Organic semiconductors with dithienofuran core monomers

Patent metadata

Field	Value
Publication number	US-10454035-B2
Application number	US-201916381865-A
Country	US
Kind code	B2
Filing date	Apr 11, 2019
Priority date	Oct 6, 2016
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

An organic semiconducting donor-acceptor (D-A) small molecule, as well as a semiconductor device that can incorporate the D-A small molecule, are disclosed. The D-A small molecule can have electron deficient substituents and R group substituents that can be C 1 -C 20 linear alkyl chains, C 2 -C 24 branched alkyl chains, hydrogen atoms, etc. The D-A small molecule can be can be synthesized in a reaction between a dithienofuran (DTF) core monomer and an electron deficient monomer. Additionally, the D-A small molecule can be part of an organic semiconducting copolymer. A semiconductor device that can incorporate the D-A small molecule in a photoactive layer is also disclosed herein. Additionally, 3,4-dibrominated furan compound that can, in some embodiments, be a precursor for the D-A small molecule is disclosed. The 3,4-dibrominated furan compound can be synthesized in a reaction involving a furan-2,5-dicarboxylic dimethyl ester (FDME), which can have a bio-renewable precursor.

First claim

What is claimed is:

1. A device comprising:
a first electrode;
a second electrode; and
semiconducting layer disposed between the first electrode and the second electrode and including a photoactive layer, wherein the photoactive layer includes a semiconducting compound of the formula:

wherein each of R is selected from a group consisting of a C 1 -C 20 linear alkyl chain, a C 2 -C 24 branched alkyl chain, and a hydrogen atom; and
wherein each of E is an electron deficient substituent selected from a group consisting of a bromoalkylthienyl-pyridylthiazole, a benzodithiazole, a pyridyldithiazole, a diketopyrrolopyrrole, a thienopyrrolodione, a thienothiophene ester, a fluorinated thienothiophene ester, a dithienotetrazine, a thienoquinoxaline, a benzoquinoxaline, and a pyridylquinoxaline.

2. The device of claim 1 , wherein the first electrode and the second electrode comprise at least one material selected from a group consisting of a metal, a metal oxide, a metal alloy, a conductive polymer, Ag nanowires, Cu nanowires, graphene, carbon nanotubes, a polymer-metal hybrid, carbon-sulfur nanotubes, nanofibers, and an organic polymer.

3. The device of claim 1 , wherein the semiconducting layer is a bilayer.

4. The device of claim 1 , wherein the semiconducting layer is a bulk heterojunction.

5. The device of claim 1 , wherein the semiconducting layer further comprises a semiconducting material selected from a group consisting of fullerenes, a polymer, and a polymer blend.

6. The device of claim 1 , wherein the semiconducting compound is synthesized in a reaction between a dithienofuran core monomer and the electron deficient monomer.

7. The device of claim 1 , wherein the device is an organic photovoltaic cell.

8. The device of claim 1 , wherein the device is a field effect transistor.

9. The device of claim 1 , wherein the device is a flexible organic photovoltaic cell.

10. The device of claim 1 , wherein the device is a light sensor.

Assignees

• IBM

Inventors

• King Scott B
• Kobilka Brandon M
• Kuczynski Joseph
• Wertz Jason T

Classifications

• C08G2261/3241

  containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole · CPC title

• C08G2261/334

  containing heteroatoms · CPC title

• C08G2261/414

  Stille reactions · CPC title

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• C08G2261/3247

  containing combinations of different heteroatoms other than nitrogen and oxygen or nitrogen and sulfur · CPC title