Organic semiconductors with dithienofuran core monomers

Patent metadata

Field	Value
Publication number	US-10680179-B2
Application number	US-201916567085-A
Country	US
Kind code	B2
Filing date	Sep 11, 2019
Priority date	Oct 6, 2016
Publication date	Jun 9, 2020
Grant date	Jun 9, 2020

Abstract

A process includes providing furan-2,5-dicarboxylic dimethyl ester (FDME), reacting the FDME with a Grignard reagent to form a bis-alkylketone furan having R groups selected from the group consisting of a C 1 -C 20 linear alkyl chain, a C 2 -C 24 branched alkyl chain, and a hydrogen atom. An additional process includes mixing a 3,4-dibrominated bis-alkylketone furan with potassium carbonate, and adding ethyl-mercaptoacetate to the mixture. This process also includes stirring the mixture to form a bis-alkyl-DTF diester fused ring structure, which is then brominated to form a dibromo-DTF compound.

First claim

What is claimed is:

1. A process of forming a semiconductor, comprising:
providing a 3,4-dibrominated bis-alkylketone furan;
forming a mixture that includes the 3,4-dibrominated bis-alkylketone furan and potassium carbonate;
adding ethyl-mercaptoacetate to the mixture;
stirring the mixture to form a bis-alkyl-dithienofuran (DTF) diester fused ring structure; and
brominating the bis-alkyl-DTF diester fused ring structure to form a dibromo-DTF compound.

2. The process of claim 1 , further comprising reacting the dibromo-DTF compound with an electron-deficient monomer to form a semiconducting small molecule.

3. The process of claim 2 , wherein the electron-deficient monomer is selected from the group consisting of a bromoalkylthienyl-pyridylthiazole, a benzodithiazole, a pyridyldithiazole, a diketopyrrolopyrrole, a thienopyrrolodione, a thienothiophene ester, a fluorinated thienothiophene ester, a dithienotetrazine, a thienothiophene ester, a fluorinated thienothiophene ester, a dithienotetrazine, a thienoquinoxaline, a benzoquinoxaline, and a pyridylquinoxaline.

4. The process of claim 1 , further comprising reacting the dibromo-DTF compound with an electron-deficient monomer to form a semiconducting copolymer.

5. The process of claim 4 , wherein the electron-deficient monomer is selected from the group consisting of a bromoalkylthienyl-pyridylthiazole, a benzodithiazole, a pyridyldithiazole, a diketopyrrolopyrrole, a thienopyrrolodione, a thienothiophene ester, a fluorinated thienothiophene ester, a dithienotetrazine, a thienothiophene ester, a fluorinated thienothiophene ester, a dithienotetrazine, a thienoquinoxaline, a benzoquinoxaline, and a pyridylquinoxaline.

6. The process of claim 1 , further comprising reacting the dibromo-DTF compound with bis(pinacolato)diboron to form a bis(boronic ester)-DTF monomer.

7. The process of claim 6 , further comprising reacting the bis(boronic ester)-DTF monomer with an electron-deficient monomer to form a semiconducting small molecule.

8. The process of claim 6 , further comprising reacting the bis(boronic ester)-DTF monomer with an electron-deficient monomer to form a semiconducting copolymer.

9. The process of claim 1 , further comprising reacting the dibromo-DTF compound with a trialkylstannane chloride to form a bis(trialkylstannyl)-DTF monomer.

10. The process of claim 9 , further comprising reacting the bis(trialkylstannyl)-DTF monomer with an electron-deficient monomer to form a semiconducting small molecule.

11. The process of claim 9 , further comprising reacting the bis(trialkylstannyl)-DTF monomer with an electron-deficient monomer to form a semiconducting copolymer.

12. The process of claim 1 , wherein the brominating uses an electrophilic bromine source.

13. The process of claim 1 , wherein the providing the 3,4-dibrominated bis-alkylketone furan comprises brominating a bis-alkylketone.

Assignees

• IBM

Inventors

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

Classifications

• C08G2261/228

  Polymers, i.e. more than 10 repeat units · CPC title

• C08G2261/94

  Applications in sensors, e.g. biosensors · CPC title

• C08G2261/414

  Stille reactions · CPC title

• C08G61/126

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

• C08G61/125

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