Dispersed solution of carbon nanotubes and method of preparing the same

• US 8,591,771 B2
• Filed: 01/19/2007
• Issued: 11/26/2013
• Est. Priority Date: 04/14/2006
• Status: Expired due to Fees

• Current Assignee: Samsung Electronics Co. Ltd.
• Original Assignee: Samsung Electronics Co. Ltd.
• Inventors: Yoon, Seon-mi, Choi, Jae-young, Paik, Un-gyu, Lee, Jin-hyon
• Primary Examiner(s): Nguyen, Tri V
• Application Number:
  US11/624,928
• Publication Number:
  US 20130187084A1
• Time in Patent Office: 2,503 Days
• Field of Search: 252500-511, 423/445.B, 427/122, 524/495, 524/496, 977/742, 977/745
• US Class Current: 252/502
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: B82Y 40/00 Manufacture or treatment of nanostructures
• CPC Class Codes: C01B 32/174 Derivatisation; Solubilisation; Dispersion in solvents

Abstract

Disclosed herein are a dispersed solution of carbon nanotubes including carbon nanotubes, an organic solvent, a spacer, and a dispersant, and a method of preparing the same. The dispersed solution of the carbon nanotubes includes both the spacer, which reduces the van der Waals force of the carbon nanotubes and prevents bundling of the carbon nanotubes, and the dispersant, which maintains the debundling and stability of the carbon nanotubes, thereby improving the dispersibility of the carbon nanotubes. The method of preparing the dispersed solution of the carbon nanotubes can easily produce a dispersed solution of carbon nanotubes without performing a separate chemical treatment.

Claims

1. A dispersed solution of carbon nanotubes, comprising:

carbon nanotubes;

an organic solvent;

a spacer; and

a dispersant,

wherein the dispersant is a compound comprising;

a head moiety comprising a substituted or unsubstituted C₅ to C₃₀ aromatic hydrocarbon group or a substituted or unsubstituted C₃ to C₃₀ heterocyclic aromatic group; and

a tail moiety comprising a repeat unit selected from the group consisting of an acrylate group, an ethylene oxide group, a propylene oxide group, and an alkyl group, wherein the head moiety and the tail moiety are connected to each other, and the molecular weight of the dispersant is less than or equal to about 20,000, wherein the dispersant is a compound represented by Formulae 9 through 11;

2. The dispersed solution of claim 1, wherein the spacer is a compound selected from the group consisting of a substituted or unsubstituted C₇ to C₃₀ polycyclic aromatic hydrocarbon compound or a substituted or unsubstituted C₃ to C₃₀ heterocyclic aromatic compound.

3. The dispersed solution of claim 2, wherein the C₇ to C₃₀ polycyclic aromatic hydrocarbon compound is a compound selected from the group consisting of pentalene, indene, naphthalene, azulene, heptalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluorathene, triphenylene, pyrene, chrycene, naphthacene, picene, perylene, pentaphene, hexacene, rubicene, coronene, trinaphthylene, heptaphene, heptacene, pyranthrene, and ovalene.

4. The dispersed solution of claim 2, wherein the C₃ to C₃₀ heterocyclic aromatic compound is a compound selected from the group consisting of thiophene, thianthrene, phenothiarsine, furan, pyran, isobenzofuran, chromene, xanthene, phenoxatin, imidazole, pyrrole, pyrazole, isothiazole, isoxazole, pyridine, pyrazine, pyrimidine, pyradizine, pyrrolizine, indolizine, indole, indazole, purine, quinolizine, isoquinoline, phthalazine, naphthylidine, quinoxaline, quinazoline, cinnoline, pteridine, carbazole, phenantridine, acridine, perimidine, phenanthroline, phenazine, phenomercazine, phenarazine, phenophosphazine, phenotellurazine, phenoselenazine, phenotiazine, phenoxazine, iso chroman, chroman, pyrrolidine, imidazolidine, pyrazolidine, piperidine, piperazine, indoline, isoindoline, morpholine, and a compound represented by Formula 1 below:

5. The dispersed solution of claim 4, wherein CY1 of Formula 1 is selected from the group consisting of

6. The dispersed solution of claim 4, wherein the compound of Formula 1 is a compound selected from the group consisting of compounds represented by Formulae 2 through 7:

7. The dispersed solution of claim 2, wherein the polycyclic aromatic hydrocarbon compound, the heterocyclic aromatic compound, or both are independently substituted by —

F, —

Cl, —

Br, —

CN, —

NO₂, or —

OH.

8. The dispersed solution of claim 1, wherein the organic solvent is selected from the group consisting of hexanol, heptanol, octanol, nonanol, decanol, acetone, methylethylketone, ethylisobutylketone, methylisobutylketone, ethyleneglycol, ethyleneglycol methylether, ethyleneglycol mono-n-propylether, propyleneglycol, propyleneglycol methylether, propyleneglycol ethylether, propyleneglycol butylether, propyleneglycol propylether, dimethylformamide, dimethylacetoamide, N-methylpyrrolidone, N-ethylpyrrolidone, dimethylsulfoxide, γ

-butyrolactone, methyl lactate, ethyl lactate, methyl β

-methoxyisobutyrate, methyl α

-hydroxyisobutyrate, aniline, N-methylaniline, hexane, terpineol, chloroform, toluene, propyleneglycol monomethylether acetate, chlorobenzene, dichlorobenzene, chloroform, and N-methyl-2-pyrrolidone, or a combination comprising at least one of the foregoing.

9. The dispersed solution of claim 1, wherein the dispersed solution comprises about 0.001 weight percent to about 5 weight percent carbon nanotubes, about 0.001 weight percent to about 5 weight percent spacer, about 0.001 weight percent to about 10 weight percent dispersant, and a balance of a weight of the dispersed solution being the organic solvent.

10. A method of preparing a dispersed solution of carbon nanotubes, the method comprising:

inserting a spacer between carbon nanotubes; and

dispersing the carbon nanotubes using a dispersant and an organic solvent,

wherein the dispersant is a compound comprising;

a head moiety comprising a substituted or unsubstituted C₅ to C₃₀ aromatic hydrocarbon group or a substituted or unsubstituted C₃ to C₃₀ heterocyclic aromatic group; and

a tail moiety comprising a repeat unit selected from the group consisting of an acrylate group, an ethylene oxide group, a propylene oxide group, and an alkyl group, wherein the head moiety and the tail moiety are connected to each other, and the molecular weight of the dispersant is less than or equal to about 20,000, wherein the dispersant is a compound represented by Formulae 9 through 11;

11. The method of claim 10, wherein the inserting the spacer between the carbon nanotubes and dispersing the nanotubes using the dispersant are performed at the same time.

12. The method of claim 10, wherein the spacer is a compound selected from the group consisting of a substituted or unsubstituted C₇ to C₃₀ polycyclic aromatic hydrocarbon compound or a substituted or unsubstituted C₃ to C₃₀ heterocyclic aromatic compound.

13. The method of claim 12, wherein the C₇ to C₃₀ polycyclic aromatic hydrocarbon compound is a compound selected from the group consisting of pentalene, indene, naphthalene, azulene, heptalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluorathene, triphenylene, pyrene, chrycene, naphthacene, picene, perylene, pentaphene, hexacene, rubicene, coronene, trinaphthylene, heptaphene, heptacene, pyranthrene, and ovalene.

14. The method of claim 12, wherein the C₃ to C₃₀ heterocyclic aromatic compound is a compound selected from the group consisting of thiophene, thianthrene, phenothiarsine, furan, pyran, isobenzofuran, chromene, xanthene, phenoxatin, imidazole, pyrrole, pyrazole, isothiazole, isoxazole, pyridine, pyrazine, pyrimidine, pyradizine, pyrrolizine, indolizine, indole, indazole, purine, quinolizine, isoquinoline, phthalazine, naphthylidine, quinoxaline, quinazoline, cinnoline, pteridine, carbazole, phenantridine, acridine, perimidine, phenanthroline, phenazine, phenomercazine, phenarazine, phenophosphazine, phenotellurazine, phenoselenazine, phenotiazine, phenoxazine, iso chroman, chroman, pyrrolidine, imidazolidine, pyrazolidine, piperidine, piperazine, indoline, isoindoline, morpholine, and a compound represented by Formula 1 below:

15. The method of claim 14, wherein CY1 of Formula 1 is selected from the group consisting of

16. The method of claim 14, wherein the compound of Formula 1 is a compound selected from the group consisting of compounds represented by Formulae 2 through 7:

17. A method of preparing a dispersed solution of carbon nanotubes, the method comprising:

adding carbon nanotubes to a solution containing a spacer to prepare a first carbon nanotube solution;

sonicating the first carbon nanotube solution;

adding a dispersant and an organic solvent to the sonicated first carbon nanotube solution to prepare a second carbon nanotube solution;

sonicating the second carbon nanotube solution;

centrifuging the sonicated second carbon nanotube solution; and

recovering a dispersed solution of the carbon nanotubes which are dispersed in the centrifuged second carbon nanotube solution,

wherein the dispersant is a compound comprising;

a head moiety comprising a substituted or unsubstituted C₅ to C₃₀ aromatic hydrocarbon group or a substituted or unsubstituted C₃ to C₃₀ heterocyclic aromatic group; and

a tail moiety comprising a repeat unit selected from the group consisting of an acrylate group, an ethylene oxide group, a propylene oxide group, and an alkyl group, wherein the head moiety and the tail moiety are connected to each other, and the molecular weight of the dispersant is less than or equal to about 20,000, wherein the dispersant is a compound represented by Formulae 9 through 11;

18. A method of preparing a dispersed solution of carbon nanotubes, the method comprising:

adding carbon nanotubes to a solution containing a spacer, an organic solvent and a dispersant to prepare a carbon nanotube solution;

sonicating the carbon nanotube solution;

centrifuging the sonicated carbon nanotube solution; and

recovering a dispersed solution of the carbon nanotubes which are dispersed in the centrifuged carbon nanotube solution,

wherein the dispersant is a compound comprising;

a head moiety comprising a substituted or unsubstituted C₅ to C₃₀ aromatic hydrocarbon group or a substituted or unsubstituted C₃ to C₃₀ heterocyclic aromatic group; and

a tail moiety comprising a repeat unit selected from the group consisting of an acrylate group, an ethylene oxide group, a propylene oxide group, and an alkyl group, wherein the head moiety and the tail moiety are connected to each other, and the molecular weight of the dispersant is less than or equal to about 20,000, wherein the dispersant is a compound represented by Formulae 9 through 11;