N-type dopants for efficient solar cells

Patent metadata

Field	Value
Publication number	US-2020194686-A1
Application number	US-201916712206-A
Country	US
Kind code	A1
Filing date	Dec 12, 2019
Priority date	Dec 12, 2018
Publication date	Jun 18, 2020
Grant date	—

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 (MAPbI 3 ) 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.

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 7 , wherein the organic compound is

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

10 . 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.

11 . 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.

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

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

14 . The composition of matter of claim 13 , 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.

15 . A device comprising the organic compound of claim 1 , wherein the device is a light emitting device, a light absorbing device, a thermoelectric device, a photodetector device or a transistor.

16 . The device of claim 15 , further comprising an active region or electron transporting layer including the organic compound.

17 . The device of claim 16 , wherein the organic compound is n-type self-doped such that the organic compound emits electromagnetic radiation in response to current, transports current in a channel of a transistor, or generates current in response to the electromagnetic radiation.

18 . The device of claim 16 , wherein the active region or the electron transporting layer includes an organic acceptor combined with the organic compound so that the organic compound n-type dopes the organic acceptor.

19 . The device of claim 15 , wherein the organic compound is non-volatile and stable in air up to a temperature of at least 200 degrees Celsius.

20 . A device, comprising:
an organic transistor, an organic light absorbing device, a solar cell device, a thermoelectric device, a photodetector device, or an organic light emitting device comprising an n-type dopant including an organic compound of the structure:

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

Assignees

• Univ California

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

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

• C07D487/16 Primary

  Peri-condensed systems · CPC title

• H01B1/04

  mainly consisting of carbon-silicon compounds, carbon or silicon · CPC title