Ultra narrow bandgap non-fullerene-acceptor based organic electronics

Patent metadata

Field	Value
Publication number	US-2023132149-A1
Application number	US-202217870628-A
Country	US
Kind code	A1
Filing date	Jul 21, 2022
Priority date	Jul 21, 2021
Publication date	Apr 27, 2023
Grant date	—

Abstract

Ultra-narrow bandgap Non Fullerene Acceptors (NFAs) comprising an A-D-A′-D-A structure or an A-D-A′-D′-A′-D-A structure were designed, synthesized, and characterized (where A, A′ are organic acceptor moieties and D and D′ are organic donor moieties). Exemplary NFA materials have narrow bandgap (0.86 eV-0.99 eV). Photovoltaic devices and Near Infrared photodetector devices based on these compositions above were synthesized with controlled amounts of solvents and additives. A photodetector having a specific detectivity of 2.41×10 12 Jones (D*) at a wavelength of 1040 nm was achieved.

First claim

1 . A composition of matter useful as an electron acceptor, comprising:
an organic semiconducting compound having an A-D-A′-D-A structure or an A-D-A′-D′-A′-D-A structure, wherein: D is a first donor moiety; D′ is a second electron donor moiety; A is a first electron acceptor moiety; and A′ is a second electron acceptor moiety.

2 . The composition of matter of claim 1 , wherein the organic semiconducting compound has the structure:

Ar or Ar1 comprise an aromatic functional group or hydrogen,
X is O, S, Se or N—R 1 ;
Y is O, S, Se, or N—R 2 ; Z is C, Si, Ge, N or P; E is O, S, Se, or N—R 3 ; and
each R, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently hydrogen or a substituted or non-substituted alkyl, aryl or alkoxy chain.

3 . The composition of matter of claim 1 , wherein the organic semiconducting compound comprises the structure:

wherein X is O, S, Se or N—R 1 , Y is O, S; Z is C, Si, Ge, N; E is O, S; each R R 1 , R 4 , R 5 and R 6 is independently hydrogen or a substituted or non-substituted alkyl, aryl or alkoxy, chain; and each Ar1 and Ar2 is independently a substituted or non-substituted aromatic functional group comprising an electron withdrawing aromatic functional group.

4 . The composition of matter of claim 3 , wherein each Ar2 is independently one of the following:

5 . The composition of matter of claim 1 , having the A-D-A′-D′-A′-D-A structure wherein:
A′ is:

D′ is:

Ar is one of the following:

D is independently one of the following:

where each R, R 2 , R 3 , R 4 , R 5 is independently hydrogen or a substituted or non-substituted alkyl, aryl or alkoxy chain.

6 . The composition of matter of claim 1 , wherein the organic semiconducting compound has the structure:

wherein each R is independently hydrogen or a substituted or non-substituted alkyl, aryl or alkoxy chain.

7 . The composition of matter of claim 1 , wherein the organic semiconducting compound has the structure:

wherein each R 1 and R 2 is independently hydrogen or a substituted or non-substituted alkyl, aryl or alkoxy chain.

8 . The composition of matter of claim 1 , wherein the organic semiconducting compound is:

where each R 4 and R 7 is independently hydrogen or a substituted or non-substituted alkyl, aryl or alkoxy chain; and each R 5 and R 6 , is independently hydrogen or a substituted or non-substituted alkyl or aryl chain.

9 . The composition of matter of claim 1 , further comprising an organic semiconducting donor combined with the electron acceptor.

10 . The composition of matter of claim 9 , wherein the organic semiconducting donor comprises:
a semiconducting compound of the structure (and isomers thereof):

wherein:
each Ar 2 is independently a substituted or non-substituted aromatic functional group, or Ar 2 is nothing and the valence of the ring is completed with hydrogen;
each Q is independently O, S Se, or N—R 4 ;
each R and R 4 is independently hydrogen or a substituted or non-substituted alkyl, aryl, alkoxy or thioether chain;
T is N, C—F, or C—Cl; and
X is C, Si, Ge, N or P, or

the semiconducting compound of the structure:

each Ar 2 is independently a substituted or non-substituted aromatic functional group, or Ar 2 is nothing and the valence of the ring is completed with hydrogen;
each Q is independently O, S Se, or N—R 4 ;
each R and R 4 is independently hydrogen or a substituted or non-substituted alkyl, aryl, alkoxy or thioether chain;
T is N, C—F, or C—Cl; and
X is C, Si, Ge, N or P,
or the semiconducting compound of the structure:

wherein:
Q is O, S, Se, N—R 4 ,
each R, R 4 is independently hydrogen or a substituted or non-substituted alkyl, aryl, alkoxy or thioether chain;
T is N, C—F, or C—Cl; and
X is C, Si, Ge, N or P,
or the organic semiconducting donor comprises the structure:

wherein:
each Ar 1 is independently a substituted or non-substituted aromatic functional group, or each Ar 1 is nothing and the valence of the ring is completed with hydrogen,
each Z is independently O, S, Se, or N—R 4 ;
each R 1 , R 4 is independently hydrogen or a substituted or non-substituted alkyl, aryl, alkoxy or thioether chain; and
each Q is independently O, S Se, or N—R 4 ,
or
the organic semiconducting donor comprises the structure:

each Ar 1 and Ar 2 is independently a substituted or non-substituted aromatic functional group, or each Ar 1 and Ar2 is independently nothing and the valence of the ring is completed with hydrogen,
each Z is independently O, S, Se, or N—R 4 ;
each R 1 , R 4 is independently hydrogen or a substituted or non-substituted alkyl, aryl, alkoxy or thioether chain; and
each Q is independently O, S Se, or N—R 4 .

11 . The composition of matter of claim 10 , wherein the electron acceptor has a bandgap less than or equal to the bandgap of the organic semiconducting donor.

12 . The composition of matter of claim 11 , wherein the organic semiconducting donor comprises a semiconducting polymer.

13 . The composition of matter of claim 9 , wherein the organic semiconducting donor comprises a semiconducting polymer having the structure:

14 . The composition of matter of claim 9 , wherein the organic semiconducting donor comprises:

Assignees

• Univ California

Inventors

• Bazan Guillermo C
• Song Seyeong
• Zhu Ziyue
• Wang Hengbin

Classifications

• H10K30/30

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

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/657 Primary

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• H10K85/111

  comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene · CPC title

• H10K85/113

  Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene · CPC title