IP Library Granted Patent US 12,150,381
Granted Patent B2
US 12,150,381 · App. 17/826,455 · Granted Nov 19, 2024

N-type dopants for efficient solar cells

Inventors: Julia Schneider (New Haven, CT); Michael L. Chabinyc (Santa Barbara, CA); Hengbin Wang (Santa Barbara, CA); Hidenori Nakayama (Goleta, CA); Kyle D. Clark (Santa Barbara, CA); Javier Read de Alaniz (Santa Barbara, CA)
Assignees: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; THE MITSUBISHI CHEMICAL CORPORATION
H10K85/6572B82Y30/00C07D487/12C07D487/16H10K85/215H01B1/04H10K30/30
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Quick Facts
Patent No.
US 12,150,381
App. No.
17/826,455
Granted
Nov 19, 2024
Kind
B2
Abstract

Triazabicylodecene can effectively n-dope a variety of organic semiconductors, including PCBM, thus increasing in-plane conductivities. We synthesized a series of TBD-based n-dopants via an N-alkylation reaction and studied the effect of various alkyl chains on the physical and device properties of the dopants. Combining two TBD moieties on a long alky chain gave a solid dopant, 2TBD-C10, with high thermal stability above 250° C. PCBM films doped by 2TBD-C10 were the most tolerant to thermal annealing and reached in-plane conductivities of 6.5×10 −2 S/cm. Furthermore, incorporating 2TBD-C10 doped PCBM as the electron transport layer (ETL) in methylammonium lead triiodide (MAPbI 3 ) based photovoltaics led to a 23% increase in performance, from 11.8% to 14.5% PCE.

Claims (32)

1. A composition of matter, comprising:

an organic compound of the structure:

wherein:

1≤m≤8;

1≤n≤8;

2≤x≤4; and

R is any substituted or non-substituted alkyl, alkenyl, alkynyl, aryl or alkoxy group; and

the

comprises an n-type dopant.

2. The composition of matter of claim 1 , wherein R contains one or more heteroatoms.

3. The composition of matter of claim 1 , wherein R contains one or more aromatic moieties.

4. The composition of matter of claim 1 , wherein:

is any of the following bicyclic structures:

5. The composition of matter of claim 1 , wherein the organic compound is a dimer (x=2) wherein each end of the R is connected to one of the

6. The composition of matter of claim 5 , wherein the organic

compound is

7. The composition of matter of claim 1 , wherein the organic compound is a trimer (x=3) wherein each end of the R is connected to one of the

8. The composition of matter of claim 1 bonded to a phenyl-C 61 -butyric acid methyl ester (PCBM), or wherein the R comprises the PCBM, so as to n-type dope the PCBM.

9. The composition of matter of claim 1 bonded to an electron acceptor, or wherein the R comprises an electron acceptor, so as to n-type dope the acceptor.

10. The composition of claim 1 bonded to a fullerene so as to form the organic compound

11. The composition of matter of claim 1 , wherein the R is selected so that the organic compound is miscible with an organic acceptor.

12. The composition of matter of claim 11 , further comprising a single phase amorphous composition including the organic compound combined with the organic acceptor, wherein the organic compound n-type dopes the organic acceptor.

13. The composition of matter of claim 1 , wherein the

comprises an n-type dopant for the R.

14. A composition of matter, comprising an organic compound of the structure:

15. A composition of matter comprising an organic compound of the structure

wherein:

1≤m≤8;

1≤n≤8;

2≤x≤4; and

R is any substituted or non-substituted alkyl, alkenyl, alkynyl, aryl or alkoxy group; and

the R comprises the fullerene, so as to n-type dope the fullerene.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2024
From: SCHNEIDER, JULIA; CHABINYC, MICHAEL L.; CLARK, KYLE D.; DE ALANIZ, JAVIER READ
To: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
Reel/Frame 068875/0254 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2024
From: WANG, HENGBIN; NAKAYAMA, HIDENORI
To: THE MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 068875/0261 →
Continuity (3)
Division 16712206 · Dec 12, 2019
Provisional Application 62778685 · Dec 12, 2018
Related Publication 20220293866A1 · Sep 15, 2022