N-type dopants for efficient solar cells

Patent metadata

Field	Value
Publication number	US-12150381-B2
Application number	US-202217826455-A
Country	US
Kind code	B2
Filing date	May 27, 2022
Priority date	Dec 12, 2018
Publication date	Nov 19, 2024
Grant date	Nov 19, 2024

Abstract

Triazabicylodecene can effectively n-dope a variety of organic semiconductors, including PCBM, thus increasing in-plane conductivities. We synthesized a series of TBD-based n-dopants via an N-alkylation reaction and studied the effect of various alkyl chains on the physical and device properties of the dopants. Combining two TBD moieties on a long alky chain gave a solid dopant, 2TBD-C10, with high thermal stability above 250° C. PCBM films doped by 2TBD-C10 were the most tolerant to thermal annealing and reached in-plane conductivities of 6.5×10−2 S/cm. Furthermore, incorporating 2TBD-C10 doped PCBM as the electron transport layer (ETL) in methylammonium lead triiodide (MAPbI3) based photovoltaics led to a 23% increase in performance, from 11.8% to 14.5% PCE.

First claim

What is claimed is:

1. A composition of matter, comprising:
an organic compound of the structure:

wherein:
1≤m≤8;
1≤n≤8;
2≤x≤4; and
R is any substituted or non-substituted alkyl, alkenyl, alkynyl, aryl or alkoxy group; and
the

comprises an n-type dopant.

2. The composition of matter of claim 1 , wherein R contains one or more heteroatoms.

3. The composition of matter of claim 1 , wherein R contains one or more aromatic moieties.

4. The composition of matter of claim 1 , wherein:

is any of the following bicyclic structures:

5. The composition of matter of claim 1 , wherein the organic compound is a dimer (x=2) wherein each end of the R is connected to one of the

6. The composition of matter of claim 5 , wherein the organic
compound is

7. The composition of matter of claim 1 , wherein the organic compound is a trimer (x=3) wherein each end of the R is connected to one of the

8. The composition of matter of claim 1 bonded to a phenyl-C 61 -butyric acid methyl ester (PCBM), or wherein the R comprises the PCBM, so as to n-type dope the PCBM.

9. The composition of matter of claim 1 bonded to an electron acceptor, or wherein the R comprises an electron acceptor, so as to n-type dope the acceptor.

10. The composition of claim 1 bonded to a fullerene so as to form the organic compound

11. The composition of matter of claim 1 , wherein the R is selected so that the organic compound is miscible with an organic acceptor.

12. The composition of matter of claim 11 , further comprising a single phase amorphous composition including the organic compound combined with the organic acceptor, wherein the organic compound n-type dopes the organic acceptor.

13. The composition of matter of claim 1 , wherein the

comprises an n-type dopant for the R.

14. A composition of matter, comprising an organic compound of the structure:

15. A composition of matter comprising an organic compound of the structure

wherein:
1≤m≤8;
1≤n≤8;
2≤x≤4; and
R is any substituted or non-substituted alkyl, alkenyl, alkynyl, aryl or alkoxy group; and
the R comprises the fullerene, so as to n-type dope the fullerene.

Assignees

• Univ California
• The Mitsubishi Chemical Corp

Inventors

• Schneider Julia
• Chabinyc Michael L
• Wang Hengbin
• Nakayama Hidenori
• Clark Kyle D
• De Alaniz Javier Read

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K30/30

  comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains · CPC title

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D487/16 Primary

  Peri-condensed systems · CPC title

• H10K85/215

  comprising substituents, e.g. PCBM · CPC title