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Chlorinated Carbon-Bridged and Silicon-Bridged Carbazole-Based Nonfullerene Acceptors Manifest Synergistic Enhancement in Ternary Organic Solar Cell with Efficiency over 15%
(1970-01-01)
Chen, Tsung-Wei
;
Yu, Jun-Yan
;
Lin, You-Wei
;
Peng, Shih-Hao
;
Wu, Shang-Hsuan
Herein, two novel nonfullerene acceptors (NFAs), DTCC-4Cl and DTSiC-4Cl, are synthesized by end-capping dithienocyclopentacarbazole (DTCC) and dithieno-silolocarbazole (DTSiC) cores with chlorinated IC (2Cl-IC) units, respectively. With the better-known advantage of having the extraordinary sigma*-pi* conjugation of silole unit embedded in the DTSiC core, DTSiC-4Cl manifests upshifted lowest unoccupied molecular orbital (LUMO), blue-shifted absorption, and increased pi-pi interaction in comparison with DTCC-4Cl. Furthermore, to elucidate the effect of bridging atoms on the photovoltaic performance, T1 is selected as the polymer donor to be blended with DTCC-4Cl and DTSiC-4Cl. T1:DTCC-4Cl-based devices exhibit a fine power conversion efficiency (PCE) of 14.43% and T1:DTSiC-4Cl-based devices exhibit a comparable PCE of 14.46%. Interestingly, the T1:DTSiC-4Cl-based devices demonstrate an additive-free feature, which is worthy of further applications. From the perspective of constructing high-performance ternary devices, DTCC-4Cl is expected to possess excellent compatibility with DTSiC-4Cl owing to its structural similarity. As anticipated, the ternary T1:DTSiC-4Cl:DTCC-4Cl-based device outperforms the binary T1:DTCC-4Cl and T1:DTSiC-4Cl-based devices, affording a decent PCE of 15.04% with aV(OC)of 0.97 V, aJ(SC) of 20.80 mA cm(-2), and an FF of 74.55% without any additive.
2-Dimensional cross-shaped tetrathienonaphthalene-based ladder-type acceptor for high-efficiency organic solar cells
(2020-06-28)
Chang, Shao-Ling
;
Cao, Fong-Yi
;
Huang, Kuo-Hsiu
;
Lee, Wei-Liang
;
Lee, Meng-Hsun
AnNC-FICnonfullerene acceptor, using a didodecylnaphthodithiophene (NDT) embedded octacyclic ladder-type donorNC, had been described previously. In this work, a new cross-shapedTC-FICnonfullerene acceptor is designed by substitution of the NDT unit in theNCskeleton with a 2-dimensional didodecyltetrathienonaphthalene (TTN) unit. The 2-dimensionalTC pi-system with two vertically fused thiophenes strengthens the electron-donating ability, promotes pi-electron delocalization and enhances intramolecular donor-acceptor charge transfer and intermolecular pi-pi interactions. As a result,TC-FICshows more red-shifted and widened absorption compared to theNC-FICcounterpart. The PBDB-T:TC-FICdevice exhibits a higher efficiency of 11.6% which greatly outperformed the corresponding PBDB-T:NC-FICdevice with an efficiency of 7.52%. The dramatic 54% enhancement in efficiency is ascribed to the improved light-harvesting ability and enhanced charge mobilities which are benefited from the central 2-dimensionalTTNmoiety. By incorporatingPC(71)BMto improve absorption and electron transport, the ternary-blend PBDB-T : TC-FIC : PC(71)BMdevice (1 : 1 : 1 in wt%) achieves a highest PCE of 13.49% with an enhancedJ(sc)of 23.80 mA cm(-2), an FF of 64.4%, and aV(oc)of 0.88 V.
Face-on reorientation of pi-conjugated polymers in thin films by surface-segregated monolayers
(2020-04-07)
Wang, Wei-Chih
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Chen, Sheng-Yuan
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Yang, Yaw-Wen
;
Hsu, Chain-Shu
;
Tajima, Keisuke
A new pi-conjugated polymer based on naphthalenediimide with a branched semifluoroalkyl side chain (FNDIT2) was synthesized and used to change the polymer orientations in thin films. X-ray photoelectron spectroscopy and near-edge X-ray absorption fine structure spectroscopy revealed that FNDIT2 spontaneously forms surface-segregated monolayers in blend films with other pi-conjugated polymers to adopt a preferred face-on orientation, with the pi-plane of the polymer aligned more parallel to the surface. Thermal annealing of the films induced further reorientation of the polymers inside the films closer to the face-on orientation, as shown by two-dimensional grazing-incidence wide-angle X-ray scattering. The induced face-on orientations in the films led to higher charge mobility in the vertical direction. This study provides a general and versatile strategy to control the molecular orientation in thin films and enhance the performance of thin-film organic electronics.
Alkaline-developable positive-type photosensitive polyimide with high mechanical strength and high resolution based on chain extendable poly(amic acid), thermally degradable cross-linker and photoacid generator
(2020-04-01)
Yeh, Yao-Ming
;
Ueda, Mitsuru
;
Hsu, Chain-Shu
;
交大名義發表
;
應用化學系
A positive-type photosensitive polyimide (PSPI) based on a chain extendable poly(amic acid) (PAA), a thermally degradable cross-linker 1,3,5-tris[(2-vinyloxy)ethoxy]benzene (TVEB), and a photoacid generator (PAG) (5-propylsulfonyloxyimino-5H-thiophene-2-ylidene)-(2-methylphenyl)acetonitrile (PTMA) has been developed. The chain extendable PAA was prepared from 3,3 ',4,4 '-biphenyltetracarboxylic dianhydride (BPDA) and 4,4 '-oxydianiline (ODA) and end-capped with di-tert-butyl dicarbonate (DIBOC) in N-methyl-2-pyrrolidone (NMP), which has a controlled molecular weight for developing in a 2.38 wt% tetramethyl ammonium hydroxide aqueous solution (TMAH( aq)) and undergoes a chain extending reaction during curing stage. The photosensitive resist solution was formulated with the polymerization solution (30 wt% in NMP), TVEB (15 wt% for the polymer), and PAG (4.5 wt% for the polymer). The PSPI showed a sensitivity of 47 mJ cm(-2) and a contrast of 5.8 when exposed to 365-nm light, followed by postexposure baking at 90 degrees C for 10 min and development with the 2.38 wt% TMAH( aq) at room temperature. A fine-positive image with 3-mu m line-and-space patterns was obtained on a 3-mu m thick film exposed to UV light at 365 nm in the contact-printed mode. After thermal curing at 350 degrees C for 1 hr, the resulting PSPI features excellent mechanical strength and elongation.
A chlorinated nonacyclic carbazole-based acceptor affords over 15% efficiency in organic solar cells
(2020-01-21)
Chen, Tsung-Wei
;
Peng, Kuan-Lin
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Lin, You-Wei
;
Su, Yi-Jia
;
Ma, Ko-Jui
In this contribution, a dithienocyclopentacarbazole (DTC)-based and two dithieno[3,2-b]thiophenecyclopentacarbazole (DTTC)-based non-fullerene acceptors (NFAs) named DTC-4F, DTTC-4F and DTTC-4Cl were exploited to elucidate the effects of conjugation extension and end group chlorination. DTTC-4F was designed through conjugation extension on the basis of DTC-4F by fusing one additional thiophene on both flanks of the heptacyclic DTC core, generating the nonacyclic DTTC core. Compared with DTC-4F, DTTC-4F features up-shifted energy levels, red-shifted absorption and enhanced pi-pi interaction. PM6:DTTC-4F exhibits a decent PCE of 13.89% with a V-OC of 0.95 V, a J(SC) of 21.66 mA cm(-2) and a FF of 67.60%. Although DTTC-4F affords a reduced FF compared to DTC-4F, a DTTC-4F-based device delivers a higher PCE than DTC-4F-based devices due to the extended absorption range of DTCC-4F in comparison with DTC-4F. Since chlorinated NFAs are known to possess stronger pi-pi interaction than fluorinated NFAs, DTTC-4Cl was therefore synthesized by end-capping DTTC core with 2Cl-IC groups instead of 2F-IC groups. Moreover, DTTC-4Cl demonstrates a red-shifted absorption in comparison with DTTC-4F, which is beneficial for light-harvesting. Overall, PM6:DTTC-4Cl affords an outstanding PCE of 15.42% with a V-OC of 0.92 V, a J(SC) of 22.64 mA cm(-2) and a FF of 74.04%, which is the record PCE observed in carbazole-based NFAs.
Fluorinated heptacyclic carbazole-based ladder-type acceptors with aliphatic side chains for efficient fullerene-free organic solar cells
(2019-05-01)
Chen, Tsung-Wei
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Hsiao, Yu-Tang
;
Lin, You-Wei
;
Chang, Chia-Chih
;
Chuang, Wei-Tsung
Molecular engineering of non-fullerene acceptors (NFAs) is a promising strategy to uncover new structure-property relationships and design principles for developing next-generation high performance n-type materials. Two dithienocyclopentacarbazole (DTC)-based NFAs, DTC(4R)-IC and DTC(4R)-4FIC, are synthesized to elucidate the effects of incorporating aliphatic side chains and 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2FIC) end groups on the thermal and optoelectronic properties of these NFAs. An inverted organic solar cell architecture of ITO/ZnO/J71:NFA/MoO3/Ag is employed. By replacing the phenyl-based side chains with aliphatic side chains on the carbon bridges of the carbazole-based core, the device containing DTC(4R)-IC exhibits an enhanced PCE of 9.61%, a V-OC of 0.94 V, a J(SC) of 16.44 mA cm(-2), and a FF of 62.00%, whereas the device containing DTC(4Ph)-IC exhibits a PCE of 7.76%. The incorporation of 2FIC end groups affords DTC(4R)-4FIC featuring better device performance relative to DTC(4R)-IC, a more red-shifted absorption edge, and a broader absorption range upon fluorination. Notably, the device fabricated with DTC(4R)-4FIC affords a V-oc of 0.82 V, a J(sc) of 18.92 mA cm(-2), a FF of 70.22% and a highest PCE of 10.89%, which is by far the highest PCE for NFA containing heptacyclic carbazole cores.
Isomerically Pure Benzothiophene-Incorporated Acceptor: Achieving Improved V-oc and J(sc) of Nonfullerene Organic Solar Cells via End Group Manipulation
(2019-09-11)
Chang, Shao-Ling
;
Hung, Kai-En
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Cao, Fong-Yi
;
Huang, Kuo-Hsiu
;
Hsu, Chain-Shu
Benzene-based 1,1-dicyanomethylene-3-indanone (IC) derivatives have been widely utilized as the end-group to construct acceptor-donor-acceptor type nonfullerene acceptors (A-D-A type NFAs). The extension of the end-group conjugation of nonfullerene acceptors (NFAs) is a rational strategy to facilitate intermolecular stacking of the end-groups which are responsible for efficient electron transportation. A bicyclic benzothiophene-based end-group acceptor, 2-(3-oxo-2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophen-1-ylidene)malononitrile, denoted as alpha-BC was designed and synthesized. The Knoevenagel condensation of the unsymmetrical 1,3-diketo-precursor with one equivalent of malononitrile selectively reacts with the keto group attached at the alpha-position of the thiophene unit, leading to the isomerically pure benzothiophene-fused alpha-BC. The well-defined alpha-BC with extended conjugation was condensed with three different ladder-type diformylated donors to form three new A-D-A NFAs named BDCPDT-BC, DTCC-BC, and ITBC, respectively. The corresponding IC-based BDCPDT-IC, DTCC-IC, and ITIC model compounds were also synthesized for comparison. The incorporation of the electron-rich benzothiophene unit in the end-group upshifts the lowest unoccupied molecular orbital energy levels of the NFAs, which beneficially enlarges the V-oc values. On the other hand, the benzothiophene unit in alpha-BC not also imparts an optical transition in the shorter wavelengths around 340-400 nm for a better light harvesting ability but also promotes the antiparallel pi-pi stacking of the end-groups for efficient electron transport. The organic photovoltaic cell devices using a PBDB-T polymer and BC-based NFAs all showed the improved V-oc and J(sc) values. The BDCPDT-BC- and DTCC-BC-based devices exhibited a power conversion efficiency (PCE) of 10.82 and 10.74%, respectively, which outperformed the corresponding BDCPDT-IC-, and DTCC-IC-based devices (9.33 and 9.25%). More importantly, the ITBC-based device delivered the highest PCE of 12.07% with a J(sc) of 19.90 mA/cm(2), a V-oc of 0.94 V, and an fill factor of 64.51%, representing a 14% improvement relative to the traditional ITIC-based device (10.05%).
Rapid Prototyping of an Open-Surface Microfluidic Platform Using Wettability-Patterned Surfaces Prepared by an Atmospheric-Pressure Plasma Jet
(2019-10-08)
Wu, She-Ting
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Huang, Chen-Yu
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Weng, Chih-Chiang
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Chang, Chia-Chih
;
Li, Bor-Ran
Open-surface microfluidics is promising in terms of enabling economical and rapid biochemical analysis for addressing challenges associated with medical diagnosis and food safety. To this end, we present a simple and economical approach to develop an open-surface microfluidic platform suitable for facile liquid transport and mixing. Customizable patterns with tailored wettability are deposited using a plasma-assisted deposition technique under atmospheric pressure. The flow of the dispensed liquid is driven by gravity, and the tilting angle of the device determines the extent of mixing. First, a hexamethyldisiloxane film was deposited to create hydrophobic patterns on glass, and then, hydrophilic acrylic acid was deposited by a patterned cardboard mask to construct a channel suitable for forming channels to transport aqueous liquids without the need of an external energy input; the liquid can be confined to designated pathways. Several designs including Y-junctions, serpentine-shaped patterns, splitting channels, and concentration gradient generation patterns are presented. The proposed method can spatially pattern a surface with a hydrophobic/hydrophilic area, which can function as a microfluidic channel, and the surface can be applied in microfluidic devices with other types of substrates.
Single-Junction Organic Solar Cell Containing a Fluorinated Heptacyclic Carbazole-Based Ladder-Type Acceptor Affords over 13% Efficiency with Solution-Processed Cross-Linkable Fullerene as an Interfacial Layer
(2019-08-28)
Chen, Tsung-Wei
;
Chang, Chia-Chih
;
Hsiao, Yu-Tang
;
Chan, ChoonKee
;
Hong, Ling
In this article, a fluorinated heptacyclic dithienocyclopentacarbazole (DTC)-based non-fullerene acceptor (NFA), DTC(4Ph)-4FIC, is synthesized and blended with J71, PBDB-T, and PBDB-TF, featuring complementary absorption and well-matched energy levels. The DTC(4Ph)-4FIC neat film exhibits face-on preference, whereas the nonfluorinated counterpart, DTC(4Ph)-IC, exhibits edge-on preference; this unique feature owing to fluorination in DTC-based NFAs is observed for the first time. More importantly, DTC(4Ph)-4FIC exhibits improved power conversion efficiencies (PCEs) of 10.92 and 10.41% in J71- and PBDB-T-containing devices, while the devices that employed DTC(4Ph)-IC afford PCEs of 7.76 and 9.48%, respectively. Because PBDB-TF is known to exhibit lower energy levels than J71 and PBDB-T, the corresponding device affords a V-OC of 0.95 V, a J(SC) of 18.29 mA cm(-2), a FF of 75.70%, and a PCE of 13.15%, which is 20 and 26% higher than J71- and PBDB-T-containing devices. Furthermore, the inverted device containing the PBDB-TF:DTC(4Ph)-4FIC blend is fabricated using cross-linkable fullerene (C-PCBSD) as the cathode interlayer, affording a decent PCE of 13.36%, with a V-OC of 0.94 V, a J(SC) of 20.20 mA cm(-2), and a FF of 70.42%.
Perovskite Grains Embraced in a Soft Fullerene Network Make Highly Efficient Flexible Solar Cells with Superior Mechanical Stability
(2019-06-01)
Li, Meng
;
Yang, Ying-Guo
;
Wang, Zhao-Kui
;
Kang, Tin
;
Wang, Qiong
Halide perovskite films processed from solution at low-temperature offer promising opportunities to make flexible solar cells. However, the brittleness of perovskite films is an issue for mechanical stability in flexible devices. Herein, photo-crosslinked [6,6]-phenylC(61)-butyric oxetane dendron ester (C-PCBOD) is used to improve the mechanical stability of methylammonium lead iodide (MAPbI(3)) perovskite films. Also, it is demonstrated that C-PCBOD passivates the grain boundaries, which reduces the formation of trap states and enhances the environmental stability of MAPbI(3). Thus, MAPbI(3) perovskite solar cells are prepared on solid and flexible substrates with record efficiencies of 20.4% and 18.1%, respectively, which are among the highest ever reported for MAPbI(3) on both flexible and solid substrates. The result of this work provides a step improvement toward stable and efficient flexible perovskite solar cells.

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