Difluorobithiophene-based donor-acceptor polymers for electronic and photonic applications

Patent metadata

Field	Value
Publication number	US-10263190-B2
Application number	US-201515516792-A
Country	US
Kind code	B2
Filing date	Oct 22, 2015
Priority date	Oct 22, 2014
Publication date	Apr 16, 2019
Grant date	Apr 16, 2019

Abstract

An organic compound, a donor-acceptor conjugated polymer, a formulation and a thin film, wherein a solution of the donor-acceptor conjugated polymer exhibits a peak optical absorption spectrum red shift of at least 100 nm when the donor-acceptor conjugated polymer solution is cooled from 140° C. to room temperature.

First claim

We claim:

1. A donor-acceptor conjugated polymer comprising one or more repeating units of the following formula:

wherein Ar is an aromatic unit selected from the group consisting of:

wherein each R is independently selected from the group consisting of straight-chain, branched, and cyclic alkyl with 2-40 C atoms, wherein one or more non-adjacent C atoms are optionally replaced by —O—, —S—, —C(O)—, —C(O—)—O—, —O—C(O)—, —O—C(O)—O—, —CR 0 ═CR 00 —, or —C≡C—, and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, or CN or denote aryl, heteroaryl, aryloxy, heteroaryloxy, arylcarbonyl, heteroarylcarbonyl, arylcarbonyloxy, heteroarylcarbonyloxy, aryloxycarbonyl, or heteroaryloxycarbonyl having 4 to 30 ring atoms unsubstituted or substituted by one or more non-aromatic groups, wherein R 0 and R 00 are independently a straight-chain, branched, or cyclic alkyl group.

2. The donor-acceptor conjugated polymer of claim 1 , wherein the average molecular weight of the conjugated donor-acceptor polymer is in a range from 20,000 to 40,000 gram/mole.

3. The donor-acceptor conjugated polymer of claim 1 , wherein a solution of the donor-acceptor conjugated polymer exhibits a peak optical absorption spectrum red shift of at least 100 nm when the donor-acceptor conjugated polymer solution is cooled from 140° C. to room temperature.

4. The donor-acceptor conjugated polymer of claim 1 , wherein a solution of the donor-acceptor conjugated polymer exhibits a peak optical absorption spectrum red shift at about 740 nm when the donor-acceptor conjugated polymer solution is cooled from 140° C. to room temperature.

5. The donor-acceptor conjugated polymer of claim 1 , further characterized in that the donor-acceptor conjugated polymer has an optical bandgap of 1.65 eV or lower.

6. The donor-acceptor conjugated polymer of claim 1 , wherein Ar is selected from a group consisting of:

7. The donor-acceptor conjugated polymer of claim 6 , having a power conversion efficiency as an acceptor in a range between 6.7 and 10.4%.

8. The donor-acceptor conjugated polymer of claim 6 , wherein a power conversion efficiency of the donor-acceptor conjugated polymer with phenyl-C 71 -butyric-acid-methyl-ester (PC 71 BM) is in a range between 2.0 and 9.0%.

9. The donor-acceptor conjugated polymer of claim 6 , wherein a fill factor of the donor-acceptor conjugated polymer with phenyl-C 71 -butyric-acid-methyl-ester (PC 71 BM) is in a range between 0.49 and 0.70.

10. The donor-acceptor conjugated polymer of claim 6 , wherein a fluorinated donor-acceptor conjugated polymer exhibited a higher fill factor and power conversion efficiency than a hydrogenated donor-acceptor conjugated polymer.

11. A formulation comprising an organic solvent, a fullerene and a donor-acceptor conjugated polymer, wherein the donor-acceptor conjugated polymer comprises one or more repeating units of the following formula:

wherein Ar is independently selected from the group consisting of:

wherein each R is independently selected from the group consisting of straight-chain, branched, and cyclic alkyl with 2-40 C atoms, wherein one or more non-adjacent C atoms are optionally replaced by —O—, —S—, —C(O)—, —C(O—)—O—, —O—C(O)—, —O—C(O)—O—, —CR 0 ═CR 00 —, or —C≡C—, and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, or CN or denote aryl, heteroaryl, aryloxy, heteroaryloxy, arylcarbonyl, heteroarylcarbonyl, arylcarbonyloxy, heteroarylcarbonyloxy, aryloxycarbonyl, or heteroaryloxycarbonyl having 4 to 30 ring atoms unsubstituted or substituted by one or more non-aromatic groups, wherein R 0 and R 00 are independently a straight-chain, branched, or cyclic alkyl group.

12. The formulation of claim 11 , wherein the fullerene is selected from the group consisting of:

wherein
each n=1, 2, 4, 5, or 6;
each Ar is independently selected from the group consisting of monocyclic, bicyclic, and polycyclic arylene, and monocyclic, bicyclic, and polycyclic heteroarylene, wherein each Ar may contain one to five of said arylene or heteroarylene each of which may be fused or linked;
each R x is independently selected from the group consisting of Ar, straight-chain, branched, and cyclic alkyl with 2-40 C atoms, wherein one or more non-adjacent C atoms are optionally replaced by —O—, —S—, —C(O)—, —C(O—)—O—, —O—C(O)—, —O—C(O)—O—, —CR 0 ═CR 00 —, or —C≡C—, and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, or CN or denote aryl, heteroaryl, aryloxy, heteroaryloxy, arylcarbonyl, heteroarylcarbonyl, arylcarbonyloxy, heteroarylcarbonyloxy, aryloxycarbonyl, or heteroaryloxycarbonyl having 4 to 30 ring atoms unsubstituted or substituted by one or more non-aromatic groups, wherein R 0 and R 00 are independently a straight-chain, branched, or cyclic alkyl group;
each R 1 is independently selected from the group consisting of straight-chain, branched, and cyclic alkyl with 2-40 C atoms, wherein one or more non-adjacent C atoms are optionally replaced by —O—, —S—, —C(O)—, —O—C(O)—, —O—C(O)—O—, —CR 0 ═CR 00 —, or —C≡C—, and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, or CN or denote aryl, heteroaryl, aryloxy, heteroaryloxy, arylcarbonyl, heteroarylcarbonyl, arylcarbonyloxy, heteroarylcarbonyloxy, aryloxycarbonyl, or heteroaryloxycarbonyl having 4 to 30 ring atoms unsubstituted or substituted by one or more non-aromatic groups, wherein the number of carbon that R′ contains is larger than 1, wherein R 0 and R 00 are independently a straight-chain, branched, or cyclic alkyl group;
each Ar 1 is independently selected from the group consisting of monocyclic, bicyclic and polycyclic heteroaryl groups, wherein each Ar 1 may contain one to five of said heteroaryl groups each of which may be fused or linked;
each Ar 2 is independently selected from aryl groups containing more than 6 atoms excluding H; and

wherein the fullerene ball represents a fullerene selected from the group consisting of C60, C70, C84, and other fullerenes.

13. An organic electronic (OE) device comprising a coating or printing ink containing the formulation according to claim 11 .

14. The OE device of claim 13 , characterized in that the OE device is an organic field effect transistor (OFET) device.

15. The OE device of claim 13 , characterized in that the OE device is an organic photovoltaic (OPV) device.

16. A thin film comprising a donor-acceptor conjugated polymer and a fullerene, wherein a solution of the donor-acceptor conjugated polymer exhibits a peak optical absorpt

Assignees

• Univ Hong Kong Sci & Tech

Inventors

• Yan He
• Li Zhengke

Classifications

• C08G2261/3241

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

• C08G2261/1412

  Saturated aliphatic units · CPC title

• C07F7/2208

  Compounds having tin linked only to carbon, hydrogen and/or halogen · CPC title

• C08G2261/18

  conjugated · CPC title

• H01L51/0047

  Electricity · mapped topic