Decomposable s-tetrazine based polymers for single walled carbon nanotube applications

Patent metadata

Field	Value
Publication number	US-10121968-B2
Application number	US-201715401421-A
Country	US
Kind code	B2
Filing date	Jan 9, 2017
Priority date	Jan 9, 2017
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

A process for purifying semiconducting single-walled carbon nanotubes (sc-SWCNTs) extracted with a conjugated polymer, the process comprising exchanging the conjugated polymer with an s-tetrazine based polymer in a processed sc-SWCNT dispersion that comprises the conjugated polymer associated with the sc-SWCNTs. The process can be used for production of thin film transistors. In addition, disclosed herein is use of an s-tetrazine based polymer for purification of semiconducting single-walled carbon nanotubes (sc-SWCNTs).

First claim

The invention claimed is:

1. A process for purifying semiconducting single-walled carbon nanotubes (sc-SWCNTs) extracted with a conjugated polymer, the process comprising exchanging the conjugated polymer with an s-tetrazine based polymer in a processed sc-SWCNT dispersion that comprises the conjugated polymer associated with the sc-SWCNTs.

2. The process of claim 1 , further comprising decomposing the s-tetrazine based polymer by photo irradiation or thermal treatment; followed by removal of the decomposition products.

3. The process of claim 1 , wherein the s-tetrazine based polymer has the following structure:

where A is O, S, Se or C═C; n is an integer from 1 to 4; R 1 is independently H, F, CN or a C 1 -C 20 linear or branched aliphatic group; Ar is one or more substituted or unsubstituted aromatic units; and, m is an integer 5 or greater.

4. The process of claim 1 , wherein the s-tetrazine based polymer is PBDTFTz:

5. The process of claim 1 , wherein the s-tetrazine based polymer is PDTSTTz:

6. The process of claim 1 , wherein the s-tetrazine based polymer is:

and wherein: R 1 and R 2 =2-ethylhexyl; or R 1 =2-ethylhexyl and R 2 =hexyl; or R 1 =hexyl and R 2 =2-ethylhexyl; or R 1 and R 2 =hexyl; or R 1 =methyl and R 2 =2-ethylhexyl.

7. The process of claim 1 , wherein the s-tetrazine based polymer is PCPDTFTz:

in which Ar=cyclopenta[2,1-b; 3.4-b′]dithiophene.

8. The process of claim 2 , wherein the decomposition products are removed by rinsing or evaporation.

9. The process of claim 1 , wherein the conjugated polymer comprises a polyfluorene.

10. The process of claim 1 , wherein the conjugated polymer comprises a polythiophene.

11. The process according to claim 1 , wherein the conjugated polymer is poly(9,9-di-n-dodecylfluorene) (PFDD).

12. The process according to claim 1 , wherein the weight ratio of the conjugated polymer to the sc-SWCNTs has a maximum value of 2.

13. The process according to claim 1 , wherein the weight ratio of the s-tetrazine based polymer to the sc-SWCNTs has a maximum value of 4.

14. The process according to claim 1 , wherein the weight ratio of the s-tetrazine based polymer to the sc-SWCNTs is between 1 and 4.

15. A method for producing thin film transistors, the method comprising:
a) exchanging a conjugated polymer with an s-tetrazine based polymer in a processed sc-SWCNT dispersion that comprises the conjugated polymer associated with the sc-SWCNTs, resulting in an associated complex of s-tetrazine/SWCNTs (15);
b) removing the displaced conjugated polymer;
c) applying the resulting dispersion to a substrate;
d) applying heat and/or UV light to decompose the s-tetrazine based polymer; and
e) removing the resulting decomposition products.

16. The method according to claim 15 , wherein the s-tetrazine based polymer has the following structure:

where A is O, S, Se or C═C; n is an integer from 1 to 4; R 1 is independently H, F, CN or a C 1 -C 20 linear or branched aliphatic group; Ar is one or more substituted or unsubstituted aromatic units; and, m is an integer 5 or greater.

17. The method of claim 16 , wherein the wherein the s-tetrazine based polymer is PBDTFTz:

18. The method of claim 16 wherein the conjugated polymer is poly(9,9-di-n-dodecylfluorene) (PFDD).

Assignees

• Nat Res Council Canada

Inventors

• Li Zhao
• Ding Jianfu
• Malenfant Patrick Roland Lucien

Classifications

• H01L51/0048

  Electricity · mapped topic

• C08G2261/228

  Polymers, i.e. more than 10 repeat units · CPC title

• C08G2261/3247

  containing combinations of different heteroatoms other than nitrogen and oxygen or nitrogen and sulfur · CPC title

• C08G2261/3221

  containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole · CPC title

• H01L51/0558

  Electricity · mapped topic