WO2020237793A1 - 有机发光二极管的发光层掺杂剂及其制备方法和电致发光器件 - Google Patents

有机发光二极管的发光层掺杂剂及其制备方法和电致发光器件 Download PDF

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WO2020237793A1
WO2020237793A1 PCT/CN2019/096000 CN2019096000W WO2020237793A1 WO 2020237793 A1 WO2020237793 A1 WO 2020237793A1 CN 2019096000 W CN2019096000 W CN 2019096000W WO 2020237793 A1 WO2020237793 A1 WO 2020237793A1
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light
emitting layer
dopant
liquid
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林亚飞
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Wuhan China Star Optoelectronics Semiconductor Display Technology Co Ltd
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Wuhan China Star Optoelectronics Semiconductor Display Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

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  • This application relates to the field of display technology, in particular to a dopant for the light-emitting layer of an organic light-emitting diode, a preparation method thereof, and an electroluminescent device.
  • OLED Organic Light Emitting Diode
  • the existing OLED display device usually includes an anode, a hole transport layer, an organic light emitting layer, an electron transport layer, and a cathode.
  • the anode transports holes to the organic light-emitting layer through the hole transport layer
  • the cathode transports electrons to the organic light-emitting layer through the electron transport layer. These holes and electrons combine in the organic light-emitting layer to generate exciting electron-hole pairs. These electron-hole pairs are further converted from an excited state to a ground state to realize OLED light emission.
  • the excited particles formed in the light-emitting layer of the OLED include singlet particles and triplet particles, and the ratio of the two is 1:3.
  • the existing OLED light-emitting layer materials are pure organic materials. Due to the effect of the potential barrier, only singlet particles can transition to the excited state to achieve light emission. This is fluorescent light emission. Therefore, the internal quantum efficiency of fluorescent light-emitting devices can only reach 25%.
  • doping heavy metal complexes in the light-emitting layer can use the spin-orbit coupling of heavy metal atoms to achieve transitional light emission of triplet particles, which is phosphorescent light emission. In theory, phosphorescent light emission can reach 100% internal quantum effectiveness.
  • the preparation of heavy metal complexes (such as metal iridium complexes) still has many problems, such as complex preparation process, low purity, and low yield.
  • the internal quantum efficiency of fluorescent light-emitting diodes is much lower than that of phosphorescent light-emitting diodes.
  • the heavy metal complexes that promote the phosphorescence of the diodes have the problems of complicated preparation process, low purity and low yield.
  • This application provides a method for preparing a dopant for a light emitting layer of an organic light emitting diode, which includes the following steps:
  • Step S1 Take the mixed reaction of o-nitrodiphenylamine and hydrazine hydrate to prepare the first intermediate; its synthesis route is as follows:
  • Step S2 Take the first intermediate and 3,5-dimethyl bromobenzene to mix and react to obtain the second intermediate; the synthesis route is as follows:
  • Step S3 Take the second intermediate and p-toluenesulfonic acid to mix and react to obtain the third intermediate; the synthesis route is as follows:
  • Step S4 Take the third intermediate and hydrated iridium trichloride to mix and react to obtain the fourth intermediate; the synthesis route is as follows:
  • Step S5 mixing and reacting the fourth intermediate and acetyl ketone to prepare the light-emitting layer dopant; its synthesis route is as follows:
  • the step S1 specifically includes:
  • Step S101 Use absolute ethanol to dissolve the o-nitrodiphenylamine to prepare a first liquid
  • Step S102 adding ferric hydroxide and hydrazine hydrate to the first liquid to react for 3-8 hours to prepare a second liquid;
  • Step S103 the second liquid is at least filtered and dried to prepare the first intermediate.
  • the amount of absolute ethanol used in step S101 is 400 parts, the amount of o-nitrodiphenylamine is 100 parts; the amount of iron hydroxide used in step S102 is 3 parts, hydrazine hydrate The amount is 58.4 parts.
  • the step S2 specifically includes:
  • Step S201 using dichloromethane to dissolve the first intermediate to prepare a third liquid
  • Step S202 adding 3,5-dimethyl bromobenzene to the third liquid to react for 2 to 4 hours to prepare a fourth liquid;
  • Step S203 The fourth liquid is at least filtered and dried to obtain the second intermediate.
  • step S201 the amount of dichloromethane used in step S201 is 530 parts; the amount of 3,5-dimethylbromobenzene used in step S202 is 83 parts.
  • the step S3 specifically includes:
  • Step S301 using toluene to dissolve the second intermediate to prepare a fifth liquid
  • Step S302 adding p-toluenesulfonic acid to the fifth liquid to react for 3-9 hours to prepare a sixth liquid;
  • Step S303 the sixth liquid is at least filtered and dried to obtain the third intermediate.
  • the amount of toluene in the step S301 is 430 parts; the amount of p-toluenesulfonic acid used in the step S302 is 8.8 parts.
  • the step S4 specifically includes:
  • Step S401 using a mixed liquid of deionized water and ethyl glycol ether to dissolve the third intermediate to prepare a seventh liquid;
  • Step S402 adding hydrated iridium trichloride to the seventh liquid and reacting for 8-16 hours to obtain an eighth liquid;
  • Step S403 the eighth liquid is at least filtered and dried to obtain the fourth intermediate.
  • the amount of deionized water used in step S401 is 230 parts, and the amount of ethyl glycol ether is 230 parts; the amount of hydrated iridium trichloride used in step S402 is 25 parts.
  • the step S5 specifically includes:
  • Step S501 dissolving the fourth intermediate with ethylene glycol ether to prepare a ninth liquid
  • Step S502 adding acetyl ketone to the ninth liquid to react for 20-30 hours to prepare a tenth liquid;
  • Step S503 the tenth liquid is at least extracted, filtered and dried to obtain the light-emitting layer dopant.
  • the amount of ethylene glycol ether used in step S501 is 480 parts; the amount of acetyl ketone used in step S502 is 24.3 parts.
  • the extractant used in the extraction is dichloromethane.
  • the present application also provides a dopant for a light-emitting layer of an organic light-emitting diode.
  • the structural formula of the dopant for the light-emitting layer includes at least structural formula 1, and the structural formula 1 is as follows:
  • the structural formula of the light-emitting layer dopant is as follows:
  • the color of the light-emitting layer dopant is red.
  • the light emitting layer dopant of the present application is applied to the light emitting layer of an organic light emitting diode.
  • the light-emitting layer dopant is a complex of heavy metal iridium.
  • the present application further provides an electroluminescent device including a light-emitting layer, the light-emitting layer is doped with a light-emitting layer dopant, and the structure of the light-emitting layer dopant includes at least structural formula 1, and the structural formula 1 is as follows:
  • the structural formula of the dopant of the light-emitting layer is as follows:
  • the electroluminescent device includes:
  • the anode layer is arranged on the substrate;
  • the hole transport layer is arranged on the anode layer
  • the light-emitting layer is disposed on the hole transport layer
  • the electron transport layer is arranged on the light-emitting layer
  • the cathode layer is arranged on the electron transport layer.
  • This application provides a light-emitting layer dopant of an organic light-emitting diode, a preparation method thereof, and an electroluminescent device made by using the light-emitting layer dopant.
  • the preparation method of the light-emitting layer dopant is simple and easy to operate. It is realized with high preparation efficiency, and can prepare high-purity light-emitting layer dopant materials; the electroluminescent device provided in this application contains the light-emitting layer dopant provided in this application, which can realize phosphorescence of light-emitting layer materials, Thereby improving the luminous efficiency of the electroluminescent device.
  • FIG. 1 is a flowchart of a method for preparing a dopant for a light-emitting layer of an organic light-emitting diode according to an embodiment of the present application;
  • FIG. 2 is a schematic diagram of the structure of an electroluminescent device provided by an embodiment of the present application.
  • Figure 3 is a luminescence spectrum diagram of an electroluminescent device provided by an embodiment of the present application.
  • FIG. 4 is a graph showing the relationship between current density and voltage of an electroluminescent device provided by an embodiment of the present application.
  • FIG. 5 is a graph showing the relationship between the luminous current efficiency and current density of the electroluminescent device provided by the embodiment of the present application.
  • Fig. 6 is a graph showing the relationship between normalized brightness and light-emitting time of an electroluminescent device provided by an embodiment of the present application.
  • the embodiment of the application provides a method for preparing a dopant for a light-emitting layer of an organic light-emitting diode.
  • the preparation process is simple and easy to operate, and the preparation efficiency is high, and a high-purity light-emitting layer dopant can be prepared.
  • a flow chart of a method for preparing a dopant for a light-emitting layer of an organic light-emitting diode includes the following steps:
  • Step S1 Take o-nitrodiphenylamine and hydrazine hydrate to mix and react to prepare the first intermediate.
  • the synthesis path of the first intermediate is as follows:
  • the amount of each substance described in this application is calculated in parts by mass, that is, the mass ratio between the substances.
  • 100 parts of substance A and 50 parts of substance B are used in the operation, which means that the ratio of the mass of substance A to the mass of substance B used in the operation is 100:50, which can be 100 grams of substance A, 50 grams of substance B, or 10 grams of substance A and 5 grams of substance B.
  • the step S1 includes the following steps:
  • Step S101 Take a three-necked bottle, add 400 parts of absolute ethanol and 100 parts of o-nitrodiphenylamine to the three-necked bottle, and dissolve the o-nitrodiphenylamine in the absolute ethanol by stirring or shaking , Prepare the first liquid.
  • Step S102 adding 3 parts of iron hydroxide to the first liquid, heating to 70-80°C, then adding 58.4 parts of hydrazine hydrate to the first liquid, keeping the temperature and stirring for 3-8 hours to make the The o-nitrodiphenylamine fully reacts with the hydrazine hydrate to prepare a second liquid.
  • the hydrazine hydrate has the formula N 2 H 4 H 2 O; .
  • the purity was 80% hydrazine hydrate; the iron hydroxide catalyst as in the step S102.
  • Step S103 cooling the second liquid to 60-70°C, filtering the second liquid, and then taking the filtrate to evaporate and concentrate, then filtering again, and drying the filtrate to obtain a first intermediate .
  • silica gel is used as a filter aid when filtering the second liquid; the temperature of evaporation and concentration is 40-50°C; the temperature of the drying treatment is 55-60°C, and the drying time is 12 hours; The amount of the first intermediate is 82 parts.
  • Step S2 The first intermediate is mixed and reacted with 3,5-dimethyl bromobenzene to prepare a second intermediate.
  • the synthesis path of the second intermediate is as follows:
  • the step S2 includes the following steps:
  • Step S201 Take a three-necked bottle, add 82 parts of the first intermediate and 530 parts of dichloromethane into the three-necked bottle, and dissolve the first intermediate in the dichloromethane by stirring or shaking. In methane, the third liquid is prepared.
  • Step S202 cooling the third liquid to 10-15°C, adding 83 parts of 3,5-dimethyl bromobenzene dropwise to the third liquid, and keeping the temperature and stirring for 2 to 4 hours to make the An intermediate is fully reacted with the 3,5-dimethyl bromobenzene to prepare the fourth liquid.
  • the step S201 and the step S202 can be performed in a nitrogen atmosphere, for example, can be performed in a glove box filled with nitrogen; the 3,5-dimethylbromobenzene can be slowly added dropwise through a dropper.
  • the dropping time may be 2 hours to ensure that the first intermediate and the 3,5-dimethylbromobenzene fully react.
  • Step S203 Filter the fourth liquid at 10-15°C, take the filtrate and rinse it in absolute ethanol, then filter again, and dry the filtrate to obtain a second intermediate.
  • the temperature of the drying treatment is 40-50° C.
  • the amount of the obtained second intermediate is 146 parts
  • the second intermediate is a white solid.
  • Step S3 Take the second intermediate and p-toluenesulfonic acid to mix and react to obtain a third intermediate.
  • the synthesis path of the third intermediate is as follows:
  • the step S3 includes the following steps:
  • Step S301 Take a three-necked bottle, add 146 parts of the second intermediate and 430 parts of toluene into the three-necked bottle, and stir or shake to completely dissolve the second intermediate in the toluene. Prepare the fifth liquid.
  • Step S302 Add 8.8 parts of p-toluenesulfonic acid to the fifth liquid, and react in a nitrogen atmosphere for 3-9 hours to fully react the second intermediate with the p-toluenesulfonic acid to prepare a sixth liquid. liquid.
  • Step S303 In a nitrogen atmosphere, heat the sixth liquid to 80°C; add 80 parts of clear water to the sixth liquid and stir for 15 minutes; use a separatory funnel to separate the water layer in the liquid; Filter the above-mentioned liquid at 80°C; after the filtrate is evaporated and concentrated, it is filtered again, and the filtrate is taken and dried to obtain the third intermediate.
  • the temperature of the evaporation concentration is 40-50°C
  • the drying treatment is a room temperature drying treatment
  • the drying treatment time is 12 hours
  • the amount of the third intermediate obtained is 130 parts
  • the The third intermediate is a white solid.
  • Step S4 mixing and reacting the third intermediate and hydrated iridium trichloride to obtain a fourth intermediate.
  • the synthetic route of the fourth intermediate is as follows:
  • the step S4 specifically includes the following steps:
  • Step S401 Take a three-necked bottle, add 41 parts of the third intermediate, 230 parts of deionized water, and 230 parts of ethylene glycol ether to the three-necked bottle in a nitrogen atmosphere, and stir or shake the The third intermediate was completely dissolved, and the seventh liquid was prepared.
  • Step S402 In a nitrogen atmosphere, add 25 parts of hydrated iridium trichloride to the seventh liquid, and heat the reaction liquid to 85-100°C for 8-16 hours to make the third intermediate and the The hydrated iridium trichloride is fully reacted to obtain the eighth liquid.
  • the hydrated iridium trichloride of formula three is IrCl 3. H 2 O.
  • Step S403 cooling the eighth liquid to below 40°C, adding 500 parts of water to the eighth liquid, extracting the liquid three times with dichloromethane, combining the organic phases, filtering the organic phases, and performing the filtrate Evaporate and concentrate, then perform and filter again, and dry the filtrate to obtain the fourth intermediate.
  • the temperature of the evaporation concentration is 40-50°C
  • the drying temperature is 40-60°C
  • the amount of the obtained fourth intermediate is 32 parts
  • the fourth intermediate is a reddish brown solid .
  • Step S5 mixing and reacting the fourth intermediate and acetyl ketone to prepare the light emitting layer dopant.
  • the synthetic route of the step S5 is as follows:
  • the step S5 specifically includes the following steps:
  • Step S501 Take a three-necked bottle, add 32 parts of the fourth intermediate and 480 parts of ethylene glycol ether into the three-necked bottle, and stir or shake to make the fourth intermediate completely dissolve in the In ethylene glycol ether, the ninth liquid was prepared.
  • the temperature at which the ethylene glycol ethyl ether dissolves the fourth intermediate is 90-100° C., so as to accelerate the dissolution rate of the fourth intermediate and increase the dissolution amount of the fourth intermediate.
  • Step S502 Add 24.3 parts of acetyl ketone to the ninth liquid at 90-100°C, and react for 20-30 hours under stirring and shaking conditions to make the fourth intermediate and the Acetyl ketone was fully reacted to obtain the tenth liquid.
  • Step S503 Cool the tenth liquid to below 40°C, add 1000 parts of water to the tenth liquid and extract three times with dichloromethane. After the organic phases are combined, the organic phases are filtered, and the filtrate is evaporated and concentrated , And then perform and filter again, and dry the filtrate to obtain the dopant for the light-emitting layer.
  • the evaporation concentration temperature is 40-50°C
  • the drying temperature is 40-60°C
  • the amount of the light-emitting layer dopant obtained is 19 parts
  • the light-emitting layer dopant is red solid.
  • the structural formula of the light-emitting layer dopant is as follows:
  • the preparation method of the light-emitting layer dopant of the organic light-emitting diode provided by the embodiment of the application is simple to operate and easy to implement.
  • the prepared light-emitting layer dopant is a complex of heavy metal iridium, which is helpful for applying it to organic light-emitting devices. To improve the luminous efficiency of light-emitting devices.
  • Another embodiment of the present application provides a light-emitting layer dopant of an organic light-emitting diode, and the structural formula of the light-emitting layer dopant includes at least structural formula 1.
  • the structural formula 1 is as follows:
  • the light-emitting layer dopant is made by using the method for preparing the light-emitting layer dopant described in the foregoing embodiment.
  • the dopant of the light-emitting layer is a red solid.
  • the structural formula of the light-emitting layer dopant is as follows:
  • PL peak is the wavelength corresponding to the photoluminescence peak
  • TGA is the thermal decomposition temperature
  • Tm is the melting point temperature
  • Eg is the energy range between the highest occupied molecular orbital and the lowest unoccupied molecular orbital
  • HOMO is the highest occupied molecular orbital.
  • Energy level LOMO is the lowest unoccupied molecular orbital energy level.
  • the light-emitting layer dopant provided in the embodiments of the present application is a complex of heavy metal iridium.
  • the light-emitting layer dopant is dispersed in the light-emitting layer.
  • the light-emitting layer can be caused to generate phosphorescent light emission, thereby improving the light-emitting efficiency of the organic light-emitting device.
  • FIG. 2 a schematic structural diagram of the electroluminescent device 20 provided by this embodiment of the present application.
  • the electroluminescent device 20 includes a substrate 21 and an anode layer. 22.
  • the substrate 21 may be a transparent glass substrate;
  • the anode layer 22 is made of indium tin oxide material;
  • the hole transport layer 23 is made of N,N-bis(naphthalene-2-yl)-N,N-
  • the electron transport layer 25 is made of 1,3,5-tris(3-(3-pyridyl)phenyl)benzene;
  • the cathode is made of bis(phenyl)biphenyl-4,4-diamine;
  • the layer 26 is made of magnesium and silver alloy;
  • the light-emitting layer 24 uses 1,3-dicarbazolylbenzene as the host material, and the light-emitting layer dopant described in the above embodiment is used as the dopant material.
  • 3 is a light emission spectrum diagram of the electroluminescent device 20, wherein the abscissa represents the wavelength of the emitted spectrum, and the ordinate represents the normalized intensity of the emission spectrum; it can be seen that the light emitted by the electroluminescent device 20 is mainly The light with a wavelength of 618nm corresponds to the EL Peak column in the above table.
  • Fig. 5 is a curve of the relationship between the luminous current efficiency and current density of the electroluminescent device 20, wherein the abscissa represents the current density of the electroluminescent device 20, and the ordinate represents the luminous current efficiency;
  • the current density of the electroluminescent device 20 is 10 mA/cm 2
  • the corresponding luminous current efficiency is 41 cd/A, which corresponds to the Eff.@J10 column in the above table.
  • the light-emitting display device 20 provided in this embodiment has a high light-emitting current efficiency, which illustrates that the light-emitting layer dopant provided in the embodiment of the present application has a beneficial effect on the light-emitting performance of the light-emitting layer 24.
  • the normalized brightness of the electroluminescent device 20 and the light-emitting time curve where the abscissa represents the light-emitting time of the electroluminescent device 20, and the ordinate represents the normalized brightness;
  • the electroluminescent device 20 continues to emit light for 80 hours (h)
  • its luminous brightness is 95% of the initial brightness, which corresponds to the LT95 column in the above table. It should be noted that the curve shown in FIG. 6 indicates that the electroluminescent device 20 has an excellent service life.
  • the electroluminescent device provided in the embodiment of the present application because it contains the dopant of the light-emitting layer provided in the embodiment of the present application, exhibits high luminous efficiency and excellent service life.

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Abstract

涉及一种有机发光二极管的发光层掺杂剂，其制备方法，和应用所述发光层掺杂剂制成的电致发光器件。所述发光层掺杂剂的制备方法操作简单、易于实现，且制备效率高，可制备出高纯度的发光层掺杂剂材料；所述的电致发光器件因为包含了所述的发光层掺杂剂，可以实现发光层材料的磷光发光，从而提高电致发光器件的发光效率。

Description

有机发光二极管的发光层掺杂剂及其制备方法和电致发光器件 技术领域
本申请涉及显示技术领域，尤其涉及一种有机发光二极管的发光层掺杂剂及其制备方法和电致发光器件。
背景技术
有机发光二极管(Organic Light Emitting Diode,OLED)显示装置以其主动发光不需要背光源、发光效率高、可视角度大、响应速度快、温度适应范围大、能耗小、更轻更薄、柔性显示等优点以及巨大的应用前景，吸引了众多研究者的关注。
现有的OLED显示装置通常包括：阳极、空穴传输层、有机发光层、电子传输层以及阴极。工作时，阳极通过空穴传输层向有机发光层传输空穴，阴极通过电子传输层向有机发光层传输电子，这些空穴和电子在有机发光层中组合产生激发性的电子-空穴对，这些电子-空穴对进一步由激发态转换为基态实现OLED的发光。
OLED的发光层中形成的激发态粒子包括单重态粒子和三重态粒子，二者的比例为1:3。而现有的OLED发光层材料为单纯的有机材料，由于势垒的作用，只有单重态粒子可以跃迁至激发态实现发光，此即为荧光发光，因此荧光发光器件的内量子效率只能达到25％。理论研究认为，在发光层中掺杂重金属配合物，可以利用重金属原子的自旋轨道耦合作用，实现三重态粒子的跃迁发光，此即为磷光发光，理论上磷光发光可以达到100％的内量子效率。然而，重金属配合物(如金属铱配合物)的制备还存在较多问题，如制备过程复杂、纯度低、产量低等。
技术问题
荧光发光二极管的内量子效率远低于磷光发光二极管的内量子效率，然而 促进二极管实现磷光发光的重金属配合物存在制备过程复杂、纯度低、产量低的问题。
技术解决方案
为了解决上述技术问题，本申请的技术方案如下：
本申请提供一种有机发光二极管的发光层掺杂剂的制备方法，其包括以下步骤：
步骤S1、取邻硝基二苯胺和水合肼混合反应，制得第一中间物；其合成路线如下：
Figure PCTCN2019096000-appb-000001
步骤S2、取所述第一中间物和3,5-二甲基溴苯混合反应，制得第二中间物；其合成路线如下：
Figure PCTCN2019096000-appb-000002
步骤S3、取所述第二中间物和对甲苯磺酸混合反应，制得第三中间物；其合成路线如下：
Figure PCTCN2019096000-appb-000003
步骤S4、取所述第三中间物和水合三氯化铱混合反应，制得第四中间物；其合成路线如下：
Figure PCTCN2019096000-appb-000004
步骤S5、取所述第四中间物和乙酰基酮混合反应，制得所述发光层掺杂剂；其合成路线如下：
Figure PCTCN2019096000-appb-000005
在本申请的发光层掺杂剂的制备方法中，所述步骤S1具体包括：
步骤S101、使用无水乙醇溶解所述邻硝基二苯胺，制得第一液体；
步骤S102、向所述第一液体中加入氢氧化铁和水合肼反应3～8小时，制得第二液体；
步骤S103、所述第二液体至少经过过滤和干燥制得所述第一中间物。
在本申请的发光层掺杂剂的制备方法中，
按质量份数，所述步骤S101中使用的无水乙醇的量为400份，邻硝基二苯胺的量为100份；所述步骤S102中使用的氢氧化铁的量为3份，水合肼的量为58.4份。
在本申请的发光层掺杂剂的制备方法中，所述步骤S2具体包括：
步骤S201、使用二氯甲烷溶解所述第一中间物，制得第三液体；
步骤S202、向所述第三液体中加入3,5-二甲基溴苯反应2～4小时，制得第四液体；
步骤S203、所述第四液体至少经过过滤和干燥制得所述第二中间物。
在本申请的发光层掺杂剂的制备方法中，
按质量份数，所述步骤S201中使用的二氯甲烷的量为530份；所述步骤S202中使用的3,5-二甲基溴苯的量为83份。
在本申请的发光层掺杂剂的制备方法中，所述步骤S3具体包括：
步骤S301、使用甲苯溶解所述第二中间物，制得第五液体；
步骤S302、向所述第五液体中加入对甲苯磺酸反应3～9小时，制得第六液体；
步骤S303、所述第六液体至少经过过滤和干燥制得所述第三中间物。
在本申请的发光层掺杂剂的制备方法中，
按质量份数，所述步骤S301中甲苯的量为430份；所述步骤S302中使用的对甲苯磺酸的量为8.8份。
在本申请的发光层掺杂剂的制备方法中，所述步骤S4具体包括：
步骤S401、使用去离子水和乙二醇乙醚的混合液溶解所述第三中间物，制得第七液体；
步骤S402、向所述第七液体中加入水合三氯化铱反应8～16小时，制得第八液体；
步骤S403、所述第八液体至少经过过滤和干燥制得所述第四中间物。
在本申请的发光层掺杂剂的制备方法中，
按质量份数，所述步骤S401中使用的去离子水的量为230份，乙二醇乙醚的量为230份；所述步骤S402中使用的水合三氯化铱的量为25份。
在本申请的发光层掺杂剂的制备方法中，所述步骤S5具体包括：
步骤S501、使用乙二醇乙醚溶解所述第四中间物，制得第九液体；
步骤S502、向所述第九液体中加入乙酰基酮反应20～30小时，制得第十液体；
步骤S503、所述第十液体至少经过萃取、过滤和干燥制得所述发光层掺杂剂。
在本申请的发光层掺杂剂的制备方法中，
按质量份数，所述步骤S501中使用的乙二醇乙醚的量为480份；所述步骤S502中使用的乙酰基酮的量为24.3份。
在本申请的发光层掺杂剂的制备方法中，所述萃取时采用的萃取剂是二氯甲烷。
本申请还提供一种有机发光二极管的发光层掺杂剂，所述发光层掺杂剂的结构式至少包含结构式1，所述结构式1如下：
Figure PCTCN2019096000-appb-000006
在本申请的发光层掺杂剂中，所述发光层掺杂剂的结构式如下：
Figure PCTCN2019096000-appb-000007
在本申请的发光层掺杂剂中，所述发光层掺杂剂的颜色为红色。
在本申请的发光层掺杂剂中，所述发光层掺杂剂应用于有机发光二极管的发光层中。
在本申请的发光层掺杂剂中，所述发光层掺杂剂为重金属铱的配合物。
本申请又提供一种电致发光器件，包括发光层，所述发光层中掺杂发光层掺杂剂，所述发光层掺杂剂的结构至少包括结构式1，所述结构式1如下：
Figure PCTCN2019096000-appb-000008
在本申请的电致发光器件中，所述发光层掺杂剂的结构式如下：
Figure PCTCN2019096000-appb-000009
在本申请的电致发光器件中，所述电致发光器件包括：
基板；
阳极层，设置于所述基板上；
空穴传输层，设置于所述阳极层上；
所述发光层，设置于所述空穴传输层上；
电子传输层，设置于所述发光层上；
阴极层，设置于所述电子传输层上。
有益效果
本申请提供了一种有机发光二极管的发光层掺杂剂及其制备方法和应用所述发光层掺杂剂制成的电致发光器件，所述发光层掺杂剂的制备方法操作简单、 易于实现，且制备效率高，可制备出高纯度的发光层掺杂剂材料；本申请提供的电致发光器件因为包含了本申请提供的发光层掺杂剂，可以实现发光层材料的磷光发光，从而提高电致发光器件的发光效率。
附图说明
为了更清楚地说明实施例或现有技术中的技术方案，下面将对实施例或现有技术描述中所需要使用的附图作简单介绍，显而易见地，下面描述中的附图仅仅是申请的一些实施例，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。
图1是本申请实施例提供的有机发光二极管的发光层掺杂剂的制备方法流程图；
图2是本申请实施例提供的电致发光器件的结构示意图；
图3是本申请实施例提供的电致发光器件的发光光谱图；
图4是本申请实施例提供的电致发光器件的电流密度与电压关系曲线图；
图5是本申请实施例提供的电致发光器件的发光电流效率与电流密度的关系曲线图；
图6是本申请实施例提供的电致发光器件的归一化亮度与发光时间的关系曲线图。
本发明的实施方式
以下各实施例的说明是参考附加的图示，用以例示本申请可用以实施的特定实施例。本申请所提到的方向用语，例如[上]、[下]、[前]、[后]、[左]、[右]、[内]、[外]、[侧面]等，仅是参考附加图式的方向。因此，使用的方向用语是用以说明及理解本申请，而非用以限制本申请。在图中，结构相似的单元是用以相同标号表示。
本申请实施例提供了一种有机发光二极管的发光层掺杂剂的制备方法，制备过程简单易操作，制备效率高，可制备出高纯度的发光层掺杂剂。
如图1所示，为本申请实施例提供的有机发光二极管的发光层掺杂剂制备方法流程图，所述制备方法包括以下步骤：
步骤S1、取邻硝基二苯胺和水合肼混合反应，制得第一中间物。
所述第一中间物的合成路径如下：
Figure PCTCN2019096000-appb-000010
需要说明的是，本申请中所述的各物质的量均按质量份数计算，即物质之间的质量比例。例如，在操作中分别使用A物质100份和B物质50份，其意思是在该操作中使用的A物质的质量与B物质的质量的比值是100:50，其可以是A物质100克、B物质50克，或A物质10克、B物质5克。
根据本申请一实施例，所述步骤S1包括以下步骤：
步骤S101、取一三口瓶，向所述三口瓶中添加400份无水乙醇和100份邻硝基二苯胺，通过搅拌或震动使所述邻硝基二苯胺溶解于所述无水乙醇中，制得第一液体。
具体地，所述邻硝基二苯胺的结构式如下：
Figure PCTCN2019096000-appb-000011
步骤S102、向所述第一液体中加入3份氢氧化铁，加热升温至70～80℃后，再向所述第一液体中加入58.4份水合肼，保温搅拌3-8小时，使所述邻硝基二苯胺与所述水合肼充分反应，制得第二液体。
具体地，所述水合肼的分子式为N 2H 4 .H 2O；所述水合肼的纯度为80％；所述氢氧化铁在所述步骤S102中作为反应的催化剂。
步骤S103、将所述第二液体降温至60～70℃，对所述第二液体进行过滤，然后取滤液蒸发浓缩，之后再次进行过滤，并对滤出物进行干燥处理，得到第一中间物。
具体地，对所述第二液体进行过滤时采用硅胶作为助滤剂；所述蒸发浓缩的温度为40～50℃；所述干燥处理的温度55～60℃，干燥的时间为12小时；得到的所述第一中间物的量为82份。
具体地，所述第一中间物的结构式如下：
Figure PCTCN2019096000-appb-000012
步骤S2、取所述第一中间物和3,5-二甲基溴苯混合反应，制得第二中间物。
所述第二中间物的合成路径如下：
Figure PCTCN2019096000-appb-000013
根据本申请一实施例，所述步骤S2包括以下步骤：
步骤S201、取一三口瓶，向所述三口瓶中加入82份的所述第一中间物和530份的二氯甲烷，通过搅拌或震动使所述第一中间物溶解于所述二氯甲烷中，制得第三液体。
步骤S202、将所述第三液体降温至10～15℃，向所述第三液体中滴加83份的3,5-二甲基溴苯，并保温搅拌2～4小时，使所述第一中间物与所述3,5-二甲基溴苯充分反应，制得第四液体。
具体地，所述步骤S201和所述步骤S202可以在氮气氛围中进行，如可以在充满氮气的手套箱中进行；所述3,5-二甲基溴苯可以通过滴管缓慢滴加入所 述第三液体中，其滴加时间可以是2小时，以保证所述第一中间物与所述3,5-二甲基溴苯充分反应。
具体地，所述3,5-二甲基溴苯的结构式如下：
Figure PCTCN2019096000-appb-000014
步骤S203、将所述第四液体在10～15℃的条件下过滤，取滤出物置于无水乙醇中漂洗，然后再次进行过滤，并对滤出物进行干燥处理，得到第二中间物。
具体地，所述干燥处理的温度为40～50℃，得到的所述第二中间物的量为146份，所述第二中间物为白色固体。
具体的，所述第二中间物的结构式如下：
Figure PCTCN2019096000-appb-000015
步骤S3、取所述第二中间物和对甲苯磺酸混合反应，制得第三中间物。
所述第三中间物的合成路径如下：
Figure PCTCN2019096000-appb-000016
根据本申请一实施例，所述步骤S3包括以下步骤：
步骤S301、取一三口瓶，向所述三口瓶中加入146份的所述第二中间物和430份的甲苯，通过搅拌或震动使所述第二中间物完全溶解于所述甲苯中，制得第五液体。
步骤S302、向所述第五液体中加入8.8份的对甲苯磺酸，在氮气氛围中反应3～9小时，使所述第二中间物与所述对甲苯磺酸充分反应，制得第六液体。
具体地，所述对甲苯磺酸的结构式如下：
Figure PCTCN2019096000-appb-000017
步骤S303、在氮气氛围中，将所述第六液体加热到80℃；向所述第六液体中加入80份的清水并搅拌15分钟；采用分液漏斗分去上述液体中的水层；在80℃条件下对上述液体进行过滤；取滤液蒸发浓缩后，再次进行过滤，取滤出物进行干燥处理，制得第三中间物。
具体地，所述蒸发浓缩的温度为40～50℃，所述干燥处理为常温干燥处理，所述干燥处理的时间为12小时；得到的所述第三中间物的量为130份，所述第三中间物为白色固体。
具体地，所述第三中间物的结构式如下：
Figure PCTCN2019096000-appb-000018
步骤S4、取所述第三中间物和水合三氯化铱混合反应，制得第四中间物。
所述第四中间物的合成路线如下：
Figure PCTCN2019096000-appb-000019
根据本申请一实施例，所述步骤S4具体包括以下步骤：
步骤S401、取一三口瓶，在氮气氛围中，向所述三口瓶中加入41份所述第三中间物、230份去离子水和230份乙二醇乙醚，通过搅拌或震动使所述第三中间物完全溶解，制得第七液体。
步骤S402、在氮气氛围中，向所述第七液体中加入25份的水合三氯化铱，并将反应液加热至85～100℃反应8～16小时，使所述第三中间物和所述水合三氯化铱充分反应，制得第八液体。
具体地，所述水合三氯化铱的分子式为IrCl 3 .H 2O。
步骤S403、将所述第八液体降温至40℃以下，向所述第八液体中加入500份水，使用二氯甲烷对上述液体萃取三次，合并有机相，过滤所述有机相，对滤液进行蒸发浓缩，然后再次进行并过滤，将滤出物烘干，得到第四中间物。
具体地，所述蒸发浓缩的温度为40～50℃，所述烘干温度为40～60℃，得到的所述第四中间物的量为32份，所述第四中间物为红褐色固体。
具体地，所述第四中间物的结构式如下：
Figure PCTCN2019096000-appb-000020
步骤S5、取所述第四中间物和乙酰基酮混合反应，制成所述发光层掺杂剂。
所述步骤S5的合成路线如下：
Figure PCTCN2019096000-appb-000021
根据本申请一实施例，所述步骤S5具体包括以下步骤：
步骤S501、取一三口瓶，向所述三口瓶中加入32份的所述第四中间物和480份的乙二醇乙醚，通过搅拌或震动使所述第四中间物完全溶解在所述乙二醇乙醚中，制得第九液体。
具体地，所述乙二醇乙醚溶解所述第四中间物时的温度为90～100℃，以加快所述第四中间物的溶解速度并且增大所述第四中间物的溶解量。
步骤S502、在90～100℃条件下，向所述第九液体中加入24.3份的乙酰基酮，并在搅拌和震动的条件下反应20～30小时，使所述第四中间物与所述乙酰基酮充分反应，制得第十液体。
具体地，所述乙酰基酮的结构式如下：
Figure PCTCN2019096000-appb-000022
步骤S503、将所述第十液体降温至40℃以下，向所述第十液体中加入1000份水并使用二氯甲烷萃取三次，合并有机相后，过滤所述有机相，对滤液进行蒸发浓缩，然后再次进行并过滤，将滤出物烘干，得到所述发光层掺杂剂。
具体地，所述蒸发浓缩的温度为40～50℃，所述烘干温度为40～60℃，得到的所述发光层掺杂剂的量为19份，所述发光层掺杂剂为红色固体。
具体地，所述发光层掺杂剂的结构式如下：
Figure PCTCN2019096000-appb-000023
本申请实施例提供的有机发光二极管的发光层掺杂剂的制备方法操作简单、易于实现，制备出的发光层掺杂剂为重金属铱的配合物，将其应用于有机发光设备中，有助于提高发光设备的发光效率。
本申请另一实施例提供了一种有机发光二极管的发光层掺杂剂，所述发光层掺杂剂的结构式至少包括结构式1。
所述结构式1如下：
Figure PCTCN2019096000-appb-000024
根据本申请一实施例，所述发光层掺杂剂为采用上述实施例中所述的发光层掺杂剂的制备方法制成。所述发光层掺杂剂为红色固体。所述发光层掺杂剂的结构式如下：
Figure PCTCN2019096000-appb-000025
对所述发光层掺杂剂的电化学能级进行测试，可以得到下表中所示的数据：
Figure PCTCN2019096000-appb-000026
其中，PL peak为光致发光峰所对应的波长，TGA为热分解温度，Tm为熔点温度，Eg为最高已占分子轨道与最低未占分子轨道的能极差，HOMO为最高已占据分子轨道能级，LOMO为最低未占分子轨道能级。
应当理解的是，本申请实施例提供的发光层掺杂剂为重金属铱的配合物，所述发光层掺杂剂应用于有机发光设备中时，将所述发光层掺杂剂分散于发光层主体材料中，可以促使所述发光层产生磷光发光，从而提高所述有机发光设备的发光效率。
本申请又一实施例提供了一种电致发光器件，如图2所示，为本申请实施例提供的电致发光器件20的结构示意图，所述电致发光器件20包括基板21、阳极层22、空穴传输层23、发光层24、电子传输层25以及阴极层26。其中，所述基板21可以是透明玻璃基板；所述阳极层22由氧化铟锡材料制成；所述空穴传输层23由N,N-二(萘-2-基)-N,N-二(苯基)联苯-4,4-二胺制成；所述电子传输层25由1,3,5-三(3-(3-吡啶基)苯基)苯制成；所述阴极层26由镁、银合金制成；所述发光层24采用1,3-二咔唑基苯作为主体材料，采用上述实施例所述的发光层掺杂剂作为掺杂剂材料。
对所述电致发光器件20进行性能测试，得到如下性能数据：
EL Peak(nm) Op.V@J10(V) Eff.@J10(cd/A) LT95(h)
618 3.5 41 80
下面结合图2至图6对上述表格中的数据进行说明：
图3为所述电致发光器件20的发光光谱图，其中横坐标代表所发射光谱的波长，纵坐标代表发射光谱的归一化强度；可见，所述电致发光器件20发射的光主要是波长618nm的光，对应上述表格中的EL Peak栏。
图4为所述电致发光器件20的电流密度与电压关系曲线，其中横坐标代表 所述电致发光器件20的工作电压，纵坐标代表其电流密度；可见，当所述电致发光器件20的电流密度为10mA/cm 2时对应的工作电压为3.5V，对应上述表格中的Op.V@J10一栏。
图5是所述电致发光器件20的发光电流效率与电流密度的关系曲线，其中横坐标代表所述电致发光器件20的电流密度，纵坐标代表其发光电流效率；可见，当所述电致发光器件20的电流密度为10mA/cm 2时对应的发光电流效率为41cd/A，对应上述表格中的Eff.@J10一栏。需要说明的是，本实施例提供的发光显示装置20具有较高的发光电流效率，说明了本申请实施例提供的发光层掺杂剂对所述发光层24的发光性能产生有益影响。
图6是所述电致发光器件20的归一化亮度与发光时间的关系曲线，其中横坐标代表所述电致发光器件20的发光时间，纵坐标代表其归一化亮度；可见，当所述电致发光器件20持续发光80小时(h)时，其发光亮度是初始亮度的95％，对应上述表格中的LT95一栏。需要说明的是，图6所示的曲线说明所述电致发光器件20具有优异的使用寿命。
综上所述，本申请实施例提供的电致发光器件，因为包含了本申请实施例提供的发光层掺杂剂，表现出较高的发光效率，以及优异的使用寿命。
需要说明的是，虽然本申请以具体实施例揭露如上，但上述实施例并非用以限制本申请，本领域的普通技术人员，在不脱离本申请的精神和范围内，均可作各种更动与润饰，因此本申请的保护范围以权利要求界定发范围为准。

Claims (20)

  1. 一种有机发光二极管的发光层掺杂剂的制备方法，其包括以下步骤：
    步骤S1、取邻硝基二苯胺和水合肼混合反应，制得第一中间物；其合成路线如下：
    Figure PCTCN2019096000-appb-100001
    步骤S2、取所述第一中间物和3,5-二甲基溴苯混合反应，制得第二中间物；其合成路线如下：
    Figure PCTCN2019096000-appb-100002
    步骤S3、取所述第二中间物和对甲苯磺酸混合反应，制得第三中间物；其合成路线如下：
    Figure PCTCN2019096000-appb-100003
    步骤S4、取所述第三中间物和水合三氯化铱混合反应，制得第四中间物；其合成路线如下：
    Figure PCTCN2019096000-appb-100004
    步骤S5、取所述第四中间物和乙酰基酮混合反应，制得所述发光层掺杂剂；其合成路线如下：
    Figure PCTCN2019096000-appb-100005
  2. 根据权利要求1所述的发光层掺杂剂的制备方法，其中，所述步骤S1具体包括：
    步骤S101、使用无水乙醇溶解所述邻硝基二苯胺，制得第一液体；
    步骤S102、向所述第一液体中加入氢氧化铁和水合肼反应3～8小时，制得第二液体；
    步骤S103、所述第二液体至少经过过滤和干燥制得所述第一中间物。
  3. 根据权利要求2所述的发光层掺杂剂的制备方法，其中，
    按质量份数，所述步骤S101中使用的无水乙醇的量为400份，邻硝基二苯胺的量为100份；所述步骤S102中使用的氢氧化铁的量为3份，水合肼的量为58.4份。
  4. 根据权利要求1所述的发光层掺杂剂的制备方法，其中，所述步骤S2具体包括：
    步骤S201、使用二氯甲烷溶解所述第一中间物，制得第三液体；
    步骤S202、向所述第三液体中加入3,5-二甲基溴苯反应2～4小时，制得第四液体；
    步骤S203、所述第四液体至少经过过滤和干燥制得所述第二中间物。
  5. 根据权利要求4所述的发光层掺杂剂的制备方法，其中，
    按质量份数，所述步骤S201中使用的二氯甲烷的量为530份；所述步骤S202中使用的3,5-二甲基溴苯的量为83份。
  6. 根据权利要求1所述的发光层掺杂剂的制备方法，其中，所述步骤S3具体包括：
    步骤S301、使用甲苯溶解所述第二中间物，制得第五液体；
    步骤S302、向所述第五液体中加入对甲苯磺酸反应3～9小时，制得第六液体；
    步骤S303、所述第六液体至少经过过滤和干燥制得所述第三中间物。
  7. 根据权利要求6所述的发光层掺杂剂的制备方法，其中，
    按质量份数，所述步骤S301中甲苯的量为430份；所述步骤S302中使用的对甲苯磺酸的量为8.8份。
  8. 根据权利要求1所述的发光层掺杂剂的制备方法，其中，所述步骤S4具体包括：
    步骤S401、使用去离子水和乙二醇乙醚的混合液溶解所述第三中间物，制得第七液体；
    步骤S402、向所述第七液体中加入水合三氯化铱反应8～16小时，制得第八液体；
    步骤S403、所述第八液体至少经过过滤和干燥制得所述第四中间物。
  9. 根据权利要求8所述的发光层掺杂剂的制备方法，其中，
    按质量份数，所述步骤S401中使用的去离子水的量为230份，乙二醇乙醚的量为230份；所述步骤S402中使用的水合三氯化铱的量为25份。
  10. 根据权利要求1所述的发光层掺杂剂的制备方法，其中，所述步骤S5具体包括：
    步骤S501、使用乙二醇乙醚溶解所述第四中间物，制得第九液体；
    步骤S502、向所述第九液体中加入乙酰基酮反应20～30小时，制得第十液 体；
    步骤S503、所述第十液体至少经过萃取、过滤和干燥制得所述发光层掺杂剂。
  11. 根据权利要求10所述的发光层掺杂剂的制备方法，其中，
    按质量份数，所述步骤S501中使用的乙二醇乙醚的量为480份；所述步骤S502中使用的乙酰基酮的量为24.3份。
  12. 根据权利要求10所述的发光层掺杂剂的制备方法，其中，所述萃取时采用的萃取剂是二氯甲烷。
  13. 一种有机发光二极管的发光层掺杂剂，其中，所述发光层掺杂剂的结构式至少包含结构式1，所述结构式1如下：
    Figure PCTCN2019096000-appb-100006
  14. 根据权利要求13所述的发光层掺杂剂，其中，所述发光层掺杂剂的结构式如下：
    Figure PCTCN2019096000-appb-100007
  15. 根据权利要求13所述的发光层掺杂剂，其中，所述发光层掺杂剂的颜色为红色。
  16. 根据权利要求13所述的发光层掺杂剂，其中，所述发光层掺杂剂应用于有机发光二极管的发光层中。
  17. 根据权利要求13所述的发光层掺杂剂，其中，所述发光层掺杂剂为重 金属铱的配合物。
  18. 一种电致发光器件，其中，包括发光层，所述发光层中掺杂发光层掺杂剂，所述发光层掺杂剂的结构至少包括结构式1，所述结构式1如下：
    Figure PCTCN2019096000-appb-100008
  19. 根据权利要求18所述的电致发光器件，其中，所述发光层掺杂剂的结构式如下：
    Figure PCTCN2019096000-appb-100009
  20. 根据权利要求18所述的电致发光器件，其中，所述电致发光器件包括：
    基板；
    阳极层，设置于所述基板上；
    空穴传输层，设置于所述阳极层上；
    所述发光层，设置于所述空穴传输层上；
    电子传输层，设置于所述发光层上；
    阴极层，设置于所述电子传输层上。
PCT/CN2019/096000 2019-05-29 2019-07-15 有机发光二极管的发光层掺杂剂及其制备方法和电致发光器件 Ceased WO2020237793A1 (zh)

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