Symmetric charge transfer compounds for organic photovoltaics
Inventors
Thompson, Mark E. • Mencke, Austin
Assignees
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Publication Number
US-12317738-B2
Publication Date
2025-05-27
Expiration Date
Abstract
The present disclosure is related to organic acceptor-donor-acceptor compounds as non-fullerene acceptors for use in organic photovoltaics.
Core Innovation
The invention relates to a symmetric non-fullerene acceptor compound represented by Formula (A-I), in which a core chromophore group represented by Formula (E-1) is connected to electron accepting groups represented by Formula (A-4) to Formula (A-9) through a linking group π. The structures use integer parameters m from 0 to 3 and p from 1 to 3, and the compound defines that each A is the same and each π is the same on both sides.
The core chromophore group E is selected from Formula (E-1) to Formula (E-22), while the electron accepting endcaps A are selected from Formula (A-1) to Formula (A-9). The π-bridge groups are defined from Formula (P-1) to Formula (P-11), with substituent definitions that allow adjacent substituents to be joined or fused to form a ring optionally substituted.
The document describes design principles for organic photovoltaics, including symmetry to eliminate a ground-state dipole, reduced HO/LU overlap, and small S1-T1 CT energy gaps. It links these structural features to the OPV device/composition including the compound, and describes high device-relevant performance ranges for open-circuit voltage (VOC), short-circuit current (JSC), external quantum efficiency (EQE), and power conversion efficiency (PCE).
Claims Coverage
The claim set covers a symmetric Formula (A-I) compound and extends to an OPV device and a formulation containing the compound. Across the independent claims, the inventive features focus on the structural constraints of the compound scaffold and its incorporation into an organic photovoltaic device and a formulation.
Symmetric non-fullerene acceptor compound with A-π-E-π-A architecture
A compound represented by Formula (A-I) where E is a core chromophore group represented by Formula (E-1), A is an electron accepting group represented by Formula (A-4) to Formula (A-9), π is a linking group, m is an integer from 0 to 3, and p is an integer from 1 to 3, with each A the same and each π the same.
Broad substituent and atom-type definitions for acceptor endcaps and core chromophore
In Formula (A-4) to Formula (A-9) and in Formula (E-1), substituent variables are defined to represent hydrogen or a selected substituent group, adjacent substituents are optionally joined or fused to form a ring optionally substituted, and atom-type variables X1 to X8 are C, Si, N or P with Z1, Z2, and Z3 independently representing CR2, NR, O, or S.
Integer-defined bridging connectivity and symmetric substitution constraints
The compound structure is parameterized by m from 0 to 3 and p from 1 to 3 and constrained such that the substituent and group choices are applied symmetrically with each A the same and each π the same on both sides.
Endcap selection restricted to specific electron accepting formulas
The electron accepting group A is selected from Formula (A-4) to Formula (A-9), with further refinement in dependent claims to specific A-formulas.
Optional additional group x selected from π-bridge-formula set
A group x is selected from Formula (P-1) through Formula (P-11), with x's substituent definitions specified by variables including R1 to R4, R, X1 to X8, and Z1 to Z2.
Across the identified claims, the inventive focus is a symmetric OPV non-fullerene acceptor compound of Formula (A-I) using a core chromophore E, electron accepting groups A, and a linking group π, with defined integer parameters m and p and broad, symmetry-preserving substituent and atom-type options. The compound is also incorporated into an OPV device and a formulation.
Stated Advantages
Symmetry is described as eliminating a ground-state dipole.
Reduced HO/LU overlap is described as relating to small S1-T1 CT energy gaps.
High open-circuit voltage (VOC), short-circuit current (JSC), external quantum efficiency (EQE), and power conversion efficiency (PCE) are described.
Improved OPV device performance versus fullerene acceptors is stated in the description.
Documented Applications
Organic photovoltaic (OPV) devices in an anode/cathode architecture with an active layer and intermediate layers, including single-junction and tandem-junction configurations.
An organic photovoltaic device including an anode and a cathode with an organic layer between them, where the organic layer comprises the claimed compound.
A formulation that includes the compound of claim 1.
OPV-related device performance examples described for BPT-based BHJ cells with reported JSC, VOC, fill factor, and PCE.
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