 and n2 are independently selected from 1 or 2, and the sum of n1 and n2 is greater than or equal to 3.
2. The spirofluorene-based oxepin organic light-emitting device according to claim 1, characterized in that, The first stack comprises a hole transport layer and an electron blocking layer. The hole transport layer contains the following compound: or ; The electron blocking layer contains the following compound: or ; The second stack comprises a hole blocking layer and an electron transport layer. The hole blocking layer contains the following compound: or ; The electron transport layer contains the following compound: or .
3. The spirofluorene-based oxepin organic light-emitting device according to claim 1, characterized in that, The host material of the light emitting layer comprises an arylamine compound represented by Formula II and an anthracene compound represented by Formula III. Formula II; Formula III; R1, R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl; L5, L6, L7 are independently selected from a single bond, substituted or unsubstituted C6-C60 arylene; Ar5, Ar6 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, C1-C40 silyl, C6-C60 aryl, C3-C60 heteroaryl; R3 is selected from substituted or unsubstituted phenyl, naphthyl, biphenyl, phenanthryl, carbazolyl or dibenzofuranyl.
4. The spirofluorene-based oxepin organic light-emitting device according to claim 3, characterized in that, The lowest unoccupied molecular orbital energy level (LUMO energy level) of the arylamine compound represented by Formula II is greater than or equal to -2 eV and less than or equal to -2.7 eV; The lowest unoccupied molecular orbital energy level (LUMO energy level) of the anthracene compound represented by Formula III is greater than or equal to -2.7 eV and less than or equal to -3.2 eV.
5. The spirofluorene-based oxepin organic light emitting device according to claim 3, wherein The highest occupied molecular orbital energy level (HOMO energy level) of the arylamine compound represented by Formula II is greater than or equal to -5.4 eV and less than or equal to -6.0 eV; The highest occupied molecular orbital energy level (HOMO energy level) of the anthracene compound represented by Formula III is greater than or equal to -5.6 eV and less than or equal to -6.0 eV.
6. The spirofluorene-based oxepin organic light-emitting device according to claim 3, wherein R1, R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C5 alkyl; L5, L6, L7 are independently selected from a single bond, substituted or unsubstituted phenylene; Ar5, Ar6 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted phenyl, biphenyl, carbazolyl, dibenzofuranyl, fluorenyl, spirofluorenyl; The substituents in Ar5, Ar6 are independently selected from one or more of deuterium, halogen, cyano, nitro, C1-C5 alkyl, phenyl.
7. The spirofluorene-based oxepin organic light-emitting device according to claim 6, characterized in that, The arylamine compound represented by Formula II has any one of the following structures: 、 、 。 8. The spirofluorene-based oxepin organic light-emitting device according to claim 3, wherein The anthracene compound represented by Formula III has any one of the following structures: 、 、 。 9. A display panel comprising the spirofluorene xanthene-based organic light emitting device according to any one of claims 1-8.
Citation Information
Patent Citations
Spirofluorenexanthenyl derivatives and organic electroluminescent device including the same
CN108218842A