CN113372361B - Organic compound and application thereof - Google Patents
Organic compound and application thereof Download PDFInfo
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Abstract
The invention provides an organic compound and application thereof, wherein the organic compound has a structure shown in a formula I, the structure of the compound provided by the invention can achieve the purpose of electron transmission, and the compound has a deeper LUMO value, can smoothly inject electrons, reduces injection potential barrier and further reduces voltage; the organic electroluminescent device has a high triplet state energy level, so that excitons in a light emitting layer can be limited in the light emitting layer, the exciton utilization rate is improved, and the device efficiency is further improved; the spiro structure can reduce intermolecular stacking, improve compound solubility, and the like. When the compound is used for manufacturing an OLED device, an amorphous film form can be presented, and degradation or attenuation caused by light scattering or crystallization induction is avoided; the uniformity of the formed film is good, and the film has no pinhole.
Description
Technical Field
The invention belongs to the field of organic electroluminescent materials, and relates to an organic compound and application thereof.
Background
The electron transport material (ETL) used in conventional electroluminescent devices is Alq3, but the electron mobility of Alq3 is relatively low (approximately at l 0) -6 cm 2 Vs) such that electron transport and hole transport of the device are not balanced. Most of the electron transport materials currently used in the market, such as batho-phenanthroline (BPhen), bathocuproine (BCP) and TmPyPB, can substantially meet the market demand of organic electroluminescent panels, but their glass transition temperature is low, generally less than 85 ℃, and the generated joule heat during device operation can cause molecular degradation and change of molecular structure, resulting in low panel efficiency and poor thermal stability. Meanwhile, the molecular structure is symmetrical and regular, and the crystal is easy to crystallize after a long time. Once the electron transport material is crystallized, the intermolecular charge jump 36800mechanism is different from the normally operating amorphous thin film mechanism, so that the electron transport performance is reduced, the electron and hole mobility of the whole device is unbalanced, the exciton formation efficiency is greatly reduced, and the exciton formation is concentrated at the interface of the electron transport layer and the light emitting layer, so that the device efficiency and the service life are seriously reduced.
Therefore, with the commercialization and practical use of electroluminescent devices, it is desired to obtain ETL materials with higher transmission efficiency and better usability, and researchers have made a lot of exploratory work in this field.
Patent applications in LG chemistry (W0 2007/011170Al and CN 101003508A) report a series of naphthoimidazole and pyrene derivatives, respectively, as electron transport and injection materials in electroluminescent devices, improving the luminous efficiency of the devices.
Kodak applications (publication nos. US 2006/0204784 and US 2007/0048545) mention hybrid electron transport layers, doped with one material with a low LUMO energy level and another electron transport material with a low ignition voltage and other materials such as metallic materials. The efficiency, the service life and the like of the device based on the mixed electron transport layer are improved.
Therefore, the electronic transmission material and/or the electronic injection material which are stably and efficiently designed and developed, have high electron mobility and high glass transition temperature, and are effectively doped with metal Yb or Liq are/is designed, the working voltage is reduced, the efficiency of the device is improved, the service life of the device is prolonged, and the electronic transmission material and/or the electronic injection material have important practical application values.
Disclosure of Invention
In view of the shortcomings of the prior art, the present invention aims to provide an organic compound and its application.
In order to achieve the purpose, the invention adopts the following technical scheme:
it is an object of the present invention to provide an organic compound having the structure of formula I:
wherein X is selected from-O, -S, -N (R) 1 )，R 1 Selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C5-C20 heteroaryl;
y is selected from-O or-S;
Z 1 -Z 5 independently selected from a C or N atom;
r is independently selected from cyano, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C2-C40 heteroaryl;
ar is independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C40 aryl or substituted or unsubstituted C2-C40 heteroaryl;
n 1 an integer selected from 1-5 (e.g., 1, 2, 3, 4, 5), n 2 An integer selected from 0-3 (e.g., 0, 1, 2, 3).
In the present invention, C1 to C20 may be C2, C3, C4, C5, C6, C8, C10, C12, C13, C14, C15, C16, C18, C19, or the like.
The C6-C40 can be C6, C8, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C32, C35, C38, C39, and the like.
The C3-C20 can be C4, C5, C6, C8, C10, C12, C13, C14, C15, C16, C18, C19, etc.
The C5-C20 can be C6, C8, C10, C12, C13, C14, C15, C16, C18, C19 and the like.
The C2-C40 can be C3, C4, C5, C6, C8, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C32, C35, C38, C39, and the like.
In the present invention, the halogen includes F, cl, br or I.
The compound provided by the invention has a skeleton structure of heteroanthracene spirofluorene heterocyclic rings, and other groups such as linker and R are connected on the skeleton, so that the compound has a deep enough LUMO energy level, is beneficial to electron transmission, and reduces potential barriers of charge injection and transmission, thereby obtaining lower device voltage; the material has a proper HOMO energy level, so that the material has certain hole blocking capability; the organic electroluminescent material has a high triplet state energy level, can effectively block excitons of a light emitting layer, limits the excitons in the light emitting layer, and improves the utilization rate of the excitons; the spiro structure of the compound can reduce intermolecular stacking, further improve the solubility of the compound and simultaneously ensure that the compound has higher glass transition temperature T g And thermal decomposition temperature T d The film is in an amorphous film form, degradation or attenuation caused by light scattering or crystallization induction is avoided, the uniformity of the formed film is good, and the formed film is free of pinholes and is more stable in device operation.
It is a second object of the present invention to provide an electron transport material comprising the organic compound according to the first object.
It is a further object of the present invention to provide a hole blocking material comprising an organic compound according to one of the objects.
It is a fourth object of the present invention to provide an OLED device comprising an anode, a cathode and an organic thin film layer between the anode and the cathode, the material of the organic thin film layer comprising an organic compound according to one of the objects.
The fifth object of the present invention is to provide a display panel including the OLED device of the fourth object.
The sixth object of the present invention is to provide an electronic device, which includes the display panel according to the fifth object.
Compared with the prior art, the invention has the following beneficial effects:
the compound provided by the invention has a skeleton structure of heteroanthracene spirofluorene heterocyclic rings, and other groups such as linker and R are connected on the skeleton, so that the compound has a deep enough LUMO energy level, is beneficial to electron transmission, and reduces potential barriers of charge injection and transmission, thereby obtaining lower device voltage; the material has a proper HOMO energy level, so that the material has certain hole blocking capability; the organic electroluminescent material has a high triplet state energy level, can effectively block excitons of a light emitting layer, limits the excitons in the light emitting layer, and improves the utilization rate of the excitons; the spiro structure of the compound can reduce intermolecular stacking, further improve the solubility of the compound, and meanwhile, the compound has higher glass transition temperature T g And thermal decomposition temperature T d The film is in an amorphous film form, degradation or attenuation caused by light scattering or crystallization induction is avoided, the uniformity of the formed film is good, and the film is pinhole-free and is more stable in device operation.
Drawings
Fig. 1 is a schematic structural diagram of an OLED device of the present invention, in which 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode, and an arrow represents a light emitting direction of the device.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitation of the present invention.
One object of the present invention is to provide an organic compound having the structure of formula I:
wherein X is selected from-O, -S, -N (R) 1 )，R 1 Selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C5-C20 heteroaryl;
y is selected from-O or-S;
Z 1 -Z 5 independently selected from a C or N atom;
r is independently selected from cyano, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C2-C40 heteroaryl;
ar is independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted C3-C20 cyclic alkyl, substituted or unsubstituted C6-C40 aryl or substituted or unsubstituted C2-C40 heteroaryl;
n 1 an integer selected from 1-5 (e.g., 1, 2, 3, 4, 5), n 2 An integer selected from 0-3 (e.g., 0, 1, 2, 3).
In the present invention, C1 to C20 may be C2, C3, C4, C5, C6, C8, C10, C12, C13, C14, C15, C16, C18, C19, or the like.
The C6 to C40 may be C6, C8, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C32, C35, C38, C39, etc.
The C3-C20 can be C4, C5, C6, C8, C10, C12, C13, C14, C15, C16, C18, C19 and the like.
The C5-C20 can be C6, C8, C10, C12, C13, C14, C15, C16, C18, C19 and the like.
The C2 to C40 may be C3, C4, C5, C6, C8, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C32, C35, C38, C39, etc.
In the present invention, the term "aryl" includes monocyclic or polycyclic (e.g., 2, 3, 4, or 5, etc. fused rings) aryl groups, illustratively including, but not limited to: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, anthracenyl indenyl, phenanthryl, pyrenyl, acenaphthenyl, triphenylene,
An acenaphthenyl group, a peryleneyl group, or the like.
The same description is referred to below, all having the same meaning.
The heteroatom in the term "heteroaryl" includes O, S, N, P, B, or Si, etc.; heteroaryl includes monocyclic or polycyclic (e.g., 2, 3, 4, or 5 fused rings) heteroaryl, illustratively including but not limited to: pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzopyrazinyl, pyridopyridyl, pyridopyrazinyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, benzimidazolyl, or phenanthrolinyl, and the like. The same description is referred to below, all having the same meaning.
In the present invention, the halogen includes F, cl, br or I. The same description is referred to below, all having the same meaning.
The compound provided by the invention has a skeleton structure of heteroanthracene spirofluorene heterocyclic rings, and other groups such as linker and R are connected on the skeleton, so that the compound has a deep enough LUMO energy level, is beneficial to electron transmission, and reduces potential barriers of charge injection and transmission, thereby obtaining lower device voltage; the material has a proper HOMO energy level, so that the material has certain hole blocking capability; utensil for cleaning buttockThe higher triplet state energy level is prepared, excitons of the light emitting layer can be effectively blocked and limited in the light emitting layer, and the exciton utilization rate is improved; the spiro structure of the compound can reduce intermolecular stacking, further improve the solubility of the compound, and meanwhile, the compound has higher glass transition temperature T g And thermal decomposition temperature T d The film is in an amorphous film form, degradation or attenuation caused by light scattering or crystallization induction is avoided, the uniformity of the formed film is good, and the film is pinhole-free and is more stable in device operation.
In one embodiment, X is selected from-O.
In one embodiment, ar is selected from hydrogen or-CN.
In one embodiment, Z 1 -Z 5 At least one of which is an N atom. For example Z 1 -Z 5 One of them being an N atom, or Z 1 -Z 5 Wherein both are N atoms, or Z 1 -Z 5 The three are N atoms.
In one embodiment, Z 1 -Z 5 All are C atoms, i.e., the organic compound has the structure shown in formula II:
wherein R is independently selected from cyano, substituted or unsubstituted aryl of C6 to C40 (e.g., C6, C8, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C32, C35, C38, C39, etc.), substituted or unsubstituted heteroaryl of C2 to C40 (e.g., C3, C4, C5, C6, C8, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C32, C35, C38, C39, etc.), n 1 An integer selected from 1 to 5 (e.g., 1, 2, 3, 4, 5), X, Y, ar and n 2 Having the same limitations as in formula I.
In one embodiment of the method of the present invention,
is selected from
Any one of the above; wherein R is 2 Is cyano or azaheterocyclyl, m is an integer from 0 to 4 (e.g., 0, 1, 2, 3, 4), X 1 Is an O atom, an S atom or
X 1 -X 10 Is selected from C or N, and X 1 -X 5 At least one of them is N, X 6 -X 10 At least one of which is N; r 3 、R 4 Independently selected from hydrogen or cyano, n 3 Is an integer of 0 to 5 (e.g., 0, 1, 2, 3, 4, 5), n 4 Is an integer of 0 to 5 (e.g., 0, 1, 2, 3, 4, 5), R 5 Is hydrogen, cyano-substituted phenyl or cyano-substituted pyridyl,
X 11 -X 16 Is selected from C or N, and X 11 -X 16 At least two of which are N, R 6 And R 7 Independently selected from phenyl, pyridyl, cyano-substituted phenyl or cyano-substituted pyridyl, n 6 Is an integer of 0 to 5 (e.g. 0, 1, 2, 3, 4, 5), n 7 Is an integer from 0 to 5 (e.g., 0, 1, 2, 3, 4, 5), and the wavy line represents the attachment site of the group.
In one embodiment, the organic compound is any one of the following compounds:
in the present invention, the organic compound having the structure shown in formula I can be prepared by the following synthetic route:
it is a second object of the present invention to provide an electron transport material comprising the organic compound according to the first object.
It is a further object of the present invention to provide a hole blocking material comprising an organic compound according to one of the objects.
It is a fourth object of the present invention to provide an OLED device comprising an anode, a cathode and an organic thin film layer between the anode and the cathode, the material of the organic thin film layer comprising an organic compound according to one of the objects.
In one embodiment, the organic thin film layer comprises an electron transport layer, the material of which comprises an organic compound as described in one of the objects.
In one embodiment, the organic thin film layer includes a hole blocking layer, and a material of the hole blocking layer includes an organic compound according to one of the objects.
In the OLED device provided by the invention, the anode material can be metal, metal alloy, metal oxide or conductive polymer; wherein the metal includes copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc., the metal alloy includes an alloy of at least two of copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc., the metal oxide includes indium oxide, zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), etc., and the conductive polymer includes polyaniline, polypyrrole, poly (3-methylthiophene), etc. In addition to the materials described above and combinations thereof that facilitate hole injection, materials known to be suitable for use as anodes are also included.
In the OLED device, the cathode material can be metal, metal alloy or multilayer metal material; wherein the metal comprises aluminum, magnesium, silver, indium, tin, titanium and the like, the alloy is formed by at least two of aluminum, magnesium, silver, indium, tin and titanium, and the multilayer metal material comprises LiF/Al and LiO 2 /Al、BaF 2 Al, etc. In addition to the materials described above and combinations thereof that facilitate electron injection, materials known to be suitable for use as cathodes are also included.
In the OLED device, the organic thin film layer includes at least one light emitting layer (EML), and may further include other functional layers, for example, any one or a combination of at least two of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Injection Layer (EIL), and an Electron Injection Layer (EIL).
The OLED device can be prepared by the following method: an anode is formed on a transparent or opaque smooth substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer. Among them, known film forming methods such as evaporation, sputtering, spin coating, dipping, ion plating, and the like can be used to form the organic thin layer.
The fifth object of the present invention is to provide a display panel including the OLED device of the fourth object.
The sixth object of the present invention is to provide an electronic device, which includes the display panel according to the fifth object.
The following examples are exemplary of several organic compounds of the present invention:
preparation of Compounds 1-9
(1)
Under nitrogen atmosphere, adding anhydrous DMSO into a reaction flask, then adding reactant a-1 (4 mmol), reactant 1-1 (4 mmol) and cesium carbonate (8 mmol) in sequence, heating to 180 ℃, and reacting overnight. After the reaction is finished, cooling to room temperature, adding dichloromethane/H2O for extraction, and collecting the organic phase by using anhydrous Na 2 SO 4 Drying, collecting filtrate by suction filtration, removing solvent by rotation, and purifying by column chromatography to obtain intermediate b-1 (yield 75%).
MALDI-TOF (m/z): calcd for C13H7BrN2O: 285.97, found: 286.20.
(2)
under nitrogen atmosphere, in a reaction flask with toluene: ethanol: water =7, 1, about 80mL of reaction solvent was added, followed by the sequential addition of K 2 CO 3 (5 mmol) aq, intermediate reactant b-1 (2 mmol), reactant 2-1 (2 mmol), and Pd (PPh) 3 ) 4 (0.1 mmol), the temperature was raised to 80 ℃ and the reaction was carried out overnight. After the reaction is finished, cooling to room temperature, adding dichloromethane/H2O for extraction, and using anhydrous Na for collected organic phase 2 SO 4 Drying, collecting filtrate by suction filtration, removing solvent by rotation and purifying by column chromatography to obtain intermediate c-1 (yield 76%).
MALDI-TOF (m/z): calcd for C19H11BrN2O: 362.01, found: 362.25.
(3)
under nitrogen atmosphere, adding the intermediate compound c-1 (1 mmol) into anhydrous THF, stirring and cooling at-78 ℃, dropwise adding 1.6M n-BuLi (1.1 mmol) and reacting for 2h at-78 ℃; slowly dropwise adding the compound 3-1 (1.2 mmol) into the low-temperature reaction liquid, and continuing to react for 2 hours at low temperature after the dropwise adding is finished, and then standing overnight at room temperature. Quenching with small amount of water, extracting with DCM/H2O, collecting organic phase and extracting with anhydrous Na 2 SO 4 Drying, filtering, collecting filtrate, and removing solvent to obtain crude product;
the crude product is added into acetic acid under nitrogen, stirred and heated, and reacted for 2 hours at 120 ℃, and then hydrochloric acid is added, and the reaction is heated and reacted for 12 hours at the temperature. Cooling and extraction, collection of the organic phase and removal of the solvent by rotation, purification by column chromatography gave intermediate d-1 (68% yield).
MALDI-TOF (m/z): calcd for C32H18N2O2: 462.14, found: 462.35.
(4)
under nitrogen atmosphere, adding acetic acid into a reaction bottle, then adding a reactant d-1 (1 mmol), N-iodosuccinimide (1.5 mmol) and trifluoroacetic acid, and heating for reacting overnight. After the reaction is complete, cooling and adding dichloromethane/H 2 Extracting with O, and collecting organic phase with anhydrous Na 2 SO 4 Drying, collecting the filtrate by suction filtration, removing the solvent by rotation, and purifying by column chromatography to obtain intermediate e-1 (yield 75%).
MALDI-TOF (m/z): calcd for C32H17IN2O2: 588.03, found: 588.30.
(5)
adding 1, 4-dioxane solvent into a reaction bottle under the nitrogen atmosphere, and then sequentially adding K 2 CO 3 (2.5 mmol) aq, intermediate e-1 (1 mmol), reaction A1 (1.2 mmol), and Pd (PPh) 3 ) 4 (0.05 mmol), the temperature was raised to 100 ℃ and the reaction was carried out overnight. After the reaction is finished, cooling to room temperature, adding dichloromethane/H 2 Extracting with O, and collecting organic phase with anhydrous Na 2 SO 4 Drying, collecting filtrate by suction filtration, removing solvent by rotation and purifying by column chromatography to obtain compound 1 (yield 75%).
MALDI-TOF (m/z): calcd for C47H27N5O2: 693.22, found: 693.45.
elemental analysis (%): calcd for C47H27N5O2: c81.37, H3.92, N10.09; test values: c81.36, H3.91, N10.12.
The following compounds in table 1 were synthesized according to the above-described analogous method:
TABLE 1
Simulated calculation of compound energy levels:
by applying Density Functional Theory (DFT), aiming at the organic compound provided by the embodiment of the invention, the distribution of molecular front line orbitals HOMO and LUMO is obtained through optimization and calculation by Guassian 09 package (Guassian Inc.) at the calculation level of B3LYP/6-31G (d), and the lowest singlet energy level S of the compound molecule is calculated based on time-containing density functional theory (TD-DFT) simulation 1 And the lowest triplet level T 1 The results are shown in table 2 below.
TABLE 2
As can be seen from Table 2, the compounds provided by the invention have deeper LUMO energy levels (-1.75 to-1.95 eV), can reduce the potential barrier of electron transport, improve the injection capability of electrons, and effectively reduce the voltage of OLED devices; the compounds have deeper HOMO energy level (-5.54-5.77 eV), which can effectively block holes and enable more holes-electrons to be compounded in a light emitting region; meanwhile, the compounds all have higher triplet state energy level (E) T1 Not less than 2.80 eV), which can block excitons of the light emitting layer and improve the exciton utilization rate. In conclusion, the compound provided by the invention can realize higher luminous efficiency. The compound provided by the invention also has a spiro structure, so that the molecules have a twisted structure, the stacking of the molecules can be reduced, the crystallization of the molecules is avoided, and the compounds are more stable in device application.
Several examples of applications of the organic compounds according to the invention in OLED devices are listed below:
application example 1:
the application example provides an OLED device, which has a structure as shown in fig. 1, and includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10, which are sequentially stacked, where arrows in fig. 1 represent the light extraction direction of the device.
The preparation method of the OLED device comprises the following specific steps:
1) A glass substrate 1 with an Indium Tin Oxide (ITO) anode 2 (thickness 100 nm) was subjected to ultrasonic treatment in isopropanol and deionized water for 30 minutes, respectively, and then exposed to ozone for about 10 minutes to clean, and the cleaned glass substrate was mounted on a vacuum deposition apparatus;
2) A compound a is evaporated on the ITO anode 2 in vacuum, the thickness of the compound a is 10nm, and the compound a is used as a hole injection layer 3;
3) A compound b was vacuum-deposited on the hole injection layer 3 to a thickness of 40nm as a hole transport layer 4;
4) A compound c is evaporated on the hole transport layer 4 in vacuum, and the thickness of the compound c is 10nm to be used as an electron blocking layer 5;
5) On the electron blocking layer 5, a compound d and a compound e are vacuum co-evaporated, the doping proportion is 5% (mass ratio), the thickness is 20nm, and the compound d and the compound e are used as a light emitting layer 6;
6) On the light-emitting layer 6, the compound 1 provided in preparation example 1 was vacuum-deposited as a hole-blocking layer 7 with a thickness of 10 nm;
7) A compound f was vacuum-evaporated on the hole-blocking layer 7 to a thickness of 30nm as an electron-transporting layer 8;
7) A compound LiF is evaporated on the electron transport layer 8 in vacuum, the thickness of the compound LiF is 2nm, and the compound LiF is used as an electron injection layer 9;
8) On the electron injection layer 9, an aluminum electrode was vacuum-deposited to a thickness of 100nm as a cathode 10.
The compounds used in the preparation of the above-described OLED devices are as follows:
performance evaluation of OLED device:
according to the current density and the brightness of the OLED device under different voltages, the current density (10 mA/cm) under a certain current density is obtained 2 ) Operating voltage V and current efficiency CE (cd/A); the lifetime LT95 (h) (at 50 mA/cm) was obtained by measuring the time taken for the luminance of the OLED device to reach 95% of the initial luminance 2 Under test conditions); the test data are shown in table 3.
TABLE 3
As can be seen from Table 3, the OLED device provided by the invention has lower driving voltage, higher luminous efficiency and longer device life, wherein the working voltage is less than or equal to 4.17V, the current efficiency CE is more than or equal to 14.4cd/A, and the life LT95 is more than or equal to 53h. Compared with the comparative example 1, the OLED device adopting the compound has the advantages that the working voltage is reduced, the efficiency is improved, the service life is prolonged, the organic compound has a deeper HOMO value, holes can be effectively blocked, the holes are limited in a light-emitting region and are compounded with electrons, the light-emitting composite region is widened, and the light-emitting efficiency of the device is improved; the LUMO energy level is deeper, so that the electron injection is smoother, and the working voltage of the device is reduced; meanwhile, the organic compound provided by the invention has good thermal stability and film forming property, is beneficial to the stability of devices, and prolongs the service life of the devices.
The applicant states that the present invention is illustrated by the above examples of the organic compounds and their applications, but the present invention is not limited to the above examples, that is, it is not meant to imply that the present invention must be implemented by means of the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. An organic compound having a structure according to formula I:
wherein X is selected from-O or-S;
y is selected from-O or-S;
ar is selected from hydrogen or cyano;
2. An organic compound according to claim 1, wherein X is selected from-O.
3. An organic compound, characterized in that the organic compound is any one of the following compounds:
4. an electron transport material comprising the organic compound according to any one of claims 1 to 3.
5. A hole blocking material characterized in that it comprises the organic compound according to any one of claims 1 to 3.
6. An OLED device comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode, wherein a material of the organic thin film layer comprises the organic compound according to any one of claims 1 to 3.
7. The OLED device of claim 6, wherein the organic thin film layer comprises an electron transport layer, and a material of the electron transport layer comprises the organic compound according to any one of claims 1 to 3.
8. The OLED device according to claim 6, wherein the organic thin film layer includes a hole blocking layer, and a material of the hole blocking layer includes the organic compound according to any one of claims 1 to 3.
9. A display panel comprising an OLED device according to any one of claims 6 to 8.
10. An electronic device characterized in that the electronic device comprises the display panel according to claim 9.
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