Organic photosensitive devices made using semi-orthogonal solvents and methods of making the same

Patent metadata

Field	Value
Publication number	US-11744138-B2
Application number	US-202016946696-A
Country	US
Kind code	B2
Filing date	Jul 1, 2020
Priority date	Jul 1, 2019
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

Disclosed herein are organic photosensitive optoelectronic device comprising a first layer comprising one or more of a first layer material, a second layer comprising one or more of a second layer material, and a third layer comprising one or more of a third layer material. The second layer may be dissolved in a semi-orthogonal solvent. The first layer and the third layer may be very slightly soluble or practically insoluble in the semi-orthogonal solvent.

First claim

What is claimed is:

1. An organic photosensitive optoelectronic device comprising:
a first layer comprising one or more of a first layer material;
a second layer comprising one or more of a second layer material; and
a third layer comprising one or more of a third layer material,
wherein the second layer is dissolved in a semi-orthogonal solvent, and
wherein the first layer and the third layer are very slightly soluble or practically insoluble in the semi-orthogonal solvent.

2. The device of claim 1 , wherein the second layer is deposited via spin coating.

3. The device of claim 1 , wherein the first layer material is chosen from perylenes, pthalocyanines, porphyrins, napthalenes, fullerenes, nanotubules, and derivatives thereof.

4. The device of claim 1 , wherein the first layer material is chosen from C 60 , C 70 , C 76 , C 82 , C 84 , and derivatives thereof.

5. The device of claim 1 , wherein the second layer material is chosen from squaraines or squaraine derivatives.

6. The device of claim 1 , wherein the second layer material is chosen from:
2,4-bis[4-N-carbazolo-2,6-dihydroxyphenyl] squaraine (CBZSQ);
2,4-bis[4-N-phenothiazino-2,6-dihydroxyphenyl] squaraine (PTSQ);
2,4-bis[4-(N,N-diphenylamino)-2,6-dihydroxyphenyl] squaraine (DPSQ);
2,4-bis[4-(N-Phenyl-1-naphthylamino)-2,6-dihydroxyphenyl] squaraine (1NPSQ);
2,4-bis[4-(N-Phenyl-2-naphthylamino)-2,6-dihydroxyphenyl] squaraine (2NPSQ);
{2-[4-(N,N-diisobutylamino)-2,6-dihydroxyphenyl]-4-diphenylamino} squaraine (USSQ);
{2-[4-(N,N-diphenylamino)-2,6-dihydroxyphenyl]-4-diphenylamino} squaraine (DPUSQ); and
diphenylamino-squarate (YSQ).

7. The device of claim 1 , wherein the third layer material is chosen from Al, Ag, Au, MoO 3 , Li, LiF, Sn, Ti, WO 3 , indium tin oxide (ITO), tin oxide (TO), gallium indium tin oxide (GITO), zinc oxide (ZO), zinc indium tin oxide (ZITO) and derivatives thereof.

8. The device of claim 1 , wherein the semi-orthogonal solvent is a heterocyclic organic compound.

9. The device of claim 1 , wherein the semi-orthogonal solvent is chosen from tetrahydrofuran and tetrahydrofuran derivatives.

10. The device of claim 1 , wherein the first layer material is chosen from C 60 , C 70 , C 76 , C 82 , C 84 , and derivatives thereof;
wherein the second layer material is chosen from CBZSQ, PTSQ, DPSQ, 1NPSQ, 2NPSQ, USSQ, DPUSQ, and YSQ;
wherein the third layer material is chosen from Al, Ag, Au, MoO 3 , Li, LiF, Sn, Ti, WO 3 , indium tin oxide (ITO), tin oxide (TO), gallium indium tin oxide (GITO), zinc oxide (ZO), zinc indium tin oxide (ZITO) and derivatives thereof; and
wherein the semi-orthogonal solvent is chosen from tetrahydrofuran or tetrahydrofuran derivatives.

11. The device of claim 1 , wherein 1 ml of the semi-orthogonal solvent dissolves about 0.05 mg or less of the first layer and the third layer at 25° C.; and
wherein 1 ml of the semi-orthogonal solvent dissolves about 100 mg or more of the second layer at 25° C.

12. The device of claim 11 , wherein the device is a bulk heterojunction organic photovoltaic device or a tandem organic photovoltaic device.

Assignees

• Univ Michigan Regents

Inventors

• Forrest Stephen R
• Lassiter Brian E
• Zimmerman Jeramy D

Classifications

• H10K71/15 Primary

  characterised by the solvent used · CPC title

• H10K30/20 Primary

  comprising organic-organic junctions, e.g. donor-acceptor junctions · CPC title

• H10K30/30

  comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains · CPC title

• H10K30/57

  comprising multiple junctions, e.g. tandem PV cells · CPC title

• H10K85/211

  Fullerenes, e.g. C60 · CPC title