CN111233840A - Quinoxaline derivative and application thereof in organic light-emitting device - Google Patents

Quinoxaline derivative and application thereof in organic light-emitting device Download PDF

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CN111233840A
CN111233840A CN201811432682.8A CN201811432682A CN111233840A CN 111233840 A CN111233840 A CN 111233840A CN 201811432682 A CN201811432682 A CN 201811432682A CN 111233840 A CN111233840 A CN 111233840A
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孙恩涛
刘叔尧
冯嘉宁
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Beijing Eternal Material Technology Co Ltd
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Abstract

The invention disclosesA novel organic compound having the structure:
Figure DDA0001882978070000011
wherein L is1And L2Each independently selected from a single bond, substituted or unsubstituted C6‑C30Arylene, substituted or unsubstituted C3‑C30One of the heteroarylenes of (a); ar (Ar)1Selected from substituted or unsubstituted C3‑C30And one of the heteroaryl groups containing at least two heteroatoms, Ar2Selected from substituted or unsubstituted C6‑C30Aryl, substituted or unsubstituted C3‑C30One of the heteroaryl groups of (a). The compound of the present invention shows excellent device performance and stability when used as a light emitting material in an OLED device. The invention also protects the organic electroluminescent device adopting the compound with the general formula.

Description

Quinoxaline derivative and application thereof in organic light-emitting device
Technical Field
The invention relates to a novel organic heterocyclic compound, in particular to a quinoxaline derivative, and also relates to an application of the compound in an organic electroluminescent device.
Background
With the continuous advance of the OLED technology in the two fields of display and lighting, people pay more attention to the research on the core materials of the OLED technology, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like. In order to prepare a light emitting device with better performance, the industry is continuously working on developing new organic electroluminescent materials to further improve the luminous efficiency and the lifetime of the device.
Through research and development for many years, organic electroluminescent materials and devices have reached the practical level, and hole transport materials, electron transport materials, luminescent materials, display device preparation technologies and the like have made great progress. Similarly, various types of electron transport materials having higher transport ability and higher stability have been reported in the past articles and patents. Generally, electron transport materials are compounds having electron-deficient nitrogen-containing heterocyclic groups, most of which have a higher electron affinity and thus a stronger electron accepting ability, but the electron mobility of common electron transport materials such as AlQ is higher than that of hole transport materials3The hole mobility of (aluminum octahydroxyquinoline) is much lower than that of a hole transport material, so that in an OLED device, the imbalance of injection and transport of carriers can be caused to cause hole and electron recombinationThe rate decreases thereby reducing the luminous efficiency of the device, and on the other hand, electron transport materials with lower electron mobility may cause the operating voltage of the device to increase thereby affecting the power efficiency, which is detrimental to the energy saving.
In the current OLED screen manufacturers, Liq (lithium octahydroxyquinoline) is widely used as a technical means for doping into an ET material layer to achieve low voltage and high efficiency of a device, and has an effect of improving the service life of the device, Liq (lithium octahydroxyquinoline) mainly has an effect of reducing a trace amount of metal lithium under the action of electrons injected from a cathode, so that an N-doping effect on an electron transport material is achieved, and thus the injection effect of electrons is significantly improved.
At present, the electron transport material traditionally used in electroluminescent devices is Alq3, but the electron mobility ratio of Alq3 is low (approximately 10-6cm 2/Vs). In order to improve the electron transport properties of electroluminescent devices, researchers have made a great deal of exploratory work. LG patent WO03/060956 discloses compounds having a benzimidazole ring and an anthracene skeleton, which suffer from high voltage and insufficient lifetime. Furthermore, KR2015024288A discloses a class of quinazoline and anthracene skeleton compounds, which have high voltage and low current efficiency. However, the above references do not specifically disclose an organic electroluminescent compound in which a quinoxaline group is introduced as an electron-deficient group into an electron transport layer structure of a material, which can significantly reduce voltage and improve current efficiency of a device.
In summary, in order to further satisfy the demand for increasing the photoelectric properties of OLED devices and the demand for energy saving of mobile electronic devices, new and efficient OLED materials need to be continuously developed, wherein the development of new electronic transmission materials with low voltage, high current efficiency and long service life is of great significance.
Disclosure of Invention
In view of the problems of the prior art, the present invention aims to provide new compounds for organic electroluminescent devices to meet the increasing demand for the photoelectric properties of OLED devices.
The invention provides a quinoxaline group-containing derivative, which is shown in the following general formula (1):
Figure 100002_1
wherein:
L1and L2Each independently selected from substituted or unsubstituted C6-C30Arylene, substituted or unsubstituted C3-C30One of the heteroarylenes of (a);
Ar1selected from substituted or unsubstituted C3-C30And one of the heteroaryl groups containing at least two heteroatoms, Ar2Selected from substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30One of the heteroaryl groups of (a);
when the above groups have substituents, the substituents are respectively and independently selected from halogen and C1-C10Alkyl or cycloalkyl of, C2-C10Alkenyl radical, C1-C6Alkoxy or thioalkoxy group of (C)6-C30Monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group of (A), C3-C30One of the monocyclic heteroaromatic group or the condensed ring heteroaromatic group of (a).
Further, L1And L2Each independently is preferably one of phenylene, pyridylene, pyrimidylene or quinolylene.
Further, Ar1And Ar2Each independently preferably has the following structure:
Figure BDA0001882978060000031
wherein R is1-R12Each independently is hydrogen, C1-C12Alkyl, halogen, C6-C30Aryl or C3-C30One of the heteroaryl groups of (1), R9、R10Each independently selected from substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30One of the heteroaryl groups of (a).
Still further, as preferable examples of the compound of the present invention, the following representative compounds can be cited:
Figure BDA0001882978060000041
Figure BDA0001882978060000051
Figure BDA0001882978060000061
Figure BDA0001882978060000071
as another aspect of the invention, the invention also provides application of the compound with the general formula as described above in an organic electroluminescent device. The compounds of the invention are preferably used as electron transport materials in organic electroluminescent devices.
As still another aspect of the present invention, the present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and an organic layer comprising at least one light-emitting layer interposed between the first electrode and the second electrode, characterized in that the organic layer contains a compound represented by the above general formula (1).
Researches show that the compound with the general formula has good film forming property and is suitable for being used as an electron transport material in an organic electroluminescent device. The principle is not clear, and it is assumed that the following reasons may be:
in the general formula design, quinoxaline is adopted as an electron-withdrawing group and is connected with pyrimidine, triazine and other structural groups with the pi electron-lacking characteristic, so that the potential barrier between the material and the cathode can be effectively reduced, and the electron injection capability of molecules is improved. Meanwhile, the heteroaryl group containing at least two heteroatoms is designed and connected in the molecular structure, and the structural group in the compound has stronger electron deficiency and larger plane conjugation, so that the compound is more favorable for the injection and transmission of electrons.
Meanwhile, the compounds have larger spatial plane structures, so that the film forming performance of the material is improved, and the glass transition temperature Tg of the material is greatly improved due to the larger spatial structure, so that the compounds have high thermal stability and chemical stability. In addition, the specific compound designed has smaller polarity compared with the compound containing the pyridine structure in the synthesis and post-treatment of the compound of the invention, so that the compound has the advantage of simple and convenient treatment.
In the invention, from the aspect of further improving the efficiency of the organic electroluminescent device, L in the general formula of the compound is preferably a single bond or an arylene group, a quinoxaline-containing structure is taken as an electron-withdrawing group, and the aryl group is connected with a quinazoline group, a triazine group and the like with a pi electron-lacking characteristic and derivatives thereof, so that the transmission efficiency of a balanced carrier can be better formed, the planarity of a molecular structure can be increased, the energy level of the molecular structure can be adjusted by different connection modes of para position or meta position, the triplet state energy level is higher, and the triplet state exciton of a light-emitting layer can be blocked, so that the purpose of improving the efficiency is achieved.
The compound is applied to an organic electroluminescent device, is used as an electron transport layer material, is favorable for reducing the voltage of the device, and is favorable for exerting excellent photoelectric efficiency and prolonging the service life. In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples.
The basic chemical materials of various chemicals used in the present invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, methylene chloride, acetic acid, potassium phosphate, sodium tert-butoxide, etc., are commercially available from Shanghai Tankatake technologies, Inc. and Xilongchemical, Inc. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
The synthesis of the compounds of the present invention is briefly described below.
Synthetic examples
Representative synthetic route:
Figure BDA0001882978060000091
more specifically, the following gives synthetic methods of representative compounds of the present invention.
Synthetic examples
Synthesis example 1:
synthesis of intermediate M-2
Figure BDA0001882978060000092
Preparation of intermediate Compound M-1
The compound 2, 3-dibromoquinoxaline (132g,0.5mol), p-chlorobenzoic acid (190g,0.75mol) and potassium carbonate (144,1.5mol) were dissolved in a flask containing toluene (2L), and 200mL of ethanol and 200mL of water were added. After nitrogen was replaced with stirring at room temperature, tetrakistriphenylphosphine palladium (3.8g,5mmol) was added. After the addition was completed, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The solvent was removed by rotation under reduced pressure, the resulting solution was dissolved in 2L of dichloromethane, and then 500mL of pure water was added for washing, followed by liquid separation, extraction of the aqueous phase with dichloromethane, combination of the organic phases, drying over anhydrous sodium sulfate, and purification by column chromatography (eluent petroleum ether: dichloromethane: 10:1 to 5:1) gave compound M-1(120g, yield 76%).
Preparation of intermediate Compound M-2
Compound M-1(120g,0.5mol), pinacol diboron ester (160g,0.75mol) and potassium acetate (135,3.0mol) were dissolved in a flask containing 1, 4-dioxane (2L), and palladium acetate (3.8g,5mmol) was added thereto with stirring at room temperature while replacing nitrogen. After the addition was completed, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The solvent was removed by rotation under reduced pressure, the resulting solution was dissolved in 2L of dichloromethane, and then 500mL of pure water was added for washing, followed by liquid separation, extraction of the aqueous phase with dichloromethane, combination of the organic phases, drying over anhydrous sodium sulfate, and purification by column chromatography (eluent petroleum ether: dichloromethane: 5:1 to 3:1) gave compound M-2(125g, yield 80%).
Synthesis example 2:
synthesis of intermediate M-4
Figure BDA0001882978060000101
Preparation of intermediate Compound M-3
The compound 2, 3-dibromoquinoxaline (132g,0.5mol), m-chlorobenzeneboronic acid (190g,0.75mol) and potassium carbonate (144,1.5mol) were dissolved in a flask containing toluene (2L), and 200mL of ethanol and 200mL of water were added. After nitrogen was replaced with stirring at room temperature, tetrakistriphenylphosphine palladium (3.8g,5mmol) was added. After the addition was completed, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The solvent was removed by rotation under reduced pressure, the resulting solution was dissolved in 2L of dichloromethane, and then 500mL of pure water was added for washing, followed by liquid separation, extraction of the aqueous phase with dichloromethane, combination of the organic phases, drying over anhydrous sodium sulfate, and purification by column chromatography (eluent petroleum ether: dichloromethane 10:1 to 5:1) gave compound M-3(128g, yield 82%).
Preparation of intermediate Compound M-4
Compound M-3(120g,0.5mol), pinacol diboron ester (160g,0.75mol) and potassium acetate (135,3.0mol) were dissolved in a flask containing 1, 4-dioxane (2L), and palladium acetate (3.8g,5mmol) was added thereto with stirring at room temperature while replacing nitrogen. After the addition was completed, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The solvent was removed by rotation under reduced pressure, the resulting solution was dissolved in 2L of dichloromethane, and then 500mL of pure water was added for washing, followed by liquid separation, extraction of the aqueous phase with dichloromethane, combination of the organic phases, drying over anhydrous sodium sulfate, and purification by column chromatography (eluent petroleum ether: dichloromethane: 5:1 to 3:1) gave compound M-4(108g, yield 65%).
Synthesis example 3
Synthesis of Compound C1
Figure BDA0001882978060000111
Intermediate M-2(13g,0.5mol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (19g,0.75mol) and potassium carbonate (14,1.5mol) were dissolved in a flask containing toluene (200mL), and 20mL of ethanol and 20mL of water were added. After nitrogen was replaced with stirring at room temperature, tetrakistriphenylphosphine palladium (0.4g,0.5mmol) was added. After the addition was completed, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The solvent was removed by evaporation under reduced pressure, the solvent was dissolved in 200mL of dichloromethane, 50mL of pure water was added for washing, the liquid separation was performed, the aqueous phase was extracted with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography (eluent petroleum ether: dichloromethane: 10:1 to 5:1) to obtain compound C1(10g, yield 60%).
Synthesis example 4
Synthesis of Compound C4
Figure BDA0001882978060000112
Intermediate M-2(12g,0.5mol), 2-chloro-4-phenyl-quinazoline (17g,0.75mol) and potassium carbonate (14,1.5mol) were dissolved in a flask containing toluene (200mL), followed by addition of 20mL of ethanol and 20mL of water. After nitrogen was replaced with stirring at room temperature, tetrakistriphenylphosphine palladium (0.4g,0.5mmol) was added. After the addition was completed, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The solvent was removed by evaporation under reduced pressure, the solvent was dissolved in 200mL of dichloromethane, 50mL of pure water was added for washing, the liquid separation was performed, the aqueous phase was extracted with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography (eluent was petroleum ether: ethyl acetate: 8:1 to 5:1) to obtain compound C4(11g, yield 62%).
Synthesis example 5
Synthesis of Compound C32
Figure BDA0001882978060000121
Intermediate M-2(12g,0.5mol), 2-phenyl-5 chloro-1, 3, 4-thiadiazole (9g,0.75mol) and potassium carbonate (14,1.5mol) were dissolved in a flask containing toluene (200mL), and 20mL of ethanol and 20mL of water were added. After nitrogen was replaced with stirring at room temperature, tetrakistriphenylphosphine palladium (0.4g,0.5mmol) was added. After the addition was completed, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The solvent was removed by evaporation under reduced pressure, the solvent was dissolved in 200mL of dichloromethane, 50mL of pure water was added for washing, the liquid separation was performed, the aqueous phase was extracted with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography (eluent petroleum ether: dichloromethane: 10:1 to 5:1) to obtain compound C32-1(12g, yield 73%).
C32-1(12g,0.5mol), 2-chloro-4-phenyl-quinazoline (8g,0.55mol), and potassium carbonate (14,1.5mol) were dissolved in a flask containing toluene (200mL), followed by 20mL of ethanol and 20mL of water. After nitrogen was replaced with stirring at room temperature, tetrakistriphenylphosphine palladium (0.4g,0.5mmol) was added. After the addition was completed, the reaction was refluxed with stirring for 6 hours, and the end of the reaction was monitored by TLC. The solvent was removed by evaporation under reduced pressure, the solvent was dissolved in 200mL of dichloromethane, 50mL of pure water was added for washing, the liquid separation was performed, the aqueous phase was extracted with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography (eluent was petroleum ether: ethyl acetate: 10:1 to 3:1) to obtain compound C32(9g, yield 59%).
Synthesis example 6
Synthesis of Compound C5
Figure BDA0001882978060000122
Intermediate M-4(13g,0.5mol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (19g,0.75mol) and potassium carbonate (14,1.5mol) were dissolved in a flask containing toluene (200mL), and 20mL of ethanol and 20mL of water were added. After nitrogen was replaced with stirring at room temperature, tetrakistriphenylphosphine palladium (0.4g,0.5mmol) was added. After the addition was completed, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The solvent was removed by evaporation under reduced pressure, the solvent was dissolved in 200mL of dichloromethane, 50mL of pure water was added for washing, the liquid separation was performed, the aqueous phase was extracted with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography (eluent petroleum ether: dichloromethane: 5:1 to 2:1) to obtain compound C5(10g, yield 68%).
Synthesis example 7
Synthesis of Compound C46
Figure BDA0001882978060000131
Intermediate M-2(13g,0.5mol), 3-bromophenanthroline (19g,0.75mol) and potassium carbonate (14,1.5mol) were dissolved in a flask containing toluene (200mL), and 20mL of ethanol and 20mL of water were added. After nitrogen was replaced with stirring at room temperature, tetrakistriphenylphosphine palladium (0.4g,0.5mmol) was added. After the addition was completed, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The solvent was removed by evaporation under reduced pressure, the solvent was dissolved in 200mL of dichloromethane, 50mL of pure water was added for washing, the liquid separation was performed, the aqueous phase was extracted with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography (eluent was petroleum ether: ethyl acetate: 3:1 to 1:1) to obtain compound C46(10g, yield 71%).
Synthesis example 8
Synthesis of Compound C54
Figure BDA0001882978060000132
Intermediate M-4(13g,0.5mol), 2-phenyl-N (4-chlorophenyl) -benzimidazole (19g,0.75mol), and potassium carbonate (14,1.5mol) were dissolved in a flask containing toluene (200mL), followed by addition of 20mL of ethanol and 20mL of water. After nitrogen was replaced with stirring at room temperature, tetrakistriphenylphosphine palladium (0.4g,0.5mmol) was added. After the addition was completed, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The solvent was removed by evaporation under reduced pressure, the solvent was dissolved in 200mL of dichloromethane, and 50mL of pure water was added for washing, followed by liquid separation, extraction of the aqueous phase with dichloromethane, combination of the organic phases, drying over anhydrous sodium sulfate, and purification by column chromatography (eluent dichloromethane: ethyl acetate: 20:1 to 8:1) gave compound C54(10g, yield 79%).
Device embodiments
Detailed description of the preferred embodiments
The OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-34; or any combination thereof.
Figure BDA0001882978060000141
Figure BDA0001882978060000151
Figure BDA0001882978060000161
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI1-HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1-HI3 described below.
Figure BDA0001882978060000162
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but is not limited to, the combination of one or more of BFH-1 through BFH-16 listed below.
Figure BDA0001882978060000171
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, combinations of one or more of BFD-1 through BFD-12 listed below.
Figure BDA0001882978060000172
Figure BDA0001882978060000181
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-57 listed below.
Figure BDA0001882978060000182
Figure BDA0001882978060000191
Figure BDA0001882978060000201
Figure BDA0001882978060000211
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, combinations of one or more of the following: LiQ, LiF, NaCl, CsF, Li2O,Cs2CO3,BaO,Na,Li,Ca。
The preparation process of the organic electroluminescent device in the embodiment of the invention is as follows:
the technical effects and advantages of the present invention are demonstrated and verified by testing practical use performance by specifically applying the compound of the present invention to an organic electroluminescent device.
To facilitate comparison of device application properties of the light emitting materials of the present invention, four prior art compounds Alq3, ET58, ET59 and ET60 shown below were used as comparative materials of the compounds of the present invention for the electron transport layer materials in the devices prepared in the comparative examples of the present invention by comparison with materials used in the prior art.
Figure BDA0001882978060000221
The organic electroluminescent device of the invention has the following specific preparation steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to less than 1 × 10-5Pa, regulating the evaporation rate of a hole transport material HT-33 to be 0.1nm/s and the evaporation rate of a hole injection material HT-32 to be 7% by using a multi-source co-evaporation method on the anode layer film, wherein the total film thickness of evaporation is 10 nm;
evaporating HT-33 on the hole injection layer in vacuum to serve as a first hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 95 nm;
evaporating HT-34 on the first hole transport layer in vacuum to serve as a second hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 20 nm;
a luminescent layer of the device is vacuum evaporated on the second hole transport layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material BFH-4 is adjusted to be 0.1nm/s, the evaporation rate of the dye BFD-4 is set in a proportion of 5%, and the total film thickness of evaporation is 36nm by using a multi-source co-evaporation method;
vacuum evaporating ET-17 on the luminescent layer to be used as a hole blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 5 nm;
on the hole blocking layer, a multi-source co-evaporation method is utilized, the evaporation rate of the representative compound in the invention or the representative compound in the prior art is adjusted to be 0.1nm/s and is set to be 100% of the evaporation rate of ET-57, and the total evaporation film thickness is 24 nm;
LiF with the thickness of 1nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 80nm is used as a cathode of the device.
The following OLED devices according to the various examples of the present invention were prepared according to the above-described process, and the materials used for preparing the devices in each example and comparative example were as follows:
example 1
An electroluminescent device was produced according to the above-mentioned production process using the compound C1 of the present invention as an electron transport layer material, and device performance test was conducted according to the device test method of the present invention described below.
Example 2
An organic electroluminescent device was produced in the same manner as in example 1, except that compound C1 was replaced with C4.
Example 3
An organic electroluminescent device was produced in the same manner as in example 1, except that compound C1 was replaced with C5.
Example 4
An organic electroluminescent device was produced in the same manner as in example 1, except that compound C1 was replaced with C32.
Example 5
An organic electroluminescent device was produced in the same manner as in example 1, except that compound C1 was replaced with C46.
Example 6
An organic electroluminescent device was produced in the same manner as in example 1, except that compound C1 was replaced with C54.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 1, except that the representative compound of the present invention, C1, was replaced with the prior art compound, Alq3。
Comparative example 2
An organic electroluminescent device was produced in the same manner as in example 1, except that the representative compound C1 of the present invention was replaced with the prior art compound ET 58.
Comparative example 3
An organic electroluminescent device was produced in the same manner as in example 1, except that the representative compound C1 of the present invention was replaced with the prior art compound ET 59.
Comparative example 4
An organic electroluminescent device was produced in the same manner as in example 1, except that the representative compound C1 of the present invention was replaced with the prior art compound ET 60.
Device testing method
The following performance measurements were performed on the organic electroluminescent devices prepared in the above examples and comparative examples:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 1 to 6 and comparative examples 1 to 4 were measured at the same luminance using a Photo-radiometer model ST-86LA model photoradiometer model PR 750 from Photo Research corporation (photoelectric instrument factory, university of beijing) and a Keithley4200 test system. Specifically, the voltage was raised at a rate of 0.1V per second, and the voltage when the luminance of the organic electroluminescent device reached 5000cd/m2, that is, the driving voltage, was measured, and the current density at that time was measured; the ratio of the luminance to the current density is the current efficiency. The life test of LT95 is as follows: the time in hours for which the luminance of the organic electroluminescent device dropped to 9500cd/m2 was measured using a luminance meter at a luminance of 10000cd/m2 with a constant current maintained.
The properties of each of the organic electroluminescent devices prepared in the above examples are shown in table 1 below.
Table 1:
Figure BDA0001882978060000241
Figure BDA0001882978060000251
as can be seen from comparison of examples 1 to 6 with comparative examples 1 to 4, the compound of the present invention was compared with Alq, which is an electron transport layer material in comparative example 1, in the case where other materials in the organic electroluminescent device structure are the same3When the organic light emitting diode is used as an electron transport layer material in an OLED device, the voltage of the device is obviously reduced, and the current efficiency and the service life of the device are greatly improved. As can be seen from comparison of examples 1-6 with comparative examples 2,3 and 4, the compound of the present invention, compared to the host material ET58 in comparative example 2, when used as an electron transport layer material in an OLED device, also has a reduced voltage, and improved current efficiency and lifetime.
The results show that the novel organic material is used as an electron transport layer material of an organic electroluminescent device, is an organic luminescent material with good performance, and is expected to be popularized and applied commercially.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (7)

1. A compound of the formula (1):
Figure 1
wherein:
L1and L2Each independently selected from substituted or unsubstituted C6-C30Arylene, substituted or unsubstituted C3-C30One of the heteroarylenes of (a);
Ar1selected from substituted or unsubstituted C3-C30And one of the heteroaryl groups containing at least two heteroatoms, Ar2Selected from substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30One of the heteroaryl groups of (a);
when the above groups have substituents, the substituents are respectively and independently selected from halogen and C1-C10Alkyl or cycloalkyl of, C2-C10Alkenyl radical, C1-C6Alkoxy or thioalkoxy group of (C)6-C30Monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group of (A), C3-C30One of the monocyclic heteroaromatic group or the condensed ring heteroaromatic group of (a).
2. The compound of formula (la) according to claim 1, wherein in formula (1), Ar1And Ar2Each independently preferably has the following structure:
Figure FDA0001882978050000012
wherein R is1-R12Each independently is hydrogen, C1-C12Alkyl, halogen, C6-C30Aryl or C3-C30One of the heteroaryl groups of (1), R9、R10Each independently selected from substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30One of the heteroaryl groups of (a).
3. A compound of formula (la) according to claim 1 or 2, wherein in formula (1):
L1and L2Each independently selected from one of phenylene, pyridylene, pyrimidylene or quinolylene.
4. A compound of formula (la) according to claim 1 or 2, selected from the compounds of the following specific structures:
Figure FDA0001882978050000021
Figure FDA0001882978050000031
Figure FDA0001882978050000041
Figure FDA0001882978050000051
5. use of a compound of the general formula according to claim 1 as electron transport material in an organic electroluminescent device.
6. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, characterized in that the organic layers comprise at least one compound represented by the general formula (1) of claim 1.
7. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, characterized in that said organic layers comprise at least one compound as claimed in claim 4.
CN201811432682.8A 2018-11-28 2018-11-28 Quinoxaline derivative and application thereof in organic light-emitting device Pending CN111233840A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021006532A1 (en) * 2019-07-05 2021-01-14 주식회사 엘지화학 Compound and organic light-emitting device including same
CN115960120A (en) * 2021-10-12 2023-04-14 南京林业大学 Preparation, electrochemical polymerization and application of D-A type monomer based on camphor quinoxaline
CN115960120B (en) * 2021-10-12 2024-05-03 南京林业大学 Preparation, electrochemical polymerization and application of D-A type monomer based on camphorquinoxaline

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021006532A1 (en) * 2019-07-05 2021-01-14 주식회사 엘지화학 Compound and organic light-emitting device including same
CN115960120A (en) * 2021-10-12 2023-04-14 南京林业大学 Preparation, electrochemical polymerization and application of D-A type monomer based on camphor quinoxaline
CN115960120B (en) * 2021-10-12 2024-05-03 南京林业大学 Preparation, electrochemical polymerization and application of D-A type monomer based on camphorquinoxaline

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