Ladder‐Type Heteroarene‐Based Organic Semiconductors

Chen, Jianhua; Yang, Kun; Zhou, Xin; Guo, Xugang

doi:10.1002/asia.201800860

Cited by 71 publications

(55 citation statements)

References 123 publications

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“…The differential scanning calorimetry (DSC) curves (Figure S1b, Supporting Information) of three polymers show no obvious thermal transition, which is typically found in ladder (or semiladder)‐type organic semiconductors. Such phenomenon is mainly attributed to the fact that the transition points of these polymers are higher than their decomposition temperatures due to their rigid backbones …”

Section: Molecular Weights and Optical And Electrochemical Propertiementioning

confidence: 99%

Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n‐Type Thin‐Film Transistors

Zhang

Tang

Sun

et al. 2019

Macromol. Rapid Commun.

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Polymer semiconductors have drawn much attention from both academia and industry due to their unique advantages for the fabrication of light-weight, largearea, low-cost, and flexible/stretchable electronic devices, such as organic thinfilm transistors (OTFTs) and organic solar cells (OSCs). [1][2][3][4][5][6][7][8][9] Recently, OTFTs have achieved promising device performance with charge carrier mobility exceeding that (0.1-1 cm 2 V −1 s −1 ) of amorphous silicon-based transistors. However, most of high-performance polymers exhibit p-type predominant or ambipolar transport characteristic in OTFT devices to date. [10][11][12][13][14][15] Due to the synthetic challenge and associated steric hindrance of highly electron-deficient building blocks, which are essential for n-type semiconductors, the development of n-type polymers far lagged behind the p-type or ambipolar analogues. [10,[16][17][18] Hence, in order to realize applications such as complementary metal-oxide-semiconductor (CMOS)-like logic circuits and all-polymer solar cells, [18][19][20] it is highly urgent to design and synthesize high-performance n-type polymer semiconductors with comparable device performance characteristics, such as charge carrier mobility and device stability.Benefiting from high electron deficiency, coplanar backbone conformation, and easy access, diketopyrrolo[3,4-c]pyrrole (DPP) is regarded as a remarkable electron-accepting building block and has been widely applied for constructing donor-acceptor (D-A) polymer semiconductors in the past decade, showing substantial charge carrier mobility in OTFT devices. [10,16,[21][22][23] The highest OTFT mobility based on DPP-incorporated polymer semiconductors has now surpassed 10 cm 2 V −1 s −1 (Figure 1a). [24] However, the electron-rich nature of the flanking thiophene moieties in DPP showed negative effects on the optimization of frontier molecular orbital (FMO) energy levels for n-type performance, resulting in a p-type dominating or ambipolar transport characteristic for most of the DPP-based copolymers (Figure 1a). [25][26][27] In this regard, copolymerizing DPP with another strong electron-acceptor co-unit should be an effective strategy for downshifting FMO energy levels, which is hence beneficial for achieving improved n-type performance due to Diketopyrrolopyrrole (DPP)-based copolymers have received considerable attention as promising semiconducting materials for high-performance organic thin-film transistors (OTFTs). However, these polymers typically exhibit p-type or ambipolar charge-transporting characteristics in OTFTs due to their high-lying highest occupied molecular orbital (HOMO) energy levels. In this work, a new series of DPP-based n-type polymers have been developed by incorporating fused bithiophene imide oligomers (BTIn) into DPP polymers. The resulting copolymers BTIn-DPP show narrow band gaps as low as 1.27 eV and gradually down-shifted frontier molecular orbital energy levels upon the increment of imide group number. Benefiting from the coplanar backbone conforma...

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Section: Molecular Weights and Optical And Electrochemical Propertiementioning

confidence: 99%

Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n‐Type Thin‐Film Transistors

Zhang

Tang

Sun

et al. 2019

Macromol. Rapid Commun.

Self Cite

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“…One attractive approach toward such materials has been the fusion of aromatic moieties into rigid, ladder‐type systems. [ 3 ] The high rigidity minimizes reorganization energy by reduction of torsional disorder, as well improving intra‐ and intermolecular charge delocalization. However, such modifications inherently reduce processability, meaning careful selection of the nature and position of suitable alkyl chains needs to be considered to facilitate solution processability while maintaining favorable charge transport properties.…”

Section: Introductionmentioning

confidence: 99%

Core Fluorination Enhances Solubility and Ambient Stability of an IDT‐Based n‐Type Semiconductor in Transistor Devices

Hodsden

Thorley

Panidi

et al. 2020

Adv Funct Materials

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The synthesis of a novel fluorinated n-type small molecule based on an indacenodithiophene core is reported. Fluorination is found to have a significant impact on the physical properties, including a surprisingly dramatic improvement in solubility, in addition to effectively stabilizing the lowest-unoccupied molecular orbital energy (−4.24 eV). Single-crystal analysis and density functional theory calculations indicate the improved solubility can be attributed to backbone torsion resulting from the positioning of the fluorine group in close proximity to the strongly electron-withdrawing dicyanomethylene group. Organic thin-film transistors made via blade coating display high electron mobility (up to 0.49 cm 2 V −1 s −1 ) along with good retention of performance in ambient conditions.

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Section: Introductionmentioning

confidence: 99%

“…Acenesh ave made as ignificant impacto no rganic functional materials due to their unique optical and electrical properties, especially as activated layersi no rganic field effect transistors (OFETs), organic light-emitting diodes (OLEDs), and organic photovoltaics (OPVs). [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] In recent years, synthetic chemists have devoted substantial efforts to studyinglinear azaacenes. [1,4,[16][17][18][19][20][21][22][23][24] However,w ith the molecular length increasing, its stability diminishes, and even decomposes.…”

Section: Introductionmentioning

confidence: 99%

Sulfur‐Containing Bent N‐Heteroacenes

Ding

Xia

Sun

et al. 2019

Chemistry A European J

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A series of novel sulfur‐containing bent N‐heteroacenes were constructed and characterized by NMR and UV/Vis spectroscopy, cyclic voltammetry, and single‐crystal X‐ray diffraction. By introducing sulfur‐containing groups (thio, sulfinyl, and sulfonyl) into bent azaacenes, their electronic delocalization was improved and frontier energy levels were modulated. The target products displayed tunable optical and electronic properties through altering the valence of sulfur and fused length of the azaacenes. For the first time, typical products were utilized as organic field effect transistor materials, affording promising results.

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Ladder‐Type Heteroarene‐Based Organic Semiconductors

Cited by 71 publications

References 123 publications

Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n‐Type Thin‐Film Transistors

Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n‐Type Thin‐Film Transistors

Core Fluorination Enhances Solubility and Ambient Stability of an IDT‐Based n‐Type Semiconductor in Transistor Devices

Sulfur‐Containing Bent N‐Heteroacenes

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