Organic semiconductor compounds and methods of use

Patent metadata

Field	Value
Publication number	US-10566539-B2
Application number	US-201515308795-A
Country	US
Kind code	B2
Filing date	May 5, 2015
Priority date	May 5, 2014
Publication date	Feb 18, 2020
Grant date	Feb 18, 2020

Abstract

Organic perylene diimide-based compounds are provided. Methods of producing the organic compounds is also provided as well as methods of their use including, among other things, their use as organic semiconductor materials.

First claim

What is claimed is:

1. An oligomer compound comprising at least one repeating monomer, wherein the compound is represented by the Formula:

wherein each R is independently selected from the group consisting of branched and unbranched alkyl groups with a total of 6-20 carbon atoms;
n is an integer from 3-10; and
wherein units are connected by ethylene bridges between bay-positions.

2. The oligomer compound of claim 1 , wherein each R is independently selected from the group consisting of branched and unbranched C 8 -C 15 alkyl groups.

3. The oligomer compound of claim 1 , wherein each R is independently selected from the group consisting of branched and unbranched C 9 -C 12 alkyl groups.

4. The oligomer compound of claim 1 , wherein at least one R is branched or unbranched C 11 H 23 .

5. The oligomer compound of claim 1 , wherein each R is independently a branched or unbranched C 11 H 23 .

6. The oligomer compound of claim 5 , wherein each R is branched C 11 H 23 .

7. The oligomer compound of claim 6 , wherein each R is:

8. The oligomer compound of claim 1 , wherein n is an integer from 3-4.

9. The oligomer compound of claim 1 , wherein the compound is represented by the formula:

10. The oligomer compound of claim 1 , wherein the compound is represented by the formula:

11. The oligomer compound of claim 1 , wherein the compound is:

12. The oligomer compound of claim 1 , wherein the compound is:

13. The oligomer compound as in claim 1 , wherein the compounds are non-planar.

14. The oligomer compound as in claim 1 , wherein the LUMO levels of the compound are between about −1 eV to about −6 eV.

15. The oligomer compound of claim 14 , wherein the LUMO levels are about −4 eV.

16. The oligomer compound as in claim 1 , wherein the electron mobilities of the compound are between about 10 −4 to about 10 −5 cm 2 V −1 s −1 .

17. The oligomer compound of claim 16 , wherein the electron mobilities are between about 10 −1 to about 10 −2 cm 2 V −1 s −1 .

18. The oligomer compound as in claim 1 , wherein the oligomer compound forms a helical, waggling, or mixed helical and waggling superstructure.

19. The oligomer compound as in claim 1 , wherein one or more carbons at positions 1, 2, 5, 6, 7, 8, 11, or 12 is substituted.

20. The oligomer compound as claim 19 , wherein one or more carbons at positions 1, 2, 5, 6, 7, 8, 11, or 12 is substituted with the group consisting of a bromine, nitrile, and ethylene glycol dimethyl ether.

21. A device comprising at least one compound of claim 1 , at least one electron donor, and optionally at least one solvent additive.

22. The device of claim 21 , wherein the electron donor is selected from the group consisting of Group IA metals, Group IA metal arenes, P3HT, poly[2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylene vinylene] (MDMO-PPV), poly(2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene vinylene) (MEH-PPV), N,N-diisopropyl-3-pentylamine, N-ethyldiisopropylamine, and 1,2,2,6,6-pentamethylpiperidine, thieno[3,4-b]thiophene/benzodithiophene (PTB7), PSBTBT, Poly[(4,8-bis[5-(2-ethylhexyl)thiophene-2-yl]benzo[1,2-b:4,5-b′]dithiophene)-2,6-diyl-alt-(4-(2-ethylhexanoyl)-thieno[3,4-b]thiophene))-2,6-diyl] (PBDTT-TT) and combinations thereof.

23. The device of claim 22 , wherein the electron donor thieno[3,4-b]thiophene/benzodithiophene (PTB7) or Poly[(4,8-bis[5-(2-ethylhexyl)thiophene-2-yl]benzo[1,2-b:4,5-b′]dithiophene)-2,6-diyl-alt-(4-(2-ethylhexanoyl)-thieno[3,4-b]thiophene))-2,6-diyl] (PBDTT-TT).

24. The device of claim 21 , wherein the solvent additive is selected from the group consisting of 1,6-dichlorohexane; 1,6-dibromohexane; 1,6-diiodohexane; diiodooctane; 1,8-dithioloctane; 1,8-dichlorooctane; 1,8-dibromooctane; 1,8-diiodooctane, decanedinitrile; 1,10-dithioldecane; 1,8-dichlorodecane; 1,8-dibromodecane; 1,8-diiododecane; chloronaphthalene, octanedithiol, 1,6-dithiolhexane; octadinitrile; dodecanedinitrile; 1-chloronaphthalene and combinations thereof.

25. The device of claim 24 , wherein solvent additive is 1,8-diiodooctane or 1-chloronaphthalene.

26. The device of claim 21 , wherein the power conversion efficiency of the device is between about 3% to about 12%.

27. The device of claim 26 , wherein the power conversion efficiency is between about 5% to about 10%.

28. The device of claim 21 , wherein the power conversion efficiency of the device is at least about 5%.

29. The device of claim 21 , where in the device is selected from the group consisting of a solar cell, an optical device, an electroluminescent device, a photovoltaic cell, a semiconducting cell, and a photodiode.

30. A process for preparing oligomer compounds, comprising coupling two or more perylene diimide monomers with an ethylene bridge to form a oligomer compound,
wherein the oligomer compound is represented by the Formula:

wherein each R is independently selected from the group consisting of branched and unbranched alkyl groups with a total of 6-20 carbon atoms;
n is an integer from 3-10; and
wherein the units are connected by ethylene bridges (C═C) between the bay positions.

31. The process of claim 30 , wherein each R is independently selected from the group consisting of branched and unbranched C 8 -C 15 alkyl groups.

32. The process of claim 30 , wherein each R is independently selected from the group consisting of branched and unbranched C 9 -C 12 alkyl groups.

33. The process of claim 30 , wherein at least one R is branched or unbranched C 11 H 23 .

34. The process of claim 30 , wherein each R is independently a branched or unbranched C 11 H 23 .

35. The process of claim 30 , wherein each R is branched C 11 H 23 .

36. The process of claim 35 , wherein each R is:

37. The process of claim 30 , wherein n is an integer from 3-4.

38. The process of claim 30 , wherein the ethylene bridge forms between the bay positions of the monomers.

39. The process of claim 30 , wherein the oligomer compound is synthesized by coupling a halogen substituted monomer or oligomer to trans-1,2-bis(tributylstannyl)ethene followed by a cyclization reaction.

40. The process of claim 39 , wherein the oligomer being coupled is a trimer.

41. The process of claim 39 , wherein the halogen is bromine or chlorine.

42. The process of claim 39

Assignees

• Univ Columbia

Inventors

• Nuckolls Colin
• Zhong Yu
• Chen Rongsheng
• Kumar Bharat
• Trinh Tuan M
• Wang Wei
• Steigerwald Michael L
• Zhu Xiaoyang
• Xiao Shenxiong
• Ng Fay
• Zhang Boyuan

Classifications

• C09B69/102

  containing a perylene dye · CPC title

• C09B23/105

  two >CH- groups · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/0047

  Electricity · mapped topic

• H01L51/4253

  Electricity · mapped topic