Polymer/fullerene formations and their use in electronic/photonic devices

Patent metadata

Field	Value
Publication number	US-10516111-B2
Application number	US-201415107596-A
Country	US
Kind code	B2
Filing date	Dec 26, 2014
Priority date	Dec 26, 2013
Publication date	Dec 24, 2019
Grant date	Dec 24, 2019

Abstract

The present subject matter relates to a formulation comprising an organic solvent, a fullerene, and a conjugated polymer, wherein a solution of the conjugated polymer exhibits a peak optical absorption spectrum red shift of at least 100 nm when the conjugated polymer solution is cooled from 120° C. to room temperature, and wherein the fullerene is not phenyl-C71-butyric-acid-methyl-ester (PC71BM). The present subject matter further relates to the use of a formulation as described above further characterized in that the fullerene is not phenyl-C61-butyric-acid-methyl-ester (PC61BM).

First claim

I claim:

1. An organic electronic (OE) device comprising a coating or printing ink containing a formulation, wherein the formulation comprises an organic solvent, a fullerene, and a conjugated polymer, wherein a solution of the conjugated polymer exhibits a peak optical absorption spectrum red shift of about 150 nm when the conjugated polymer solution is cooled from 120° C. to room temperature, wherein the fullerene is not phenyl-C71-butyric-acid-methyl-ester (PC71BM), and wherein the conjugated polymer comprises one or more repeating units selected from the group consisting of:

wherein
each X 1 is independently selected from the group consisting of S and Se;
each R is independently selected from the group consisting of C 8-23 branched alkyl groups;
each X 3 is independently selected from the group consisting of F, Cl, H, and Br;
each Ar 2 is independently selected from the group consisting of unsubstituted or substituted monocyclic, bicyclic, and polycyclic arylene, and monocyclic, bicyclic, and polycyclic heteroarylene, wherein each Ar 1 and Ar 2 may contain one to five of said arylene or heteroarylene each of which may be fused or linked;
wherein the conjugated polymer is not poly(3-hexylthiophene-2,5-diyl) (P3HT);
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)—, —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 the number of carbon that R 1 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.

2. The organic electronic (OE) device of claim 1 , further characterized in that the fullerene is not phenyl-C61-butyric-acid-methyl-ester (PC61BM).

3. The organic electronic (OE) device of claim 1 , wherein
each X 1 is independently selected from the group consisting of S and Se;
each X 3 is independently selected from the group consisting of Cl and F;
each R is independently selected from the group consisting of C 8-23 branched alkyl groups; and
each Ar 2 is independently selected from the group consisting of substituted or unsubstituted bithiophene.

4. The organic electronic (OE) device of claim 3 , wherein the conjugated polymer comprises one or more repeating units with a formula of:

wherein
each X 2 is independently selected from the group consisting of S and O;
each X 3 is independently selected from the group consisting of Cl and F;
each R is independently selected from the group consisting of C 17-23 branched alkyl groups; and
each Ar 2 is independently selected from the group consisting of substituted or unsubstituted bithiophene.

5. The organic electronic (OE) device of claim 3 , wherein the conjugated polymer comprises one or more repeating units with a formula of:

wherein
each R is independently selected from the group consisting of C 17-23 branched alkyl groups; and
each Ar 2 is independently selected from the group consisting of substituted or unsubstituted bithiophene.

6. The organic electronic (OE) device of claim 1 , further characterized in that the conjugated polymer has an optical bandgap of 1.8 eV or lower.

7. The organic electronic (OE) device of claim 1 , wherein the fullerene is 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.

8. The organic electronic (OE) device of claim 7 , wherein the fullerene is selected from the group consisting of:

9. The organic electronic (OE) device of claim 1 , wherein the fullerene is selected from the group consisting of:

wherein
each n=1−6;
each m=1, 2, 4, 5, or 6;
each q=1−6; and
each R 1 and R 2 is independently selected from the group consisting of C1-6 straight and branched chain alkyl groups;
wherein the fullerene ball represents a fullerene from the group consisting of C60, C70, C84, and othe

Assignees

• Univ Hong Kong Sci & Tech

Inventors

• Yan He

Classifications

• C01B32/156

  After-treatment · CPC title

• C08G2261/91

  Photovoltaic applications · CPC title

• C08G2261/92

  TFT applications · CPC title

• C08G61/123

  derived from five-membered heterocyclic compounds · CPC title

• C08G2261/146

  Side-chains containing halogens · CPC title