Organic semiconductors with dithienofuran core monomers

US10312444B2 · US · B2

Patent metadata
FieldValue
Publication numberUS-10312444-B2
Application numberUS-201615287713-A
CountryUS
Kind codeB2
Filing dateOct 6, 2016
Priority dateOct 6, 2016
Publication dateJun 4, 2019
Grant dateJun 4, 2019

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  1. Title

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  2. Abstract

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  5. First independent claim

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Abstract

Official abstract text for this publication.

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

Opening claim text (preview).

What is claimed is: 1. 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 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 C 1 -C 20 linear alkyl chain, the C 2 -C 24 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. 2. The semiconducting compound of claim 1 , wherein the semiconducting compound is part of a semiconducting copolymer. 3. A 3,4-dibrominated furan compound of the formula: wherein each of R is selected from a group consisting of a C 1 -C 20 linear alkyl chain, a and C 2 -C 24 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. 4. 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.

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Classifications

  • containing heteroatoms · CPC title

  • containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene · CPC title

  • Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

  • Stille reactions · CPC title

  • Ortho-condensed systems · CPC title

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What does patent US10312444B2 cover?
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 …
Who is the assignee on this patent?
IBM
What technology area does this patent fall under?
Primary CPC classification C08G61/122. Mapped technology areas include Chemistry & Metallurgy.
When was this patent published?
Publication date Tue Jun 04 2019 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
What related patents are in patentsdb?
We list 4 related publications on this page (citations in our corpus or others sharing the same primary CPC).