Browsing by Author "Hsu, Chain-Shu"

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2-Dimensional cross-shaped tetrathienonaphthalene-based ladder-type acceptor for high-efficiency organic solar cells
(2020-06-28)
Chang, Shao-Ling
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Cao, Fong-Yi
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Huang, Kuo-Hsiu
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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.
A chlorinated nonacyclic carbazole-based acceptor affords over 15% efficiency in organic solar cells
(2020-01-21)
Chen, Tsung-Wei
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Peng, Kuan-Lin
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Lin, You-Wei
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Su, Yi-Jia
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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.
A crosslinked fullerene matrix doped with an ionic fullerene as a cathodic buffer layer toward high-performance and thermally stable polymer and organic metallohalide perovskite solar cells
(2015-01-01)
Chao, Yi-Hsiang
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Huang, Yi-You
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Chang, Jen-Yun
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Peng, Shih-Hao
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Tu, Wei-Yi
In this study, we developed a new cathodic buffer layer consisting of a cross-linked [6,6]-phenyl-C-61-butyric styryl dendron ester (C-PCBSD) matrix and an ionic FPI dopant. The incorporation of FPI can improve the electron mobility via an anion induced charge transfer (AIET) mechanism, while maintaining the solvent-resistant properties of the crosslinked layer. ZnO combined with the C-PCBSD/FPI layer can effectively and universally improve the performance of bulk-heterojunction polymer solar cells (BHJPSCs), planar heterojunction polymer solar cells (PHJPSCs), and organic metallohalide perovskite solar cells (OMPSCs). Furthermore, the insertion of the C-PCBSD/FPI layer can improve the thermal stability of the device by preventing the residual moisture in ZnO from diffusing into the CH3NH3PbI3 layer in OMPSCs.
A Facile PDMS-Assisted Crystallization for the Crystal-Engineering of C-60 Single-Crystal Organic Field-Effect Transistors
(2015-08-05)
Wu, Kuan-Yi
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Wu, Tzu-Yi
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Chang, Shu-Ting
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Hsu, Chain-Shu
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Wang, Chien-Lung
A High-Mobility Low-Bandgap Copolymer for Efficient Solar Cells
(2010-12-15)
Ding, Ping
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Chu, Cheng-Che
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Liu, Bo
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Peng, Bo
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Zou, Yingping
A new high-mobility low-bandgap polymer, PBDT-DODTBT, based on benzodithiophene and 5,6-bis(octyloxy)-4,7-di(thiophen-2-yl) benzothiadiazole has been synthesized through a standard Stille coupling reaction. The polymer is soluble in common organic solvents, such as chloroform, tetrahydrofuran, and chlorobenzene and has excellent film forming properties. Preliminary studies of the copolymer showed the charge mobility as high as 7.15 x 10(-3) cm(2).V(-1). s(-1) from SCLC measurement. Initial photovoltaic cells based on the composite structure of ITO/PEDOT: PSS/PBDT-DODTBT: (alpha)PC(71)BM (1:2)/Ca/Al showed an open-circuit voltage of 0.76 V, a power conversion efficiency of 4.02%, and a short-circuit current of 8.96mA.cm(-2).
A new ladder-type benzodi(cyclopentadithiophene)-based donor-acceptor polymer and a modified hole-collecting PEDOT: PSS layer to achieve tandem solar cells with an open-circuit voltage of 1.62 V
(2013)
Chen, Yung-Lung
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Kao, Wei-Shun
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Tsai, Che-En
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Lai, Yu-Ying
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Cheng, Yen-Ju
We have developed a new ladder-type conjugated polymer PBDCPDT-FBT and a robust interconnecting layer (ICL) integrating a hole-collecting m-PEDOT:PSS layer with an electron-collecting ZnO layer. The inverted device using PBDCPDT-FBT exhibited a high power conversion efficiency (PCE) of 5.76% with a V-oc of 0.81 V, a J(sc) of 12.82 mA cm(-2), and a FF of 55.5%. The inverted tandem device incorporating the PBDCPDT-FBT and ICL achieves a V-oc of 1.62 V leading to a PCE of 7.08%.
A New Ladder-Type Germanium-Bridged Dithienocarbazole Arene and Its Donor-Acceptor Conjugated Copolymers: Synthesis, Molecular Properties, and photovoltaic Applications
(2014-11-11)
Jwo, Pei-Chi
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Lai, Yu-Ying
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Tsai, Che-En
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Lai, Yun-Yu
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Liang, Wei-Wei
We have developed a new germanium-bridged heptacyclic arene, dithienogermolocarbazole (DTGC), in which two outer thiophene subunits are covalently fastened to the central 2,7-carbazole core by two dibutylgermanium bridges. The germole moieties embedded in the DTGC structure were successfully constructed by one-pot nucleophilic cyclization in a high yield of 88%. Because of the relatively lower polarity of carbongermanium bonds, the DTGC unit is chemically stable under basic conditions, rendering its more versatile functionalization. Comparison of germanium-bridged DTGC with the carbon-bridged DTCC (dithienocyclopentacarbazole) and silicon-bridged DTSC (dithienosilolocarbazole) analogues reveals that the HOMO energy level of DTGC lies between those of DTCC and DTSC and so does the LUMO energy level of DTGC. Density functional theory (DFT) calculations suggest that DTSC and DTGC have more bent structures than DTCC, which plays an important role in determining their frontier orbital energies. The structural disparity could be amplified in their corresponding polymers. The DTGC unit was copolymerized with four different comonomers, including benzothiadiazole (BT), dithienylbenzothiadiazole (DTBT), difluorobenzothiadiazole (FBT), and dithienyldifluorobenzothiadiazole (DTFBT) to yield a series of new alternating donoracceptor copolymers, poly(dithienogermolo-carbazole-alt-benzothiadiazole) (PDTGCBT), poly(dithienogermolocarbazole-alt-dithienylbenzothiadiazole) (PDTGCDTBT), poly(dithienogermolocarbazole-alt-difluorobenzothiadiazole) (PDTGCFBT), and poly(dithienogermolocarbazole-alt-dithienyldifluorobenzothiadiazole) (PDTGCDTFBT). Because of the two additional thiophene rings in the repeating units on the backbone to facilitate pi-electron delocalization, PDTGCFDTBT showed a lower optical band gap than PDTGCFBT. Furthermore, PDTGCDTFBT also showed the lower-lying LUMO and HOMO energy levels than PDTGCDTBT as a result of the electron-withdrawing fluorine atoms. Consequently, the bulk heterojunction solar cell incorporating PDTGCDTFBT delivered the highest performance with V-oc of 0.84 V, Jsc of 9.87 mA/cm(2), FF of 48.8%, and PCE of 4.05%. By adding 3 vol % 1-chloronaphthalene to tailor the morphology, the solar cell using PDTGCDTFBT with higher molecular weight exhibited the improved efficiency of 4.50% with a V-oc of 0.84 V, a J(sc) of 11.19 mA/cm(2), and an FF of 47.7%.
A New Pentacyclic Indacenodiselenophene Arene and Its Donor-Acceptor Copolymers for Solution-Processable Polymer Solar Cells and Transistors: Synthesis, Characterization, and Investigation of Alkyl/Alkoxy Side-Chain Effect
(2013-10-08)
Chang, Huan-Hsuan
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Tsai, Che-En
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Lai, Yu-Ying
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Liang, Wei-Wei
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Hsu, So-Lin
A pentacyclic indacenodiselenophene (IDS) arene was synthesized via intramolecular Friedel-Craft cyclization of the selenophene moieties. This IDS framework was used as a model system to investigate the alkyl/alkoxy side-chain effect by preparing IDS-OCH8 and IDS-C-6, where the side chains on the sp(3) carbon in the cyclopentadienyl ring are 4-octyloxyphenyl groups and 4-hexylphenyl groups, respectively. The SnIDS-OCH8 and Sn-IDS-C-6 monomers were copolymerized with 4,7dibromo-2,1,3-benzothiadiazole (BT), 4,7-diiodo-5,6-difluoro-2,1,3-benzothiadiazole (FBT) and 1,3-dibromothieno[3,4-dpyrrole-4,6-dione (TPD) acceptor monomers by Stil le polycondensation to afford five new IDS-based donor acceptor alternating copolymers, PIDSBT-OCH8, PIDSBTC6) PIDSFBT-OCH8, PIDSFBT-C-6, and PIDSTPD-C-6. Despite the fact that the octyloxy and hexyl side chains play a negligible role in the optical and electrochemical properties of the resulting polymers, the solar cell performance is highly associated with the side chains of the polymers. Under similar device fabrication conditions, the PIDSBT-C-6 and PIDSFBT-C-6-based devices showed much improved efficiencies than the corresponding PIDSBT-OCH8, and PIDSFBT-OCH8-based devices (2.6% and 1.9% vs 3.8% and 3.9%). The improvement is mainly the result of much enhanced J(sc) values. Consistently, PIDSBT-C-6 and PIDSFBT-C-6 exhibited much higher FET hole mobilites than the corresponding PIDSBT-OCH8, and PIDSFBT-OCH8. These results clearly revealed that the 4-hexylphenyl group is a more suitable side chain than the 4-octyloxyphenyl group in the IDS system, and the side-chain dependent mobility of the polymers is the dominating factor to determine the photocurrents and efficiencies of PSCs. PIDSBT-C-6 exhibited a high hole mobility of 0.08 cm(2) V-1 s(-1) and PIDSTPD-C-6:PC71BM (1:4 in wt %)-based solar cell with 5 v% chloronaphthalene (CN) delivered a V-oc of 0.92 V, a J(sc) of 9.77 mA/cm(2), an FF of 51%, and a highest PCE of 4.6%. This work not only discloses a new selenophene-containing ladder-type IDS structure and its copolymers but also provides useful insights into the allcyl/alkoxy side-chain effect for future design of conjugated polymers.
A New sp2-sp2 Dialkylethylene-Bridged Heptacyclic Ladder-Type Arene for High Efficiency Polymer Solar Cells
(2013-04-01)
Wu, Jhong-Sian
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Lai, Yu-Ying
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Cheng, Yen-Ju
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Chang, Chih-Yu
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Wang, Chien-Lung
A new dithienobenzo-carbazole (DTBC) heptacyclic arene using sp2-sp2 dialkylethylene moiety as the bridge was successfully synthesized by Suzuki-Miyaura cross-coupling reaction. This facile benzoannulation planarizes the conjugated framework with the concomitant introduction of four octyl substituents, making the newly designed copolymer PDTBCDTBT exhibit solution processability, superior absorption ability, lower-lying HOMO energy level, and crystalline nature. The solar cell using PDTBCDTBT has produced a high efficiency of 6.2%, which outperforms the corresponding sp3-hybridized C-bridged, Si-bridged and N-bridged analogous polymers.
A Pentacyclic Nitrogen-Bridged Thienyl-Phenylene-Thienyl Arene for Donor-Acceptor Copolymers: Synthesis, Characterization, and Applications in Field-Effect Transistors and Polymer Solar Cells
(2012-09-01)
Tseng, Cheng-An
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Wu, Jhong-Sian
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Lin, Tai-Yen
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Kao, Wei-Shun
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Wu, Cheng-En
A pentacyclic benzodipyrrolothiophene (BDPT) unit, in which two outer thiophene rings are covalently fastened with the central phenylene ring by nitrogen bridges, was synthesized. The two pyrrole units embedded in BDPT were constructed by using one-pot palladium-catalyzed amination. The coplanar stannylated Sn-BDPT building block was copolymerized with electron-deficient thieno[3,4-c]pyrrole-4,6-dione (TPD), benzothiadiazole (BT), and dithienyl-diketopyrrolopyrrole (DPP) acceptors by Stille polymerization. The bridging nitrogen atoms make the BDPT motif highly electron-abundant and structurally coplanar, which allows for tailoring the optical and electronic properties of the resultant polymers. Strong photoinduced charge-transfer with significant band-broadening in the solid state and relatively higher oxidation potential are characteristic of the BDPT-based polymers. Poly(benzodipyrrolothiophene-alt-benzothiadiazole) (PBDPTBT) achieved the highest field-effect hole mobility of up to 0.02 cm2?V-1?s-1. The photovoltaic device using the PBDPTBT/PC71BM blend (1:3, w/w) exhibited a Voc of 0.6 V, a Jsc of 10.34 mA?cm-2, and a FF of 50?%, leading to a decent PCE of 3.08?%. Encouragingly, the device incorporating poly(benzodipyrrolothiophene-alt-thienopyrrolodione) (PBDPTTPD)/PC71BM (1:3, w/w) composite delivered a highest PCE of 3.72?%. The enhanced performance arises from the lower-lying HOMO value of PBDPTTPD to yield a higher Voc of 0.72 V.
A Supramolecular "Double-Cable" Structure with a 129(44) Helix in a Columnar Porphyrin-C-60 Dyad and its Application in Polymer Solar Cells
(2012-11-01)
Wang, Chien-Lung
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Zhang, Wen-Bin
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Sun, Hao-Jan
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Van Horn, Ryan M.
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Kulkarni, Rahul R.
A novel porphyrin-C-60 dyad (PCD1) is designed and synthesized to investigate and manipulate the supramolecular structure where geometrically isotropic [such as [60]fullerene (C-60)] and anisotropic [such as porphyrin (Por)] units coexist. It is observed that PCD1 possesses an enantiomeric phase behavior. The melting temperature of the stable PCD1 thermotropic phase is 160 degrees C with a latent heat (Delta H) of 18.5 kJ mol(-1). The phase formation is majorly driven by the cooperative intermolecular PorPor and C60C60 interactions. Structural analysis reveals that this stable phase possesses a supramolecular double-cable structure with one p-type Por core columnar channel and three helical n-type C-60 peripheral channels. These double-cable columns further pack into a hexagonal lattice with a = b = 4.65 nm, c = 41.3 nm, alpha = beta = 90 degrees and gamma = 120 degrees. The column repeat unit is determined to possess a 129(44) helix. With both donor (D; Pro) and acceptor (A; C-60) units having their own connecting channels as well as the large D/A interface within the supramoleculassr double-cable structure, PCD1 has photogenerated carriers with longer lifetimes compared to the conventional electron acceptor [6,6]-phenyl-C-61-butyric acid methyl ester. A phase-separated columnar morphology is observed in a bulk-heterojunction (BHJ) material made by the physical blend of a low band-gap conjugated polymer, [poly[2,6-(4,4-bis-(2-ethylhexyl)-4H-cyclopenta [2,1-b;3,4-b']-dithiophene)-alt-4,7-(2,1,3-benzothia-diazole)] (PCPDTBT), and PCD1. With a specific phase structure in the solid state and in the blend, PCD1 is shown to be a promising candidate as a new electron acceptor in high performance BHJ polymer solar cells.
A Versatile Fluoro-Containing Low-Bandgap Polymer for Efficient Semitransparent and Tandem Polymer Solar Cells
(2013-10-01)
Chang, Chih-Yu
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Zuo, Lijian
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Yip, Hin-Lap
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Li, Yongxi
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Li, Chang-Zhi
The versatility of a fluoro-containing low band-gap polymer, poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene)-alt-4,7-(5-fluoro-2,1,3-benzothia-diazole)] (PCPDTFBT) in organic photovoltaics (OPVs) applications is demonstrated. High boiling point 1,3,5-trichlorobenzene (TCB) is used as a solvent to manipulate PCPDTFBT:[6,6]-phenyl-C-71-butyric acid methyl ester (PC71BM) active layer morphology to obtain high-performance single-junction devices. It promotes the crystallization of PCPDTFBT polymer, thus improving the charge-transport properties of the active layer. By combining the morphological manipulation with interfacial optimization and device engineering, the single-junction device exhibits both good air stability and high power-conversion efficiency (PCE, of 6.6%). This represents one of the highest PCE valuesfor cyclopenta[2,1-b;3,4-b']dithiophene (CPDT)-based OPVs. This polymer is also utilized for constructing semitransparent solar cells and double-junction tandem solar cells to demonstrate high PCEs of 5.0% and 8.2%, respectively.
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
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Ueda, Mitsuru
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Hsu, Chain-Shu
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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.
Alternating and Diblock Donor-Acceptor Conjugated Polymers Based on Diindeno[1,2-b:2 ',1 '-d]thiophene Structure: Synthesis, Characterization, and Photovoltaic Applications
(2010)
Chen, Chiu-Hsiang
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Cheng, Yen-Ju
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Dubosc, Martin
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Hsieh, Chao-Hsiang
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Chu, Cheng-Che
Pentacyclic diindeno[1,2':2',1'-d]thiophene (DIDT) unit is a rigid and coplanar conjugated molecule. To the best of our knowledge, this attractive molecule has never been incorporated into a polymer and thus its application in polymer solar cells has never been explored. For the first time, we report the detailed synthesis of the tetra-alkylated DIDT molecule leading to its dibromo-and diboronic ester derivatives, which are the key monomers for preparation of DIDT-based polymers. Two donor-acceptor alternating polymers, poly(diindenothiophene-alt-benzothiadiazole) PDIDTBT and poly-(diindenothiophene-alt-dithienylbenzothiadiazole) PDIDTDTBT, were synthesized by using Suzuki polymerization. Copolymer PTDIDTTBT was also prepared by using Stille polymerization. Although PTDIDTTBT is prepared through a manner of random polymerization, we found that the different reactivities of the dibromo-monomers lead to the resulting polymer having a block copolymer arrangement. With the higher structural regularity, PTDIDTTBT, symbolized as (thiophene-alt-DIDT)(0.5)-block-(thiophene-alt-BT)(0.5), shows the higher degree of crystallization, stronger pi-pi stacking, and broader absorption spectrum in the solid state, as compared to its alternating PDIDTDTBT analogue. Bulk heterojunction photovoltaic cells based on ITO/PEDOT:PSS/polymer:PC(71)BM/Ca/Al configuration were fabricated and characterized. PDIDTDTBT/PC(71)BM and PTDIDTTBT/PC(71)BM systems exhibited promising power-conversion efficiencies (PCEs) of 1.65% and 2.00%, respectively. Owing to the complementary absorption spectra, as well as the compatible structures of PDIDTDTBT and PTDIDTTBT, the PCE of the device based on the ternary blend PDIDTDTBT/PTDIDTTBT/PC(71)BM was further improved to 2.40%.
Alternating Copolymers Incorporating Cyclopenta[2,1-b:3,4-b ']dithiophene Unit and Organic Dyes for Photovoltaic Applications
(2011-04-15)
Cheng, Yen-Ju
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Hung, Lung-Chang
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Cao, Fong-Yi
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Kao, Wei-Shun
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Chang, Chih-Yu
We have synthesized six p-type copolymers, CPDT-co-TPADCN, CPDT-co-TPADTA, CPDT-co-TPATCN, CPDT-coDFADCN, CPDT-co-DFADTA, and CPDT-co-DFATCN, consisting of a cyclopenta[2,1-b:3,4-b']dithiophene (CPDT) unit and an organic dye in an alternating arrangement. Triphenylamine (TPA) or difluorenylphenyl amine (DFA) units serve as the electron donors, whereas dicyanovinyl (DCN), 1,3-diethyl-2-thiobarbituric acid, or tricyanovinyl (TCN) units act as the electron acceptors in the dyes. The target polymers were prepared via Stille coupling, followed by postfunctionalization to introduce the electron acceptors to the side chains. Because of the strongest withdrawing ability of TCN acceptor to induce efficient intramolecular charge transfer, CPDT-co-TPATCN and CPDT-co-DFATCN exhibit the broader absorption spectra covering from 400 to 900 nm and the narrower optical band gaps of 1.34 eV. However, the CPDT-co-TPATCN:PC(71)BM and CPDT-co-DFATCN:PC(71)BM based solar cells showed the power conversion efficiencies (PCEs) of 0.22 and 0.31%, respectively, due to the inefficient exciton dissociation. The DFA-based polymers possess deeper-lying HOMO energy levels than the TPA-based polymer analogues, leading to the higher V(oc) values and better efficiencies. The device based on CPDT-co-DFADTA:PC(71)BM blend achieved the best PCE of 1.38% with a V(oc) of 0.7 V, a J(sc) of 4.57 mA/cm(2), and a fill factor of 0.43. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49:1791-1801, 2011
Analysis of metal ion impurities in liquid crystals using high resolution inductively coupled plasma mass spectrometry
(2012-11-01)
Hung, Huan-Yi
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Lu, Chien-Wei
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Lee, Cheng-Yu
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Hsu, Chain-Shu
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Hsieh, You-Zung
We have developed a method, using high resolution inductively coupled plasma mass spectrometry (HR-ICP-MS), to directly analyze metal ion impurities in liquid crystals (LCs). From measurements of resistivity, a commonly used technique for quality control of liquid crystal display (LCD) cells, we found that the resistivities of the LCs decreased significantly upon progressing through the different stages of the LCD cell manufacturing process. We determined the levels of metal ion impurities in the LCs through direct loading of diluted LC samples into the HR-ICP-MS system at a steady flow rate. Solutions featuring LC contents of 10% (v/v) were formed by dissolving each LC in isopropanol (IPA) containing acetone as a modifier. We quantified the trace metal ion impurities in the LC samples using a certified standard of metal ions diluted in IPA (external calibration) without the need for digestion pretreatment. Next, we compared the levels of metal ion impurities with the resistivities of the LCs at the different stages of the LCD cell manufacturing process. We confirmed that the resistivities of the LCs decreased as the total levels of metal ion impurities in the LCs increased. The total content of metal ion impurities added into the LC was higher in the siphoning process than in the one-drop filling process during the fabrication of LCD cells. The HR-ICP-MS method could, therefore, be used to directly measure metal ion impurities in LCs during the LCD cell manufacturing process, potentially replacing resistivity measurements of LCs as a means of quality control. We suggest setting 1400 ng L-1 as the limit of the total metal ion concentration in LCs used for LCD cell manufacturing. We used the HR-ICP-MS method to analyze a stained LCD panel to confirm that the content of metal ion impurities was indeed significantly greater in the stained area of the defected LCD. HR-ICP-MS appears to be a promising technique for the direct and effective analyses of metal ion impurities in LCs.
Angular-Shaped 4,9-Dialkyl - and -Naphthodithiophene-Based Donor-Acceptor Copolymers: Investigation of Isomeric Structural Effects on Molecular Properties and Performance of Field-Effect Transistors and Photovoltaics
(2015-10-14)
Cheng, Sheng-Wen
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Chiou, De-Yang
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Tsai, Che-En
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Liang, Wei-Wei
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Lai, Yu-Ying
Two angular-shaped 4,9-didodecyl -aNDT and 4,9-didodecyl -aNDT isomeric structures have been regiospecifically designed and synthesized. The distannylated -aNDT and -aNDT monomers are copolymerized with the Br-DTNT monomer by the Stille coupling to furnish two isomeric copolymers, PNDTDTNT and PNDTDTNT, respectively. The geometric shape and coplanarity of the isomeric -aNDT and -aNDT segments in the polymers play a decisive role in determining their macroscopic device performance. Theoretical calculations show that PNDTDTNT possesses more linear polymeric backbone and higher coplanarity than PNDTDTNT. The less curved conjugated main chain facilitates stronger intermolecular - interactions, resulting in more redshifted absorption spectra of PNDTDTNT in both solution and thin film compared to the PNDTDTNT counterpart. 2D wide-angle X-ray diffraction analysis reveals that PNDTDTNT has more ordered -stacking and lamellar stacking than PNDTDTNT as a result of the lesser curvature of the PNDTDTNT backbone. Consistently, PNDTDTNT exhibits a greater field effect transistor hole mobility of 0.214 cm(2) V-1 s(-1) than PNDTDTNT with a mobility of 0.038 cm(2) V-1 s(-1). More significantly, the solar cell device incorporating the PNDTDTNT:PC71BM blend delivers a superior power conversion efficiency (PCE) of 8.01% that outperforms the PNDTDTNT:PC71BM-based device with a moderate PCE of 3.6%.
Angular-Shaped 4,9-Dialkylnaphthodithiophene-Based Donor-Acceptor Copolymers for Efficient Polymer Solar Cells and High-Mobility Field-Effect Transistors
(2015-04-14)
Cheng, Sheng-Wen
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Tsai, Che-En
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Liang, Wei-Wei
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Chen, Yung-Lung
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Cao, Fong-Yi
Although the tetracyclic angular-shaped naphthodithiophenes (aNDTs) derivatives are an emergent building block for constructing promising semiconductor conjugated polymers, the absence of aliphatic side chains as solubilizing groups on the aNDTs greatly restricted their further application toward polymer synthesis. To create a new class of aNDT-based polymers for widespread applications in solution-processable OFETs and PSCs, side-chain engineering of the aNDT-based structures plays a pivotal role in improving solubility and optimizing electronic/steric properties associated with the resultant solar cell characteristics. In this research, we developed an efficient and straightforward methodology to construct the angular naphthodithophene core with regiospecific introduction of two aliphatic chains at its 4,9-positions via a base-induced double 6p-cyclization. For the first time, the corresponding 2,7-distannylated-4,9-dialkylated aNDT monomers were polymerized with FBT and DPP acceptors to make two new PaNDTDTFBT and PaNDTDPP donor-acceptor copolymers. The photovoltaic devices based on the PaNDTDTFBT:PC71BM blend not only showed a promising PCE of 6.52% with conventional configuration but also achieved a higher PCE of 6.86% with inverted configuration. Moreover, PaNDTDPP with strong intermolecular interaction achieved a high FET hole mobility of 0.202 cm(2) V-1 s(-1).
Anthradithiophene-based liquid crystal molecules: High carrier mobilities enhanced by rubbed polyimides for the application in organic field-effect transistors
(2018-06-01)
Wang, Wei-Chih
;
Yeh, Tien-Tien
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Liau, Wei-Lung
;
Chen, Jiun-Tai
;
Hsu, Chain-Shu
We synthesize three liquid crystal molecules with angular anthradithiophene (a-ADT) as the core for the application in organic film-effect transistors (OFETs). Thiophene-octyl group and thiophene-dodecyl group are introduced on both sides of the a-ADT core to yield compounds Bis-C8T-a-ADT and Bis-C12T-a-ADT. Moreover, thiophene-dodecyl group is attached to the a-ADT core on one side to yield compound C12T-a-ADT. The synthesized compounds are measured by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) to determine their mesomorphic properties. Compound Bis-C8T-a-ADT shows nematic and smectic A phases while both compounds Bis-C12T-a-ADT and C12T-a-ADT reveal smectic A phases. The optical and electrochemical properties of the compounds are characterized by UV-vis spectroscopy and cyclic voltammetry (CV). The HOMO levels for Bis-C8T-a-ADT and Bis-C12T-a-ADT are estimated to be -5.27 eV while the HOMO level of C12T-a-ADT is estimated to be -5.34 eV. The low-lying HOMO levels of the molecules indicate their great oxidation stability in OFET devices. The carrier mobilities are observed to increase 10-1000 times using rubbed polyimide (PI), resulting from the better arrangements of the liquid crystal molecules, and excellent carrier mobilities of 1.06 and 1.02 cm(2)/Vs are obtained from compounds Bis-C12T-a-ADT and C12T-a-ADT, respectively.
Applications of functional fullerene materials in polymer solar cells
(2014-06-01)
Lai, Yu-Ying
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Cheng, Yen-Ju
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Hsu, Chain-Shu
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應用化學系
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Department of Applied Chemistry
Bulk heterojunction (BHJ) polymer solar cells (PSCs) on the basis of polymer: fullerene blends have delivered numerous impressive results in the last decade and thus have drawn much attention of the scientific and industrial communities. However, BHJ PSCs often suffer from several intrinsic problems, such as the low open-circuit voltage (V-oc), energetically-unfavorable and chemically-incompatible interfaces, and morphological phase separation of the polymer: fullerene blend driven by thermal treatment, hindering further advancement. In this review, we summarize the recent progress on applications of fullerene-based materials in the BHJ PSCs. Bis-adduct fullerenes possessing high-lying LUMO energy levels can substitute for mono-substituted fullerenes and higher Voc values can thus be achieved. Incorporation of an n-type fullerene interlayer between inorganic and organic active layers in either inverted or conventional PSCs can help in minimization of charge recombination losses at the interface and improvement of charge transfer from the active layer to the inorganic layer, thus resulting in superior PCEs. The optimal active-layer morphology can be maintained through several approaches, such as in situ polymerization of cross-linkable fullerenes, suppression of large-scale PC61BM aggregation by a polyethylene glycol-functionalized fullerene, supramolecular pentafluorophenyl-fullerene stabilization, and light-induced oligomerization of fullerenes. The morphological phase separation of the active-layer materials can thus be minimized. The research of employing fullerene materials will continue playing a critical role in BHJ PSCs. With further investigation and advancement in this field, it is expected that the ultimate goal of commercialization can be realized.