A wide‐bandgap polymer, (poly[(2,6‐(4,8‐bis(5‐(2‐ethylhexyl)thiophen‐2‐yl)‐benzo[1,2‐b:4,5‐b′]dithiophene))‐alt‐(2,5‐(methyl thiophene carboxylate))]) (3MT‐Th), is synthesized to obtain a complementary broad range absorption when harmonized with 3,9‐bis(2‐methylene‐(3‐(1,1‐dicyanomethylene)‐indanone))‐5,5,11,11‐tetrakis(4‐hexylphenyl)‐dithieno[2,3‐d:2′,3′‐d′]‐s‐indaceno[1,2‐b:5,6‐b′]dithiophene (ITIC). The synthesized regiorandom 3MT‐Th polymer shows good solubility in nonhalogenated solvents. A film of 3MT‐Th:ITIC can be employed for forming an active layer in a polymer solar cell (PSC), with the blend solution containing toluene with 0.25% diphenylether as a nonhalogenated additive. The corresponding PSC devices display a power conversion efficiency of 9.73%. Moreover, the 3MT‐Th‐based PSCs exhibit excellent shelf‐life time of over 1000 h and are operationally stable under continuous light illumination. Therefore, methyl thiophene‐3‐carboxylate in 3MT‐Th is a promising new accepting unit for constructing p‐type polymers used for high‐performance nonfullerene‐type PSCs.
New thienothiophene-flanked diketopyrrolopyrrole and thiophene-containing π-extended conjugated polymers with various branched alkyl side-chains were successfully synthesized. 2-Octyldodecyl, 2-decyltetradecyl, 2-tetradecylhexadecyl, 2-hexadecyloctadecyl, and 2-octadecyldocosyl groups were selected as the side-chain moieties and were anchored to the N-positions of the thienothiophene-flanked diketopyrrolopyrrole unit. All five polymers were found to be soluble owing to the bulkiness of the side chains. The thin-film transistor based on the 2-tetradecylhexadecyl-substituted polymer showed the highest hole mobility of 1.92 cm2 V(-1) s(-1) due to it having the smallest π-π stacking distance between the polymer chains, which was determined by grazing incidence X-ray diffraction. Bulk heterojunction polymer solar cells incorporating [6,6]-phenyl-C71-butyric acid methyl ester as the n-type molecule and the additive 1,8-diiodooctane (1 vol %) were also constructed from the synthesized polymers without thermal annealing; the device containing the 2-octyldodecyl-substituted polymer exhibited the highest power conversion efficiency of 5.8%. Although all the polymers showed similar physical properties, their device performance was clearly influenced by the sizes of the branched alkyl side-chain groups.
New small molecules having modified acceptor strength and π-conjugation length and containing dicyanovinylene (DCV) and tricyanovinylene (TCV) as a strongly electron-accepting unit with indacenodithiophene, IDT(DCV), IDT(TCV), and IDTT(TCV), were synthesized and studied in terms of their applicability to polymer solar cells with PTB7-Th as an electron-donating polymer. Intriguingly, the blended films containing IDT(TCV) and IDTT(TCV) exhibited superior shelf life stabilities of more than 1000 h without any reduction in the initial power conversion efficiency. The low-lying lowest unoccupied molecular orbital energy levels and robust internal morphologies of small TCV-containing molecules could afford excellent shelf life stability.
In this work, three-armed luminogens IAcTr-out and IAcTr-in were synthesized and used as emitters bearing triazine and indenoacridine moieties in thermally activated delayed fluorescence organic light-emitting diodes (OLEDs). These molecules could form a uniform thin film via the solution process and also allowed the subsequent deposition of an electron transporting layer either by vacuum deposition or by an all-solution coating method. Intriguingly, the new luminogens displayed aggregation-induced emission (AIE), which is a unique photophysical phenomenon. As a nondoped emitting layer (EML), IAcTr-in showed external quantum efficiencies (EQEs) of 11.8% for the hybrid-solution processed OLED and 10.9% for the all-solution processed OLED with a low efficiency roll-off. This was evident by the higher photoluminescence quantum yield and higher rate constant of reverse intersystem crossing of IAcTr-in, as compared to IAcTr-out. These AIE luminogens were used as dopants and mixed with the well-known host material 1,3-bis( N-carbazolyl)benzene (mCP) to produce a high-efficiency OLED with a two-component EML. The maximum EQE of 17.5% was obtained when using EML with IAcTr-out doping (25 wt %) into mCP, and the OLED with EML bearing IAcTr-in and mCP showed a higher maximum EQE of 18.4% as in the case of the nondoped EML-based device.
We synthesized five different donor−acceptor (D−A) conjugated polymers bearing diketopyrrolopyrrole (DPP) acceptors and acene donors in the repeating groups via the Suzuki and Stille coupling methods. To investigate the effect of acene donor moieties on static and dynamic charge transport properties, pyrene, naphthodithiophene, benzodithiophene, dithieno[3,2-b:2′,3′-d]thiophene (DTT), and thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene (TTTT) were selected and introduced into the structure of the polymer repeating group. Among the five polymers, the polymer PDPPTTTT bearing TTTT donor units exhibited the highest hole mobility, ∼3.2 cm 2 V −1 s −1 (I on /I off > 10 6 ) in the thin film transistors. The five polymers had different mobilities and exhibited different charge transport dynamic responses. The response was investigated by applying a pulsed bias to thin film transistors loaded with a resistor. The resistor loaded (RL) inverter made of PDPPTTTT operates well, maintaining a fairly high switching voltage ratio at a relatively high frequency. The PDPPTTTT-based RL inverter also had the fastest switching behavior with a relatively small decay time of 1.86 ms. From this study, the structure of the donor moiety in the D−A conjugated polymer was found to strongly affect the optical property, internal morphology of the polymer film, charge carrier mobility, and charge transport dynamics in electronic devices.
New M- and V-shaped perylene diimide (PDI)-based small molecules using a non-conjugated 1,1-diphenylcyclohexane linker (CP-M and CP-V, respectively) were designed and synthesized as new n-type acceptors for nonfullerene-based polymer solar cells. The blended film with poly[(2,5-bis(2-hexyldecyloxy)phenylene)-alt-(5,6-difluoro-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole)] (PPDT2FBT) and CP-V displayed a higher power conversion efficiency of 5.28% due to higher short circuit current and fill factor values.
New regular and random diketopyrrolopyrrole (DPP)-based terpolymers (i.e., Reg-PBDPPT and Ran-PBDPPT, respectively) bearing DPP as an electron deficient unit and 2,2'-bithiophene and (E)-1,2-di(thiophen-2-yl)ethene as electron donating units were designed and synthesized, and their performance in photovoltaic cells was investigated precisely. The absorption properties and highest occupied molecular orbital (HOMO) of Reg-PBDPPT were found to be different from those of Ran-PBDPPT. The results of grazing incidence X-ray diffraction experiments revealed that Ran-PBDPPT typically had a predominantly edge-on chain orientation on the substrate, whereas Reg-PBDPPT showed mixed chain orientation both in pristine and thermally annealed films. Although Reg-PBDPPT exhibited a lower degree of edge-on chain orientation on the substrate, the corresponding TFTs showed a high hole mobility of 0.42-0.96 cm(2) V(-1) s(-1) and maintained a high current on/off ratio (>10(6)). A polymer solar cell (PSC) composed of Reg-PBDPPT and PC71BM exhibited power conversion efficiencies (PCE) of 5.24-5.45%, which were higher than those of the Ran-PBDPPT-based PSCs. The enhanced efficiency was supported by an increase in the short circuit current, which is strongly related to the unique internal crystalline morphology and pronounced nanophase segregation behavior in the blend films. These results obviously manifested that this synthetic strategy for regular conjugated terpolymers could be employed to control morphological properties to obtain high-performance PSCs.
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