Hydrophilic conjugated polymers, and methods of preparation and use thereof

Patent metadata

Field	Value
Publication number	US-10147553-B2
Application number	US-201715457971-A
Country	US
Kind code	B2
Filing date	Mar 13, 2017
Priority date	Mar 14, 2016
Publication date	Dec 4, 2018
Grant date	Dec 4, 2018

Abstract

The invention provides novel hydrophilic conjugated polymers, e.g., hydrophilic poly(arylene vinylenes) or PAVs, and preparation thereof, and methods and devices for their application in photovoltaics, and the resulting improved solar cells.

First claim

What is claimed is:

1. A polymer comprising the structural formula:

wherein Q is:

wherein
each R 1 , R 2 , R 3 and R 4 is independently H or an electron-withdrawing group; provided that at least two of R 1 , R 2 , R 3 and R 4 are electron-withdrawing groups;
each of R 5 , R 6 , R 7 and R 8 is independently selected from H, —R, —OR and —SR, provided at least two of R 5 , R 6 , R 7 and R 8 are selected from —R, —OR and —SR, wherein R comprises a group selected from cationic moiety, anionic moiety, zwitterionic moiety and a neutral moiety comprising a moiety selected from ethylene oxide and ethyleneglycol groups; and
n is an integer from 2 to 4,000.

2. The polymer of claim 1 , wherein each electron-withdrawing group is selected from F, carboxylic acid, ester, amide, cyano (CN), trifluoromethyl (CF 3 ), and nitro (NO 2 ).

3. The polymer of claim 2 , wherein each electron-withdrawing group is F.

4. The polymer of claim 1 , wherein Q is:

5. The polymer of claim 4 , wherein each of R 1 , R 2 , R 3 and R 4 is F.

6. The polymer of claim 1 , wherein Q is:

7. The polymer of claim 6 , wherein each of R 3 and R 4 is F.

8. The polymer of claim 1 , wherein each of R 5 and R 8 is H and each of R 6 and R 7 is selected from —R, —OR and —SR.

9. The polymer of claim 8 , wherein R is selected from:

wherein each of i, j, and k is independently an integer from about 1 to about 20, X − is an anionic counter ion and M + is a cationic counter ion.

10. The polymer of claim 1 , wherein the structural unit has the formula:

wherein R is selected from

11. The polymer of claim 1 , wherein the structural unit has the formula:

wherein R is selected from

12. The polymer of claim 1 , wherein the structural unit has the formula:

wherein R is selected from

13. The polymer of claim 1 , wherein R comprises a zwitterionic moiety.

14. The polymer of claim 13 , wherein R further comprises one or more of a cationic moiety, an anionic moiety and a neutral moiety.

15. A polymerization method, comprising:
reacting a first monomer of the formula

with a second monomer of the formula

wherein
each R′ is independently a C 1 -C 3 alkyl group;
Q is:

wherein
each R 1 , R 2 , R 3 and R 4 is independently H or an electron-withdrawing group; provided that at least two of R 1 , R 2 , R 3 and R 4 are electron-withdrawing groups; and
each of R 5 , R 6 , R 7 and R 8 is independently selected from H, —R, —OR and —SR, provided at least two of R 5 , R 6 , R 7 and R 8 are selected from —R, —OR and —SR, wherein R comprises a group selected from cationic moiety, anionic moiety, zwitterionic moiety and a neutral moiety comprising a moiety selected from ethylene oxide and ethyleneglycol groups.

16. The polymer of claim 1 , having a molecular weight from about 1 kDa to about 2,000 kDa.

17. A material comprising a polymer of claim 1 .

18. An article of manufacture comprising a polymer of claim 1 , wherein the article is a solar cell.

19. The article of claim 18 , wherein the solar cell is an inverted Perovskite solar cell.

20. An inverted Perovskite solar cell comprising a hole-extraction layer, wherein the hole-extraction layer comprises a polymer or is prepared from a polymer of the structural formula:

wherein Q is:

wherein
each R 1 , R 2 , R 3 and R 4 is independently H or an electron-withdrawing group; provided that at least two of R 1 , R 2 , R 3 and R 4 are electron-withdrawing groups;
each of R 5 , R 6 , R 7 and R 8 is independently selected from H, —R, —OR and —SR, provided at least two of R 5 , R 6 , R 7 and R 8 are selected from —R, —OR and —SR, wherein R comprises a group selected from cationic moiety, anionic moiety, zwitterionic moiety and a neutral moiety comprising a moiety selected from ethylene oxide and ethyleneglycol groups; and
n is an integer from 2 to 4,000.

Assignees

• Univ Massachusetts

Inventors

• Emrick Todd
• Page Zachariah A
• Liu Yao
• Russell Thomas P

Classifications

• C08G2261/344

  containing heteroatoms · CPC title

• H01L51/0043

  Electricity · mapped topic

• H01L51/0047

  Electricity · mapped topic

• C08G2261/146

  Side-chains containing halogens · CPC title

• H01L51/0036

  Electricity · mapped topic