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Now showing 1 - 6 of 6

Synthesis and Electroluminescence Properties of White-Light Single Polyfluorenes with High-Molecular Weight by Click Reaction
(2011-08-01)
Lo, Chih-Nan
;
Hsu, Chain-Shu
;
應用化學系
;
Department of Applied Chemistry
We reported a new way to synthesize single-chain white light-emitting polyfluorene (WPF) with an increased molecular weight using azide-alkyne click reaction. Four basic polymers with specific end-capping, which exhibited high-glass transition temperatures (T(g) > 100 degrees C) and excellent thermal stability, were used as foundations of the WPF's synthesis; a blue-light polymer (PFB2) end-capped with azide groups can easily react with acetylene end-capped polymers (PFB1, PFG1, and PFR1, which are emitting blue-, green- and red-light, respectively) to form triazole-ring linkages in polar solvents such as N,N-dimethylforamide/toluene co-solvent at moderate temperature of 100 degrees C, even without metal-catalyst. Several WPFs that consist of these four basic polymers in certain ratios were derived, and the polymer light-emitting diode device based on the high-molecular weight WPF was achieved and demonstrated a maximum brightness of 7551 cd/m(2) (at 12.5 V) and a maximum yield of 5.5 cd/A with Commission Internationale de l'Eclairage coordinates of (0.30, 0.33) using fine-tuned WPF5 as emitting material. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 3355-3365, 2011
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
;
Wu, Jhong-Sian
;
Lin, Tai-Yen
;
Kao, Wei-Shun
;
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.
Effects of thiophene units on substituted benzothiadiazole and benzodithiophene copolymers for photovoltaic applications
(2012-09-05)
Ding, Ping
;
Zou, Yingping
;
Chu, Cheng-Che
;
Xiao, Dequan
;
Hsu, Chain-Shu
Two conjugated copolymers, poly{4,7-[5,6-bis(octyloxy)]benzo(c)(1,2,5)thiadiazole-alt-4,8-di(2-ethylhexyloxyl)benzo[1,2-b:3,4-b]dithiophene} (P1) and poly(2-{5-[5,6-bis(octyloxy)-4-(thiophen-2-yl)benzo(c)(1,2,5)thiadiazol-7-yl] thiophen-2-yl}-4,8-di(2-ethylhexyloxyl)benzo(1,2-b:3,4-b)dithiophene) (P2), composed of benzodithiophene and 5,6-dioctyloxybenzothiadiazole derivatives with or without thiophene units were synthesized via a Stille cross-coupling polymerization reaction. These copolymers are promising for applications in bulk heterojunction solar cells because of their good solubility, proper thermal stability, moderate hole mobility, and low band gap. The photovoltaic properties of these copolymers were investigated on the basis of blends of the different polymer/(6,6)-phenyl-C71-butyric acid methyl ester (PC71BM) weight ratios under AM1.5G illumination at 100 mW/cm2. The device with indium tin oxide/poly(3,4-ethylene dioxythiophene):poly(styrene sulfonate)/P2:PC71BM (1 : 2 w/w)/Ca/Al gave a relatively better photovoltaic performance with a power conversion efficiency of 1.55%. (C) 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012
Dithienocyclopentathieno[3,2-b]thiophene Hexacyclic Arene for Solution-Processed Organic Field-Effect Transistors and Photovoltaic Applications
(2012-04-01)
Cheng, Yen-Ju
;
Chen, Chiu-Hsiang
;
Lin, Tai-Yen
;
Hsu, Chain-Shu
;
應用化學系
We have developed a ladder-type dithienocyclopentathieno[3,2-b]thiophene (DTCTT) hexacyclic unit in which the central thieno[3,2-b]thiophene ring was covalently fastened to two adjacent thiophene rings through carbon bridges, thereby forming two connected cyclopentadithiophene (CPDT) units in a hexacyclic coplanar structure. This stannylated Sn-DTCTT building block was copolymerized with three electron-deficient acceptors, dibromo-thieno[3,4-c]pyrrole-4,6-dione (TPD), dibromo-benzothiadiazole (BT), and dibromo-phenanthrenequinoxaline (PQX), by Stille polymerization, thereby furnishing a new class of alternating donoracceptor copolymers: PDTCTTTPD, PDTCTTBT, and PDTCTTPQX, respectively. Field-effect transistors based on PDTCTTPQX and PDTCTTBT yielded high hole mobilities of 0.017 and 0.053 cm2?V-1?s-1, respectively, which are among the highest performances among amorphous donoracceptor copolymers. A bulk heterojunction solar cell that incorporated PDTCTTTPD with the lower-lying HOMO energy level delivered a higher Voc value of 0.72 V and a power conversion efficiency (PCE) value of 2.59?%.
Alternating Copolymers Incorporating Cyclopenta[2,1-b:3,4-b ']dithiophene Unit and Organic Dyes for Photovoltaic Applications
(2011-04-15)
Cheng, Yen-Ju
;
Hung, Lung-Chang
;
Cao, Fong-Yi
;
Kao, Wei-Shun
;
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
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
;
Cheng, Yen-Ju
;
Dubosc, Martin
;
Hsieh, Chao-Hsiang
;
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%.

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