Functionalized pyranopyran-derived acceptors for donor-acceptor polymers

Patent metadata

Field	Value
Publication number	US-10084136-B2
Application number	US-201715722064-A
Country	US
Kind code	B2
Filing date	Oct 2, 2017
Priority date	Jun 22, 2016
Publication date	Sep 25, 2018
Grant date	Sep 25, 2018

Abstract

An organic photovoltaic device includes an anode and a cathode. The organic photovoltaic device includes an active layer between the anode and the cathode. The active layer includes a p-type material. The p-type material includes a donor-acceptor (DA) polymer. An acceptor unit of the DA polymer includes a functionalized pyranopyran-dione compound or a functionalized naphthyridine-dione compound.

First claim

The invention claimed is:

1. A donor-acceptor (DA) polymer comprising:
a sequence:

wherein D is an electron-rich donor unit, A is an electron-deficient acceptor unit, and n is an integer between 4 and 200,000, and
wherein A includes a functionalized naphthyridine-dione unit
wherein D comprises one of:

and
wherein R is a linear or branched group having from 2 to 40 carbons, and wherein the group is an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof,
the functionalized naphthyridine-dione unit comprises:

wherein R 1 is an unsaturated heterocyclic group;
wherein R 2 is hydrogen, a halogen, or a linear or branched first group having from 2 to 40 carbons, the first group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof, and
wherein R 5 is an independently selected linear or branched second group having from 2 to 40 carbons, the second group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof.

2. The DA polymer of claim 1 , wherein the unsaturated heterocyclic group comprises:

wherein X is sulfur, oxygen, or selenium;
wherein R 3 is hydrogen or a linear or branched third group having from 1 to 40 carbons, the third group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof; and
wherein R 4 is hydrogen or a linear or branched fourth group having from 1 to 40 carbons, the fourth group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof.

3. The DA polymer of claim 1 , wherein the halogen of R 2 is fluorine.

4. The DA polymer of claim 1 , wherein the DA polymer is polymerized from D monomers and A monomers using Stille cross coupling reactions or Suzuki cross-coupling reactions.

5. The DA polymer of claim 1 , wherein the DA polymer comprises a p-type material of a solar cell.

6. An organic photovoltaic device comprising:
an anode;
a cathode; and
an active layer between the anode and the cathode, wherein the active layer comprises a p-type material, wherein the p-type material includes a donor-acceptor (DA) polymer, and wherein an acceptor unit of the DA polymer comprises a functionalized naphthyridine-dione compound,
wherein D comprises one of:

and
wherein R is a linear or branched group having from 2 to 40 carbons, and wherein the group is an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof,
the functionalized naphthyridine-dione unit comprises:

wherein R 1 is an unsaturated heterocyclic group;
wherein R 2 is hydrogen, a halogen, or a linear or branched first group having from 2 to 40 carbons, the first group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof, and
wherein R 5 is an independently selected linear or branched second group having from 2 to 40 carbons, the second group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof.

7. The organic photovoltaic device of claim 6 , wherein the unsaturated heterocyclic group comprises:

wherein X is sulfur, oxygen, or selenium;
wherein R 3 is hydrogen or a linear or branched third group having from 1 to 40 carbons, the third group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof; and
wherein R 4 is hydrogen or a linear or branched fourth group having from 1 to 40 carbons, the fourth group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof.

8. A method comprising:
reacting diethyl acetylene dicarboxylate or dimethyl acetylene dicarboxylate with iodine and hydrogen peroxide to yield a fumarate;
reacting the fumarate with alkynyl compounds including heterocyclic groups to produce a bis-alkynylfumarate;
subjecting the bis-alkynylfumarate to iodocyclization conditions to produce a functionalized diiodopyranopyran-dione;
replacing the iodines of the functionalized diiodopyranopyran-dione with other functional groups;
adding cross-coupling moieties to the heterocyclic groups to produce functionalized pyranopyran-dione monomer; and
reacting the functionalized pyranopyran-dione monomer with an alkylamine to produce functionalized naphthyridine-dione monomer.

9. The method of claim 8 , wherein the heterocyclic groups include thiophene groups, furan groups, or selenophene groups.

10. The method of claim 8 , wherein the diethyl acetylene dicarboxylate is derived from a bio-renewable resource of succinic acid.

11. The method of claim 8 , wherein the cross-coupling moieties include bromine, and wherein the functionalized pyranopyran-dione monomer comprises:

wherein X is one of oxygen, sulfur, and selenium;
wherein R 2 is hydrogen, a halogen, or a linear or branched first group having from 2 to 40 carbons, the first group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof;
wherein R 3 is hydrogen or a linear or branched second group having from 1 to 40 carbons, the second group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof; and
wherein R 4 is hydrogen or a linear or branched third group having from 1 to 40 carbons, the third group including an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylamino group, a carbonyl group, or combinations thereof.

Assignees

• IBM

Inventors

• Kobilka Brandon M
• Wertz Jason T

Classifications

• C08G61/126

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

• H01L51/4253

  Electricity · mapped topic

• C08G2261/514

  Electron transport · CPC title

• C08G2261/314

  Condensed aromatic systems, e.g. perylene, anthracene or pyrene · CPC title

• C08G2261/3241

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