Narrow bandgap non-fullerene acceptors and devices including narrow bandgap non-fullerene acceptors

Patent metadata

Field	Value
Publication number	US-11233207-B2
Application number	US-201816179294-A
Country	US
Kind code	B2
Filing date	Nov 2, 2018
Priority date	Nov 2, 2017
Publication date	Jan 25, 2022
Grant date	Jan 25, 2022

Abstract

Organic devices comprising an organic semiconducting acceptor motif coupled to a donor motif. Examples include IOTIC-2F, ITOTIC-2F, COTIC-4F, and SiOTIC-4F as acceptor materials. The acceptor materials have narrow bandgap (1.1 eV-1.3 eV), strong near-IR absorption and high solar cell EQE in near infrared (IR) region. The acceptor materials may also be used as the absorbing/light sensitive region in an IR photodetector.

First claim

What is claimed is:

1. An organic device, comprising:
an active region comprising an organic semiconducting acceptor molecule having a structure:

wherein:
each Ar is independently a substituted or non-substituted aromatic functional group, or each Ar is independently nothing and the valence of its respective thiophene ring is completed with hydrogen;
X is C, Si, Ge, N or P; Y is O, S, Se or N—R 3 ;
Z is O, S, Se, or N—R 3 ;
each R 1 , R 2 , and R 3 is independently hydrogen or a substituted or non-substituted alkyl, aryl or alkoxy chain;
R 4 is either a hydrogen or the same as Z—R 2 ; and
A is an acceptor moiety.

2. The device of claim 1 , wherein the dithiophene has side chains soluble in a solvent used to solution process the device.

3. The device of claim 1 , wherein the organic semiconducting acceptor molecule has the structure:

wherein R is a solubilizing chain comprising a substituted or non-Substituted alkyl, aryl or alkoxy chain.

4. The device of claim 1 , wherein— the organic semiconducting molecule has the structure:

wherein X is C, Si, Ge, N or P; Y is O, S or Se; Z is O or S.

5. The device of claim 1 ,—wherein:
the R, R 1 , R 2 , R 3 and/or R 4 ; each comprise a substituted or non-substituted alkyl, aryl or alkoxy chain including, but not limited to, a C 6 -C 50 substituted or non-substituted alkyl or alkoxy chain, —(CH 2 CH 2 O) n (n=2˜30), C 6 H 5 , —C n F (2n+1) (n=2˜50),—(CH 2 ) n N(CH 3 ) 3 Br (n=2˜50), 2-ethylhexyl, PhC m H 2m+1 (m=1-50), —(CH 2 ) n N(C 2 H 5 ) 2 (n=2˜50), —(CH 2 ) n Si(C m H 2m+l ) 3 (m, n=1 to 50), or —(CH 2 ) n Si(OSi(C m H 2m+1 ) 3 ) x (C p H 2p+1 ) y (m, n, p=1 to 50, x+y=3).

6. The device of claim 1 , wherein A is a compound of the structure:

Y and Z are each independently CH, CF, N, C—CN or C—OR, and
X═O, S, Se, or N—R where R is H or a solubilizing chain.

7. The device of claim 1 , wherein A is a compound of the structure:

X 1 and X 2 are each independently O, S, or a malonitrile,
Y is one or more halogens, —CN, or any solubilizing chain, and
Ar is any aryl unit.

8. The device of claim 1 , further comprising an organic semiconducting donor molecule.

9. The device of claim 8 , wherein the donor molecule comprises PTB7-Th or PBDB-T.

10. The device of claim 1 , wherein the active region is a sensing element in the photodetector comprising an infrared photodetector.

11. The device of claim 1 , further comprising:
an organic semiconducting donor molecule forming heterojunction with the organic semiconducting acceptor molecule;
a first electrode coupled to the organic semiconducting acceptor molecule to receive electrons in electron-hole pairs generated in response to electromagnetic radiation;
a second electrode coupled to the organic semiconducting donor molecule to receive holes in the electron-hole pairs, wherein:
the device comprises a photodetector having an external quantum efficiency (EQE) above 50% in the wavelength range of 900-950 nm when the second electrode is biased negatively with respect to the first electrode.

12. The device of claim 1 , wherein the device has an external quantum efficiency (EQE) above 55% in the wavelength range of 600-1000 nm.

13. The device of claim 1 ,—wherein A is a compound of the structure:

X 1 , X 2 , and X 3 are each independently a halogen, CN, alkoxy, alkylthio, N-annulated (a ring comprising N), or S—annulated (a ring comprising S),
Y 1 , Y 2 , Y 3 , and Y 4 are each independent S or O, and
R 1 and R 2 are each independently H or a solubilizing chain.

14. The device of claim 1 , wherein A is a compound of the structure:

15. A composition of matter, comprising:
a molecule of the structure:

wherein R is a solubilizing chain comprising a substituted or non-substituted alkyl, aryl or alkoxy chain.

16. A composition of matter, comprising an organic semiconducting molecule having a structure:

wherein:
each Ar is independently a substituted or non-substituted aromatic functional group, or each Ar is independently nothing and the valence of its respective thiophene ring is completed with hydrogen;
X is C, Si, Ge, N or P; Y is O, S, Se or N—R 3 ;
Z is O, S, Se, or N—R 3 ;
each R 1 , R 2 , and R 3 is independently hydrogen or a substituted or non-substituted alkyl, aryl or alkoxy chain;
R 4 is either a hydrogen or the same as Z—R 2 ; and
A is an acceptor moiety.

17. The composition of matter of claim 16 , wherein the organic semiconducting molecule has the structure:

wherein X is C, Si, Ge, N or P; Y is O, S or Se; Z is O or S.

18. The composition of matter of claim 16 , wherein:
the R, R 1 , R 2 , R 3 and/or R 4 each comprise a substituted or non-substituted alkyl, aryl or alkoxy chain including, but not limited to, a C 6 -C 50 substituted or non-substituted alkyl or alkoxy chain, —(CH 2 CH 2 O)n (n=2˜30), C 6 H 5 , —C n F (2n+1) (n=2 ˜50), —(CH 2 ) n N(CH 3 ) 3 Br(n=2˜50), 2-ethylhexyl, PhC m H 2m+1 (m=1-50), —(CH 2 ) n N(C 2 H 5 ) 2 (n=2˜50), —(CH 2 ) n Si(C m H 2m+1 ) 3 (m, n=1 to 50), or —(CH 2 ) n Si(OSi(C m H 2m+1 ) 3 ) x (C p H 2p+1 ) y (m, n, p=1 to 50, x+y=3).

19. The composition of matter of claim 16 , wherein A is a compound of the structure:

Y and Z are each independently CH, CF, N, C—CN or C—OR, and
X═O, S, Se, or N—R where R is H or a solubilizing chain.

20. The composition of matter of claim 16 , wherein A is a compound of the structure:

X 1 and X 2 are each independently O, S, or a malonitrile,
Y is one or more halogens, —CN, or any solubilizing chain, and
Ar is any aryl unit.

21. The composition of matter of claim 16 , wherein A is a compound of the structure:

X 1 , X 2 , and X 3 are each independently a halogen, CN, alkoxy, alkylthio, N—annulated (a ring comprising N), or S— annulated (a ring comprising S),
Y 1 , Y 2 , Y 3 , and Y 4 are each independent S or O, and

Assignees

• Univ California

Inventors

• Seifrid Martin
• Bazan Guillermo C
• Lee Jaewon
• Nguyen Thuc-Quyen
• Luginbuhl Benjamin R

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

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K85/621 Primary

  Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide · CPC title

• Y02E10/549

  Organic PV cells · CPC title