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

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

R 1 and R 2 are each independently H or a solubilizing chain.

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

R 1 and R 2 are each independently H or a solubilizing chain, and

Ar is any aryl unit.

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

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

R is H or any solubilizing chain,

Y 1 and Y 2 are each independently S, O, or a malonitrile, and

Ar is any aryl unit.

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

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

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

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

27. The composition of matter of claim 16 , wherein A is an acceptor moiety comprising (3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (IC).

28. The device of claim 1 , wherein the device is an organic solar cell.

29. The device of claim 1 , wherein A is an acceptor moiety comprising (3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (IC).

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

R 1 and R 2 are each independently H or a solubilizing chain, and

Ar is any aryl unit.

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

R is H or any solubilizing chain,

Y 1 and Y 2 are each independently S, O, or a malonitrile, and

Ar is any aryl unit.