CN109761221A - Organic matter, method and the application of separating-purifying semiconductor single-walled carbon - Google Patents
Organic matter, method and the application of separating-purifying semiconductor single-walled carbon Download PDFInfo
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- CN109761221A CN109761221A CN201711096920.8A CN201711096920A CN109761221A CN 109761221 A CN109761221 A CN 109761221A CN 201711096920 A CN201711096920 A CN 201711096920A CN 109761221 A CN109761221 A CN 109761221A
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Abstract
The present invention relates to the organic matter of separating-purifying semiconductor single-walled carbon, method and applications, and wherein process for separation and purification includes: step (1): benzene thiophene substance and the raw material comprising semiconductor single-walled carbon are put into organic solvent；And step (2): handling the organic solvent, isolates semiconductor single-walled carbon therein.Organic matter of the present invention is benzene thiophene substance, can be used for the fields such as semiconductor devices, integrated circuit, display driving, transparent conductive film, biology/chemical sensitisation, infrared acquisition and infrared therapeutic.Method of the invention can reduce the cost that semiconductor single-walled carbon is separated from raw material, improve yield, improve the purity of semiconductor single-walled carbon.
Description
Technical field
The invention belongs to the organic of technical field of nano material more particularly to separating-purifying semiconductor single-walled carbon
Object, method and application.
Background technique
Carbon nanotube is a kind of nanometer material in semiconductor devices, integrated circuit and biologic medical with great potential
Material.How carbon nanotube is dispersed to separation from impure raw material, is the important research content in the field.
Currently, mainly in a solvent being separated carbon nanotube from impurity using dispersing agent, finding suitable dispersing agent is
The main direction of studying of current this field.
Professor Bao Zhenan of Stanford Univ USA proposes carbon nanotube using the separation of polythiophene class substance.U.S.'s prestige this
The Michael S.Arnold and IBM of Kang Xing university isolates carbon nanotube using the copolymer of fluorenes and pyridine.
Chinese patent application publication No. is that the patent application of CN106629670A discloses a kind of Gemini type dispersing agent point
The method of carbon nanotube is dissipated, this method is modified carbon nano tube surface by series of process process, makes carbon nanotube group
Aggressiveness is thoroughly unfolded into dispersion liquid.The main implementation steps of this method are as follows: (1) bis- (tetradecane of Carbon nano-tube dispersant 4,4-
Base) diphenyl-methane disulfonate solution preparation；(2) decentralized processing of carbon nanotube.
It is relatively simple to can be used in the isolated substance classes of carbon nanotube dispersion at present, also, above several technical solutions
There are the disadvantages such as expensive, carbon nanotube low yield, purity is low, cause these schemes that can not promote and apply.
Based on the above technical problem, the present invention provides a kind of organic matter of separating-purifying semiconductor single-walled carbon, divides
From method of purification and application.
Summary of the invention
The present invention provides a kind of organic matter of separating-purifying semiconductor single-walled carbon, process for separation and purification and answer
With to solve in the prior art, the molecular species of the substance for separating semiconductor single-walled carbon nanotube is single, price is high
It is expensive, the low technological deficiency of the semiconductor single-walled carbon low yield isolated, purity.
According to an aspect of the invention, there is provided a kind of method of separating-purifying semiconductor single-walled carbon, comprising:
Step (1): benzene thiophene substance and the raw material comprising semiconductor single-walled carbon are put into organic solvent；
And
Step (2): handling the organic solvent, isolates semiconductor single-walled carbon therein.
According to another aspect of the present invention, at least one including following substance: the benzene thiophene substance includes
Benzene thiophene small molecule, benzene thiophene polymer, benzene thiophene analog copolymer and the benzene thiophene class of alkyl chain
Derivative；The benzene thiophene analog derivative refers to the derivative of the benzene thiophene small molecule comprising alkyl chain, benzo two
The derivative of thiophen polymer, the derivative of benzene thiophene analog copolymer are comprising small point of the benzene thiophene of alkyl chain
Shown in the structural formula such as following formula (1) of son:
In formula (1), R=is the alkyl chain of different length, such as :-C8H17,-C9H19,-C26H53Deng.By designing benzene
The length of the alkyl chain of 1,4-Dithiapentalene small molecule can adjust the yield of semiconductor carbon nanometer tube, and long alkyl chains are longer, yield
It is higher.
According to another aspect of the invention, the benzene thiophene analog copolymer, comprising: benzene thiophene and carbazole or
The copolymer of fluorenes or pyridine or thiophene or benzo [2,1,3] thiadiazoles -4,8- diyl.
According to another aspect of the invention, the model of the mass ratio of benzene thiophene substance and the raw material comprising carbon nanotube
It encloses for 0.1:1 to 20:1.
According to another aspect of the invention, the organic solvent be toluene, dimethylbenzene, chloroform, tetrahydrofuran, hexamethylene,
One of hexahydrotoluene, ethyl cyclohexane, N-methyl pyrrolidones and dimethyl sulfoxide.
According to another aspect of the invention, the organic solvent is handled, semiconductor single-walled carbon therein is isolated,
Include: step (2-1): the organic solvent is ultrasonically treated, extracts the dispersion liquid formed after ultrasonic treatment；Step (2-2):
Centrifugal treating is made to the dispersion liquid, extracts the supernatant formed after centrifugal treating, the supernatant includes to separate from raw material
Carbon nanotube out.
According to another aspect of the invention, the ultrasonic power range used when being ultrasonically treated to the organic solvent is 20
Watt~1500 watts, when ultrasonic treatment, is 5 minutes~300 minutes a length of.
According to another aspect of the invention, the centrifugal speed range used when making centrifugal treating to the dispersion liquid is 3000
Revolutions per minute~100000 revolutions per minute, when centrifugal treating, are 0.5 hour~300 hours a length of.
The present invention also provides the organic matter according to used in above-mentioned process for separation and purification, the organic matter is two thiophene of benzo
Pheno substance, the benzene thiophene substance include at least one of following substance: the benzene thiophene comprising alkyl chain is small
Molecule, benzene thiophene polymer, benzene thiophene analog copolymer and benzene thiophene analog derivative；The benzene thiophene
Analog derivative refers to the derivative of benzene thiophene small molecule comprising alkyl chain, the derivative of benzene thiophene polymer, benzene
The derivative of 1,4-Dithiapentalene analog copolymer.
According to another aspect of the invention, the organic solvent be toluene, dimethylbenzene, chloroform, tetrahydrofuran, hexamethylene,
One of hexahydrotoluene, ethyl cyclohexane, N-methyl pyrrolidones and dimethyl sulfoxide.
Wherein, shown in the structural formula such as following formula (1) of the benzene thiophene small molecule comprising alkyl chain:
(R=is the alkyl chain of different length, such as :-C8H17,-C9H19,-C26H53)
The present invention also provides the concrete application of above-mentioned organic matter, the organic matter for semiconductor devices, integrated circuit,
Show driving, transparent conductive film, biology/chemical sensitisation, infrared acquisition and infrared therapeutic.
In the present invention, using benzene thiophene substance separating semiconductor single-walled carbon nanotube in organic solvent, compare
In the prior art using modes separating semiconductor single-walled carbon nanotubes such as the copolymers of polythiophene class substance or fluorenes and pyridine, expand
Opened up the substance classes that separating semiconductor single-walled carbon nanotube is able to use, meanwhile, have lower cost, higher yield and
Better separation purity.
Detailed description of the invention
Fig. 1 is the effect detection schematic diagram of separating semiconductor single-walled carbon nanotube provided by the invention.
Specific embodiment
The present invention provides a kind of methods of separating semiconductor single-walled carbon nanotube, to provide a kind of inexpensive, high yield
The semiconductor single-walled carbon separation scheme of rate, high-purity.
Embodiments of the present invention are described more detail below.
In the first embodiment of the present invention, the method for separating semiconductor single-walled carbon nanotube includes:
Step (1): benzene thiophene substance and the raw material comprising semiconductor single-walled carbon are put into organic solvent；
Step (2): handling the organic solvent, isolates semiconductor single-walled carbon therein.
Preferably, benzene thiophene substance used in step (1), at least one including following substance: comprising appointing
Benzene thiophene small molecule, benzene thiophene polymer, benzene thiophene analog copolymer and the benzo of the alkyl chain for length of anticipating
Dithiophene analog derivative.
The structure of the benzene thiophene small molecule referred in present embodiment are as follows:
Wherein, R represents the optional alkyl chain of length.Preferably, the long alkyl chains of benzene thiophene small molecule are C8~C26；Such as:
R=-C8H17 ,-C9H19 ,-C26H53.
Preferably, the benzene thiophene analog copolymer referred in present embodiment, comprising: with carbazole or fluorenes or pyridine or
The copolymer of thiophene or benzo [2,1,3] thiadiazoles -4,8- diyl.
Preferably, in step (1), the quality of benzene thiophene substance and the raw material comprising semiconductor single-walled carbon
The range of ratio is 0.1:1 to 20:1.It should be noted that the above proportional region is only the preferred embodiment of the present invention, for
Embodiment using the quality than other mass ratioes other than range, can equally play separating semiconductor single-walled carbon nanotube
Technical effect.
Preferably, the organic solvent used in present embodiment are as follows: toluene, dimethylbenzene, chloroform, tetrahydrofuran, hexamethylene,
One of hexahydrotoluene, ethyl cyclohexane, N-methyl pyrrolidones and dimethyl sulfoxide.
Preferably, present embodiment step (2) specifically includes:
Step (2-1): being ultrasonically treated the organic solvent, extracts the dispersion liquid formed after ultrasonic treatment；
Step (2-2): centrifugal treating is made to the dispersion liquid, extracts the supernatant formed after centrifugal treating, the supernatant
Liquid includes the semiconductor single-walled carbon isolated from raw material.
Preferably, the ultrasonic power range used when being ultrasonically treated to the organic solvent is excellent for 20 watts~1500 watts
Selection of land ultrasonic power is 150 watts, and when ultrasonic treatment is 5 minutes~300 minutes a length of, 30 minutes a length of when being preferably ultrasonically treated.
Preferably, the centrifugal speed range used when making centrifugal treating to the dispersion liquid is 3000 revolutions per minute~100000
Revolutions per minute, preferably centrifugal speed are 8000 revolutions per minute, and when centrifugal treating is 0.5 hour~300 hours a length of, preferably at centrifugation
A length of 2 hours when reason.
The present invention also provides the organic matter according to used in above-mentioned process for separation and purification, the organic matter is two thiophene of benzo
Pheno substance, the benzene thiophene substance include at least one of following substance: the benzene thiophene comprising alkyl chain is small
Molecule, benzene thiophene polymer, benzene thiophene analog copolymer and benzene thiophene analog derivative；The benzene thiophene
Analog derivative refers to the derivative of benzene thiophene small molecule comprising alkyl chain, the derivative of benzene thiophene polymer, benzene
The derivative of 1,4-Dithiapentalene analog copolymer.
Preferably, the organic solvent is toluene, dimethylbenzene, chloroform, tetrahydrofuran, hexamethylene, hexahydrotoluene, ethyl
One of hexamethylene, N-methyl pyrrolidones and dimethyl sulfoxide.
Hereinafter, will be illustrated to the embodiment of the present invention.
Embodiment one
A kind of method of separating semiconductor single-walled carbon nanotube includes the following steps: 1, by small point of 100mg benzene thiophene
Son puts into 100ml toluene according to the ratio of 1:1 with carbon nanometer tube material and mixes, wherein benzene thiophene small molecule includes length
The alkyl chain that degree is 8；2,30 minutes ultrasonic at 150 watts (W) with Ultrasonic cell smash；3, dispersion liquid centrifugation is taken out, from
8000 revolutions per minute of heart speed (rpm), centrifugation time 2 hours (h)；4, after being centrifuged, supernatant is taken, is suspended with high-purity in supernatant
Carbon nanotube.
Embodiment two
A kind of method of separating semiconductor single-walled carbon nanotube includes the following steps: 1,100mg benzene thiophene polymer
It puts into 100ml toluene and mixes according to the ratio of 0.5:1 with carbon nanometer tube material；2, with Ultrasonic cell smash at 500W
Ultrasound 45 minutes；3, dispersion liquid centrifugation, centrifugal speed 12000rpm, centrifugation time 2h are taken out；4, after being centrifuged, supernatant is taken, on
The carbon nanotube of high-purity is suspended in clear liquid.
Embodiment three
A kind of method of separating semiconductor single-walled carbon nanotube, includes the following steps: 1,100mg carbazole-benzene thiophene
Copolymer and carbon nanometer tube material are put into 100ml toluene according to the ratio of 0.1:1 to be mixed；2, existed with Ultrasonic cell smash
Ultrasound 300 minutes under 20W；3, dispersion liquid centrifugation, centrifugal speed 100000rpm, centrifugation time 0.5h are taken out；4, it after being centrifuged, takes
Supernatant is suspended with the carbon nanotube of high-purity in supernatant.
Example IV
A kind of method of separating semiconductor single-walled carbon nanotube includes the following steps: that 1,100mg benzene thiophene and carbon are received
Mitron raw material puts into 100ml toluene according to the ratio of 20:1 and mixes；2, with Ultrasonic cell smash ultrasonic 5 at 1500W
Minute；3, dispersion liquid centrifugation, centrifugal speed 3000rpm, centrifugation time 300h are taken out；4, after being centrifuged, supernatant is taken, in supernatant
It is suspended with the carbon nanotube of high-purity.
Embodiment five
A kind of method of separating semiconductor single-walled carbon nanotube includes the following steps: 1,100mg indone-carbazole-benzo two
Thiophene copolymers and carbon nanometer tube material are put into 1000ml toluene according to the ratio of 10:1 to be mixed；2, it is crushed with supersonic cell
Instrument ultrasound 45 minutes at 500W；3, dispersion liquid centrifugation, centrifugal speed 12000rpm, centrifugation time 2h are taken out；4, it after being centrifuged, takes
Supernatant is suspended with the carbon nanotube of high-purity in supernatant.
Embodiment six
A kind of method of separating semiconductor single-walled carbon nanotube includes the following steps: 1, by small point of 100mg benzene thiophene
Son puts into 500ml toluene according to the ratio of 1:1 with carbon nanometer tube material and mixes, wherein benzene thiophene small molecule includes length
The alkyl chain that degree is 26；2,30 minutes ultrasonic at 150 watts (W) with Ultrasonic cell smash；3, dispersion liquid centrifugation is taken out, from
8000 revolutions per minute of heart speed (rpm), centrifugation time 2 hours (h)；4, after being centrifuged, supernatant is taken, is suspended with high-purity in supernatant
Carbon nanotube.
The embodiment of the present invention uses benzene thiophene substance separating semiconductor single-wall carbon tube, using benzene thiophene class
Substance can purify out the semiconductor single-walled carbon of high-purity, have the characteristics that high yield, also, benzene thiophene class object
The molecular solution of matter is easy to get, and cost is relatively low.
Fig. 1 is the result detected to the carbon nanotube gone out using scheme separating-purifying provided by the invention.According to Fig. 1
Shown in relationship between wavelength and carbon nanotube absorbance, those skilled in the art it can be found that, metallicity carbon area under control domain does not have
Occur the characteristic peak of metallicity carbon pipe, the purity for the semiconductor single-walled carbon that this feature description separating-purifying goes out
It is high；Also, the maximum absorption peak that absorbance is shown in figure reaches 1.65, illustrates that semiconductor single-walled carbon yield is high.
The technical effect comparing result of the embodiment of the present invention and prior art is as shown in table 1:
1 embodiment of the present invention of table and prior art Contrast on effect result
In conclusion the semiconductor single-walled carbon purity is high that the present invention is obtained using benzene thiophene substance, is closed
At at low cost, suitable industrial production；It is passed in semiconductor devices, integrated circuit, display driving, transparent conductive film, biology/chemistry
The fields such as sense, infrared acquisition, infrared therapeutic have a broad prospect of the use.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art
Mind and range.In this way, if these modifications and changes of the present invention belongs to the range of the claims in the present invention and its equivalent technologies
Within, then the present invention is also intended to include these modifications and variations.
Claims (10)
1. a kind of method of separating-purifying semiconductor single-walled carbon characterized by comprising
Step (1): benzene thiophene substance and the raw material comprising semiconductor single-walled carbon are put into organic solvent；And
Step (2): handling the organic solvent, isolates semiconductor single-walled carbon therein.
2. the method as described in claim 1, which is characterized in that the benzene thiophene substance, extremely including following substance
Few one kind: benzene thiophene small molecule, benzene thiophene polymer, benzene thiophene analog copolymer and benzene comprising alkyl chain
1,4-Dithiapentalene analog derivative；The benzene thiophene analog derivative refers to the derivative of the benzene thiophene small molecule comprising alkyl chain
Object, the derivative of benzene thiophene polymer, benzene thiophene analog copolymer derivative.
3. method according to claim 2, which is characterized in that the benzene thiophene analog copolymer, including following substance
It is at least one: the copolymer of benzene thiophene and carbazole, fluorenes, pyridine, thiophene or benzo [2,1,3] thiadiazoles -4,8- diyl.
4. the method as described in claim 1, which is characterized in that in step (1), benzene thiophene substance with comprising partly leading
The mass ratio of the raw material of body single-walled carbon nanotube is 0.1:1 to 20:1.
5. method according to any of claims 1-4, which is characterized in that the organic solvent are as follows: toluene, dimethylbenzene, chlorine
At least one in imitative, tetrahydrofuran, hexamethylene, hexahydrotoluene, ethyl cyclohexane, N-methyl pyrrolidones and dimethyl sulfoxide
Kind.
6. method as claimed in claim 5, which is characterized in that in step (2), handle the organic solvent, isolate it
In semiconductor single-walled carbon, comprising:
Step (2-1): being ultrasonically treated the organic solvent, extracts the dispersion liquid formed after ultrasonic treatment；
Step (2-2): centrifugal treating is made to the dispersion liquid, extracts the supernatant formed after centrifugal treating, the supernatant packet
Containing the semiconductor single-walled carbon isolated from raw material.
7. method as claimed in claim 6, which is characterized in that in step (2-1), be ultrasonically treated to the organic solvent
The ultrasonic power range of Shi Caiyong is 20 watts~1500 watts, and when ultrasonic treatment is 5 minutes~300 minutes a length of.
8. the method for claim 7, which is characterized in that in step (2-2), when making centrifugal treating to the dispersion liquid
For the centrifugal speed range used for 3000 revolutions per minute~100000 revolutions per minute, when centrifugal treating, is 0.5 hour~300 hours a length of.
9. a kind of separating-purifying semiconductor single-walled carbon as used in any one of claim 1-8 the method is organic
Object, which is characterized in that the organic matter is benzene thiophene substance, and the benzene thiophene substance includes following substance
It is at least one: benzene thiophene small molecule, benzene thiophene polymer, benzene thiophene analog copolymer comprising alkyl chain and
Benzene thiophene analog derivative；The benzene thiophene analog derivative refers to spreading out for the benzene thiophene small molecule comprising alkyl chain
The derivative of biology, the derivative of benzene thiophene polymer, benzene thiophene analog copolymer.
10. the application of organic matter as claimed in claim 9, which is characterized in that the organic matter is for semiconductor devices, collection
At circuit, display driving, transparent conductive film, biology/chemical sensitisation, infrared acquisition and infrared therapeutic.
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| CN112174118A (en) * | 2020-10-14 | 2021-01-05 | 西安交通大学 | Separation method of large-diameter semiconductor single-walled carbon nanotubes |
| CN112591735A (en) * | 2020-12-23 | 2021-04-02 | 北京大学 | Semiconductor type single-walled carbon nanotube purification method |
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