- Star-shaped magnesium tetraethynylporphyrin bearing four peripheral electron-accepting diketopyrrolopyrrole functionalities for organic solar cells
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Magnesium tetraethynylporphyrins bearing four electron-deficient diketopyrrolopyrrole (DPP; Mg-TEP-DPP4) units were synthesized by Sonogashira coupling, and their optical and electrochemical properties were investigated. The energy levels were effectively tuned by DPP with or without electron-withdrawing end-caps. Importantly, all the Mg-TEP-DPP4 molecules have broad absorption bands across the visible and near-infrared regions. The time-dependent excited state features of Mg-TEP-DPP4 and their kinetics were investigated by femtosecond transient absorption spectroscopy in combination with multiwavelength and global/target analyses of time-resolved spectra. Importantly, the charge-separated state was demonstrated to undergo recombination within 253 ps in benzonitrile. Bulk heterojunction organic solar cells fabricated with Mg-TEP-DPP4:PC61BM exhibited a power conversion efficiency of 7.40% after solvent vapor annealing, which enabled balanced charge carrier transport, reduced charge recombination, and favorable charge separation and collection.
- Wang, Huan,Yue, Qihui,Nakagawa, Takafumi,Zieleniewska, Anna,Okada, Hiroshi,Ogumi, Keisuke,Ueno, Hiroshi,Guldi, Dirk M.,Zhu, Xiaozhang,Matsuo, Yutaka
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- High-mobility n-type organic transistors based on a crystallized diketopyrrolopyrrole derivative
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A new high-performing small molecule n-channel semiconductor based on diketopyrrolopyrrole (DPP), 2,2′-(5,5′-(2,5-bis(2-ethylhexyl)-3,6- dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(thiophene-5,2-diyl)) bis(methan-1-yl-1-ylidene)dimalononitrile (DPP-T-DCV), is successfully synthesized. The frontier molecular orbitals in this designed structure are elaborately tuned by introducing a strong electron-accepting functionality (dicyanovinyl). The well-defined lamellar structures of the crystals display a uniform terrace step height corresponding to a molecular monolayer in the solid-state. As a result of this tuning and the remarkable crystallinity derived from the conformational planarity, organic field-effect transistors (OFETs) based on dense-packed solution-processed single-crystals of DPP-T-DCV exhibit an electron mobility (μe) up to 0.96 cm2 V-1 s-1, one of the highest values yet obtained for DPP derivative-based n-channel OFETs. Polycrystalline OFETs show promise (with an μe up to 0.64 cm2 V-1 s-1) for practical utility in organic device applications. Copyright
- Yoon, Won Sik,Park, Sang Kyu,Cho, Illhun,Oh, Jeong-A,Kim, Jong H.,Park, Soo Young
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- The effect of side-chain substitution on the aggregation and photovoltaic performance of diketopyrrolopyrrole-alt-dicarboxylic ester bithiophene polymers
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Using a dicarboxylic ester bithiophene (DCBT) co-monomer, electron-withdrawing ester groups are introduced on the two central thiophene rings of an alternating donor-acceptor polymer (PDPP4T) consisting of diketopyrrolopyrrole (DPP) and quaterthiophene (4T) to increase the oxidation potential and reduce the photon energy loss in solar cells. To counteract the increased solubility of the PDPPDCBT polymers owing to the ester side chains, linear instead of branched side chains were used on the DPP monomer. The length of the ester side chains was varied to study their effect on the optoelectronic properties, morphology and photovoltaic performance of these polymers in bulk-heterojunction blends with PC71BM as acceptor. The molecular weight of PDPPDCBT is limited, because the bisstannyl-DPP monomer could not be completely purified from mono-functional analogues. By using a non-stoichiometric monomer ratio or a branching unit, the molecular weights were improved to ～35 kDa. A maximum power conversion efficiency of PCE = 5.7% was obtained. Compared to the parent PDPP4T (PCE 7.0%), the photon energy loss for the best PDPPDCBT was reduced from 0.79 to 0.76 eV, but the photon-to-electron quantum efficiency was reduced, as a consequence of a too coarse phase separation, as studied with two-dimensional grazing-incidence X-ray scattering and transmission electron microscopy.
- Heuvel, Ruurd,Colberts,Li, Junyu,Wienk, Martijn M.,Janssen, René A. J.
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- Donor-fullerene dyads for energy cascade organic solar cells
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Organic bulk heterojunction (BHJ) solar cells require broad absorption of the incident solar spectrum by the donor and acceptor in the blend. Fullerene derivatives with covalently linked dyes, referred to as dyads, were designed to have strong optical absorption and appropriate electronic levels for electron transfer with common donor polymers in BHJs. Dyads with dyes based on diketopyrrolopyrrole and benzothiadiazole were synthesized using either a methanofullerene or a fulleropyrrolidine linkage. The performance of these dyad acceptors in BHJ solar cells with poly(3-hexylthiophene) (P3HT) and a low optical gap co-polymer of thiophene and diketopyrrolopyrrole (PDPP2FT) were examined. Although the solar power conversion efficiencies were low, charge generation from the molecular dye in the dyad could be observed in BHJs with PDPP2FT. The low power conversion efficiency was attributed to the morphology of the BHJs based on grazing incidence wide angle X-ray scattering patterns. Density functional theory was used to examine the charge transfer states between the donor and the dyad. The lowest energy charge-transfer state was found to be a transition from the donor polymer to the fullerene portion of the dyad.
- Cowart, John S.,Liman, Christopher,Garnica, Amanda,Page, Zachariah A.,Lim, Eunhee,Zope, Rajendra R.,Baruah, Tunna,Hawker, Craig J.,Chabinyc, Michael L.
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- Substantial photovoltaic response and morphology tuning in benzo[1,2-b:6,5-b′]dithiophene (bBDT) molecular donors
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The influence of solubilizing substituents on the photovoltaic performance and thin-film blend morphology of new benzo[1,2-b:6,5-b′]dithiophene (bBDT) based small molecule donor semiconductors is investigated. Solar cells based on bBDT(TDPP)2-PC71BM with two different types of side chains exhibit high power conversion efficiencies, up to 5.53%. This journal is the Partner Organisations 2014.
- Harschneck, Tobias,Zhou, Nanjia,Manley, Eric F.,Lou, Sylvia J.,Yu, Xinge,Butler, Melanie R.,Timalsina, Amod,Turrisi, Riccardo,Ratner, Mark A.,Chen, Lin X.,Chang, Robert P. H.,Facchetti, Antonio,Marks, Tobin J.
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- Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells
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Two novel π-conjugated small molecules based on the electron-deficient diketopyrrolopyrrole (DPP) and the electron-rich fused tetrathienoacene (TTA) frameworks are synthesized and characterized. As verified in the bandgap compression of these chromophores by electrochemistry and density functional theory (DFT) computation, these DPP-TAA derivatives exhibit substantial conjugation and ideal MO energetics for light absorption. The large fused TTA core and strong intermolecular SS interactions enforce excellent molecular planarity, favoring a close-packed thin film morphologies for efficient charge transport, as indicated by grazing incidence wide angle X-ray scattering (GIWAXS), atomic force microscopy (AFM), and transmission electron microscopy (TEM) analysis. Top-gate/bottom-contact thin film transistors based on these systems exhibit hole mobilities approaching 0.1 cm2 V-1 s-1. Organic photovoltaic cells based on DDPP-TTAR:PC71BM blends achieve power conversion efficiencies (PCE) > 4% by systematic morphology tuning and judicious solvent additive selection.
- Zhou, Nanjia,Vegiraju, Sureshraju,Yu, Xinge,Manley, Eric F.,Butler, Melanie R.,Leonardi, Matthew J.,Guo, Peijun,Zhao, Wei,Hu, Yan,Prabakaran, Kumaresan,Chang, Robert P. H.,Ratner, Mark A.,Chen, Lin X.,Facchetti, Antonio,Chen, Ming-Chou,Marks, Tobin J.
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- A Phototheranostic Strategy to Continuously Deliver Singlet Oxygen in the Dark and Hypoxic Tumor Microenvironment
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Continuous irradiation during photodynamic therapy (PDT) inevitably induces tumor hypoxia, thereby weakening the PDT effect. In PDT-induced hypoxia, providing singlet oxygen from stored chemical energy may enhance the cell-killing effect and boost the therapeutic effect. Herein, we present a phototheranostic (DPPTPE?PEG-Py NPs) prepared by using a 2-pyridone-based diblock polymer (PEG-Py) to encapsulate a semiconducting, heavy-atom-free pyrrolopyrrolidone-tetraphenylethylene (DPPTPE) with high singlet-oxygen-generation ability both in dichloromethane and water. The PEG-Py can trap the 1O2 generated from DPPTPE under laser irradiation and form a stable intermediate of endoperoxide, which can then release 1O2 in the dark, hypoxic tumor microenvironment. Furthermore, fluorescence-imaging-guided phototherapy demonstrates that this phototheranostic could completely inhibit tumor growth with the help of laser irradiation.
- Chen, Xiaoyuan,Cheng, Yaya,Deng, Liming,Dong, Xiaochen,Fan, Wenpei,He, Liangcan,Huang, Wei,Li, Ling,Ma, Yuanyuan,Mu, Jing,Tang, Wei,Yang, Zhen,Zhu, Jianwei,Zou, Jianhua
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- A versatile star-shaped organic semiconductor based on benzodithiophene and diketopyrrolopyrrole
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We report the synthesis of a new star-shaped π-conjugated oligomer, BDT(DPP)4, containing a benzodithiophene core and four diketopyrrolopyrrole arms. The thermal, electrochemical and optical properties are characterized and the results complemented by computational studies. The utility of the molecule is demonstrated in both solar cell and field-effect transistor devices. In the former, BDT(DPP)4 displays low efficiency when used as an acceptor in blends with poly(3-hexylthiophene) but exhibits promising performance as a donor, in blends with either a fullerene or a non-fullerene acceptor. In field-effect transistors BDT(DPP)4 exhibits typical p-type transistor behavior, which is in accordance with its better donor performance in solar cell devices.
- He, Qiao,Shahid, Munazza,Panidi, Julianna,Marsh, Adam V.,Huang, Wentao,Daboczi, Matyas,Kim, Ji-Seon,Fei, Zhuping,Anthopoulos, Thomas D.,Heeney, Martin
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- Towards more sustainable synthesis of diketopyrrolopyrroles
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The alkylation of 1,4-diketo-3,6-arylpyrrolo[3,4-c]pyrroles (ArDPP) is one of the most important steps in the synthesis of soluble materials based on these molecules and the polymers derived from them (that are employed widely in putative organic solar ce
- Pop, Flavia,Humphreys, Joshua,Schwarz, Jesper,Brown, Liam,Van Den Berg, Ashmiani,Amabilino, David B.
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- Family of diazapentalene chromophores and narrow-band-gap polymers: Synthesis, halochromism, halofluorism, and visible-near infrared photodetectivity
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A family of pyrrolo[3,4-c]pyrrol-1(2H)-one (PPO) and 2,5-diazapentalene (DAP) chromophores and DAP-containing polymers were synthesized, and their optical and electrochemical properties were studied. PPO and DAP chromophores are readily obtained by chemical transformation of the lactam unit in diketopyrrolopyrrole (DPP) dyes and can be used as versatile building blocks for construction of a variety of conjugated low-band-gap compounds and polymers. In comparison with the DPP chromophores, PPO and DAP chromophores have narrower energy gaps and low-lying HOMO levels in the order DPP > PPO > DAP. Interestingly, the PPO and DAP chromophores exhibit unique visible and near-infrared halochromic and halofluoric properties. The emission spectrum of DAP-containing polymer 6d covers the telecommunication window including the wavelength of 1310 nm. The photodetector with a device configuration of ITO/PEDOT:PSS (35 nm)/active layer (100 nm)/Al (100 nm) was fabricated using a blend of polymer 6d and [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) in a weight ratio of 1:3 as the active layer and exhibited photocurrent spectral response from 400 to 1000 nm and the detectivity in an order of 1011 Jones at 800 nm.
- Qian, Gang,Qi, Ji,Davey, James A.,Wright, James S.,Wang, Zhi Yuan
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- Charge separation and singlet fission in covalently linked diketopyrrolopyrrole derivatives and triphenylamine triad in solution
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A covalently linked push-pull type triad containing two unsymmetrical electron donors, triphenylamine (TPA) and benzothiophene (BT), and diketopyrrolopyrrole (DPP), an electron acceptor, through thiophene spacer has been synthesized (BT-DPP-TPA(7)) and ultrafast relaxation dynamics of the triad has been explored in solution phase by various spectroscopic methods. Steady-state and time-resolved emission studies show the efficient fluorescence quenching of the DPP entity of as prepared BT-DPP-TPA(7) triad. The negative free energy values comprising the redox potentials and singlet state energy of BT-DPP-TPA(7) revealed the probability of electron transfer from the singlet ground state of TPA to the excited singlet state of DPP. Femtosecond transient absorption (fsTA) spectroscopic studies confirmed the formation of charge separation state by detecting triphenylamine radical cation as electron-transfer transients. The rate of charge separation, kCS, is (109?108 s?1) observed to be increasing from nonpolar to polar solvents and the rate of charge recombination, kCR, was found to be slower (μs time scale) in polar solvents like DMF and chloroform, than that in hexane, non-polar solvent (ns time scale). This novel aspect could be due to asymmetrically designed push-pull type triad, a feature that was not evident in push-pull triad constructed using symmetric TPA as electron donors. Furthermore, fsTA studies also demonstrate, for the first time, that the DPP derivatives, TDPP(4) and BT-DPP-TPA(7), both undergo singlet fission (SF) event (S→TT) in 100?200 ps time scale in solution phase for the solution of concentration above ～100 μM. These results may pave the new avenue for device design comprising DPP derivatives.
- Bangal, Prakriti Ranjan,Chakali, Madhu,Dyaga, Bharath,Mandal, Haraprasad,Rao, V. Jayathirtha,Venkatesan, Munisamy
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- Mono-/Bimetallic Neutral Iridium(III) Complexes Bearing Diketopyrrolopyrrole-Substituted N-Heterocyclic Carbene Ligands: Synthesis and Photophysics
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The synthesis and photophysics (UV-vis absorption, emission, and transient absorption) of four neutral heteroleptic cyclometalated iridium(III) complexes (Ir-1-Ir-4) incorporating thiophene/selenophene-diketopyrrolopyrrole (DPP)-substituted N-heterocyclic carbene (NHC) ancillary ligands are reported. The effects of thiophene versus selenophene substitution on DPP and bis- versus monoiridium(III) complexation on the photophysics of these complexes were systematically investigated via spectroscopic techniques and density functional theory calculations. All complexes exhibited strong vibronically resolved absorption in the regions of 500-700 nm and fluorescence at 600-770 nm, and both are predominantly originated from the DPP-NHC ligand. Complexation induced a pronounced red shift of this low-energy absorption band and the fluorescence band with respect to their corresponding ligands due to the improved planarity and extended π-conjugation in the DPP-NHC ligand. Replacing the thiophene units by selenophenes and/or biscomplexation led to the red-shifted absorption and fluorescence spectra, accompanied by the reduced fluorescence lifetime and quantum yield and enhanced population of the triplet excited states, as reflected by the stronger triplet excited-state absorption and singlet oxygen generation.
- Hobbie, Erik K.,Kilina, Svetlana V.,Lystrom, Levi,Pan, Yanxiong,Sun, Wenfang,Sun, Xinyang,Thomas, Salim A.,Wang, Hua,Xu, Wan,Yang, Zhongyu
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p. 15278 - 15290
(2021/10/20)
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- Improved crystallinity of the asymmetrical diketopyrrolopyrrole derivatives by the adamantane substitution
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Alkylation of diketopyrrolopyrroles (DPPs) is a powerful tool for increasing the solubility and processability of these pigments. Moreover, alkylation contributes to solid state packing and structural ordering of DPPs. In this study, the influence of the alkylation and solubilization side group engineering to DPPs on the thermal and optical properties was systematically investigated. Two series (each containing 3 derivatives: N,N'-, N,O′- and O,O′-substituted examples) of alkylated DPPs by 2-ethylhexyl and ethyladamantyl substituents were synthesized. Separation of all formed DPP derivatives was accomplished in order to perform an in-depth study of their physicochemical properties. DSC measurements revealed that the O-substitution caused a decrease in the thermal stability of DPP derivatives. On the contrary, an ethyladamantyl side chain, as a rigid alicyclic substituent, contributed very effectively to the increase of the melting point and thermal stability. The new results provide insights into the development of DPP-alkylated regioisomers and their thermal and optical properties.
- Cigánek, Martin,Heinrichová, Patricie,Kovalenko, Alexander,Ku?erík, Ji?í,Vala, Martin,Weiter, Martin,Kraj?ovi?, Jozef
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- D-A-D type organic photo-thermal small molecular material and preparation method thereof
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The invention provides a D-A-D type organic photo-thermal small molecular material and a preparation method thereof. The D-A-D type organic photo-thermal small molecular material contains an electronwithdrawing group 2,1,3-benzothiadiazole and an electron donating group 3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c] pyrrole-1,4-dione. The preparation method comprises the steps: substituting H ona thiophene ring of bromo-isooctane substituted 3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione with N-bromo-succinimide, and carrying out a reaction with 2,1,3-benzothiadiazole-4,7-bis(pinacol borate) through Suzuki reaction to obtain the target product. With the introduction of an alkyl chain on the side chain of the electron donating group, the solubility of the organic photo-thermal material in the organic solvent is improved, the problem of poor solubility of the organic polymer is overcome, and favorable light stability is achieved.
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- ORGANIC DYES, COMPOSITIONS AND DYE-SENSITIZED SOLAR CELLS
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The present invention relates to a liquid crystal display device. The present invention relates to an organic dye, a composition including the same, and a dye-sensitized solar cell twisted π-spacer and DPP-based core unit introduced therein, and to a composition and a dye-sensitized solar cell including the same.
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- Synthesis of novel 3,6-dithienyl diketopyrrolopyrrole dyes by direct C-H arylation
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Direct C-H arylation coupling is potentially a more economical and sustainable process than conventional cross-coupling. However, this method has found limited application in the synthesis of organic dyes for dye-sensitized solar cells. Although direct C-H arylation is not an universal solution to any cross-coupling reactions, it efficiently complements conventional sp2-sp2 bond formation and can provide shorter and more efficient routes to diketopyrrolopyrrole dyes. Here, we have applied palladium catalyzed direct C-H arylation in the synthesis of five new 3,6-dithienyl diketopyrrolopyrrole dyes. All prepared sensitizers display broad absorption from 350 nm up to 800 nm with high molar extinction coefficients. The dye-sensitized solar cells based on these dyes exhibit a power conversion efficiency in the range of 2.9 to 3.4%.
- Almenningen, David Moe,Gautun, Odd Reidar,Hoff, B?rd Helge,Venkatraman, Vishwesh,Yemene, Amsalu Efrem
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- Perfluorobutyl substituted compound as well as preparation method and application thereof (by machine translation)
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The invention discloses a perfluorobutyl substituted compound as well as a preparation method and application; and a preparation method and application thereof. The chemical structural formula of the compound is as shown in formula (III), (VI), (X), wherein R is a branched alkane or a straight-chain alkane having 8~16 carbon atoms, and the compound has better dissolving performance, and the yield of each step is higher than the unitunityl ?. 10%. There is better air stability compared to compounds which are not substituted with fluoroalkyl groups, for example. The LUMO, HOMO energy level and the like are reduced, so that electron injection and transmission, and the maximum absorption wavelength in the field, of organic field effect transistors (OFET), organic solar cells (OPV), have potential application prospects. (by machine translation)
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- Diketopyrrolopyrrole derivative and application thereof
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The invention provides a diketopyrrolopyrrole derivative and application thereof as well as relates to a diketopyrrolopyrrole derivative. The structural formula of the diketopyrrolopyrrole derivativeis as shown in a formula (I): the formula (I) is as shown in the description; in the formula (I), R1 is selected from a group as shown in a formula (I-a), a formula (I-b), a formula (I-c), a formula (I-d) or a formula (I-e) (the formulas are as shown in the description); and in the formula (I-a), the formula (I-b), the formula (I-c), the formula (I-d) and the formula (I-e), * shows connection position. The diketopyrrolopyrrole derivative has excellent photoelectric property and can be applied in the field of organic photoelectric functional devices.
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- Aggregation-induced emission near-infrared emission diketopyrrolopyrrole compound and preparation method thereof
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The invention discloses an aggregation-induced emission near-infrared emission diketopyrrolopyrrole compound and a preparation method thereof. The method comprises the steps that 3,6-dithiophene diketopyrrolopyrrole reacts with twice molar weight of alkyl
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Paragraph 0035; 0042
(2019/01/07)
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- Substituent-eliminable diketopyrrolopyrrole derivative, organic semiconductor material precursor solution, organic semiconductor material, and organic semiconductor material film
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A substituent-eliminable diketopyrrolopyrrole derivative represented by the following formula (I) is provided. In the formula (I), R represents a substituted or unsubstituted alkyl group; X represents a substituted or unsubstituted alkyl group; Ar represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group; and n represents an integer of from 1 to 4.
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- Synthesis and Characterization of Diketopyrrolopyrrole-based D-π-A-π-D Small Molecules for Organic Solar Cell Applications
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Four new small molecules – CTDP, BCTDP, CFDP, and BCFDP having D-π-A-π-D molecular architecture, possessing carbazole and benzocarbazole as electron donors, diketopyrrolopyrrole core as acceptor and thiophene/furan acting as spacer/bridge between donor (carbazole and benzocarbazole) and acceptor (diketopyrrolopyrrole) units are synthesized. All the four compounds exhibited absorption in the range of 300 to 700 nm, and, in particular, more intense absorption found in the 500 to 660 nm region. The estimated band gaps are found to be 1.92 eV for CTDP, 1.92 eV for BCTDP, 1.94 eV for CFDP, and 1.92 eV for BCFDP from their intersection point of absorption and emission spectra. The electrochemical studies revealed that the highest occupied molecular orbital/lowest unoccupied molecular orbital energy levels of all the four compounds, CTDP (?5.03/?3.65 eV), BCTDP (?5.03/?3.65 eV), CFDP (?4.94/?3.65 eV), and BCFDP (?4.90/?3.62 eV) are well matched with PCBM and expected to be act as donor materials in small molecule bulk hetero junction organic solar cells. All the compounds are thermally stable up to 382–416°C.
- Sivakumar, Gangala,Sasikumar, Mayarambakam,Rao, Vaidya Jayathirtha
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p. 1983 - 1994
(2017/05/29)
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- Multichromophore Donor Materials Derived from Diketopyrrolopyrrole and Phenoxazine: Design, Synthesis, and Photovoltaic Performance
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Herein two conjugated donor molecules, TDPP-POCN and FDPP-POCN, with planar diketopyrrolopyrrole (DPP) as the core building-block acceptor unit and phenoxazine-capped acrylonitriles as arms are designed and synthesized. Solution-processed bulk-heterojunction organic solar cells based on blends of the small-molecule donors and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) exhibit promising photovoltaic device performance with a maximum power conversion efficiency up to 4.8 % for TDPP-POCN and 3.4 % for FDPP-POCN under the illumination of AM1.5G, 100 mW cm–2. To the best of our knowledge, this is the highest efficiency reported so far in DPP–phenoxazine-based systems and among acrylonitrile-bridged donor-π-acceptor-π-donor-structured small-molecule donors for solution-processed small-molecule-based organic solar cells.
- Narayanaswamy, Kamatham,Yadagiri, Bommaramoni,Bagui, Anirban,Gupta, Vinay,Singh, Surya Prakash
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p. 4896 - 4904
(2017/09/13)
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- Benzocarbazoles three thiophene compound and its preparation and use
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The invention relates to benzo terthiophene compound as well as a preparation method and usage thereof. The structure of the benzo terthiophene compound is expressed by a formula I, and in the formula, the definition of X is described in the description.
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Paragraph 0204-0206
(2016/11/07)
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- Narrow band-gap donor-acceptor copolymers based on diketopyrrolopyrrole and diphenylethene: Synthesis, characterization and application in field effect transistor
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Three low band-gap diketopyrrolopyrrole based polymers with varying donor groups of furan, thiophene and phenyl were synthesized and then copolymerized with diphenylethene. We investigate the influence of different donor groups and comonomers on the band-gap and field effect transistors. The efficient synthesis of the diketopyrrolopyrrole based copolymers was clearly characterized by a variety of measurements. Two dimensional Grazing Incident X-ray Diffraction was measured to prove that furan and thiophene based copolymers have ordered edge-on structure. These copolymers exhibited strong π-π stacking and excellent hole mobilities when applied in the electric double layer field effect transistors. The high mobility of 2.36 cm2 V-1 s-1 with an on/off ratio of 103 was achieved.
- Zhu, Haoyun,Huang, Wei,Huang, Yuli,Yang, Junwei,Wang, Weizhi
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- B thienyl pyrrolo pyrrole dione-naphthyl conjugated derivative and its preparation method and application
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The invention discloses a preparation method of a bithienyl pyrrolopyrroledione-naphthyl conjugated derivative and an application of the derivative as a small molecule electronic donor material in a photoelectric conversion active layer in organic bulk heterojunction solar batteries. Due to coupling of bithienyl pyrrolopyrroledione and a naphthyl derivative, the prepared material has good visible-near infrared light absorption property and high hole mobility, solubility and photoelectric conversion efficiency. According to the preparation method of the derivative, a target product is obtained through reaction of Suzuki coupling and the like. The derivative is simple in synthesis method, explicit in structure and easy to purify, high photoelectric conversion property is realized in simple molecules, and the derivative has the potential application prospect in the aspect of application in low-cost organic solar batteries.
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- Synthesis and Spectroscopic Investigation of Diketopyrrolopyrrole - Spiropyran Dyad for Fluorescent Switch Application
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We report the synthesis and characterization of a new fluorescent dyad SP-DPP-SP(9) via efficient palladium-catalyzed Sonogashira coupling of prop-2-yn-1-yl 3-(3′,3’dimethyl-6-nitrospiro[chromene-2,2′-indolin]-1′-yl)propanoatespiropyran, SP(8), a well known photochromic accepter, with 3,6-bis(5-bromothiophen-2-yl)-2,5-bis((R)-2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, DPP(4), a highly fluorescent donor. Under visible light exposure the SP unit is in a closed hydrophobic form, whereas under UV irradiation it converts to a polar, hydrophilic open form named Merocyanine (MC), which is responsible for functioning of photo-switch application. The photochemistry pertaining to fluorescence switch, ‘on/off’ behaviour, of model dyad SP-DPP-SP(9) is experimentally analyzed in solution as well as in solid state in polymer matrices by photoluminescence(PL) and absorption spectroscopy. After absorption of UV light the spiropyran unit of the dyad under goes the rupture of the spiro C-O bond leading to the formation of MC. The absorption band of MC fairly overlaps to the fluorescence of DPP unit resulting quenching of fluorescence via fluorescence resonance energy transfer from exited DPP unit to ground state MC. In contrary, the fluorescence of DPP is fully regained upon transformation of MC to SP by exposure to visible light or thermal stimuli. Hence, the fluorescence intensity of dyad 9 is regulated by reversible conversion among the two states of the photochromic spiropyran units and the fluorescence resonance energy transfer (FRET) between the MC form of SP and the DPP unit. Conversely, these scrutiny of the experiment express that the design of dyad 9 is viable as efficient fluorescent switch molecule in many probable commercial applications, such as, logic gates and photonic and optical communications.
- Doddi, Siva,Narayanaswamy,Ramakrishna, Bheerappagari,Singh, Surya Prakash,Bangal, Prakriti Ranjan
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p. 1939 - 1949
(2016/11/06)
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- NOVEL COMPOUND AND PHOTOELECTRIC CONVERSION DEVICE HAVING THE SAME
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The present specification of the photoelectric conversion element is the life, efficiency, electrochemical stability and thermal stability can be compound, said compound number. under public affairs including photoelectric conversion element. Specifically photoelectric conversion region of. under public affairs number organic solar cell. (by machine translation)
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Paragraph 0194-0196
(2017/04/21)
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- Hetero aromatic donors as effective terminal groups for DPP based organic solar cells
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Four new solution-processable donor-acceptor-donor (D-A-D) structured low bandgap small molecules (CSDPP5, CSDPP6, CSDPP7 and CSDPP8) with diketopyrrolopyrrole as central acceptor unit and phenoxazine (POZ) or carbazole (CBZ) as terminal units were designed, synthesized and characterized. The new small molecules have been employed as donors along with the PC71BM as electron acceptor in solution processed BHJ organic solar cells, showed broad absorption bands with suitable electrochemical energy levels. When the BHJ active layer was cast from THF solvent, the optimal power conversion efficiencies obtained with CSDPP5, CSDPP6, CSDPP7 and CSDPP8 are 2.97% 3.06%, 2.42% and 2.43% respectively. The PCE of the devices when processed with DIO/THF solvent, have been further enhanced to 4.69%, 4.14% for CSDPP6:PC71BM and CSDPP8:PC71BM active layers respectively. The enhancement in PCE has been attributed to change in nanoscale morphology and more balanced charge transport resulting from increased hole mobility.
- Reddy, Marri Anil,Kumar, Ch. Pavan,Ashok, Akudari,Sharma, Abhishek,Sharma,Chandrasekharam, Malapaka
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p. 9023 - 9036
(2016/02/05)
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- “N-alkyl diketopyrrolopyrrole-based fluorophores for luminescent solar concentrators: Effect of the alkyl chain on dye efficiency”
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We report on the preparation of luminescent solar concentrators (LSCs) made of poly(methyl methacrylate) (PMMA) thin films doped with six new diketopyrrolopyrrole (DPP) fluorophores obtained in good yields by using simple N-alkylation and direct C[sbnd]H
- Lucarelli, Jonathan,Lessi, Marco,Manzini, Chiara,Minei, Pierpaolo,Bellina, Fabio,Pucci, Andrea
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p. 154 - 162
(2016/09/07)
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- Air-stable ambipolar organic field-effect transistors based on naphthalenediimide-diketopyrrolopyrrole copolymers
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Two air-stable polymeric semiconductors were rationally designed and synthesized, namely PNDI-DPP and PNDI-T(DPP)T, containing naphthalenediimide (NDI) units and diketopyrrolopyrrole (DPP). The coplanar thiophene-substituted DPP moieties act as donors rather than acceptors, even though DPP is an electron-deficient core. In a bottom-gate/top-contact device architecture, the effect of changing the number of thiophene linkers on the performance of the two completely different OFETs was investigated. PNDI-T(DPP)T presented unipolar p-type behaviour with an average hole mobility of 0.02 cm2 V-1 s-1, while PNDI-DPP exhibited ambipolar transport with average electron and hole mobilities of 5.7 × 10-3 and 1.6 × 10-3 cm2 V-1 s-1, respectively. Moreover, OFETs based on the two polymers showed good air-stability with negligible changes after being stored under ambient conditions for over 3 months. This journal is
- Wang, Ping,Li, Hui,Gu, Chunling,Dong, Huanli,Xu, Zhenzhen,Fu, Hongbing
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p. 19520 - 19527
(2015/05/05)
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- UNIMOLECULAR AND ORGANIC SOLAR CELL COMPRISING THE SAME
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Provided are a single molecule and an organic solar cell including the single molecule. Specifically, the single molecule has an end represented by chemical formula 1 and includes at least two units selected from the group consisting of units represented by chemical formula 2, wherein the two units are the same or different from each other.COPYRIGHT KIPO 2015
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Paragraph 0499-0502
(2016/10/09)
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- Panchromatic Push-Pull Dyes of Elongated Form from Triphenylamine, Diketopyrrolopyrrole, and Tetracyanobutadiene Modules
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Several symmetrical and unsymmetrical thiophene-functionalized diketopyrrolopyrrole chromophores bearing a bis(p-methoxyphenyl)-p-phenylamine substituent were synthesized through palladium-catalyzed cross-coupling reactions. Mono-substitution and di-substitution occur using either alkyne or borolane groups, allowing the preparation of mixed systems. The alkyne derivatives could be prepared in high yields, and are versatile building blocks for the [2+2] cyAcloaddition of tetracyanoethylene, leading to 1,1,4,4-tetracyanobuta-1,3-diene derivatives. These interesting push-pull molecules exhibit a rich redox activity, which is understandable in light of the behavior of appropriate reference compounds. These innovative and rationally designed scaffolds are highly colored, exhibiting high absorption coefficients and spanning an absorption range of more than 600A nm of the UV/Vis electromagnetic spectrum.
- Heyer, Elodie,Ziessel, Raymond
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supporting information
p. 2109 - 2116
(2015/09/15)
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- ORGANIC MATERIAL AND PHOTOELECTRIC CONVERSION ELEMENT
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PROBLEM TO BE SOLVED: To provide a new organic material having a high open voltage used for an organic thin film solar battery system, capable of absorbing light in a wide wavelength range and excellent in charge transport performance. SOLUTION: Provided
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Paragraph 0070-0074
(2016/10/07)
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- Synthesis and optical properties of photovoltaic materials based on the ambipolar dithienonaphthothiadiazole unit
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Dithieno[3′2′:5,6;2′′,3′′:7,8]naphtho[2,3-c][1,2,5]thiadiazole (DTNT) was designed to control the band energies of the polymers for photovoltaic materials. Electrochemical analysis showed that DTNT acts as both an electron donor and an electron acceptor, revealing the ambipolar nature of the DTNT unit. The direct arylation polymerization of DTNT with 2,2′-bithiophene (BTh) and 3,6-bis(2-thienyl)pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) afforded four polymers that differed in either the unit of copolymerization or the chosen side chains. In the PDTNT-BTh series, a shoulder absorption band was observed at a longer wavelength than the intense absorption band. The PDTNT-DPP series exhibited a narrow band gap of less than 1.4 eV and a low HOMO energy of -5.43 eV. An organic photovoltaic cell that contained a PDTNT-BTh polymer with 2-ethylhexyl groups and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as an active layer afforded the best performance among the studied compounds, with a JSC of 6.98 mA cm-3, a VOC of 0.758 V, a FF of 0.52, and a PCE of 2.76%.
- Nakanishi, Tatsuaki,Shirai, Yasuhiro,Han, Liyuan
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supporting information
p. 4229 - 4238
(2015/03/04)
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- Synthesis and properties of Zn2+/Cd2+-directed self-assembled metallo-supramolecular polymers based on 1,4-diketo-pyrrolo[3,4-c]pyrrole (DPP) derivatives
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New building blocks based on 1,4-diketopyrrolo[3,4-c]pyrrole (DPP), 2,5-bis(2-ethylhexyl)-3,6-bis(5-[p-(2,2':6′,2′′-terpyridine-4′-yl) phenyl]thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (M1) and 2,5-bis(2-ethylhexyl)-3,6-bis(4-[p-(2,2′:6′,2′′-terpyridine-4′-yl) phenyl]phenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (M2) were synthesized by the Suzuki Pd-catalyzed cross-coupling reaction. Under moderate conditions, directed self-assembly polymerizations by the transition metal ions Zn2+ and Cd2+, respectively, were carried out. The metallo-supramolecular polymers P1Zn, P1Cd, P2Zn and P2Cd were obtained and fully characterized. The supramolecular polymers P2Zn and P2Cd, containing DPP modified by a phenyl unit, showed absorption maxima at about 504 and 506 nm in films. In contrast, the polymers P1Zn and P1Cd, in which the thiophene moiety-modified DPP was introduced, exhibited strong and broad visible absorption over 300-800 nm with maxima at about 601 and 598 nm and shoulder peaks at about 665 and 671 nm, respectively. The low band gaps estimated from CV of 1.52, 1.51, 1.58 and 1.58 eV for P1Zn, P1Cd, P2Zn and P2Cd, respectively, are also reported.
- Chen, Xuegang,Guo, Kai,Li, Fanchao,Zhou, Li,Qiao, Hongbin
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p. 58027 - 58035
(2015/01/16)
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- Diketopyrrolopyrrole-based acceptor-acceptor conjugated polymers: The importance of comonomer on their charge transportation nature
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Besides the donor-acceptor (D-A) type, acceptor-acceptor (A-A) polymers are another class of important alternative conjugated copolymers, but have been less studied in the past. In this study, two kinds of A-A polymers, P1 and P2, have been designed and synthesized based on diketopyrrolopyrrole in combination with the second electron-deficient unit, perylenediimide or thieno[3,4-c] pyrrole-4,6-dione. UV-vis absorption spectroscopy revealed that these two kinds of polymers have a band gap of 1.28-1.33 eV. Their highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels are around -5.6 and -4.0 eV for P1 polymers, whereas -5.4 and -3.7 eV for P2 polymers, respectively. Density functional theory study disclosed that P1 backbone is in a vastly twisting state, whereas that of P2 is completely planar. Furthermore, organic field-effect transistor devices were fabricated using these two kinds of polymers as the active material. Of interest, the devices based on P1 polymers displayed n-channel behaviors with an electron mobility in the order of 10 -4 cm2 V-1 s-1. In contrast, the P2-based devices exhibited only p-channel charge transportation characteristics with a hole mobility in the order of 10-3 cm2 V -1 s-1.
- Ge, Cong-Wu,Mei, Chong-Yu,Ling, Jun,Zhao, Fu-Gang,Li, Hong-Jiao,Liang, Long,Wang, Jin-Tu,Yu, Jin-Cheng,Shao, Wei,Xie, Yong-Shu,Li, Wei-Shi
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p. 2356 - 2366
(2014/07/21)
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- Alternating copolymers of diketopyrrolopyrrole or benzothiadiazole and alkoxy-substituted oligothiophenes: Spectroscopic, electrochemical and spectroelectrochemical investigations
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A series of solution processable semiconducting donor-acceptor (DA) copolymers consisting of either diketopyrrolopyrrole or benzothiadiazole A units and alkoxy- or alkyl-substituted oligothiophene D units were synthesized. For all prepared copolymers the measured XPS spectra (C1s, S2p, N1s and O1s) were in a very good agreement with the expected chemical constitution. Spectroscopic studies of the synthesized copolymers showed that their optical band gaps were governed by the presence of the alkoxy substituents whose electron donating properties led to additional gap narrowing yielding semiconductors with band gaps of below 1.3 eV in the case of the polymers with the diketopyrrolopyrrole A unit. The same trend was observed with the electrochemical band gaps, whose values were however found to be ca. 0.4 eV superior to the corresponding optical band gaps values. Vibrational model was calculated for two of the synthesized copolymers with the goal to unequivocally attribute the observed Raman modes and to support the interpretation of the spectral changes induced by the electrochemical oxidation. It was established that the electrochemical oxidative doping of the copolymer with the benzothiadiazole A unit is limited to the oligothiophene segment in which the charge of the formed polycation is localized. To the contrary, in the case of the polymer with the diketopyrrolopyrrole A segment the charge imposed on the oligothiophene segment delocalizes towards the diketopyrrolopyrrole unit. These findings are in perfect agreement with the UV-vis-NIR spectroelectrochemistry data which show strong localization of electrochemically created charge carriers in the benzothiadiazole - oligothiophene copolymer and their metallic-like delocalization in the diketopyrrolopyrrole one. The latter seems to be very interesting not only as a potential low band gap component of organic photovoltaic cells but also, in the doped state, as electronic conductor of metallic character.
- Gora,Krzywiec,Mieczkowski,Rodrigues Maia,Louarn,Zagorska,Pron
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supporting information
p. 211 - 220
(2015/03/03)
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- Synthesis, molecular and photovoltaic properties of an indolo[3,2-b]indole- based acceptor-donor-acceptor small molecule
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Indolo[3,2-b]indole, containing two fused indole units, is an unexplored but promising electron-rich molecule for constructing donor-acceptor materials due to its planar, symmetric, and extended conjugated structure. We have successfully developed a new synthetic pathway to prepare 2,7-diboronic ester-indolo[3,2-b]indole, which was then reacted with dithienodiketopyrrolo- pyrrole acceptor to afford a new acceptor-donor-acceptor (A-D-A) conjugated molecule, 2,7-bis(dithienodiketopyrrolo-pyrrole)indolo[3,2-b]indole (2,7-DPPIIDPP). II is used to stand for indolo[3,2-b]indole in order to emphasize that this compound is constructed from two indole units. The A-D-A linkage through the 2,7-positions of II not only preserves the phenylene units in the para-conjugation but also renders stronger electron-donating strength. This material exhibited good thermal stability, high crystallinity, and broad UV/Vis absorption. The solution-processed bulk heterojunction device using the configuration of ITO/PEDOT:PSS/2,7-DPPIIDPP:PC71BM/Ca/Al exhibited a Voc of 0.72 V, a Jsc of 6.88 mA/cm2, and an FF of 49.6 %, leading to a power conversion efficiency (PCE) of 2.45 %. A new acceptor-donor-acceptor conjugated molecule, 2,7-bis(dithienodiketopyrrolo- pyrrole)indolo[3,2-b]indole (2,7-DPPIIDPP) was designed and synthesized. This material exhibited good thermal stability, high crystallinity, and broad UV/Vis absorption. The solution-processed bulk heterojunction device using the configuration of ITO/PEDOT:PSS/ 2,7-DPPIIDPP:PC71BM/Ca/Al was characterized. Copyright
- Lai, Yu-Ying,Yeh, Jyun-Ming,Tsai, Che-En,Cheng, Yen-Ju
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p. 5076 - 5084
(2013/11/06)
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- Self-organizing mesomorphic diketopyrrolopyrrole derivatives for efficient solution-processed organic solar cells
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We describe the synthesis, self-organization, and photovoltaic properties of diketopyrrolopyrrole (DPP)-based mesomorphic small-molecule materials, 3,6-bis{5-(4-alkylphenyl)thiophen-2-yl}-2,5-di(2-ethylhexyl)-pyrrolo[3,4-c] pyrrole-1,4-diones (DPP-TP6 and DPP-TP12), which have strong visible absorption characteristics. The effects of varying terminal alkyl chains on the self-assembling properties and photovoltaic device performances have been studied. With the appropriate ratio of the lengths of the alkyl chains to its rigid DPP core, DPP-TP6 exhibits liquid-crystalline properties and forms well-developed nanostructured bulk heterojunction (BHJ) architectures with a fullerene derivative (PC71BM). Organic solar cells (OSCs) employing BHJ DPP-TP6:PC71BM films show a power conversion efficiency as high as 4.3% with a high open-circuit voltage of 0.93 V and a fill factor of 0.55. These results demonstrate that liquid-crystalline organization to direct molecular self-assembly is a promising strategy for fabricating high-performance solution-processed small-molecule OSCs.
- Shin, Woong,Yasuda, Takuma,Watanabe, Go,Yang, Yu Seok,Adachi, Chihaya
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p. 2549 - 2556
(2013/07/26)
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- Synthesis and applications of novel low bandgap star-burst molecules containing a triphenylamine core and dialkylated diketopyrrolopyrrole arms for organic photovoltaics
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In this study, we used facile synthetic routes to construct two well-defined starburst donor/acceptor conjugated small molecules with broad absorption features; in TPAKP-2 and TPAKP-3, triphenylamine (TPA) moieties served as electron donor core units and dialkylated diketopyrrolopyrrole (DKP) moieties with symmetrical thiophene units served as electron acceptors, in 1:2 and 1:3 ratios, respectively. Our investigation of the photophysical properties indicated that the absorption bands of TPAKP-2, and TPAKP-3 extended up to 793 nm, with low optical band gaps of 1.56 and 1.65 eV respectively. Under illumination with AM 1.5 white light (100 mW cm-2), we investigated the performance of bulk heterojunction (BHJ) photovoltaic devices incorporating an active layer of an electron-donor small molecule (TPAKP-2 or TPAKP-3) blended with an electron acceptor: [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) or [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) at various weight ratios. The photovoltaic device containing the donor TPAKP-3 and the acceptor PC71BM at a 1:3 weight ratio exhibited the best power conversion efficiency (1.81%), with an open circuit voltage of 0.66 V, a short circuit current density of 7.93 mA cm -2, and a fill factor of 34.7%.
- Sahu, Duryodhan,Tsai, Chia-Hua,Wei, Hung-Yu,Ho, Kuo-Chuan,Chang, Feng-Chih,Chu, Chih-Wei
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p. 7945 - 7953
(2012/07/17)
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- Structure-properties relationships in conjugated molecules based on diketopyrrolopyrrole for organic photovoltaics
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Conjugated systems built by connecting two electron-donor side-chains to a diketopyrrolopyrrole (DPP) core have been synthesized and evaluated as donor material in heterojunction organic solar cells. The effects of composition of the side-chain on the electronic properties of the conjugated system have been analyzed on first series of compounds containing various combinations of benzofuran, benzothiophene, thiophene and furan units. In a second series of compounds, the keto groups of DPP have been replaced by one or two thioketo groups. Results of UV-vis absorption spectroscopy, fluorescence emission spectroscopy and cyclic voltammetry show that the composition of the side-chain has little effect on the HOMO and LUMO levels of the system, but strongly affects the sensitivity of the material toward thermal treatment and thus indirectly the performances of the resulting solar cells. On the other hand, replacement of the keto groups of DPP by thioketo ones leads at the same time to significant reduction of the band gap due to a decrease of the LUMO level, to a quenching of fluorescence and to dramatic decrease of the photovoltaic activity of the molecule.
- Ripaud, Emilie,Demeter, Dora,Rousseau, Théodulf,Boucard-Cétol, Emmanuel,Allain, Magali,Po, Riccardo,Leriche, Philippe,Roncali, Jean
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p. 126 - 133
(2012/07/28)
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- Metal-free and fluorescent diketopyrrolopyrrole fluorophores for dye-sensitized solar cells
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Novel metal-free and fluorescent dipyrrolopyrrole (DPP) dyes consisting of a central bis(lactam)-bearing pendent benzyl or branched hydrocarbon groups as solubilizing fragments and two orthogonal side arms (dimethylaminopropyne and benzoate anion) have been designed and synthesized. The UV/Vis absorption spectra recorded in THF are dominated by intense low-energy π-π absorptions centered at 488 nm or 602 nm, respectively, for the phenyl- or thiophene-based DPP dyes. The fluorescence spectra also display broad bands at 555 nm (τF= 0.57 and ΦF=4.6 ns) for the phenyl- and at 624 nm (ΦF=0.31 and ΦF=3.5 ns) for the thiophene-based molecular structures. Under standard global AM 1.5G irradiation a maximum photon-to-electron conversion efficiency of 2.54% was achieved with dye-sensitized solar cells based on nanocrystalline TiO2 (Jsc=7.5 mAcm-2, Voc=0.49 V, and FF=0.70) for the phenyl-based DPP dye and 1.89% (Jsc=7.1 mAcm-2, Voc= 0.41 V, and FF=0.65) for the thiophene-based DPP dye.
- Hablot, Delphine,Islam, Ashraful,Han, Liyuan,Ziessel, Raymond
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p. 462 - 469
(2014/01/17)
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- Synthesis and characterization of a narrow-bandgap polymer containing alternating cyclopentadithiophene and diketo-pyrrolo-pyrrole units for solar cell applications
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We have synthesized a narrow-bandgap conjugated polymer (PCTDPP) containing alternating cyclopentadithiophene (CT) and diketo-pyrrolo-pyrrole (DPP) units by Suzuki coupling. This PCTDPP exhibits a low band gap of 1.31 eV and a broad absorption band from 350 to 1000 nm, which allows it to absorb more available photons from sunlight. A bulk heterojunction polymer solar cell incorporating PCTDPP and C70 at a blend ratio of 1:3 exhibited a high short-circuit current of 10.87 mA/cm2 and a power conversion efficiency of 2.27%.
- Chen, Guan-Yu,Chiang, Chien-Ming,Kekuda, Dhananjay,Lan, Shang-Che,Chu, Chih-Wei,Wei, Kung-Hwa
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experimental part
p. 1669 - 1675
(2011/02/16)
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- Incorporation of furan into low band-gap polymers for efficient solar cells
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The design, synthesis, and characterization of the first examples of furan-containing low band-gap polymers, PDPP2FT and PDPP3F, with substantial power conversion efficiencies in organic solar cells are reported. Inserting furan moieties in the backbone of the conjugated polymers enables the use of relatively small solubilizing side chains because of the significant contribution of the furan rings to overall polymer solubility in common organic solvents. Bulk heterojunction solar cells fabricated from furan-containing polymers and PC71BM as the acceptor showed power conversion efficiencies reaching 5.0%.
- Woo, Claire H.,Beaujuge, Pierre M.,Holcombe, Thomas W.,Lee, Olivia P.,Frechet, Jean M. J.
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supporting information; experimental part
p. 15547 - 15549
(2011/02/21)
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- PYRROLOPYRROLE DERIVATIVES, THEIR MANUFACTURE AND USE
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The present invention relates to compounds of the formula (I) wherein the substituents are as defined in claim 1, and their use as organic semiconductor in organic devices, like diodes, organic field effect transistors and/or a solar cells. The compounds of the formula I have excellent solubility in organic solvents. High efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when said compounds are used in semiconductor devices or organic photovoltaic (PV) devices (solar cells).
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Page/Page column 33; 34
(2009/05/30)
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- DIKETOPYRROLOPYRROLE POLYMERS AS ORGANIC SEMICONDUCTORS
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The present invention relates to polymers comprising a repeating unit of the formula (l) and their use as organic semiconductor in organic devices, especially a diode, an organic field effect transistor and/or a solar cell, or a device containing a diode and/or an organic field effect transistor, and/or a solar cell. The polymers according to the invention have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers according to the invention are used in semiconductor devices or organic photovoltaic (PV) devices (solar cells).
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Page/Page column 43
(2008/06/13)
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