Efficient solar cells via sulfur-fused helical perylene diimides design concept

Patent metadata

Field	Value
Publication number	US-11245077-B2
Application number	US-201916250440-A
Country	US
Kind code	B2
Filing date	Jan 17, 2019
Priority date	Jan 17, 2018
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

Sulfur-fused perylene diimides (PDIs) having the formula 2PDI-nS, wherein n is an integer. Such sulfur-fused PDIs (e.g., 2PDI-2S, 2PDI-3S, and 2PDI-4S) are incorporated as electron acceptors in an active region of a bulk heterojunction solar cell and/or as an electron transport layer. Example solar cells exhibit a power conversion efficiency above 5% and a fill factor above 70% (a record high for non-fullerene bulk heterojunction solar cell devices) when 2PDI-nS is used as the electron acceptor. In addition, the solar cells exhibit low open circuit voltage (Voc) loss.

First claim

What is claimed is:

1. A composition of matter, comprising:
a compound including fused perylene diimides (PDIs) having the structure:

wherein the R are independently hydrogen, an alkyl group, an aryl group, or a solubilizing chain, and
wherein, in each of the compounds comprising X, at least one X is S-S, the other X is S or S-S, R′ is nothing, Y is C, Si, or Ge; Z is N or P; R 1 to R 16 are each independently hydrogen, an alkyl group, or an aryl group (R 1 to R 16 can be the same or different); R 21 is nothing, an alkylene group, or an arylene group; R 23 is a trivalent aliphatic or a trivalent aromatic group; the R 24 are each independently a tetravalent aliphatic group or a tetravalent aromatic group; n=0 to 10; and
if a substituent (Y, Z, R, R′, R 1 -R 24 ) occurs more than one time in a compound, it can be different or the same in each occurrence.

2. The composition of matter of claim 1 , wherein the compound comprises 2PDI-3S.

3. The composition of matter of claim 1 , wherein the compound comprises 2PDI-4S.

4. A device comprising the composition of matter of claim 1 combined with a donor molecule, wherein the fused PDIs are electron acceptors.

5. The device of claim 4 , wherein the donor molecule is at least one compound selected from PTB7-Th or from the list of compounds illustrated in FIGS. 28A-28D .

6. The device of claim 4 , wherein the device is a solar cell having an active region including the fused PDIs combined with the donor molecule.

7. A device comprising the composition of matter of claim 1 , further comprising an electron transport layer including the fused PDIs.

8. The device of claim 1 , further comprising an electromagnetic radiation absorbing active region coupled to the electron transport layer, wherein the active region comprises an organic-inorganic hybrid perovskite (PVSK).

9. The device of claim 8 , wherein the device is a solar cell having a fill factor exceeding 57%.

10. The device of claim 9 , wherein:
the solar cell has a power conversion efficiency (PCE) of at least 11%, and
an external quantum efficiency (EQE) of greater than 70%,
when the active region of the solar cell absorbs the electromagnetic radiation having a wavelength in a range of 350-750 nm under 1 Sun irradiation.

11. The device of claim 4 , wherein the device is a photodetector having a sensing element comprising the fused PDIs combined with the donor molecule.

12. A device comprising the composition of matter of claim 1 , wherein:
the device comprises an active layer or electron transport layer comprising the fused PDIs, and
the active layer or the electron transport layer is amorphous and has a mobility greater than 10 −2 cm 2 /Vs.

13. The device of claim 12 , wherein the device is an n-type field effect transistor.

14. A solar cell device, comprising:
an anode;
an anode interface/hole transport layer on the anode;
an electron transport layer comprising a compound having at least one structure selected from:

wherein:
the R are independently hydrogen, an alkyl group, an aryl group, or a solubilizing chain;
in each structure comprising X, at least one X is S-S, the other X is S or S-S, R′ is nothing, Y is C, Si, or Ge; Z is N or P; R 1 to R 16 are each independently hydrogen, an alkyl group, or an aryl group (R 1 to R 16 can be the same or different); R 21 is nothing, an alkylene group, or an arylene group; R 23 is a trivalent aliphatic or a trivalent aromatic group; the R 24 are each independently a tetravalent aliphatic group or a tetravalent aromatic group; n=0 to 10; and
if a substituent (Y, Z, R, R′, R 1 -R 24 ) occurs more than one time in a compound, it can be different or the same in each occurrence;
a cathode on the electron transport layer;
an active absorbing region between the electron transport layer and the anode interface/hole transport layer, the active absorbing region comprising an organic-inorganic hybrid perovskite (PVSK), wherein, in response to electromagnetic radiation absorbed in the PVSK, the active absorbing region:
outputs electrons through the electron transport layer to the cathode, and
outputs holes through the hole interface/hole transport layer to the anode, so as to generate electric power.

15. The device of claim 14 , wherein the compound comprises 2PDI-3S.

16. The device of claim 14 , wherein the compound comprises 2PDI-4S.

17. The device of claim 14 , wherein the compound in the electron transport layer has a composition such that a power conversion efficiency (PCE), short circuit current (J SC ) and/or fill factor (FF) of the device do not decrease after 400 hours of continuous operation of the device under 1 Sun illumination, as com

Assignees

• Univ California
• The Mitsubishi Chemical Corp A Japanese Corp

Inventors

• Wudl Fred
• Zheng Yonghao
• Wang Hengbin
• Nakayama Hidenori
• Chabinyc Michael

Classifications

• H10K85/50

  Organic perovskites; Hybrid organic-inorganic perovskites [HOIP], e.g. CH3NH3PbI3 · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K71/40

  Thermal treatment, e.g. annealing in the presence of a solvent vapour · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K85/615 Primary

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title