CN111303134A - Organic light-emitting material and organic electroluminescent device - Google Patents

Organic light-emitting material and organic electroluminescent device Download PDF

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CN111303134A
CN111303134A CN202010220313.3A CN202010220313A CN111303134A CN 111303134 A CN111303134 A CN 111303134A CN 202010220313 A CN202010220313 A CN 202010220313A CN 111303134 A CN111303134 A CN 111303134A
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邢其锋
丰佩川
孙伟
胡灵峰
陈跃
陈义丽
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Yantai Xianhua Chem Tech Co ltd
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Abstract

The application provides a novel organic luminescent material which is used for a luminescent main body material and an electron transport layer material of an organic electroluminescent device. The application also provides an organic electroluminescent device, which comprises the novel organic luminescent material.

Description

Organic light-emitting material and organic electroluminescent device
Technical Field
The present application relates to an organic light emitting material and an organic electroluminescent device using the same.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light when excited by a current and an electric field under the action of an electric field, and is a light emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage dc driving, full curing, wide viewing angle, light weight, simple composition and process, etc., and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, and has a large viewing angle, low power, a response speed 1000 times that of the liquid crystal display, and a manufacturing cost lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
With the continuous advance of the OLED technology in the two fields of lighting and display, people pay more attention to the research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.
Organic electroluminescent materials have many advantages over inorganic luminescent materials, such as: the processing performance is good, a film can be formed on any substrate by an evaporation or spin coating method, and flexible display and large-area display can be realized; the optical property, the electrical property, the stability and the like of the material can be adjusted by changing the structure of molecules, and the selection of the material has a large space. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. The phosphorescent host materials used at present often have single carrier transport capability, such as hole-based transport hosts and electron-based transport hosts, but the single carrier transport capability may cause mismatching of electrons and holes in the light emitting layer, thereby causing severe efficiency roll-off and shortened lifetime.
A class of host materials is reported in patent CN10563695a9, but the injection effect is not good and the device voltage is higher due to the problem of energy level matching; a similar structure was also reported in CN106255687A, but the light emission efficiency was not good.
Disclosure of Invention
To this end, an object of the present application is to provide an organic light emitting material, and an organic electroluminescent device using the same.
A first aspect of the present application provides an organic light-emitting material comprising a compound having a structure represented by the following general formula (i):
Figure BDA0002425838060000021
wherein the content of the first and second substances,
R1-R4independently of one another, from hydrogen, deuterium, C1-C6 alkyl, C6-C30 arylamine, C6-C30 aryl or C6-C30 heteroaryl, wherein the C6-C30 arylamine, C6-C30 aryl and C6-C30 heteroaryl are, independently of one another, unsubstituted or substituted by one or more Ra, wherein adjacent R's are1-R4Can be connected into a ring;
x is selected from O, S, CR5R6、NR7Wherein R is5、R6Independently of one another, from C1-C10 alkyl, C1-C6 cycloalkyl, C6-C30 aryl which is unsubstituted or substituted by Ra, C3-C30 heteroaryl which is unsubstituted or substituted by Ra, R7Selected from the group consisting of C6-C30 aryl unsubstituted or substituted with Ra, C3-C30 heteroaryl unsubstituted or substituted with Ra;
Ar1、Ar2independently of one another, from a C5-C30 nitrogen-containing heteroaryl group, which is unsubstituted or substituted by one or more C5-C30 alkyl groups;
L1、L2selected from a bond, C6-C30 arylene, or C6-C30 heteroarylene.
The substituents Ra of the various radicals may be identical or different and are chosen, independently of one another, from hydrogen, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl or naphthyl.
Preferably, R1-R4Independently of one another, from hydrogen, deuterium, methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups.
Preferably, R5And R6Independently of one another, from methyl, ethyl, cyclopentyl, cyclohexyl, the following groups which are unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups.
Preferably, R7Selected from the following unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazolylAnd (4) clustering.
Preferably, Ar1、Ar2Independently of one another, from the group consisting of pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl.
Preferably, L1、L2Independently of one another, from a chemical bond or a subunit of a compound which is unsubstituted or substituted by Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, carbazole.
More preferably, the organic light emitting material comprises a compound selected from the group consisting of compounds represented by a1-a50 as follows:
Figure BDA0002425838060000031
Figure BDA0002425838060000041
Figure BDA0002425838060000051
the second aspect of the present application also provides an organic electroluminescent device comprising the organic luminescent material of the present application.
The organic luminescent material of the present application can be used as a luminescent host material or an electron transport material in an organic electroluminescent device.
The application provides an organic luminescent material, has 2, 4-disubstituted dibenzofuran derivative's parent structure, and the bond energy between the atom is high, has good thermal stability, is favorable to the solid-state of intermolecular to pile up, uses as luminescent layer material and can effectively improve the life-span of material, is used for electron transport material can keep very high electron transport efficiency, promotes luminous efficiency.
The 2, 4-disubstituted dibenzofuran derivative is applied to a light-emitting layer and an electron transport layer, has a proper energy level with adjacent layers, is favorable for injecting holes and electrons, can effectively reduce the starting voltage, and can realize good luminous efficiency in a device due to higher exciton migration rate. The compound has a large conjugated plane, is beneficial to molecular accumulation, shows good thermodynamic stability and shows long service life in a device. When the composite material is used as a main body material of a light-emitting layer, the Highest Occupied Molecular Orbital (HOMO) and the Lowest Unoccupied Molecular Orbital (LUMO) energy levels are overlapped on dibenzofuran, so that the main body structure of the composite material has partial Thermal Activation Delayed Fluorescence (TADF) property, the utilization rate of energy is improved, and the light-emitting efficiency of a device is improved.
Meanwhile, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for industrial production.
Detailed Description
The organic luminescent material of the present application can be used as a luminescent host material or an electron transport material in an organic electroluminescent device.
In the present application, there is no particular limitation on the kind and structure of the organic electroluminescent device as long as the organic light emitting material provided herein can be used. For convenience, the present application is described with an organic light emitting diode as an example, but this is not meant to limit the scope of the present application in any way. It is understood that all organic electroluminescent devices capable of using the organic light emitting material of the present application are within the scope of the present application.
In general, an organic light emitting diode includes first and second electrodes on a substrate, and an organic material layer between the electrodes, which may be a multi-layered structure. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
In the present application, the substrate is not particularly limited, and conventional substrates used in organic electroluminescent devices in the related art, for example, glass, polymer materials, and glass and polymer materials with TFT components and the like may be used.
In the present application, the anode material is not particularly limited, and may be Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) known in the art2) Transparent conductive materials such as zinc oxide (ZnO), metal materials such as silver and its alloys, aluminum and its alloys, organic conductive materials such as PEDOT (poly-3, 4-ethylenedioxythiophene), and multilayer structures of the above materials.
In the present application, the cathode material is not particularly limited, and may be selected from, for example, but not limited to, a magnesium silver mixture, metal such as LiF/Al, ITO, a metal mixture, an oxide, and the like.
In the present application, the organic electroluminescent diode (OLED) may further include a hole injection layer, a hole transport layer, and the like between the light emitting layer and the anode, and these layers may use, but are not limited to, at least one of HT1-HT31 listed below, and these materials may be used alone or in combination of a plurality of them.
Figure BDA0002425838060000061
Figure BDA0002425838060000071
Figure BDA0002425838060000081
The light-emitting layer of the OLED device can include a host material and a light-emitting dye, where the host material includes, but is not limited to, one or more combinations of the conventional materials shown in GPH1-GPH80 below. The organic light-emitting material of the present application, when used as a host material, may be used in combination with one or more of these materials.
Figure BDA0002425838060000082
Figure BDA0002425838060000091
Figure BDA0002425838060000101
In a preferred embodiment of the present application, the light-emitting layer employs the technique of phosphorescent electroluminescence. The light-emitting layer is doped with a phosphorescent dopant, and the phosphorescent dopant can be selected from but not limited to a combination of one or more of RPD-1 to RPD-28 listed below.
Figure BDA0002425838060000111
Figure BDA0002425838060000121
The electron transport layer materials include, but are not limited to, combinations of one or more of the ET1-ET57 materials listed below. The organic light-emitting material of the present application, when used as an electron transport layer material, may be used in combination with one or more of these materials.
Figure BDA0002425838060000122
Figure BDA0002425838060000131
Figure BDA0002425838060000141
In addition, an electron injection layer between the electron transport layer and the cathode can be further included in the OLED device, and the material of the electron injection layer is not particularly limited, and for example, LiQ, LiF, NaCl, CsF in the prior art can be included but not limited thereto、Li2O、Cs2CO3One or a combination of more of materials such as BaO, Na, Li, Ca and the like.
In the present application, the following two materials were used for comparative experiments with the organic light emitting material of the present application.
Figure BDA0002425838060000151
The method for synthesizing the compound of the present application is not particularly limited, and the synthesis can be carried out by any method known to those skilled in the art. The following illustrates the synthesis of the compounds of the present application.
Synthetic examples
Synthesis example 1: synthesis of Compound A1
Figure BDA0002425838060000152
100mmol of 2-iodo-3-chloro-5-bromo-fluorobenzene, 110mmol of o-hydroxyphenylboronic acid, 40g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol, 200ml of water and 1 mol% of Pd (PPh3)4The solution is heated to reflux and reacted for 8 hours, and the reaction is finished. The reaction solution was extracted with ethyl acetate and the organic phase was concentrated to give M1 as a yellow solid. Wherein, Pd (PPh3)4The amount of addition of (a) is 1 mol% of 2-iodo-3-chloro-5-bromo-fluorobenzene.
100mmol of M1 was dissolved in 500ml of DMF solution, 300mmol of sodium tert-butoxide was added, and the mixture was heated to 120 ℃ and reacted for 12 hours. Water was added to the reaction solution, ethyl acetate was added for extraction, and the organic phase was concentrated to give intermediate M2.
Dissolving 100mmol of intermediate M2 in 500ml of THF solution, adding 110mmol of butyl lithium at-78 ℃, reacting for 1h at controlled temperature, dropwise adding trimethyl borate, controlling the temperature, naturally heating, and reacting for 12 h. Water was added to the reaction solution, ethyl acetate was added for extraction, and the organic phase was concentrated to give intermediate M3.
100mmol of M3, 110mmol of 2-chloro-3-phenylquinoxaline, 40g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol, 200ml of water and 1 mol% of Pd (PPh3)4Heating the solution of (1)And (4) refluxing, reacting for 8h, and finishing the reaction. The reaction solution was extracted with ethyl acetate and the organic phase was concentrated to give M4 as a yellow solid. Wherein, Pd (PPh3)4Was added in an amount of 1 mol% based on M3.
A solution of 100mmol of raw material M, 110mmol of diphenylamine, 1 mol% of Pd (dba), 1 mol% of tri-tert-butylphosphine, 40g of sodium tert-butoxide (300mmol) and 800ml of toluene is heated to reflux and reacted for 8 hours, and the reaction is finished. Extracting the reaction liquid with ethyl acetate, concentrating the organic phase, and separating by column chromatography to obtain yellow solid M5. Wherein Pd (dba) and tri-tert-butylphosphine are added in an amount of 1 mol% based on M, respectively.
A solution of 100mmol of M4, 110mmol of M5, 1 mol% of Pd (dba), 1 mol% of tri-tert-butylphosphine, 40g of sodium tert-butoxide (300mmol) and 800ml of toluene was heated to reflux and reacted for 8 hours, after which the reaction was completed. Extracting the reaction liquid with ethyl acetate, concentrating the organic phase, and separating by column chromatography to obtain yellow solid A1. Wherein Pd (dba) and tri-tert-butylphosphine were added in an amount of 1 mol% based on M4, respectively.
1H NMR(400MHz,Chloroform)δ8.77(s,1H),8.53(d,J＝7.2Hz,2H),8.16–7.74(m,6H),7.80-7.67(m,3H),7.60(d,J＝10.0Hz,5H),7.55–7.47(m,7H),7.35-7.08(m,7H),7.00(s,1H).
Synthesis example 2: synthesis of Compound A6
Figure BDA0002425838060000161
100mmol of 2-iodo-3-chloro-5-bromo-fluorobenzene, 110mmol of o-hydroxyphenylboronic acid, 1 mol% of Pd (PPh3)440g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol and 200ml of water are heated to reflux and reacted for 8 hours, and the reaction is finished. The reaction solution was extracted with ethyl acetate and the organic phase was concentrated to give M1 as a yellow solid. Wherein, Pd (PPh3)4The amount of the compound (b) added is 1 mol% of 2-iodo-3-chloro-5-bromo-aniline.
100mmol of M1 was dissolved in 500ml of DMF solution, 300mmol of sodium tert-butoxide was added, and the mixture was heated to 120 ℃ and reacted for 12 hours. Water was added to the reaction solution, ethyl acetate was added for extraction, and the organic phase was concentrated to give intermediate M2.
Dissolving 100mmol of M2 in 500ml of THF solution, adding 110mmol of butyl lithium at-78 ℃, reacting for 1h at a controlled temperature, dropwise adding trimethyl borate, controlling the temperature, naturally heating, and reacting for 12 h. Water was added to the reaction solution, ethyl acetate was added for extraction, and the organic phase was concentrated to give intermediate M3.
100mmol of M3, 110mmol of 2-chloro-4, 6-diphenyltriazine, 1 mol% of Pd (PPh3)440g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol and 200ml of water are heated to reflux and reacted for 8 hours, and the reaction is finished. The reaction solution was extracted with ethyl acetate and the organic phase was concentrated to give M4 as a yellow solid. Wherein, Pd (PPh3)4Was added in an amount of 1 mol% based on M3.
100mmol of M4, 110mmol of 2-boronate triphenylene, 1 mol% of Pd (PPh3)440g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol and 200ml of water are heated to reflux and reacted for 8 hours, and the reaction is finished. The reaction solution was extracted with ethyl acetate and the organic phase was concentrated to give yellow solid A6. Wherein, Pd (PPh3)4Was added in an amount of 1 mol% based on M4.
1H NMR(CDCl3,400MHz)δ8.69-8.46(m,6H),8.34(dd,J＝12.0,8.0Hz,6H),7.98-7.70(m,4H),7.64(s,1H),7.62–7.48(m,9H),,7.31(s,1H).
Synthetic example 3: synthesis of Compound A14
Figure BDA0002425838060000171
100mmol of 2-iodo-3-chloro-5-bromo-fluorobenzene, 110mmol of o-hydroxyphenylboronic acid, 1 mol% of Pd (PPh3)440g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol and 200ml of water are heated to reflux and reacted for 8 hours, and the reaction is finished. The reaction solution was extracted with ethyl acetate and the organic phase was concentrated to give M1 as a yellow solid. Wherein, Pd (PPh3)4The amount of addition of (a) is 1 mol% of 2-iodo-3-chloro-5-bromo-fluorobenzene.
100mmol of intermediate M1 was dissolved in 500ml of DMF solution, 300mmol of sodium tert-butoxide was added, and the mixture was heated to 120 ℃ and reacted for 12 hours. Water was added to the reaction solution, ethyl acetate was added for extraction, and the organic phase was concentrated to give intermediate M2.
100mmol of M2 was dissolved in chloroform, 110mmol of iodine was added, and the mixture was stirred at room temperature and reacted for 3 hours. After the reaction is finished, adding water into the reaction solution, separating an organic phase, and concentrating to obtain an intermediate M3
A solution of 100mmol of M3, 110mmol of diphenylamine, 1 mol% of tri-tert-butylphosphine, 1 mol% of Pd (dba), 40g of sodium tert-butoxide (300mmol) and 800ml of toluene is heated to reflux and reacted for 8 hours, after which the reaction is completed. Extracting the reaction liquid with ethyl acetate, concentrating the organic phase, and separating by column chromatography to obtain yellow solid M4. Wherein Pd (dba) and sodium tert-butoxide are added in an amount of 1 mol% based on M3.
Dissolving 100mmol of M4 in 500ml of THF solution, adding 110mmol of butyl lithium at-78 ℃, reacting for 1h at a controlled temperature, dropwise adding trimethyl borate, controlling the temperature, naturally heating, and reacting for 12 h. Water was added to the reaction solution, ethyl acetate was added for extraction, and the organic phase was concentrated to give intermediate M5.
100mmol of M5, 110mmol of 2-chloro-3-phenylquinoxaline, 1 mol% of Pd (PPh3)440g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol and 200ml of water are heated to reflux and reacted for 8 hours, and the reaction is finished. The reaction solution was extracted with ethyl acetate and the organic phase was concentrated to give M6 as a yellow solid. Wherein, Pd (PPh3)4Was added in an amount of 1 mol% based on M5.
100mmol of M6, 110mmol of dibenzothiophene-2-boronic acid, 1 mol% of Pd (PPh3)440g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol and 200ml of water are heated to reflux and reacted for 8 hours, and the reaction is finished. The reaction solution was extracted with ethyl acetate, the organic phase was concentrated and recrystallized from toluene to give yellow solid A14. Wherein, Pd (PPh3)4Was added in an amount of 1 mol% based on M6.
1H NMR(CDCl3,400MHz)δ8.62(s,1H),8.54(t,J＝12.4Hz,2H),8.40-8.22(m,3H),8.12-8.03(m,5H),8.09–7.84(m,6H),7.80(s,1H),7.67(s,1H),7.58(d,J＝12.0Hz,2H),7.46-7.32(m,5H),7.27–7.07(m,4H),7.00(s,1H).
Synthetic example 4: synthesis of Compound A31
Figure BDA0002425838060000191
100mmol of 2-iodo-3-chloro-5-bromo-fluorobenzene, 110mmol of o-hydroxyphenylboronic acid, 1 mol% of Pd (PPh3)440g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol and 200ml of water, heating to reflux, and reacting for 8 hours. The reaction solution was extracted with ethyl acetate and the organic phase was concentrated to give M1 as a yellow solid. Wherein, Pd (PPh3)4The amount of addition of (a) is 1 mol% of 2-iodo-3-chloro-5-bromo-fluorobenzene.
100mmol of intermediate M1 was dissolved in 500ml of DMF solution, 300mmol of sodium tert-butoxide was added, and the mixture was heated to 120 ℃ and reacted for 12 hours. Water was added to the reaction solution, ethyl acetate was added for extraction, and the organic phase was concentrated to give intermediate M2.
Dissolving 100mmol of intermediate M2 in 500ml of THF solution at-78 ℃, adding 110mmol of butyl lithium, controlling the temperature to react for 1h, dropwise adding trimethyl borate, controlling the temperature, naturally heating, and reacting for 12 h. Water was added to the reaction solution, ethyl acetate was added for extraction, and the organic phase was concentrated to give intermediate M3.
100mmol of M3, 110mmol of 2-chloro-4, 6-diphenyltriazine, 1 mol% of Pd (PPh3)440g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol and 200ml of water are heated to reflux and reacted for 8 hours, and the reaction is finished. The reaction solution was extracted with ethyl acetate and the organic phase was concentrated to give M4 as a yellow solid. Wherein, Pd (PPh3)4Was added in an amount of 1 mol% based on M3.
In 100mmol of M4, 110mmol of 2- (4-phenylboronic acid) -N-phenyl-benzimidazole, 1 mol% of Pd (PPh3)440g of sodium carbonate (300mmol), 800ml of toluene, 200ml of ethanol and 200ml of water are heated to reflux and reacted for 8 hours, and the reaction is finished. The reaction solution is extracted by ethyl acetate, the organic phase is concentrated, and the yellow solid A31 is obtained by toluene recrystallization. Wherein, Pd (PPh3)4Was added in an amount of 1 mol% based on M4.
1H NMR(CDCl3,400MHz)δ8.62–8.38(m,6H),8.38(d,J＝6.4Hz,2H),8.36(s,1H),7.97(d,J＝10.0Hz,2H),7.81(s,1H),7.62-7.40(m,9H),7.38(d,J＝8.0Hz,2H),7.33–7.18(m,6H).
Other compounds of the present application can be synthesized by selecting suitable starting materials according to the above-mentioned concept of synthetic examples 1 to 4, and also by selecting any other suitable methods and starting materials.
The second aspect of the present application also provides an organic electroluminescent device comprising the organic luminescent material provided by the present application.
In the present application, the method of manufacturing the OLED device is not particularly limited, and may be manufactured using any method known in the art.
The following examples illustrate the organic light emitting materials of the present application as host light emitting materials and electron transporting materials. When used as a host light emitting material, the other materials in the OLED device are not limited and any material known in the art may be used. Also, when the organic light emitting material of the present application is used as an electron transport material, other materials in the OLED device are not limited at all, and any materials known in the art may be used.
Example 1
Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing in deionized water, carrying out ultrasonic oil removal in an acetone-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 solar beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to less than 10 DEG-5Vacuum evaporating HT-11 on the anode layer film to form a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT-5 material on the hole injection layer in vacuum to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 80 nm;
a luminescent layer of the device is vacuum evaporated on the hole transport layer, the luminescent layer comprises a main material A1 and a dye material RPD-1, evaporation is carried out by a multi-source co-evaporation method, the evaporation rate of the main material A1 is adjusted to be 0.1nm/s, the evaporation rate of the dye RPD-1 is 3% of the evaporation rate of A1, and the total thickness of the evaporated film is 30 nm;
vacuum evaporating an electron transport layer on the light-emitting layer, wherein an ET42 material is selected as the electron transport layer, the evaporation rate is 0.1nm/s, and the total film thickness is 30 nm;
LiF with the thickness of 0.5nm 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 150nm is used as a cathode of the device.
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the organic electroluminescent devices obtained in examples and comparative examples were measured for driving voltage and current efficiency and lifetime at the same luminance using a digital source meter and a luminance meter, and specifically, the luminance of the organic electroluminescent devices reached 5000cd/m when the voltage was increased at a rate of 0.1V/sec2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m2The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance2Time in hours.
Examples 2 to 6
The organic light emitting materials a6, a12, a19, a24 and a29 of the present application were used as light emitting layer host materials, respectively, and the rest were the same as in example 1. The test results are shown in Table 1.
Comparative examples 1 and 2
R1 and R2 were used as the light-emitting layer host materials, respectively, and the rest was the same as in example 1. The test results are shown in Table 1.
Table 1 organic electroluminescent device performance results
Figure BDA0002425838060000211
The data in the table show that the novel organic material prepared by the method is used as the main material of the organic electroluminescent device, can effectively reduce the driving voltage, improve the current efficiency and prolong the service life of the device, and is a main material with good performance.
In addition, the compound is used as an electron transport layer material to replace ET42 applied in the device structure, and the device structure prepared by the same preparation method is subjected to performance test under the same conditions.
Example 7
Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing in deionized water, carrying out ultrasonic oil removal in an acetone-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 solar beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to less than 10 DEG-5Vacuum evaporating HT-11 on the anode layer film to form a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT-5 material on the hole injection layer in vacuum to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 80 nm;
a luminescent layer of the device is vacuum evaporated on the hole transport layer, the luminescent layer comprises a main material GPH-4 and a dye material RPD-1, evaporation is carried out by using a multi-source co-evaporation method, the evaporation rate of the main material GPH-4 is adjusted to be 0.1nm/s, the evaporation rate of the dye RPD-1 is 3% of the evaporation rate of the main material, and the total film thickness of the evaporation is 30 nm;
vacuum evaporating an electron transport layer on the luminescent layer, wherein a material A31 is selected as an electron transport layer material, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 30 nm;
LiF with the thickness of 0.5nm 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 150nm is used as a cathode of the device.
The performance test was carried out in the same manner as in example 1, and the results are shown in Table 2.
Examples 8 to 11
The same as in example 7 except that A31, A35, A38, A40 and A44 of the present application were used as electron transporting materials, and the test results are shown in Table 2.
Comparative example 3
ET42 was used as the electron transporting material, and the test results were shown in table 2, except that the same material as in example 7 was used.
Table 2 organic electroluminescent device performance results
Figure BDA0002425838060000231
As can be seen from the data in Table 2, the novel organic material prepared by the method is used for the electron transport material of the organic electroluminescent device, can effectively reduce the driving voltage, improve the current efficiency and prolong the service life of the device, and is an electron transport material with good performance.
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 of this invention are intended to be covered by the scope of the invention as expressed herein.

Claims (10)

1. An organic light-emitting material comprising a compound having a structure represented by the following general formula (I):
Figure FDA0002425838050000011
wherein the content of the first and second substances,
R1-R4independently of one another, from hydrogen, deuterium, C1-C6 alkyl, C6-C30 arylamine, C6-C30 aryl or C3-C30 heteroaryl, wherein said C6-C30 arylamine, C6-C30 aryl and C3-C30 heteroaryl are independently of one another unsubstituted or substituted by one or more Ra; wherein adjacent R1-R4Can be connected into a ring;
x is selected from O, S, CR5R6、NR7Wherein R is5、R6Independently of one another, from C1-C10 alkyl, C1-C6 cycloalkyl, C6-C30 aryl which is unsubstituted or substituted by Ra, C3-C30 heteroaryl which is unsubstituted or substituted by Ra, R7Selected from the group consisting of C6-C30 aryl unsubstituted or substituted with Ra, C3-C30 heteroaryl unsubstituted or substituted with Ra;
Ar1、Ar2independently of one another, from a C5-C30 nitrogen-containing heteroaryl group, which is unsubstituted or substituted by one or more C5-C30 alkyl groups;
L1、L2selected from a chemical bond, C6-C30 arylene, or C6-C30 heteroarylene;
the substituents Ra of the various radicals may be identical or different and are chosen, independently of one another, from hydrogen, halogen, nitro, cyano, C1-C4Any one of alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
2. The organic light-emitting material according to claim 1, wherein R is1-R4Independently of one another, from hydrogen, deuterium, methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups.
3. The organic light-emitting material according to claim 1, wherein R is5And R6Independently of one another, from methyl, ethyl, cyclopentyl, cyclohexyl, the following groups which are unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups.
4. The organic light-emitting material according to claim 1, wherein R is7Selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups, unsubstituted or substituted with Ra.
5. The organic light-emitting material according to claim 1, wherein Ar is1、Ar2Independently of one another, from the group consisting of pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl.
6. The organic light-emitting material according to claim 1, wherein L is1、L2Independently of one another, from a chemical bond or a subunit of a compound which is unsubstituted or substituted by Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, carbazole.
7. The organic light-emitting material according to any one of claims 1 to 6, wherein the organic light-emitting material comprises a compound selected from the group consisting of compounds represented by A1-A50:
Figure FDA0002425838050000021
Figure FDA0002425838050000031
Figure FDA0002425838050000041
8. an organic electroluminescent device comprising the organic light-emitting material as claimed in any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the organic light emitting material is used as a light emitting layer host material.
10. The organic electroluminescent device according to claim 8, wherein the organic luminescent material is used as an electron transport material.
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