π-Extended Isoindigo-Based Derivative: A Promising Electron-Deficient Building Block for Polymer Semiconductors

Xu, Long; Zhao, Zhiyuan; Xiao, Mingchao; Yang, Jie; Xiao, Jian; Yi, Zhengran; Wang, Shuai; Liu, Yunqi

doi:10.1021/acsami.7b13570

Cited by 30 publications

(21 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These imply the enhanced film crystallinity with the aid of high annealing temperature. All the polymers exhibited bimodal orientation with both edge‐on and face‐on molecular orientations with respect to the substrate, as evidenced by the observation of (010) diffractions along both the in‐plane and out‐of‐plane directions (Figure ; Figure S6, Supporting Information) . Recent studies on some D–A polymers have proved that the bimodal orientation films would be able to form 3D conduction channels, leading to superior OFET performance.…”

Section: Resultsmentioning

confidence: 91%

See 1 more Smart Citation

Diketopyrrolopyrrole‐Based Conjugated Polymers Synthesized via Direct Arylation Polycondensation for High Mobility Pure n‐Channel Organic Field‐Effect Transistors

Guo

Bai

Jiang

et al. 2018

Adv Funct Materials

109

View full text Add to dashboard Cite

High-performance unipolar n-type conjugated polymers (CPs) are critical for the development of organic electronics. In the current paper, four "weak donor-strong acceptor" n-type CPs based on pyridine flanked diketopyrrolopyrrole (PyDPP), namely PPyDPP1-4FBT, PPyDPP2-4FBT, PPyDPP1-4FTVT, and PPyDPP2-4FTVT, are synthesized via direct arylation polycondensation by using 3,3′,4,4′-tetrafluoro-2,2′-bithiophene (4FBT) or (E)-1,2-bis(3,4difluorothien-2-yl)ethene (4FTVT) as weak donor unit. All four polymers exhibit low-lying highest occupied molecular orbital (≈ −5.90 eV) and lowest unoccupied molecular orbital energy levels (≈ −3.70 eV). Top-gate/ bottom-contact organic field-effect transistors based on all four polymers display unipolar n-channel characteristics with electron mobility (µ e ) above 1 cm 2 V −1 s −1 in air, and presented linear |I SD | 1/2 −V GS plots and weak dependence of the extracted moblity on gate voltage (V GS ), indicative of the reliability of the extracted mobility values. Importantly, the devices based on PPyDPP1-4FBT and PPyDPP2-4FBT show a pure unipolar n-channel transistor behavior as revealed by the typical unipolar n-channel output characteristics and clear off-regimes in transfer characteristics. Attributed to its high crystallinity and favorable thin film morphology, PPyDPP2-4FBT shows the highest µ e of 2.45 cm 2 V −1 s −1 , which is among the highest for unipolar n-type CPs reported to date. This is also the first report for DPP based pure n-type CPs with µ e greater than 1 cm 2 V −1 s −1 .

show abstract

Section: Resultsmentioning

confidence: 91%

“…The high content of face‐on molecular orientation in the PPyDPP2‐4FTVT thin film may somewhat be detrimental to charge transport in OFETs. [22a]…”

Section: Resultsmentioning

confidence: 99%

Diketopyrrolopyrrole‐Based Conjugated Polymers Synthesized via Direct Arylation Polycondensation for High Mobility Pure n‐Channel Organic Field‐Effect Transistors

Guo

Bai

Jiang

et al. 2018

Adv Funct Materials

109

View full text Add to dashboard Cite

show abstract

“…Therefore, we develop an effective synthetic method to obtain a regioregular monomer (FIBI) with a 2FBT group in the middle of the bisoindigo. Here, We used a relatively novel synthetic method to insert a 2FBT group in the middle of the 2FIID as a new acceptor (FIBI) . The molar mass of FIBI is 2299 g mol −1 , which is among the highest values reported for monomers of D–A‐type polymeric semiconductors .…”

Section: Ofet Parameters Calculated From the Saturation Regime (Vds =mentioning

confidence: 99%

Fast Deposition of Aligning Edge‐On Polymers for High‐Mobility Ambipolar Transistors

et al. 2018

Self Cite

View full text Add to dashboard Cite

In recent years, with the rapid growth of the demand for practical applications of organic electronics, organic fieldeffect transistors (OFETs) have been intensively studied due to their potential applications in logic circuits, [1] wearable electronics, [2,3] biomedical applications, [4] sensors, [5][6][7] etc. The high mobility of transistors is the key to achieving these applications. Both hole-transport (p-type) and electron-transport (n-type) polymeric materials are needed in low-energy consumption circuits. Since balanced ambipolar polymers are potentially one of the best choices for low-cost complementary metal-oxide-semiconductor (CMOS) circuits, many efforts have been made to design new polymers. [8] In fact, in addition to molecular structures, arrangement of molecules, and morphology of semiconductor films are also important factors that influence the carrier transporting in OFETs. [9,10] There are several methods for achieving ordered semiconductor films. [11][12][13][14] For example, nanogrooved substrates are used to improve the consistency of molecular arrangement in the thin film through capillary effects on polymer chain. [15,16] Postrubbing annealing process was also introduced to get ordered polymer films. [17] However, in order to obtain well-assembled molecules, these methods do require relatively long-time processes.Actually, among various solution processes for oriented semiconductor films, costly and time-consuming methods are not acceptable by industry, which prefers to some meniscusguided coating methods such as blade-coating or bar-coating methods. [18] These two methods display good compatibility with roll-to-roll (R2R) printing processes, extremely high-efficiency using semiconductor materials and are simple to operate. In recent years, some large-area oriented films of p-or n-type organic molecule [6,19,20] and polymers [21][22][23][24][25] have been prepared by these two methods. Compared to the blade-coating method, the contact portion of the bar with the substrate is smooth, and the adverse effect of blade's sharp edge can be reduced. When the bar moving slowly, thanks to the low relative molecular weight and strong intermolecular interaction forces, the mole cules can be spontaneously ordered by the influence of the Marangoni flow. [20,23,26] However, under the same preparation conditions, the Marangoni flow cannot drive the spontaneous ordering of the polymers, and the polymer molecules often Fast deposition of aligning ambipolar polymers for high-performance organic field-effect transistors (OFETs) and inverter circuits are highly desired for both scientific studies and industry applications. Here, large-area and ordered polymer films are prepared by a bar-coating method at a rate of 120 mm s −1 in air. Atomic force microscopy and grazing-incidence wide-angle X-ray scattering analysis indicate uniform edge-on poly(fluoroisoindigodifluorobithiophene-fluoroisoindigo-bithiophene) (PFIBI-BT) in 11.7 ± 1 nm film (≈5 layers). The elongated, uniformly oriented grains can reduce the ...

show abstract

“…Meanwhile, fluorine atoms were introduced to further enhance the planarity and lower the energy levels. [ 157 ] As a result, P96 showed excellent ambipolar transport with hole and electron mobilities of 1.03 and 1.82 cm 2 V −1 s −1 , respectively. [ 157 ] Using M1 as the acceptor unit ( P97 ) could also reduce the steric hindrance and increase charge transport.…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Wei

Zhang

2021

Adv Funct Materials

View full text Add to dashboard Cite

(1 of 33)benzothiadiazole (BT), [8,9] naphthalene diimide (NDI), [10,11] and isoindigo. [12][13][14] Isoindigo is an isomer of the wellknown industrial dye indigo and can be directly isolated from nature. [15,16] The structural difference between isoindigo and indigo is the relative positions of the nitrogen atom and the carbonyl group. In the indigo molecule, the nitrogen atoms are not connected to the carbonyl groups. Moreover, the nitrogen atoms in isoindigo molecule are connected with carbonyl groups. In 2012, indigo was reported as the active layer material of organic fieldeffect transistors (OFETs), which exhibited well-balanced ambipolar transport. [17] However, the H-bonded indigo showed extremely low solubility. For achieving good solution processibility, solubilizing side chains are introduced on the nitrogen atoms, which on the other hand break the intramolecular hydrogen bond, thereby reducing the molecular conjugation and limiting the electronics applications. [18] By contrast, the side chains on isoindigo do not break the hydrogen bond, and thus isoindigo is considered as a superior building block for organic electronic materials. [18,19] Since isoindigo was first used in organic electronics in 2010, [20] isoindigo-derived conjugated polymers have attracted considerable attention and have been developed rapidly due to the strong electron deficiency and high molecular planarity of isoindigo unit. [12,21] Moreover, compared with DPP, BT or NDI, isoindigo has a π-framework that can be readily modified. The structural feature of isoindigo endows itself many modification sites, including the side chains attached to the lactam nitrogen atoms, the center double bond, and the phenyl rings. More than twenty isoindigo derivatives have been reported. [22][23][24][25][26][27][28] Based on isoindigo and its derivatives, various isoindigo-derived conjugated polymers have been synthesized and many of them showed excellent performance. For example, using isoindigo-derived conjugated polymers, the hole and electron mobilities of p-and n-type OFETs have reached 14.4 and 14.9 cm 2 V −1 s −1 , respectively, and some ambipolar OFETs exhibited high hole/electron mobilities of up to 5.97/7.07 cm 2 V −1 s −1 . [29][30][31] The power conversion efficiencies (PCEs) of fullerene-containing organic photovoltaics (OPVs) and all-polymer solar cells (all-PSCs) based on isoindigo-derived polymers have exceeded 10% and 7%, respectively. [32,33] Furthermore, various structural modification

show abstract

π-Extended Isoindigo-Based Derivative: A Promising Electron-Deficient Building Block for Polymer Semiconductors

Cited by 30 publications

References 34 publications

Diketopyrrolopyrrole‐Based Conjugated Polymers Synthesized via Direct Arylation Polycondensation for High Mobility Pure n‐Channel Organic Field‐Effect Transistors

Diketopyrrolopyrrole‐Based Conjugated Polymers Synthesized via Direct Arylation Polycondensation for High Mobility Pure n‐Channel Organic Field‐Effect Transistors

Fast Deposition of Aligning Edge‐On Polymers for High‐Mobility Ambipolar Transistors

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Contact Info

Product

Resources

About