Electron acceptors based on alpha-position substituted PDI for OPV solar cells

Patent metadata

Field	Value
Publication number	US-10818849-B2
Application number	US-201616067501-A
Country	US
Kind code	B2
Filing date	Dec 29, 2016
Priority date	Dec 29, 2015
Publication date	Oct 27, 2020
Grant date	Oct 27, 2020

Abstract

The present disclosure relates to α-substituted perylene diimide (PDI) derivatives as small molecular and polymerized electron acceptors in organic photovoltaic cells.

First claim

What is claimed is:

1. A molecular acceptor of formula A:

where R 1 is selected from: C 1 -C 30 linear or branched chain alkyl;
x is an integer selected from: 2, 4 and 6;

wherein when Ar a is bonded at 1, and x is 2, Ar a is selected from: a bond,

wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 , if present, are each independently selected from: C 1 -C 30 linear or branched chain alkyl, and

wherein R 11 , if present, is C 1 -C 30 linear or branched chain alkyl;

or when Ar a is bonded at 1, and x is 4, Ar a is selected from:

or when Ar a is bonded at 1, and x is 6, Ar a is selected from:

or when Ar a is bonded at 2 and 3 and x is 2, Ar a is selected from:

wherein R 12 and R 13 , if present, are selected from: C 1 -C 30 linear or branched chain alkyl; and
wherein y is an integer selected from 1 and 3;

or when Ar a is bonded at 2 and 3 and x is 4, Ar a is selected from:

or when Ar a is bonded at 2 and 3 and x is 6, Ar a is:

2. A molecular acceptor of formula I:

where R 1 is selected from: C 1 -C 30 linear or branched chain alkyl;
x is an integer selected from: 2, 4 and 6;

wherein when x is 2, Ar is selected from: a bond,

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 , if present, are each independently selected from:
C 1 -C 30 linear or branched chain alkyl, and

R 11 , if present, is C 1 -C 30 linear or branched chain alkyl;

or when x is 4, Ar is selected from:

or when x is 6, Ar is selected from:

3. The molecular acceptor of claim 2 further selected from an acceptor of formula II:

where R 1 is a selected from: C 1 -C 30 linear or branched chain alkyl; and
Ar 1 is selected from: a bond,

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 , if present, are each independently selected from a: C 1 -C 30 linear or branched chain alkyl, and

R 11 , if present, is C 1 -C 30 linear or branched chain alkyl.

4. The molecular acceptor of claim 3 further selected from:

5. The molecular acceptor of claim 4 having a power conversion efficiency of greater than 4.92%.

6. The molecular acceptor of claim 1 further selected from an acceptor of formula VI:

where R 1 is a selected from: C 1 -C 30 linear or branched chain alkyl; and

when Ar 5 is bonded at 1, Ar 5 is selected from: a bond

wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 , if present, are each independently selected from: C 1 -C 30 linear or branched chain alkyl, and

wherein R 11 , if present, is C 1 -C 30 linear or branched chain alkyl;

or wherein when Ar 5 is bonded at 2 and 3, where Ar 5 is selected from:

wherein R 12 and R 13 , if present, are selected from: C 1 -C 30 linear or branched chain alkyl; and
wherein y is an integer selected from 1 and 3.

7. The molecular acceptor of claim 6 further selected from an acceptor of formula VII:

where R 1 is a selected from: C 1 -C 30 linear or branched chain alkyl; and
wherein Ar 6 is selected from:

wherein R 12 and R 13 , if present, are selected from: C 1 -C 30 linear or branched chain alkyl; and
wherein y is an integer selected from 1 and 3.

8. The molecular acceptor of claim 7 further selected from:

wherein EH is 2-ethyl hexyl.

9. The molecular acceptor of claim 8 having a power conversion efficiency of greater than 5.59%.

10. A molecular acceptor of claim 1 , further selected from an acceptor of formula IX:

where R 1 is C 1 -C 30 linear or branched chain alkyl; and
wherein when Ar 8 is bonded at 1, Ar 8 is selected from

or when Ar 8 is bonded at 2 and 3, Ar 8 is selected from:

Assignees

• Univ Chicago

Inventors

• Zhao Donglin
• Wu Qinghe
• Yu Luping
• Cai Zhengxu

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/6572

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

• C09B57/00 Primary

  Other synthetic dyes of known constitution · CPC title

• H10F19/50

  Integrated devices comprising at least one photovoltaic cell and other types of semiconductor or solid-state components (H10F19/75 takes precedence) · CPC title

• C09B3/14

  Perylene derivatives · CPC title