CN111983119B - Detection method of organic electroluminescent material - Google Patents
Detection method of organic electroluminescent material Download PDFInfo
- Publication number
- CN111983119B CN111983119B CN202010879911.1A CN202010879911A CN111983119B CN 111983119 B CN111983119 B CN 111983119B CN 202010879911 A CN202010879911 A CN 202010879911A CN 111983119 B CN111983119 B CN 111983119B
- Authority
- CN
- China
- Prior art keywords
- mobile phase
- detection
- sample
- detection method
- chromatographic column
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/60—Construction of the column
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/30—Control of physical parameters of the fluid carrier of temperature
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/32—Control of physical parameters of the fluid carrier of pressure or speed
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/34—Control of physical parameters of the fluid carrier of fluid composition, e.g. gradient
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/32—Control of physical parameters of the fluid carrier of pressure or speed
- G01N2030/324—Control of physical parameters of the fluid carrier of pressure or speed speed, flow rate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electroluminescent Light Sources (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention provides a detection method of an organic electroluminescent material, which comprises the following steps: detecting a sample to be detected by ultra-high performance liquid chromatography combined with mass spectrometry; the chromatographic column of the ultra-high performance liquid chromatography is a phenyl chromatographic column. The detection method realizes effective separation and qualitative and quantitative detection of the sample through the control and optimization of a specific test system, a chromatographic column and chromatographic conditions and the combination of the specific test system, the chromatographic column and a mass spectrum, shortens the analysis time to be within 30min, has short analysis time, good detection precision and accuracy, consumes less organic solvent, and effectively solves the defects of high detection cost and large amount of waste liquid caused by purchasing the organic solvent. The detection method has the advantages of high separation degree and high accuracy, is short in detection time, low in cost and more environment-friendly, can particularly realize accurate separation and detection of the organic electroluminescent material containing the triphenylamine group, and has wide application prospect.
Description
Technical Field
The invention belongs to the technical field of chemical detection, and particularly relates to a detection method of an organic electroluminescent material.
Background
Organic electroluminescent materials have been one of the hot research points in the field of optoelectronic information functional materials. After decades of development, breakthrough progress has been made, and the conversion efficiency, stability and the like of the material are greatly improved. The organic electroluminescent material has many kinds, and most of the compounds for the organic electroluminescent material contain aryl, heteroaryl or arylamine groups, and have good thermal stability and glass transition temperature T g High in light emitting efficiency, not easy to crystallize, good in film forming property and the like, and is widely applied to a light emitting layer, an electron transport layer, an electron blocking layer, a hole transport layer or a hole blocking layer of an electroluminescent device.
The compound used for the organic electroluminescent material is generally obtained by synthesizing a small molecular electroluminescent raw material through an intermediate, and the quality of a synthesized product directly influences the stability and the luminous efficiency of the material. Therefore, it is very important to perform a rapid, efficient and accurate content detection liquid chromatography method. The detection methods commonly used at present mainly comprise an ultraviolet spectrophotometry method, a high performance liquid chromatography method, a gas chromatography-mass spectrometry method, a liquid chromatography-tandem mass spectrometry method and the like.
The diamine monomer 4- (3, 5-diaminobenzoic acid methyl ester group) triphenylamine containing triphenylamine groups is synthesized by taking triphenylamine as a raw material, and characterization and analysis are carried out on a synthesized product through Fourier infrared spectroscopy, nuclear magnetic resonance and fluorescence spectroscopy, so that the diamine monomer is confirmed to be obtained (see synthesis and performance characterization of polyimide containing triphenylamine groups, Dorong, Master academic thesis of southeast university, 2009). Wangbangrong and the like synthesize a diamine monomer containing carbazole and triphenylamine groups, a series of polyimides containing triphenylamine and the triphenylamine groups are prepared by polymerization with different dianhydrides, and the influence of the molecular structure of the material on the electrical property is preliminarily researched. The molecular weight and the thermal property of the prepared polymer are researched, and the electric property of the polymer is characterized by using the ultraviolet absorption spectrum and an electrochemical workstation (see synthesis and characterization of a polyimide photovoltaic material containing a triphenylamine hole transport group side chain suspended ruthenium metal complex, summary of academic discussions of the eighth organic solid electronic process and the organic photoelectric functional material of Chinese, 2010). However, the above series of characterizations can only qualitatively analyze the synthesized product, but cannot effectively separate and quantitatively detect the product and the raw material, so that a new method needs to be searched and developed for further characterizing the synthesized product containing triarylamines.
The high performance liquid chromatography has the advantages of good selectivity, high detection sensitivity, high speed and the like, and is widely applied to the fields of medicines, foods, cosmetics and the like. CN109975438A discloses a method for detecting content of-NH based on liquid chromatograph 2 or/and-NH group fluorene photoelectric material. Adopting High Performance Liquid Chromatography (HPLC) to match with a chromatographic column: venusil XBP C18 with the specification of 4.6mm multiplied by 150mm and 5 μm; the mobile phase is as follows: the volume ratio is methanol: adding triethylamine with volume ratio of 0.1% to 80:20 to successfully react with the solution containing-NH 2 or/and-NH group fluorene photoelectric materials are detected, and target products are successfully and effectively separated, but the method still has too long analysis time, so that more waste liquid is generated, and the separation degree has great improvement space.
Therefore, it is a research focus in the field to develop a detection method based on a liquid chromatograph with good separation effect, short analysis time and high test accuracy to meet the detection requirements of organic electroluminescent materials.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a detection method of an organic electroluminescent material, which detects a sample to be detected by ultra-high performance liquid chromatography combined with mass spectrometry and selects a phenyl chromatographic column, thereby improving the separation degree of the sample to be detected and realizing qualitative and quantitative detection of the organic electroluminescent material in a short time.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a detection method of an organic electroluminescent material, which comprises the following steps: detecting a sample to be detected by ultra-high performance liquid chromatography combined with mass spectrometry; the chromatographic column of the ultra-high performance liquid chromatography is a phenyl chromatographic column.
The detection method provided by the invention is carried out by adopting ultra-high performance liquid chromatography combined with mass spectrometry and matched with a specific phenyl chromatographic column, is particularly suitable for synthetic products with large molecular weight and high boiling point in organic electroluminescent materials, and has the characteristics of good separation effect, short analysis time and high accuracy.
In the present invention, the packing particle size of the phenyl chromatographic column is 1.6-3 μm, such as 1.7 μm, 1.8 μm, 1.9 μm, 2.0 μm, 2.1 μm, 2.2 μm, 2.3 μm, 2.4 μm, 2.5 μm, 2.6 μm, 2.7 μm, 2.8 μm or 2.9 μm, and the specific values therebetween are limited to space and for simplicity, and the present invention does not exhaust the specific values included in the range, preferably 1.7-2.5 μm.
As a preferred technical scheme of the invention, the filler particle size of the phenyl chromatographic column is 1.6-3 μm; if the particle size of the filler is beyond the range, the separation time is long and the separation effect is relatively poor due to the overlarge particle size of the filler; too small a filler particle size can cause too much pressure and the detection system cannot bear it.
Preferably, the phenyl chromatography column has the specification: 3.0 mm. times.100 mm, 2.5. mu.m.
In the invention, the mobile phase A of the ultra-high performance liquid chromatography comprises an aqueous solution containing 0.1% formic acid.
Preferably, the mobile phase B of the ultra-high performance liquid chromatography comprises an acetonitrile solution containing 0.1% formic acid.
Preferably, the analytical gradient of the ultra-high performance liquid chromatography is as follows: 0-14 min, 50-90% of mobile phase B; 14-17 min, 90% of mobile phase B; 17-20 min, 90-50% of mobile phase B.
Preferably, the analytical gradient of the ultra high performance liquid chromatography is: 0-12 min, 50-90% of mobile phase B; 12-17 min, 90% of mobile phase B; 17-20 min, 90-50% of mobile phase B.
Preferably, the analytical gradient of the ultra-high performance liquid chromatography is as follows: 0-8 min, 50-90% of mobile phase B; 8-17 min, 90% of mobile phase B; 17-20 min, 90-50% of mobile phase B.
Preferably, the analysis time of the ultra performance liquid chromatography is 10-30 min, such as 12min, 14min, 16min, 18min, 20min, 22min, 24min, 26min or 28min, and specific values therebetween, for brevity and conciseness, the invention is not exhaustive.
Preferably, the detection wavelength of the ultra-high performance liquid chromatography is 254 nm.
Preferably, the flow rate of the phenyl chromatography column is 0.2 to 0.6mL/min, such as 0.25mL/min, 0.3mL/min, 0.35mL/min, 0.4mL/min, 0.45mL/min, 0.5mL/min, or 0.55mL/min, and specific values therebetween, for brevity and conciseness, the present invention is not exhaustive of the specific values included in the ranges.
The detection method provided by the invention has the advantages that through the control and optimization of a specific test system and chromatographic conditions, the analysis time is shortened to be within 30min, the solvent consumed by analyzing one sample is about 10mL, the detection solvent consumption and the waste liquid output are obviously reduced, on one hand, the reagent cost required by detection is reduced, on the other hand, more industrial three wastes are avoided, and the detection method is more environment-friendly.
Preferably, the column temperature of the phenyl chromatography column is 40 ℃.
In the present invention, the concentration of the sample to be tested is 0.5-1.5 mg/mL, such as 0.6mg/mL, 0.7mg/mL, 0.8mg/mL, 0.9mg/mL, 1.0mg/mL, 1.1mg/mL, 1.2mg/mL, 1.3mg/mL or 1.4mg/mL, and specific points therebetween, including space and simplicity, are not exhaustive.
Preferably, the sample to be detected is a solution of an organic electroluminescent material.
Preferably, the solvent of the solution comprises dichloromethane.
Preferably, the sample to be tested has a sample injection volume of 0.5-1.5 μ L, such as 0.6 μ L, 0.7 μ L, 0.8 μ L, 0.9 μ L, 1.0 μ L, 1.1 μ L, 1.2 μ L, 1.3 μ L or 1.4 μ L, and specific values therebetween, which is not limited by space and for brevity, the present invention is not exhaustive of the specific values included in the range.
In the present invention, the relative molecular mass of the organic electroluminescent material is 200 to 900, such as 250, 300, 350, 400, 450, 500, 550, 600, 650, 700, 750, 800 or 850, and the specific values therebetween are limited to the space and for the sake of brevity, and the specific values included in the range are not exhaustive.
Preferably, the organic electroluminescent material is an organic compound containing at least one of C6-C30 aryl, C3-C20 heteroaryl or C6-C30 arylamine.
The C6 to C30 aryl groups include aryl groups of C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, illustratively including but not limited to phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, or the like.
The C3 to C20 heteroaryl group includes heteroaryl groups of C6, C9, C10, C12, C14, C16, C18, C20 and the like, and exemplarily includes but is not limited to pyridyl, furyl, thienyl, carbazolyl, indolyl, acridinyl, hydrogenated acridinyl, quinolyl, isoquinolyl, phenothiazinyl, phenoxazinyl and the like.
The C6-C30 arylamine group includes arylamine groups of C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28 and the like, and exemplarily includes but is not limited to a toluidine group, a diphenylamine group, a xylidine group, a triphenylamine group, a naphthylamine group, a benzylamine group, a diphenyl p-phenylene diamine group or a phenethylamine group and the like.
In the present invention, the ion mode of the mass spectrum is a positive ion mode.
Preferably, the corona needle current of the mass spectrum is 10 μ Α.
Preferably, the cone hole voltage of the mass spectrum is 10 kV;
preferably, the source temperature of the mass spectrum is 120 ℃;
preferably, the desolvation gas temperature of the mass spectrum is 350 ℃;
preferably, the blowback gas flow speed of the mass spectrum is 50L/min;
preferably, the mass spectrum has a desolventizing gas flow rate of 500L/min.
In the invention, the detection method comprises the following steps: detecting an organic compound containing a sample to be detected by ultra-high performance liquid chromatography-mass spectrometry; the chromatographic column of the ultra-high performance liquid chromatography is a phenyl chromatographic column; the particle size of the filler of the phenyl chromatographic column is 1.6-3 mu m;
the sample to be detected is a solution of an organic electroluminescent material, and the sample injection volume is 0.5-1.5 mu L; the concentration of the solution is 0.5-1.5 mg/mL; the relative molecular mass of the organic electroluminescent material is 200-900, and the organic electroluminescent material is an organic compound containing at least one of C6-C30 aryl, C3-C20 heteroaryl or C6-C30 arylamine;
the chromatographic conditions of the ultra-high performance liquid chromatography comprise: the analysis time is 10-30 min, the detection wavelength is 254nm, the flow rate is 0.2-0.6 mL/min, the column temperature is 40 ℃, the mobile phase A comprises an aqueous solution containing 0.1% formic acid, and the mobile phase B comprises an acetonitrile solution containing 0.1% formic acid;
the conditions of the mass spectrum include: the ion mode is positive ion mode, corona needle current is 10 μ A, taper hole voltage is 10kV, source temperature is 120 deg.C, desolvation gas temperature is 350 deg.C, back blowing gas flow rate is 50L/min, and desolvation gas flow rate is 500L/min.
Compared with the prior art, the invention has the following beneficial effects:
the detection method provided by the invention realizes the detection of the organic electroluminescent material by adopting the ultra-high performance liquid chromatography-mass spectrometry, realizes the effective separation and qualitative and quantitative detection of the sample by the control and optimization of a specific test system, a chromatographic column and chromatographic conditions and the combination of the specific test system, the chromatographic column and the mass spectrometry, shortens the analysis time to be within 30min, has short analysis time, good detection precision and accuracy and less consumption of organic solvent, and effectively solves the defects of high detection cost and large amount of waste liquid caused by purchasing the organic solvent. The detection method has the advantages of high resolution and high accuracy, is short in detection time, low in cost and more environment-friendly, can be used for particularly realizing the precise separation and detection of the organic electroluminescent material containing the triphenylamine group, and has wide application prospects.
Drawings
FIG. 1 is a chromatogram obtained by the detection method provided in example 1, in which 1 represents the peak of 1-bromo-3-fluoro-4-iodobenzene and 2 represents the peak of the objective compound;
FIG. 2 is a mass spectrum of 1-bromo-3-fluoro-4-iodobenzene obtained by the detection method provided in example 1;
FIG. 3 is a mass spectrum of the target compound obtained by the detection method provided in example 1;
FIG. 4 is a chromatogram obtained by the detection method provided in example 2, in which 1 represents a peak of 1-bromo-3-fluoro-4-iodobenzene and 2 represents a peak of the objective compound;
FIG. 5 is a chromatogram obtained by the detection method provided in comparative example 1, in which 1 represents the peak of 1-bromo-3-fluoro-4-iodobenzene and 2 represents the peak of the objective compound;
FIG. 6 is a chromatogram obtained by the detection method provided in comparative example 2, in which 1 represents the peak of 1-bromo-3-fluoro-4-iodobenzene and 2 represents the peak of the objective compound.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
A detection method of an organic electroluminescent material comprises the following steps:
(1) sample pretreatment: taking a mixture containing 1-bromo-3-fluoro-4-iodobenzene and a target compound
Putting 1mg of the mixture into a 2mL automatic sample injector vial, adding 1mL of dichloromethane, ultrasonically dissolving until the mixture is clear and transparent, and taking 1 mu L of the mixture for sample loading test; wherein, 1-bromo-3-fluoro-4-iodobenzene is the main raw material for preparing the target compound;
(2) and (3) detection process: detecting by ultra performance liquid chromatography-mass spectrometry, wherein the test system is Waters Aqulity H-class (UPLC), the chromatographic column is Phenyl chromatographic column BEH Phenyl with specification of 3.0mm × 100mm and 2.5 μm; the chromatographic conditions were as follows: the detection wavelength is 254nm, the flow rate is 0.5mL/min, the column temperature is 40 ℃, the mobile phase A is an aqueous solution containing 0.1% formic acid, the mobile phase B is an acetonitrile solution containing 0.1% formic acid, and the analytical gradient is as follows: 0-12 min, 50-90% of mobile phase B; 12-17 min, 90% of mobile phase B; 17-20 min, 90-50% of mobile phase B;
mass spectrometry conditions were as follows: an atmospheric pressure chemical ionization source (APCI), wherein the ion mode is a positive ion mode, the corona needle current is 10 muA, the taper hole voltage is 10kV, the source temperature is 120 ℃, the desolvation gas temperature is 350 ℃, the back blowing gas flow rate is 50L/min, and the desolvation gas flow rate is 500L/min.
The chromatogram obtained by the detection method provided in this example is shown in FIG. 1, where 1 represents the peak of 1-bromo-3-fluoro-4-iodobenzene, and 2 represents the target compound
As can be seen from the figure, the separation peak of 1-bromo-3-fluoro-4-iodobenzene appears at the time of 7.5 min; when the time is 8min, a separation peak of the target compound appears, which indicates that the baseline separation of the 1-bromo-3-fluoro-4-iodobenzene and the target compound can be realized within 8min by the detection method provided by the embodiment; mass spectrometry is performed on the 1-bromo-3-fluoro-4-iodobenzene and the target compound separated by the detection method provided in this example 1, and the results are shown in fig. 2 and fig. 3, where fig. 2 is a mass spectrum of the 1-bromo-3-fluoro-4-iodobenzene, fig. 3 is a mass spectrum of the target compound, and peaks of the 1-bromo-3-fluoro-4-iodobenzene and isotopes thereof can be clearly observed from fig. 2; the peaks of the target compound and the isotope thereof can be obviously observed from fig. 3, and the impurity peaks of the two mass spectrograms are few, which shows that the separated materials are pure, and further verifies the separation result.
Example 2
A detection method of an organic electroluminescent material comprises the following steps:
(1) sample pretreatment: taking a mixture containing 1-bromo-3-fluoro-4-iodobenzene and a target product
1mg of the mixture was placed in a 2mL autosamplerAdding 1mL of dichloromethane into the bottle, dissolving the dichloromethane by ultrasonic waves until the dichloromethane is clear and transparent, and taking 1 mu L of dichloromethane for sample loading test;
(2) and (3) detection process: detecting by ultra performance liquid chromatography-mass spectrometry, wherein the test system is Waters Aqulity H-class (UPLC), the chromatographic column is Phenyl chromatographic column BEH Phenyl with specification of 3.0mm × 100mm and 2.5 μm; the chromatographic conditions were as follows: the detection wavelength is 254nm, the flow rate is 0.5mL/min, the column temperature is 40 ℃, the mobile phase A is an aqueous solution containing 0.1% formic acid, the mobile phase B is an acetonitrile solution containing 0.1% formic acid, and the analytical gradient is as follows: 0-8 min, 50-90% of mobile phase B; 8-17 min, 90% of mobile phase B; 17-20 min, 90-50% of mobile phase B; other conditions and procedures were the same as in example 1;
the chromatogram obtained by the detection method provided in this example is shown in FIG. 4, where 1 represents the peak of 1-bromo-3-fluoro-4-iodobenzene, and 2 represents the target compound
The peak of (2) can be seen from the figure, when the time is 5.8min, a separation peak of 1-bromo-3-fluoro-4-iodobenzene appears; when the time is 6.2min, a separation peak of the target compound appears, which indicates that baseline separation of the 1-bromo-3-fluoro-4-iodobenzene and the target compound is completed at this time, in this example, the chromatographic conditions are further optimized on the basis of example 1, so that baseline separation of two materials is achieved in a shorter time, and the working efficiency is higher.
Comparative example 1
(1) Sample pretreatment: taking the mixture containing 1-bromo-3-fluoro-4-iodobenzene and a target product
Putting 1mg of the mixture into a 2mL automatic sample injector vial, adding 1mL of dichloromethane, ultrasonically dissolving until the mixture is clear and transparent, and taking 5 mu L of the mixture for sample loading test;
(2) and (3) detection process: adopting a High Performance Liquid Chromatograph (HPLC), wherein the test system is Shimadzu LC2030(HPLC), the chromatographic column is Shim pack GIST C18, and the specification is 4.6mm multiplied by 150mm and 5 mu m; the chromatographic conditions were as follows: the detection wavelength is 254nm, the flow rate is 2.0mL/min, the column temperature is 40 ℃, the mobile phase A is an aqueous solution containing 0.1% formic acid, the mobile phase B is an acetonitrile solution containing 0.1% formic acid, and the analytical gradient is as follows: 0-30 min, 50-90% of mobile phase B; 30-50 min, 90% of mobile phase B; 90-50% of mobile phase B in 50-60 min;
the chromatogram obtained by the detection method provided in this comparative example is shown in FIG. 5, in which 1 represents the peak of 1-bromo-3-fluoro-4-iodobenzene, and 2 represents the target compound
The peak of (2) can be seen from the figure, when the time is 19.5min, the peaks of the two materials are still difficult to distinguish, which indicates that the two materials can not be separated; the detection method provided by the embodiment 1 of the invention can realize the baseline separation of the two materials within 8 min; in addition, in the comparative example, a single needle sample consumes 120mL of solvent, consumes more solvent, has higher cost and causes more waste liquid; in contrast, in the detection method provided by embodiment 1 of the present invention, the solvent dosage of a single needle sample is only 10mL, so that the detection method provided by the present invention has more excellent separation and detection effects and less organic solvent dosage.
Comparative example 2
A detection method of an organic electroluminescent material comprises the following steps:
(1) sample pretreatment: taking a mixture containing 1-bromo-3-fluoro-4-iodobenzene and a target product
1mg of the mixture of (1) was placed in a 2mL autosampler vial, 1mL of dichloromethane was added, the mixture was ultrasonically dissolved to be clear and transparent, and 1. mu.L of the mixture was sampled for testing:
(2) and (3) detection process: adopting an Ultra Performance Liquid Chromatograph (UPLC), wherein the testing system is Waters Aqulity H-class, the chromatographic column is BEH C18, and the specification is 3.0mm multiplied by 100mm and 2.5 mu m; the chromatographic conditions were as follows: the detection wavelength is 254nm, the flow rate is 0.5mL/min, the column temperature is 40 ℃, the mobile phase A is an aqueous solution containing 0.1% formic acid, the mobile phase B is an acetonitrile solution containing 0.1% formic acid, and the analytical gradient is as follows: 0-12 min, 50-90% of mobile phase B; 12-17 min, 90% of mobile phase B; 17-20 min, 90-50% of mobile phase B;
the chromatogram obtained by the detection method provided by the comparative example is shown in fig. 6, wherein 1 represents the peak of 1-bromo-3-fluoro-4-iodobenzene, and 2 represents the peak of the target compound, and as can be seen from fig. 6, when the retention time is 8.5min, the peaks of the two materials are separated, but do not reach the baseline, so that an accurate analysis result cannot be obtained, which indicates that an ideal detection result cannot be obtained by adopting an ultra-high performance liquid chromatograph in combination with a conventional C18 chromatographic column; the detection method provided by the invention can realize separation of two materials and reach a baseline by ultra-high performance liquid chromatography and matching with a specific phenyl chromatographic column when the retention time is 8min, thereby illustrating the advantages of the detection method provided by the invention.
The applicant states that the present invention is illustrated by the above examples, but the present invention is not limited to the above process steps, which means that the present invention must not be dependent on the above process steps to be implemented. It will be apparent to those skilled in the art that any modification of the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific modes and the like, which are within the scope and disclosure of the present invention, are contemplated by the present invention.
Claims (2)
1. A detection method of an organic electroluminescent material is characterized by comprising the following steps:
(1) sample pretreatment: taking a mixture containing 1-bromo-3-fluoro-4-iodobenzene and a target compound
The sample to be tested is dissolved by dichloromethane in an ultrasonic mode until the sample is clear and transparent, and 1 mu L of the sample is taken for sample loading test;
(2) ultra-high performance liquid chromatography detection: detecting by ultra-high performance liquid chromatography-mass spectrometry, wherein the chromatographic column is a Phenyl chromatographic column BEH Phenyl with the specification of 3.0mm multiplied by 100mm and 2.5 mu m; the chromatographic conditions were as follows: the detection wavelength is 254nm, the flow rate is 0.5mL/min, the column temperature is 40 ℃, the mobile phase A is an aqueous solution containing 0.1% formic acid, and the mobile phase B is an acetonitrile solution containing 0.1% formic acid;
the analytical gradient was: 0-12 min, 50-90% of mobile phase B; 12-17 min, 90% of mobile phase B; 17-20 min, 90-50% of mobile phase B; or 0-8 min, 50-90% of mobile phase B; 8-17 min, 90% of mobile phase B; 17-20 min, 90-50% of mobile phase B;
(3) and (4) detecting by mass spectrometry.
2. The detection method according to claim 1, wherein the ion mode of the mass spectrometry is a positive ion mode, the corona needle current is 10 μ A, the taper hole voltage is 10kV, the source temperature is 120 ℃, the desolvation gas temperature is 350 ℃, the back-blowing gas flow rate is 50L/min, and the desolvation gas flow rate is 500L/min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010879911.1A CN111983119B (en) | 2020-08-27 | 2020-08-27 | Detection method of organic electroluminescent material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010879911.1A CN111983119B (en) | 2020-08-27 | 2020-08-27 | Detection method of organic electroluminescent material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111983119A CN111983119A (en) | 2020-11-24 |
| CN111983119B true CN111983119B (en) | 2022-09-06 |
Family
ID=73439975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010879911.1A Active CN111983119B (en) | 2020-08-27 | 2020-08-27 | Detection method of organic electroluminescent material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111983119B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109975438A (en) * | 2017-12-28 | 2019-07-05 | 广东阿格蕾雅光电材料有限公司 | One kind containing-NH based on liquid chromatograph detection2Or/and the method for-NH group fluorene kind derivative content |
| CN111307991A (en) * | 2020-04-07 | 2020-06-19 | 中钢集团南京新材料研究院有限公司 | Method for simultaneously detecting bromobenzene and carbazole compounds by adopting high performance liquid chromatography |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6406632B1 (en) * | 1998-04-03 | 2002-06-18 | Symyx Technologies, Inc. | Rapid characterization of polymers |
| CN108129394B (en) * | 2017-12-21 | 2020-09-15 | 北京燕化集联光电技术有限公司 | Organic electroluminescent material and preparation method and application thereof |
| CN108084180A (en) * | 2017-12-26 | 2018-05-29 | 南京高光半导体材料有限公司 | A kind of novel electroluminescent compound and the organic electroluminescence device using the organic electroluminescent compounds |
-
2020
- 2020-08-27 CN CN202010879911.1A patent/CN111983119B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109975438A (en) * | 2017-12-28 | 2019-07-05 | 广东阿格蕾雅光电材料有限公司 | One kind containing-NH based on liquid chromatograph detection2Or/and the method for-NH group fluorene kind derivative content |
| CN111307991A (en) * | 2020-04-07 | 2020-06-19 | 中钢集团南京新材料研究院有限公司 | Method for simultaneously detecting bromobenzene and carbazole compounds by adopting high performance liquid chromatography |
Non-Patent Citations (1)
| Title |
|---|
| 苯并花DNA加合物anti-BPDE-N2-dG四种立体异构体的合成及色谱分离;赵旭霞等;《分析测试学报》;20200331;第39卷(第3期);第315-321页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111983119A (en) | 2020-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Madrakian et al. | Turn-off fluorescence of amino-functionalized carbon quantum dots as effective fluorescent probes for determination of isotretinoin | |
| Xie et al. | Selective detection of chloramphenicol in milk based on a molecularly imprinted polymer–surface‐enhanced Raman spectroscopic nanosensor | |
| Hashemi et al. | Separation and determination of ciprofloxacin in seawater, human blood plasma and tablet samples using molecularly imprinted polymer pipette‐tip solid phase extraction and its optimization by response surface methodology | |
| Yoon et al. | Absolute stereochemical determination of chiral carboxylates using an achiral molecular tweezer | |
| Hori et al. | Synthesis of nanometer‐scale porphyrin wheels of variable size | |
| Pascal et al. | Synthesis, Electrochemistry, and Photophysics of Aza‐BODIPY Porphyrin Dyes | |
| CN109879776A (en) | A kind of application of the sour cyanines derivative in water solubility side and its synthetic method and detection aldehyde compound | |
| Kong et al. | Dimalononitrile-containing probe based on aggregation-enhanced emission features for the multi-mode fluorescence detection of volatile amines | |
| Kong et al. | Open‐tubular capillary electrochromatography using carboxylatopillar [5] arene as stationary phase | |
| Jiang et al. | Design of a naphthalimide-based probe for acrolein detection in foods and cells | |
| Qi et al. | Visualization of enantioselective recognition and separation of chiral acids by aggregation‐induced emission chiral diamine | |
| Kataria et al. | Pyrazine-based hollow spherical self-assemblies: A portable tool for detection of volatile organic amines | |
| CN111983119B (en) | Detection method of organic electroluminescent material | |
| Zeng et al. | A new disubstituted polyacetylene for the detection of α‐amino acids | |
| Ladner et al. | Excited state photoreaction between the indole side chain of tryptophan and halocompounds generates new fluorophores and unique modifications | |
| Lv et al. | A novel color-coded sensor array for visual recognition and traceability investigation of multiple antibiotics | |
| Pillai et al. | Dendrimers as Nd3+ ligands: Effect of Generation on the Efficiency of the Sensitized Lanthanide Emission | |
| Chen et al. | Probing receptor–anion interactions by ratiometric chemosensors containing pyrrolecarboxamide interacting sites | |
| Scarduelli et al. | Methane oligomerization in a dielectric barrier discharge at atmospheric pressure | |
| You et al. | Determination of amines using 2-(11H-benzo [a] carbazol-11-yl) ethyl chloroformate (BCEC-Cl) as labeling reagent by HPLC with fluorescence detection and identification with APCI/MS | |
| Portenkirchner et al. | Photoinduced Energy Transfer from Poly (N‐vinylcarbazole) to Tricarbonylchloro‐(2, 2′‐bipyridyl) rhenium (I) | |
| He et al. | A turn-on fluorescence molecularly imprinted sensor based on covalent organic framework for specific and visual detection of α-dicarbonyl compounds | |
| CN103808822A (en) | LC-QTOF (Liquid Chromatography-Quadrupole Time Of Flight) analysis method for distinguishing resveratrol of different resources | |
| Hu et al. | Tetraphenylethene functionalized polyhedral oligomeric silsesquioxane fluorescent probe for rapid and selective trifluralin sensing in vegetables and fruits | |
| Bello et al. | Interactions of compounds adsorbed on an 80%. alpha.-cyclodextrin-sodium chloride mixture investigated by diffuse reflectance and luminescence spectrometry |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20210106 Address after: Room A2, building 6, No.2, Lane 189, Canghai Road, Ningbo hi tech Zone, Ningbo City, Zhejiang Province Applicant after: NINGBO LUMILAN ADVANCED MATERIALS Co.,Ltd. Applicant after: NINGBO DINGHAO PHOTOELECTRIC MATERIAL TECHNOLOGY Co.,Ltd. Applicant after: Ningbo Institute of Northwest University of Technology Address before: Room A2, building 6, No.2, Lane 189, Canghai Road, Ningbo hi tech Zone, Ningbo City, Zhejiang Province Applicant before: NINGBO LUMILAN ADVANCED MATERIALS Co.,Ltd. Applicant before: NINGBO DINGHAO PHOTOELECTRIC MATERIAL TECHNOLOGY Co.,Ltd. |
|
| TA01 | Transfer of patent application right | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |