CN112812065A - Method for separating nano palladium, copper and iron particles from phenanthroimidazole derivative - Google Patents

Method for separating nano palladium, copper and iron particles from phenanthroimidazole derivative Download PDF

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CN112812065A
CN112812065A CN202110053589.1A CN202110053589A CN112812065A CN 112812065 A CN112812065 A CN 112812065A CN 202110053589 A CN202110053589 A CN 202110053589A CN 112812065 A CN112812065 A CN 112812065A
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phenanthroimidazole
copper
phenanthroimidazole derivative
iron particles
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罗正鸿
潘德韬
周寅宁
张希宝
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Shanghai Jiaotong University
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Abstract

The invention provides a method for separating nano palladium, copper and iron particles from a phenanthroimidazole derivative, which specifically comprises the following steps: 1) mixing the crude phenanthroimidazole derivative product with a solvent to obtain a solution; 2) carrying out magnetic separation on the solution by adopting a micro-channel reactor, wherein the inner wall of a channel of the micro-channel reactor is made of a magnetic material; 3) and cooling the liquid subjected to magnetic separation, crystallizing and separating out, wherein the separated crystal is the phenanthroimidazole derivative. The method adopts the reactor with the inner wall material of the ferrite soft magnetic material, when the solution flows through the reactor, trace nano copper, palladium and iron particles embedded in the gaps of the crude phenanthroimidazole derivative photoelectric material are adsorbed on the wall surface of the magnetic material, so that the effect of purifying the phenanthroimidazole derivative photoelectric material is achieved, the separation method is simple to operate, no foreign impurities are introduced, and the continuous separation of the phenanthroimidazole derivative can be realized.

Description

Method for separating nano palladium, copper and iron particles from phenanthroimidazole derivative
Technical Field
The invention belongs to the field of material separation, and particularly relates to a method for separating nano palladium, copper and iron particles from a phenanthroimidazole derivative.
Background
The organic light emitting diode display technology (OLED) has the advantages of low power consumption, high contrast, wide temperature range, bright color, capability of realizing ultra-light and thin, integrated touch function, high curvature, strong impact resistance and the like, and shows a strong market development trend in recent years, and the demand of the OLED is in rapid growth. The organic photoelectric material is the upstream supporting industry of the OLED industry and is concerned by companies and research institutions at home and abroad. Among them, blue phosphorescent materials have high luminous efficiency, but have insufficient chromaticity and lifetime for practical use. In order to achieve long-term working stability of the device, the organic blue light material should have electronic grade high purity, photochemical stability, high quantum efficiency, good thermal stability, film forming property and non-crystallinity.
The phenanthroimidazole derivative is an important blue light phosphorescent material, and the molecular structure of the phenanthroimidazole derivative determines that the phenanthroimidazole derivative has ultrahigh electron-hole transmission capability and has great commercial application potential. However, during the synthesis of the material, it is difficult to avoid catalyst residues, resulting in trace (less than 10ppm) of free nano-metallic palladium, copper and iron particles being embedded in the material voids. Since the organic light emitting display device operates under an external voltage and the organic light emitting material is in an excited state, a very small amount of impurities and the like in a light emitting layer with a thickness of only tens of nanometers may cause defects, which causes a great reduction in device efficiency and seriously affects the reliability of the light emitting display device.
If the phenanthroimidazole derivative organic photoelectric material is purified by adopting conventional separation means such as column chromatography, recrystallization and the like, a large amount of organic solvent is required, the purification steps are complicated, the risk of secondary introduction of impurities is increased, and the difficulty and the cost of separation operation are further increased. Therefore, the development of related purification technology can effectively remove trace nano metal palladium, copper and iron particles embedded in the gaps of the phenanthroimidazole derivative blue-light material, and the method has important significance for improving the stability and the luminous efficiency and industrial application.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, the present invention aims to provide a method for separating nano palladium, copper and iron particles from a phenanthroimidazole derivative, which utilizes the characteristic that nano metal particles have magnetism and adopts a microchannel reactor with a magnetic material to realize separation, thereby solving the problems existing in the prior art.
To achieve the above objects and other related objects, the present invention is achieved by the following technical solutions.
One of the purposes of the invention is to provide a method for separating nano palladium, copper and iron particles from phenanthroimidazole derivatives, which comprises the following steps:
1) mixing the crude phenanthroimidazole derivative product with a solvent to obtain a solution;
2) carrying out magnetic separation on the solution by adopting a micro-channel reactor, wherein the inner wall of a channel of the micro-channel reactor is made of a magnetic material;
3) and cooling the liquid subjected to magnetic separation, crystallizing and separating out, wherein the separated crystal is the phenanthroimidazole derivative.
The method is suitable for separating trace amount of nano palladium, copper and iron particles from the phenanthroimidazole derivative, is simpler and more convenient, and has operability.
Preferably, the structural formula of the phenanthroimidazole derivative is as follows:
Figure BDA0002900049240000021
wherein R is1、R2、R4And R5Is one selected from the group consisting of H, a linear or branched alkyl group having 1 to 10 carbons, a linear or branched alkoxy group having 1 to 10 carbons, an aryl group having 1 to 10 carbons and a heterocyclic aryl group having 1 to 10 carbons, wherein R is1And R5Different;
R3is one selected from the group consisting of F, Cl, H, a linear or branched alkyl group having 1 to 10 carbons, a linear or branched alkoxy group having 1 to 10 carbons, an aryl group having 1 to 10 carbons and a heterocyclic aryl group having 1 to 10 carbons;
the structural formula of the straight-chain or branched-chain alkyl containing 1 to 10 carbons is selected from:
Figure BDA0002900049240000022
the general structural formula of the straight-chain or branched-chain alkoxy containing 1-10 carbons is selected from:
Figure BDA0002900049240000023
the aryl group having 1 to 10 carbons has a general structural formula selected from:
Figure BDA0002900049240000031
the heterocyclic aryl group containing 1 to 10 carbons has a general structural formula selected from:
Figure BDA0002900049240000032
R6is one selected from triphenylamine group and derivatives thereof, diphenylamine group and derivatives thereof, carbazolyl group and derivatives thereof, and N-phenylcarbazolyl group and derivatives thereof.
The structural general formula of the triphenylamine group and the derivative thereof is as follows:
Figure BDA0002900049240000033
the structural general formula of the diphenylamine group and the derivative thereof is as follows:
Figure BDA0002900049240000034
the carbazolyl and the derivative thereof have the structural general formula:
Figure BDA0002900049240000035
the structural general formula of the N-phenylcarbazolyl and the derivative thereof is as follows:
Figure BDA0002900049240000041
wherein R is7、R8And R9Independently selected from H, F, Cl, straight chain or branched chain alkyl containing 1-10 carbons and straight chain or branched chain alkoxy containing 1-10 carbons.
More preferably, the phenanthroimidazole derivative is specifically selected from one or more of the following structures:
Figure BDA0002900049240000042
Figure BDA0002900049240000051
preferably, the solvent is one or more of dichloromethane, xylene, tetrahydrofuran or benzene.
Preferably, the mass volume ratio of the crude phenanthroimidazole derivative to the solvent is 1g (1-10) ml.
More preferably, the mass volume ratio of the crude phenanthroimidazole derivative to the solvent is 1g (3-5) ml.
Preferably, in the step 2), the channel of the microchannel reactor is spiral, the pipe diameter of the channel of the microchannel reactor is 0.1 mm-0.5 mm, and the length of the channel of the microchannel reactor is 0.1 m-1 m.
Preferably, in step 2), the magnetic material is a ferrite soft magnetic material. More preferably, the soft magnetic material comprises one of manganese zinc ferrite, nickel zinc ferrite, zinc ferrite and manganese magnesium zinc ferrite. The total content of nano palladium, copper and iron in the crude product of the phenanthroimidazole derivative is less than 10ppm, and the crude product has good adsorption selectivity on nano-sized palladium, copper and iron particles through a ferrite soft magnetic material.
Preferably, in step 2), the flow rate of the solution in the channel of the microchannel reactor is 0.1ml/s to 1 ml/s.
More preferably, the flow rate of the solution is between 0.1ml/s and 0.6 ml/s.
Preferably, in the step 2), during magnetic separation, the microchannel reactor is placed in an ultrasonic environment for ultrasonic treatment, and heat preservation is performed simultaneously.
More preferably, the ultrasonic frequency is 20 KHz-80 KHz, and the heat preservation temperature is 10 ℃ to 25 ℃.
Further preferably, the ultrasonic frequency is 60 KHz-80 KHz, and the heat preservation temperature is 15 ℃ to 20 ℃.
Preferably, in the step 3), the temperature is reduced to-10 ℃ to 10 ℃, and the temperature reduction rate is 10 ℃/h to 40 ℃/h.
More preferably, the temperature is reduced to-10-0 ℃ at a rate of 10-30 ℃/h.
Compared with the prior art, the invention has the following beneficial effects:
1. the invention adopts a reactor with soft magnetic material as the inner wall material, when the crude phenanthroimidazole derivative solution flows through the reactor, trace nano metal particles of copper, palladium and iron embedded in gaps of the phenanthroimidazole derivative are adsorbed on the wall surface of the magnetic material, and are completely separated from the solution at the outlet of the spiral microchannel reactor, so that the effect of purifying the phenanthroimidazole derivative is achieved.
2. The spiral microchannel reactor is placed in an ultrasonic environment during magnetic separation, and the movement of molecules and metal particles in a solution is enhanced by an ultrasonic external field with certain frequency under the action of an ultrasonic field, so that the probability of the metal particles being adsorbed on a wall surface is improved, and the aim of efficiently separating in a short time is fulfilled.
3. The method can realize continuous separation of the phenanthroimidazole derivative, and has the advantages of simple steps, high efficiency and convenience.
Detailed Description
The following description of the embodiments of the present invention is provided for illustrative purposes, and other advantages and effects of the present invention will become apparent to those skilled in the art from the present disclosure.
Before the present embodiments are further described, it is to be understood that the scope of the invention is not limited to the particular embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention. Test methods in which specific conditions are not specified in the following examples are generally carried out under conventional conditions or under conditions recommended by the respective manufacturers.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition to the specific methods, devices, and materials used in the examples, any methods, devices, and materials similar or equivalent to those described in the examples may be used in the practice of the invention in addition to the specific methods, devices, and materials used in the examples, in keeping with the knowledge of one skilled in the art and with the description of the invention.
The invention relates to a device used in a method for separating nano palladium, copper and iron particles from a phenanthroimidazole derivative.
In a specific case of using the above-mentioned apparatus for separating nano palladium, copper and iron particles from the phenanthroimidazole derivative,
filling the phenanthroimidazole derivative crude product and a solvent into a raw material bottle to obtain a solution, pumping the solution into a spiral microchannel reactor through a peristaltic pump, placing the spiral microchannel reactor into an ultrasonic device for ultrasonic treatment and heat preservation, enabling trace nano-metal copper, palladium and iron contained in the phenanthroimidazole derivative crude product to be adsorbed by a magnetic material on the inner wall of a pipeline of the spiral microchannel reactor when the solution flows through the spiral microchannel reactor at a certain flow rate, enabling the liquid flowing out of an outlet of the spiral microchannel reactor to enter a cooling crystallization device, and separating out crystals through cooling, wherein the separated crystals are the phenanthroimidazole derivative.
Examples 1 to 6 in the present application were carried out by using the above-mentioned apparatus, but it should be noted that the apparatus is not limited to the apparatus exemplified in the present invention for the purpose of achieving the present invention in the present application, and any reactor, apparatus or equipment may be used as long as the conditions of the present invention are satisfied.
Example 1
In this embodiment, the method for separating nano palladium, copper and iron particles from the phenanthroimidazole derivative includes the following steps:
1) dissolving 1g of a crude product of the phenanthroimidazole derivative in 1ml of dichloromethane to obtain a solution; wherein the contents of nano palladium, copper and iron in the crude phenanthroimidazole derivative product are 1.5ppm, 2ppm and 2.2ppm respectively.
2) The solution is continuously injected into a spiral microchannel reactor with the inner wall made of ferrite soft magnetic material at the flow rate of 0.1ml/s, and the microchannel reactor is placed in an ultrasonic environment of 20KHz, and the heat preservation temperature is 10 ℃.
3) And cooling the liquid subjected to magnetic separation to 10 ℃ at a cooling rate of 10 ℃/h to separate out crystals, wherein the separated crystals are high-purity phenanthroimidazole derivatives. The ICP-MS analysis results show that the total content of total iron, copper and palladium in the crude phenanthroimidazole derivative is less than 1 ppb.
In this example, the molecular structure of the phenanthroimidazole derivative is as follows:
Figure BDA0002900049240000071
example 2
In this embodiment, the method for separating nano palladium, copper and iron particles from the phenanthroimidazole derivative includes the following steps:
1) dissolving 1g of a crude product of the phenanthroimidazole derivative in 8ml of dichloromethane to obtain a solution; wherein, the contents of nano palladium, copper and iron in the crude product of the phenanthroimidazole derivative are 4.1ppm, 2ppm and 1.5ppm respectively.
2) The solution was continuously injected into a helical microchannel reactor with an inner wall of ferrite soft magnetic material at a flow rate of 0.5ml/s, and the microchannel reactor was placed in a 40KHz ultrasonic environment, maintaining the temperature at 20 ℃.
3) And (3) cooling the liquid subjected to magnetic separation to 0 ℃ at a cooling rate of 10 ℃/h to separate out crystals, wherein the separated out crystals are high-purity phenanthroimidazole derivatives. The ICP-MS analysis result shows that the total content of iron, copper and palladium in the crude product of the phenanthroimidazole derivative material is less than 1 ppb.
In this example, the molecular structure of the phenanthroimidazole derivative is as follows:
Figure BDA0002900049240000081
example 3
In this embodiment, the method for separating nano palladium, copper and iron particles from the phenanthroimidazole derivative includes the following steps:
1) dissolving 0.1g of a crude product of the phenanthroimidazole derivative in 1ml of dichloromethane to obtain a solution; wherein, the contents of nano palladium, copper and iron in the crude product of the phenanthroimidazole derivative are 1.3ppm, 5.8ppm and 1.2ppm respectively.
2) The solution was continuously injected into a helical microchannel reactor with an inner wall of ferrite soft magnetic material at a flow rate of 0.1ml/s, and the microchannel reactor was placed in an ultrasonic field of 60KHz, maintaining the temperature at 20 ℃.
3) And (3) cooling the liquid subjected to magnetic separation to-5 ℃ at a cooling rate of 10 ℃/h to separate out crystals, wherein the separated crystals are high-purity phenanthroimidazole derivatives. The ICP-MS analysis results show that the total content of iron, copper and palladium in the crude phenanthroimidazole derivative is less than 1 ppb.
In this example, the molecular structure of the phenanthroimidazole derivative is as follows:
Figure BDA0002900049240000091
example 4
In this embodiment, the method for separating nano palladium, copper and iron particles from the phenanthroimidazole derivative includes the following steps:
1) dissolving 0.01g of the crude phenanthroimidazole derivative product in 10ml of tetrahydrofuran to obtain a solution; wherein, the contents of nano palladium, copper and iron in the crude product of the phenanthroimidazole derivative are 1ppm, 1.8ppm and 6.4ppm respectively.
2) The solution was continuously injected into a helical microchannel reactor with an inner wall of ferrite soft magnetic material at a flow rate of 0.1ml/s, and the microchannel reactor was placed in an ultrasonic field of 80KHz, maintaining the temperature at 20 ℃.
3) And cooling the liquid subjected to magnetic separation to-10 ℃ at a cooling rate of 10 ℃/h to separate out crystals, wherein the separated crystals are high-purity phenanthroimidazole derivative materials. The ICP-MS analysis result shows that the total content of iron, copper and palladium in the crude product of the phenanthroimidazole derivative material is less than 1 ppb.
In this example, the molecular structure of the phenanthroimidazole derivative is as follows:
Figure BDA0002900049240000092
example 5
In this embodiment, the method for separating nano palladium, copper and iron particles from the phenanthroimidazole derivative includes the following steps:
1) dissolving 1g of a crude phenanthroimidazole derivative product in 11ml of xylene to obtain a solution; wherein, the contents of nano palladium, copper and iron in the crude product of the phenanthroimidazole derivative material are 3.7ppm, 2.6ppm and 2.4ppm respectively.
2) The solution is continuously injected into a spiral microchannel reactor with the inner wall made of ferrite soft magnetic material at the flow rate of 1ml/s, and the microchannel reactor is placed in a 60KHz ultrasonic environment, and the temperature is kept at 25 ℃.
3) And (3) cooling the liquid subjected to magnetic separation to-10 ℃ at a cooling rate of 40 ℃/h to separate out crystals, wherein the separated crystals are high-purity phenanthroimidazole derivatives. The ICP-MS analysis results show that the total content of iron, copper and palladium in the crude phenanthroimidazole derivative is less than 1 ppb.
In this example, the molecular structure of the phenanthroimidazole derivative is as follows:
Figure BDA0002900049240000101
example 6
In this embodiment, the method for separating nano palladium, copper and iron particles from the phenanthroimidazole derivative includes the following steps:
1) dissolving 0.1g of a crude phenanthroimidazole derivative product in 1ml of benzene to obtain a solution; wherein, the contents of nano palladium, copper and iron particles in the crude product of the phenanthroimidazole derivative are 1ppm, 1.1ppm and 1.6ppm respectively.
2) The solution was continuously injected into a helical microchannel reactor with an inner wall of ferrite soft magnetic material at a flow rate of 0.5ml/s, and the whole microchannel reactor was placed in an ultrasonic environment of 80KHz, maintaining the temperature at 20 ℃.
3) And (3) cooling the liquid subjected to magnetic separation to-10 ℃ at a cooling rate of 30 ℃/h to separate out crystals, wherein the separated crystals are high-purity phenanthroimidazole derivatives. The ICP-MS analysis results show that the total content of iron, copper and palladium in the crude phenanthroimidazole derivative is less than 1 ppb.
In this example, the molecular structure of the phenanthroimidazole derivative is as follows:
Figure BDA0002900049240000102
the foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.

Claims (10)

1. A method for separating nano palladium, copper and iron particles from a phenanthroimidazole derivative is characterized by comprising the following steps:
1) mixing the crude phenanthroimidazole derivative product with a solvent to obtain a solution;
2) carrying out magnetic separation on the solution by adopting a micro-channel reactor, wherein the inner wall of a channel of the micro-channel reactor is made of a magnetic material;
3) and cooling the liquid subjected to magnetic separation, crystallizing and separating out, wherein the separated crystal is the phenanthroimidazole derivative.
2. The method for separating nano palladium, copper and iron particles from phenanthroimidazole derivative according to claim 1, characterized in that the structural general formula of the phenanthroimidazole derivative is as follows:
Figure FDA0002900049230000011
wherein R is1、R2、R4And R5Is one selected from the group consisting of H, a linear or branched alkyl group having 1 to 10 carbons, a linear or branched alkoxy group having 1 to 10 carbons, an aryl group having 1 to 10 carbons and a heterocyclic aryl group having 1 to 10 carbons, wherein R is1And R5Different;
R3is one selected from the group consisting of F, Cl, H, a linear or branched alkyl group having 1 to 10 carbons, a linear or branched alkoxy group having 1 to 10 carbons, an aryl group having 1 to 10 carbons and a heterocyclic aryl group having 1 to 10 carbons;
R6is one selected from triphenylamine group and derivatives thereof, diphenylamine group and derivatives thereof, carbazolyl group and derivatives thereof, and N-phenylcarbazolyl group and derivatives thereof.
3. The method for separating nano palladium, copper and iron particles from phenanthroimidazole derivative according to claim 1, characterized in that the solvent is one or several kinds of dichloromethane, xylene, tetrahydrofuran or benzene.
4. The method for separating nano palladium, copper and iron particles from the phenanthroimidazole derivative according to claim 1, wherein the mass-to-volume ratio of the phenanthroimidazole derivative crude product to the solvent is 1g (1-10) ml.
5. The method for separating nano palladium, copper and iron from phenanthroimidazole derivatives as claimed in claim 1, wherein in step 2), the channel of the microchannel reactor is spiral, the tube diameter of the channel of the microchannel reactor is 0.1 mm-0.5 mm, and the length of the channel is 0.1 m-1 m.
6. The method for separating nano palladium, copper and iron particles from phenanthroimidazole derivative according to claim 1, characterized in that in step 2), the magnetic material is ferrite soft magnetic material.
7. The method for separating nano palladium, copper and iron particles from phenanthroimidazole derivative according to claim 1, characterized in that,
in the step 2), the flow rate of the solution in the channel of the microchannel reactor is 0.1 ml/s-1 ml/s.
8. The method for separating nano palladium, copper and iron particles from phenanthroimidazole derivative according to claim 1, characterized in that,
in the step 2), during magnetic separation, the microchannel reactor is placed in an ultrasonic environment for ultrasonic treatment, and heat preservation is carried out simultaneously.
9. The method for separating nano palladium, copper and iron particles from phenanthroimidazole derivative according to claim 8, characterized in that the ultrasonic frequency is 20 KHz-80 KHz and the holding temperature is 10-25 ℃.
10. The method for separating nano palladium, copper and iron particles from phenanthroimidazole derivatives according to claim 1, characterized in that in step 3), the temperature is reduced to-10 ℃ to 10 ℃ and the rate of temperature reduction is 10 ℃/h to 40 ℃/h.
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Citations (2)

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CN103403557A (en) * 2010-10-28 2013-11-20 耶鲁大学 Microfluidic processing of target species in ferrofluids
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