Polymer Solar Cells Based on the Copolymers of Naphtho[1,2‐<i>c</i>:5,6‐<i>c</i>]bis(1,2,5‐thiadiazole) and Alkoxylphenyl Substituted Benzodithiophene with High Open‐Circuit Voltages

Liu, Liqian; Zhang, Guichuan; He, Baitian; Huang, Fei

doi:10.1002/cjoc.201500265

Cited by 12 publications

(6 citation statements)

References 34 publications

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“…In 2011, Huang, Cao, and co‐workers firstly reported the synthesis of an NTz‐based D–A polymer, PBDT‐DTNT, where benzodithiophene was employed as the donor unit . They then synthesized some other BDT‐NTz polymers (PBDT‐C12NT, PBDTNTz‐1 and ‐2), and NTz polymers with various fused aromatics such as fluorene (PF‐C12NT and PAF‐C12NT), carbazole (PCz‐C12NT), and indacenodithiophene (PIDT‐EHNT, ‐DTNT, and ‐C12NT) . Very recently, the same group synthesized a thienothiophene–NTz polymer system (NT812 and NT1014) .…”

Section: Ntz Polymers With Donor Unitsmentioning

confidence: 99%

Naphthobischalcogenadiazole Conjugated Polymers: Emerging Materials for Organic Electronics

Osaka

Takimiya

2017

Advanced Materials

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Semiconducting polymers can function as both p-type (hole-transporting) and n-type (electron-transporting) materials in those devices. [17][18][19] In OFETs, holes and electrons are injected into the semiconducting polymer at the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), respectively. [10] Those charge carriers are then transported between the source and drain electrodes through the assembled polymer backbones. [20,21] In OPVs, [22] the semiconducting polymer absorbs the sunlight within the polymer absorption range (or the sunlight energy above the polymer bandgap (E g )), generating excitons where the hole and electron are strongly bounded. These excitons then diffuse into the interface of the p-type semiconducting polymer and the n-type material (typically methanofullerenes, [23] but can also be n-type semiconducting polymers [24] or small molecules [25] ), at which the excitons dissociate into free holes and electrons. [23,26,27] Those charge carriers are then transported to the electrodes through the materials domains. Therefore, regardless of the device types, the electronic properties and the charge transport properties are the most important characteristics of the polymers.With respect to the electronic structure, E g and HOMO and LUMO energy levels (E HOMO and E LUMO ) are important parameters for semiconducting polymers. [28] As E g qualitatively indicates the extent of π-electron delocalization along the conjugated backbone, a narrow E g is supposed to be preferable for charge transport, especially along the backbone. E g is more important for OPVs, i.e., a narrow E g is highly desired in order to maximize sunlight harvesting. Deep E HOMO , which refers to large ionization potential (IP), is essential for the p-type semiconducting polymer. This provides oxidative stability of the material [29] as well as higher open-circuit voltage (V OC ) in OPVs that is proportional to the energy difference between the HOMO of the p-type material and LUMO of the n-type material. [30] On the other hand, deep E LUMO , which refers to large electron affinity (EA), is essential for the n-type semiconducting polymer since this offers stable electron transport in ambient conditions. [31] The E LUMO is also important for p-type semiconducting polymers when they are used in OPVs. As narrow E g and deep E HOMO are required for p-type semiconducting poly mers in OPVs, their E LUMO must be deepened. It should be noted, however, the E LUMO of the p-type semiconducting π-Conjugated polymers are an important class of materials for organic electronics. In the past decade, numerous polymers with donor-acceptor molecular structures have been developed and used as the active materials for organic devices, such as organic field-effect transistors (OFETs) and organic photovoltaics (OPVs). The choice of the building unit is the primary step for designing the polymers. Benzochalcogenadiazoles (BXzs) are one of the most familiar acceptor building units studied in this area. As their doubl...

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Section: Ntz Polymers With Donor Unitsmentioning

confidence: 99%

Naphthobischalcogenadiazole Conjugated Polymers: Emerging Materials for Organic Electronics

Osaka

Takimiya

2017

Advanced Materials

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“…The functions of ethynylene linkages are three-fold: (1) introducing SP1 carbon hybridization to lower the highest occupied molecular orbital (HOMO) energy level due to more S electron components; [26] (2) improving the planarity of the molecules, and thus enhancing inter-molecular π-π stacking and facilitating charge transport; and (3) avoiding the threat from highly toxic stannyl intermediates or the potential chemical accidents from lithiation reactions. [27][28][29] And the BHJ solar cells based on BEDPP and NEDPP without using solvent additive and any post-treatments for the active layers exhibit PCEs of 1.48% and 2.31%, respectively, both with very high open circuit voltages (V OC ) values close to 1.0 V. [30,31] …”

Section: Introductionmentioning

confidence: 99%

A‐π‐D‐π‐A type Small Molecules Using Ethynylene Linkages for Organic Solar Cells with High Open‐circuit Voltages

et al. 2016

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Introducing ethynylene linkages in a conjugated molecule can deepen the HOMO level, decrease the steric constraints and better delocalize the π electrons and so on, which are beneficial for organic solar cells. Furthermore, the typical method of introducing acetylene linkages by Sonogashira reactions can avoid the usage of toxic stannyl intermediates and potentially dangerous lithiation reactions. In this study, two simple small molecules BEDPP and NEDPP are designed and synthesized, in which two diketopyrrolopyrrole units are symmetrically connected to benzene and naphthalene cores, respectively, via acetylene linkages. And the BHJ (Bulk Heterojunction) solar cells based on BEDPP and NEDPP without using solvent additive and without any post-treatment for the active layers provide us power conversion efficiencies of 1.48% and 2.31% with remarkably high open circuit voltages up to 0.90 and 0.98 V, respectively.

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“…As for the electron-poor acceptor units in the D−A photovoltaic polymers, isoindigo (ID) has attracted much attention because of its strong electron-withdrawing ability and the inherent advantages of its two indolone structures [ 21 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 ]. Naphtho[1,2- c :5,6- c ′]bis[1,2,5]thiadiazole (NT), a benzothiadiazole-fused heteroaromatic unit, exhibited potential application in designing D–A conjugated polymers due to its thermal stability, broad optical absorption, and high electron-withdrawing effect [ 38 , 39 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photovoltaic Properties of 2D-Conjugated Polymers Based on Alkylthiothienyl-Substituted Benzodithiophene and Different Accepting Units

Wang

Cheng

et al. 2018

Polymers

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Abstract:Two new low bandgap conjugated polymers, PBDTS-ID and PBDTS-DTNT, containing isoindigo (ID) and naphtho [1,2-c:5,6-c ]bis[1,2,5]thiadiazole (NT), respectively, as an electron-deficient unit and alkylthiothienyl-substituted benzodithiophene (BDTS) as an electron-rich unit, were designed and synthesized by palladium-catalyzed Stille polycondensation. Both polymers showed good thermal stability up to 330 • C and broad absorption ranging from 300 to 842 nm. Electrochemical measurement revealed that PBDTS-ID and PBDTS-DTNT exhibited relatively low-lying highest occupied molecular orbital energy levels at −5.40 and −5.24 eV, respectively. These features might be beneficial for obtaining reasonable high open-circuit voltage and high short-circuit current. Polymer solar cells (PSCs) were fabricated with an inverted structure of indium-tin oxide/poly(ethylenimine ethoxylate)/polymer:PC 71 BM/MoO 3 /Ag. As a preliminary result, the PSCs based on PBDTS-ID and PBDTS-DTNT exhibited moderate power conversion efficiencies of 2.70% and 2.71%, respectively.

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Polymer Solar Cells Based on the Copolymers of Naphtho[1,2‐c:5,6‐c]bis(1,2,5‐thiadiazole) and Alkoxylphenyl Substituted Benzodithiophene with High Open‐Circuit Voltages

Cited by 12 publications

References 34 publications

Naphthobischalcogenadiazole Conjugated Polymers: Emerging Materials for Organic Electronics

Naphthobischalcogenadiazole Conjugated Polymers: Emerging Materials for Organic Electronics

A‐π‐D‐π‐A type Small Molecules Using Ethynylene Linkages for Organic Solar Cells with High Open‐circuit Voltages

Synthesis and Photovoltaic Properties of 2D-Conjugated Polymers Based on Alkylthiothienyl-Substituted Benzodithiophene and Different Accepting Units

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