IP Library Granted Patent US 11,744,138
Granted Patent B2
US 11,744,138 · App. 16/946,696 · Granted Aug 29, 2023

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

Inventors: Stephen R. Forrest (Ann Arbor, MI); Brian E. Lassiter (Ypsilanti, MI); Jeramy D. Zimmerman (Ann Arbor, MI)
Assignee: The Regents of the University of Michigan
H10K71/15H10K30/30H10K30/57H10K85/211H10K85/221H10K85/631H10K85/633H10K85/657H10K85/6572
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Quick Facts
Patent No.
US 11,744,138
App. No.
16/946,696
Granted
Aug 29, 2023
Kind
B2
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.

Claims (29)

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.

Assignments (2)
CONFIRMATORY LICENSE Recorded Jan 23, 2024
From: UNIVERSITY OF MICHIGAN
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 066362/0280 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: FORREST, STEPHEN R.; LASSITER, BRIAN E.; ZIMMERMAN, JERAMY D.
To: THE REGENTS OF THE UNIVERSITY OF MICHIGAN
Reel/Frame 053839/0655 →
Continuity (2)
Provisional Application 62869365 · Jul 1, 2019
Related Publication 20210005815A1 · Jan 7, 2021