# US 10,312,444 B2 · Organic semiconductors with dithienofuran core monomers

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- Number: US 10,312,444 B2
- Document ID: US10312444B2
- Status: Granted
- Kind: B2
- Application number: 15/287,713
- Filed: 2016-10-06
- Published: 2018-04-12
- Granted: 2019-06-04
- Earliest claimed: 2016-10-06
- Assignees: International Business Machines Corporation
- Applicants: International Business Machines Corporation
- Inventors: Scott B. King; Brandon M. Kobilka; Joseph Kuczynski; Jason T. Wertz
- Web page: https://patentgrep.com/patent/US10312444B2

## CPC

- C08G 61/122: {derived from five- or six-membered heterocyclic compounds, other than imides}
- C07D 307/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 495/14: Ortho-condensed systems
- C08G 61/125: {with a five-membered ring containing one oxygen atom in the ring}
- C08G 61/126: {with a five-membered ring containing one sulfur atom in the ring}
- H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene}
- H10K 85/151: {Copolymers}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- C08G 2261/228: Polymers, i.e. more than 10 repeat units
- C08G 2261/3222: containing one or more oxygen atoms as the only heteroatom, e.g. furan
- C08G 2261/3241: containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
- C08G 2261/3242: containing one or more oxygen atoms as the only heteroatom, e.g. benzofuran
- C08G 2261/3243: containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
- C08G 2261/3246: containing nitrogen and sulfur as heteroatoms
- C08G 2261/3247: containing combinations of different heteroatoms other than nitrogen and oxygen or nitrogen and sulfur
- C08G 2261/334: containing heteroatoms
- C08G 2261/411: Suzuki reactions
- C08G 2261/414: Stille reactions
- C08G 2261/91: Photovoltaic applications
- C08G 2261/92: TFT applications
- C08G 2261/94: Applications in sensors, e.g. biosensors
- H10K 10/484: {characterised by the channel regions}
- H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K 30/50: Photovoltaic [PV] devices
- Y02E 10/549: Organic PV cells
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## 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 C1-C20 linear alkyl chains, C2-C24 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.

## Claims

### Claim 1

A semiconducting compound of the formula:
wherein each of R is selected from a group consisting of a C1-C20 linear alkyl chain, a C2-C24 branched alkyl chain, and a hydrogen atom; and
wherein each of E is an electron deficient monomer attached in a reaction between the electron deficient monomer and a dithienofuran core monomer of the formula:
wherein each of R is selected from the group consisting of the C1-C20 linear alkyl chain, the C2-C24 branched alkyl chain, and the hydrogen atom, and each of Z is selected from a group consisting of a bromo substituent, a boronic ester substituent, and a trimethylstannyl substituent, and wherein the electron deficient monomer is 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.

### Claim 2 (depends on 1)

The semiconducting compound of claim 1, wherein the semiconducting compound is part of a semiconducting copolymer.

### Claim 3

A 3,4-dibrominated furan compound of the formula:
wherein each of R is selected from a group consisting of a C1-C20 linear alkyl chain, a and C2-C24 branched alkyl chain; and
wherein the 3,4-dibrominated furan compound is synthesized in a reaction involving a compound having a bio-renewable precursor selected from a group consisting of fructose, an aldaric acid, and furan-2,5-dicarboxylic acid.

### Claim 4 (depends on 3)

The 3,4-dibrominated furan compound of claim 3, wherein the compound having the bio-renewable precursor is a furan-2,5-dicarboxylic dimethyl ester.