- Synthesis and properties of air-stable n-channel semiconductors based on MEH-PPV derivatives containing benzo[c]cinnoline moieties
-
In this study we synthesized three novel poly[2-methoxy-5-(2-ethylhexyloxy) -1,4-phenylenevinylene] (MEH-PPV) derivatives that differ in terms of their ratios of heterocyclic benzo[c]cinnoline moieties: P50 containing only MEH-PPV/benzo[c]cinnolinevinylene (BZCV) alternating segments and P25 and P10 containing both MEH-PPV/BZCV alternating segments and MEH-PPV block segments. UV-Vis and PL spectra of these polymers revealed values of λUVmax and λPLmax that ranged from 440 to 489 and from 492 to 551 nm, respectively; these wavelengths blue-shifted upon incorporating additional benzo[c]cinnoline moieties. We also observed energy transfer from the MEH-PPV/BZCV alternating segments to the MEH-PPV block segments. P50, which featured an alternating structure in its main chain, displayed a solvatochromic effect, emitting green light in non-polar solvents and yellow light in polar solvents. The HOMO and LUMO energy levels of these polymers, measured using cyclic voltammetry, ranged from -5.11 to -5.62 and from -3.08 to -3.31 eV, respectively. The incorporation of electron-withdrawing benzo[c]cinnoline moieties enhanced the electron affinity and improved the oxidative stability of the polymers. A bottom-gate, top-contact organic field-effect transistor (OFET) based on P50 exhibited n-channel behavior under ambient conditions, with an electron mobility of 7.8 × 10-3 cm2 V-1 s-1 and an on/off ratio greater than 104. No significant variation in electron mobility can be observed after this OEFT was stored under ambient conditions up to 30 days. To the best of our knowledge, this is the first time that air-stable n-channel MEH-PPV derivatives have ever been reported. It indicated that p-type MEH-PPV can be transformed into n-type materials upon incorporation of benzo[c]cinnoline moieties. This journal is the Partner Organisations 2014.
- Chen, Jyh-Chien,Wu, Hsin-Chung,Chiang, Chi-Jui,Chen, Tuo,Xing, Li
-
-
Read Online
- Investigations on the electrochemical properties of new conjugated polymers containing benzo[c]cinnoline and oxadiazole moieties
-
A four-step route was designed to synthesize 3,8-benzo[c]cinnoline dicarboxylic acid (4). New conjugated polymers, POXD (I) and POXD (T), containing benzo[c]cinnoline and oxadiazole moieties, were obtained by thermal cyclodehydration of their soluble polyhydrazide precursors PHA (I) and PHA (T), respectively. Two reduction peaks were observed for these new conjugated polymers during CV cathodic scan. From the CV voltammograms combined with the results from molecular simulation, we concluded that the first reduction occurred at oxadiazole moiety and benzo[c]cinnoline moiety was responsible for the second reduction. It indicates that oxadiazole has stronger electron affinity than benzo[c]cinnoline. We proposed a mechanism to explain this two-stage reduction process. Due to the planar and electron-accepting ability of benzo[c]cinnoline and oxadiazole moieties, POXD (I) and POXD (T) exhibited very low LUMO (-3.42 and -3.45 eV) and HOMO (-6.23 and -6.27 eV) energy levels. They can be used as hole-blocking or electron-injection layers for OLED applications.
- Chen, Jyh-Chien,Wu, Hsin-Chung,Chiang, Chi-Jui,Peng, Li-Chia,Chen, Tuo,Xing, Li,Liu, Shun-Wei
-
-
Read Online
- Organic light-emitting device
-
An organic light-emitting device includes a first electrode and a second electrode facing the first electrode. An organic layer is disposed between the first electrode and the second electrode. The organic layer includes an emission layer, a first compound and a second compound.
- -
-
Page/Page column 187-188
(2021/07/08)
-
- Asymmetric pyrene derivatives comprising amine group including pyridinyl group and organic light-emitting diode including the same
-
The present invention relates to pyrene derivatives represented by the following chemical formula A or the following chemical formula B, and an organic light-emitting diode including the same, wherein substituents Py, Ar1 to Ar3, Z and m are the same as d
- -
-
Paragraph 0392-0396
(2021/04/20)
-
- PYRENE DERIVATIVES AND ORGANIC ELECTRO LUMINESCENT DEVICE COMPRISING SAME
-
The present invention relates to a pyrene based derivative compound of an asymmetric structure and an organic electroluminescent device comprising the same. The pyrene derivative according to the present invention is characterized by being represented by chemical formula A through chemical formula B. The pyrene derivative compound according to the present invention exhibits remarkably improved blue color purity as compared to an organic electroluminescent device using an existing pyrene based aryl amine derivative compound while being able to realize full color since life characteristic and luminance characteristic are excellent, thereby being able to be used in various display devices.
- -
-
Paragraph 0339; 0340-0343
(2020/04/10)
-
- Asymmetric pyrene derivatives comprising amine group including heteroaryl group and organic light-emitting diode including the same
-
The present invention relates to a pyrene derivative represented by [chemical formula A] or [chemical formula B], and an organic light emitting diode comprising the same, wherein substituents Py_1, Py_2, Ar_1, Ar_2, Z, and m are defined in the detailed de
- -
-
Paragraph 0341-0345
(2020/11/24)
-
- Asymmetric pyrene derivatives comprising heteroaryl amine group and organic light-emitting diode including the same
-
The present invention relates to a pyrene derivative represented by [chemical formula A] or [chemical formula B], and an organic light emitting diode comprising the same, wherein substituents Py, Het_1 to Het_3, Z, and m are defined in the detailed description of the invention.
- -
-
Paragraph 0405-0409
(2020/12/16)
-
- Asymmetric pyrene derivatives comprising aryl amine group and organic light-emitting diode including the same
-
The present invention relates to asymmetric pyrene derivatives represented by chemical formula A or chemical formula B and to an organic light-emitting device including the same, wherein substituents of Ar1, Ar2, Ar3, Ar4, Z and m are as defined in the detailed description of the present invention.
- -
-
Paragraph 0284-0288
(2020/12/18)
-
- Asymmetric pyrene derivatives comprising amine group including pyridinyl group and organic light-emitting diode including the same
-
The present invention relates to a pyrene derivative represented by Chemical formula A and an organic light emitting device comprising the same. The substituents Py1, Py2, Ar1, Ar2, Z, and m are as defined in the detailed description.
- -
-
Paragraph 0327; 0328-0331
(2021/01/29)
-
- Asymmetric pyrene derivatives comprising amine group including heteroaryl group and naphthyl group and organic light-emitting diode including the same
-
The present invention relates to a pyrene derivative represented by [chemical formula A] or [chemical formula B], and an organic light emitting diode comprising the same, wherein substituents Py_1, Py_2, Naph_1, and Naph_2, and m are as defined in the detailed description of the invention.
- -
-
Paragraph 0264-0268
(2021/02/02)
-
- Pyrene derivatives having substituted groups and organic light-emitting diode including the same
-
The present invention relates to a novel compound and an organic electroluminescent device comprising the same as luminous substances, and more specifically, to a novel compound represented by formula A or formula B and an organic electroluminescent device comprising the same.
- -
-
Paragraph 0206; 0207; 0231-0236
(2020/04/21)
-
- Compound taking benzo[c]cinnoline as receptor and application thereof
-
The invention discloses a compound taking benzo[c]cinnoline as a receptor, and belongs to the technical field of organic electroluminescent functional materials and devices. The structural general formula of the compound is shown as a formula (I), and in
- -
-
Paragraph 0041-0044
(2020/09/10)
-
- Compound, display panel and display device
-
The present invention belongs to the technical field of OLEDs, and provides an azapyrene compound having a structure represented by a chemical formula 1 (as shown in the specification), wherein X1-X4independently represent an N atom or C-Ra, 1-2 of X1-X4 are N atoms, X1 and X2 are not nitrogen atoms at the same time, and X3 and X4 are not nitrogen atoms at the same time; Ra is mainly selected from hydrogen, deuterium and Cl-C10 alkyl; Ar1 and Ar2 are each independently selected from a C6-C30 aryl group and a C3-C30 heteroaryl group; m and n are each independently selected from 0, 1, 2, 3, andm and n are not 0 at the same time; L1 and L2 are independently a single bond, a C6-C30 arylene group and a C3-C30 heteroarylene group; and p and q are each independently selected from 0, 1, 2. The compound has a high refractive index, can effectively improve the external quantum efficiency (EQE) of an organic light-emitting device when used as a CPL material, has a very small extinction coefficient in a blue light region (400-450 nm), hardly absorbs blue light, and is beneficial to improving the luminous efficiency. The invention further provides a display panel and a display device.
- -
-
Paragraph 0055-0059
(2020/05/14)
-
- Photophysical properties and optical power limiting ability of Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at different positions
-
Two series of Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at different positions have been synthesized. In the absorption spectra, the Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at 3,6-position have blue-shift with respect to the corresponding analogs bearing fluorene-type ligands with ethynyl units at 2,7-position, showing better transparency in the visible light region. Moreover, the Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at 3,6-position show stronger triplet emission than corresponding analogs bearing fluorene-type ligands with ethynyl units at 2,7-position in the photoluminescent (PL) spectra. Furthermore, these Pt(II) polyynes were applied to optical power limiting (OPL) field. The Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at 2,7-position show better OPL performance than the corresponding analogs with fluorene-type ligands of ethynyl units at 3,6-position. Therefore, changing the position of the ethynyl units in fluorene-type ligands can not only effectively control the photophysical properties of the Pt(II) polyynes, but also has an important effect on their OPL ability.
- Tian, Zhuanzhuan,Yang, Xiaolong,Liu, Boao,Zhong, Daokun,Zhou, Guijiang
-
supporting information
p. 28 - 36
(2019/06/05)
-
- Pyrene derivatives having substituted groups and organic light-emitting diode including the same
-
The present invention relates to a novel compound and an organic electroluminescent device including the same as luminous substances, and more specifically, to a novel compound represented by formula A or formula B and an organic electroluminescent device
- -
-
Paragraph 0207; 0208; 0233-0237
(2019/07/25)
-
- Pyrene derivative compounds and organic light-emitting diode including the same
-
PURPOSE: A pyrene derivative compound is provided to provide an organic electroluminescence device operable at low voltage and having improved luminous efficiency by having stable and excellent luminous properties. CONSTITUTION: A pyrene derivative compound is represented by chemical formula 1-5. An organic electroluminescence device comprises an anode, a cathode, an electroluminescent layer comprising the compound and inserted between the anode and the cathode. Between the anode and the cathode, one or more layers selected from a hole injection layer, a hole transport layer, an electron block layer, a hole block layer, an electron transport layer and an electron injection layer. The one or more layers are formed by a monomer evaporation method of a solution process.
- -
-
Paragraph 0122; 0141-0145
(2019/08/30)
-
- Pyrene derivatives having substituted cyclic amine groups and organic light-emitting diode including the same
-
The present invention relates to a novel compound and an organic electroluminescent device comprising the same as luminous substances, and more specifically, to a novel compound represented by formula A or formula B and an organic electroluminescent device comprising the same.
- -
-
Paragraph 0217; 0218; 0241-0246
(2019/08/30)
-
- Synthesis, Characterization, and Properties of Diazapyrenes via Bischler-Napieralski Reaction
-
Via Bischler-Napieralski cyclization of amide precursors as the key step, a series of diazapyrene derivatives were designed and successfully synthesized. Their crystal structures, optoelectronic properties, and acid-responsive feature were investigated, which demonstrated that the doping of nitrogen atoms to the pyrene framework remarkably modulates their physical and chemical properties.
- Han, Yi,Hu, Zhenzhu,Liu, Meifang,Li, Mengwei,Wang, Tingting,Chen, Yulan
-
p. 3953 - 3959
(2019/04/10)
-
- Double-(S, S - dioxo - dibenzo thiophene) and high output compound and its preparation method and application
-
The invention discloses a bi(S,S-dioxo-dibenzothiophene) five-membered ring compound and a preparation method and application thereof. The existence of bi-sulfuryl in the bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is more beneficial for improving the electron affinity of molecules. Alkyl chains are introduced on a five-membered ring, so that the solubility of monomers in an organic solvent can be obviously improved. The plane conjugacy of the compound is better, and is beneficial for the transmission of a current carrier. Higher D-A mutual effect existing in the molecules of the compound endows higher fluorescence of the material. The bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is synthesized and obtained through common organic chemistry reactions such as substitution reactions, Suzuki coupling and ring-closure reactions and oxidation reactions. The compound has good solubility in the organic solvent, and is suitable for solution processing. The compound has wide application prospects in the fields of organic luminescence display, organic photovoltaic cells and organic field-effect tubes.
- -
-
Paragraph 0044-0047
(2019/06/26)
-
- Compound, OLED display panel, and display device
-
The invention relates to the technical field of organic electroluminescent materials, and especially relates to a compound, an OLED display panel, and a display device. The provided compound has a structure represented by a formula (I) or a formula (II).
- -
-
Paragraph 0121; 0122
(2019/10/04)
-
- Deep-blue emitting poly(2′,3′,6′,7′-tetraoctyl-2,7-spirosilabifluorene) simultaneously with good color purity and high external quantum efficiency
-
A deep-blue emitting poly(2′,3′,6′,7′-tetraoctyl-2,7-spirosilabifluorene), namely PSSiBF, has been newly developed for PLEDs. Unlike the previously-reported alkyl-functionalized P27SiF, the unwanted aggregation can be effectively prevented in PSSiBF due t
- Xu, Xiushang,Bai, Keyan,Ding, Junqiao,Wang, Lixiang
-
-
- Optimal Binding of Acetylene to a Nitro-Decorated Metal-Organic Framework
-
We report the first example of crystallographic observation of acetylene binding to -NO2 groups in a metal-organic framework (MOF). Functionalization of MFM-102 with -NO2 groups on phenyl groups leads to a 15% reduction in BET surfac
- Duong, Thien D.,Sapchenko, Sergey A.,Da Silva, Ivan,Godfrey, Harry G. W.,Cheng, Yongqiang,Daemen, Luke L.,Manuel, Pascal,Ramirez-Cuesta, Anibal J.,Yang, Sihai,Schr?der, Martin
-
supporting information
p. 16006 - 16009
(2018/11/25)
-
- Flipping the Switch: Fast Photoisomerization in a Confined Environment
-
Stimuli-responsive materials are vital for addressing emerging demands in the advanced technology sector as well as current industrial challenges. Here, we report for the first time that coordinative integration of photoresponsive building blocks possessing photochromic spiropyran and diarylethene moieties within a rigid scaffold of metal-organic frameworks (MOFs) could control photophysics, in particular, cycloreversion kinetics, with a level of control that is not accessible in the solid state or solution. On the series of photoactive materials, we demonstrated for the first time that photoisomerization rates of photochromic compounds could be tuned within almost 2 orders of magnitude. Moreover, cycloreversion rates of photoresponsive derivatives could be modulated as a function of the framework structure. Furthermore, through MOF engineering we were able to achieve complete isomerization for coordinatively immobilized spiropyran derivatives, typically exhibiting limited photoswitching behavior in the solid state. For instance, spectroscopic analysis revealed that the novel monosubstituted spiropyran derivative grafted to the backbone of the MOF pillar exhibits a remarkable photoisomerization rate of 0.16 s-1, typical for cycloreversion in solution. We also applied the acquired fundamental principles toward mapping of changes in material properties, which could provide a pathway for monitoring material aging or structural deterioration.
- Williams, Derek E.,Martin, Corey R.,Dolgopolova, Ekaterina A.,Swifton, Anton,Godfrey, Danielle C.,Ejegbavwo, Otega A.,Pellechia, Perry J.,Smith, Mark D.,Shustova, Natalia B.
-
supporting information
p. 7611 - 7622
(2018/06/06)
-
- COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
-
A compound having a high glass transition temperature, high electric stability, and/or high luminescent efficiency, and an organic light-emitting device including an emitting layer including the compound, which is represented by Formula 1: In Formula 1, A may be a moiety formed by fusing a substituted or unsubstituted indole group, as represented by Formula 1-1: When the compound represented by Formula 1 is used as a material for an emitting layer, an organic light emitting device including the compound may exhibit decreased driving voltage and improved efficiency and lifespan, as compared to OLEDs containing compounds that are available in the related art.
- -
-
Paragraph 0223-0224
(2017/03/28)
-
- Facile synthesis of a hole transporting material with a silafluorene core for efficient mesoscopic CH3NH3PbI3 perovskite solar cells
-
A novel electron-rich small-molecule, 4,4′-(5,5-dihexyl-5H-dibenzo[b,d]silole-3,7-diyl)bis(N,N-bis(4-methoxyphenyl)aniline) (S101), containing silafluorene as the core with arylamine side groups, has been synthesized via a short efficient route. When S101 was incorporated into a CH3NH3PbI3 perovskite solar cell as a hole transporting material (HTM), a short circuit photocurrent density (Jsc) of 18.9 mA cm-2, an open circuit voltage (Voc) of 0.92 V, and a fill factor (FF) of 0.65 contributing to an overall power conversion efficiency (PCE) of ~11% which is comparable to the PCE obtained using the current state-of-the-art HTM 2,2′,7,7′-tetrakis(N,N′-di-p-methoxyphenylamine)-9,9′-spirobifluorene (spiro-OMeTAD) (η = 12.3%) were obtained. S101 is thus a promising HTM with the potential to replace the expensive spiro-OMeTAD due to its comparable performance and much simpler and less expensive synthesis route.
- Krishna, Anurag,Sabba, Dharani,Yin, Jun,Bruno, Annalisa,Antila, Liisa J.,Soci, Cesare,Mhaisalkar, Subodh,Grimsdale, Andrew C.
-
supporting information
p. 8750 - 8754
(2016/06/14)
-
- To induce the aggregation of silicon fluorene-based light-emitting molecule and its preparation method and application
-
The invention discloses a silafluorene-based aggregation-induced emission molecule as well as a preparation method and application thereof. The general structural formula of the silafluorene-based aggregation-induced emission molecule is as shown in the s
- -
-
Paragraph 0026; 0027
(2017/05/05)
-
- New organic electroluminescent compounds and the use of the compound of the organic electroluminescent device
-
Provided are a novel organic electroluminescent compound and an organic electroluminescent device using the same. When used as a host material of an organic electroluminescent material of an OLED device, the organic electroluminescent compound disclosed herein exhibits good luminous efficiency and excellent life property as compared to the existing host material. Therefore, it may be used to manufacture OLEDs having very superior operation life.
- -
-
Paragraph 0067; 0068; 0069
(2016/10/07)
-
- Water-soluble poly(2,7-dibenzosilole) as an ultra-bright fluorescent label for antibody-based flow cytometry
-
A series of novel water-soluble PEGylated dibenzosilole-based conjugated polymers were prepared as ultra-bright fluorescent labels for biomolecules. Due to their superior solubility and brightness, antibody conjugates labeled with functionalized polymers
- Wang, Xin,Hu, Yi-Zhen,Chen, Aimei,Wu, Yexin,Aggeler, Robert,Low, Quentin,Kang, Hee Chol,Gee, Kyle R.
-
supporting information
p. 4022 - 4024
(2016/03/15)
-
- New AIEgens containing tetraphenylethene and silole moieties: Tunable intramolecular conjugation, aggregation-induced emission characteristics and good device performance
-
Three aggregation-induced emission luminogens (Si-pTPE, Si-tPE and Si-mTPE) were successfully obtained by the covalent incorporation of tetraphenylethene into a dibenzosilole core. Through sharing a benzene ring and changing the linkage mode between TPE a
- Yang, Jie,Sun, Ning,Huang, Jing,Li, Qianqian,Peng, Qian,Tang, Xi,Dong, Yongqiang,Ma, Dongge,Li, Zhen
-
p. 2624 - 2631
(2015/03/18)
-
- Novel organic electroluminescent compounds and organic electroluminescent device using the same
-
The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device containing the same. More specifically, the organic light-emitting compound according to the present invention is selected from the following chemical formula 1 to 6. andlt;Img id = andPrime;i0030andPrime; he = andPrime;86andPrime; wi = andPrime;125andPrime; file = andPrime;pat00030.jpgandPrime; img-format = andPrime;jpgandPrime; /andgt; [In formula 1 to 6, X and Y are each independently selected from N (R_1), C (R_2) (R_3) and Si (R_4) (R_5), wherein one of either X or Y must be N (R_1); the other is C (R_2) (R_3) or Si (R_4) (R_5); and Z_1 to Z_8 are each independently selected from C (R_6) and N, wherein R_6 can be different from each other and adjacent R_6 may be bonded to each other to form a ring.] The organic light-emitting compound according to the present invention is used as a host material of the organic light-emitting material in OLED devices and shows good luminous efficiency and excellent life properties of material, compared with conventional host materials, thereby being advantageous in producing an OLED having a very good operating life.COPYRIGHT KIPO 2015
- -
-
Paragraph 0059-0061
(2017/04/14)
-
- Synthesis and characterization of arylamino end-capped silafluorenes for blue to deep-blue organic light-emitting diodes (OLEDs)
-
Diphenylamino- or cabazolyl-endcapped silafluorene derivatives which show a wide energy band gap, a high fluorescence quantum yield and high stability have been designed, synthesized, and characterized. Double layer electroluminescent devices of these silafluorene derivatives exhibited efficient blue emission. The non-doped double layer OLEDs containing TDMS, TDPS, CDMS, or CDPS exhibited better electroluminescence efficiencies than those of the devices using the reference emitter DPFL-NPB, among which the best device was with TDPS, which showed a maximum current efficiency of 1.62 cd A-1 and an external quantum efficiency (EQE) of 1.36%. The solution processed device using TDPS as dopant exhibited a high performance with an EQE of 2.48% and an obviously low turn-on voltage of 4 V, when compared to the results of the reference device. The replacement of the carbon atom of the fluorene unit with a silicon atom could lower the energy gap effectively and improve the thermal stability as well as optical performances. The results indicate that the end-capped arylamino groups affect the organic light-emitting diode (OLED) performances greatly and aryl or alkyl substitution on the 9-position of a silafluorene unit is also crucial to the OLED performances of this kind of silafluorene.
- Chen, Shao Fu,Tian, Yuan,Peng, Jinghong,Zhang, Huarong,Feng, Xin Jiang,Zhang, Haixia,Xu, Xinjun,Li, Lidong,Gao, Jianhua
-
supporting information
p. 6822 - 6830
(2015/07/02)
-
- Bottom-Up Synthesis of Necklace-Like Graphene Nanoribbons
-
Graphene nanoribbons (GNRs) with an unprecedented "necklace-like" structure were synthesized through a bottom-up chemical approach, based on the oxidative cyclodehydrogenation of tailor-made polyphenylene precursors. A polycyclic aromatic hydrocarbon cons
- Schwab, Matthias Georg,Narita, Akimitsu,Osella, Silvio,Hu, Yunbin,Maghsoumi, Ali,Mavrinsky, Alexey,Pisula, Wojciech,Castiglioni, Chiara,Tommasini, Matteo,Beljonne, David,Feng, Xinliang,Müllen, Klaus
-
supporting information
p. 2134 - 2138
(2015/10/05)
-
- Cyclic kinetics during thermal equilibration of an axially chiral bis-spiropyran
-
A compound combining the features of a molecular rotor and a photoswitch was synthesized and was shown to exist as three diastereomers, which interconvert via a reversible cyclic reaction scheme. Each of the three diastereomers was isolated, and by following the equilibration kinetics, activation barriers for all reactions were calculated. The results indicate that the properties of molecular switches depend heavily on their immediate chemical environment. The conclusions are important in the context of designing new switchable molecules and materials.
- Kundu, Pintu K.,Lerner, Avishai,Ku?anda, Kristina,Leitus, Gregory,Klajn, Rafal
-
supporting information
p. 11276 - 11279
(2014/10/15)
-
- The tuning of the energy levels of dibenzosilole copolymers and applications in organic electronics
-
An understanding of the structure-function relationships of conjugated polymers is an invaluable resource for the successful design of new materials for use in organic electronics. To this end, we report the synthesis, characterisation and optoelectronic properties of a range of new alternating copolymers of dibenzosilole. Suzuki polycondensation reactions were used to afford a series of eight conjugated materials by the respective combination of either a 3,6- or 2,7-linked 9,9-dioctyldibenzosilole with 3,6-linked-N- octylcarbazole, triarylamine, oxadiazole and triazole monomers. The copolymers were fully characterised using 1H, 13C{1H} NMR spectroscopy, size exclusion chromatography (SEC), differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The photophysical properties were determined using UV-Vis spectroscopy, photoluminescence (PL) measurements, cyclic voltammetry (CV) and photoelectron emission spectroscopy in air (PESA). The spectroscopic and electrochemical measurements were used to determine the materials' HOMO and LUMO energies and the values were correlated with the copolymer composition and structure. A selection of the copolymers (P4, P5 and P8) were evaluated as the active layer within single-layer polymer light emitting diodes (PLEDs), with the configuration: glass/ITO/PEDOT:PSS/emissive layer/Ba/Al, which gave low intensity electroluminescence. The selected copolymers were also evaluated as the organic semiconductor in bottom-gate, bottom-contact organic field effect transistors (OFETs). The best performing devices gave a maximum mobility of 3 × 10-4 cm2 V-1 s-1 and on/off current ratios of 105. The Royal Society of Chemistry 2011.
- Keyworth, Colin W.,Chan, Khai Leok,Labram, John G.,Anthopoulos, Thomas D.,Watkins, Scott E.,McKiernan, Mary,White, Andrew J. P.,Holmes, Andrew B.,Williams, Charlotte K.
-
supporting information; experimental part
p. 11800 - 11814
(2011/11/07)
-
- ELECTRON DONATING ORGANIC MATERIAL, MATERIAL FOR PHOTOVOLTAIC ELEMENT, AND PHOTOVOLTAIC ELEMENT
-
The invention aims at providing a photovoltaic device with high photoelectric conversion efficiency. The aim is attained by an electron donating organic material containing a benzothiadiazole compound in which (a) a benzothiadiazole skeleton and an oligothiophene skeleton are contained, (b) a band gap (Eg) is 1.8 eV or less, and (c) the level of the highest occupied molecular orbital (HOMO) is -4.8 eV or less, wherein said benzothiadiazole compound is formed by covalently combining the benzothiadiazole skeleton and the oligothiophene skeleton alternately, the proportion between the benzothiadiazole skeleton and the oligothiophene skeleton is within a range of 1:1 to 1:2 (however, excluding 1:1), and the number of thiophene rings contained in an oligothiophene skeleton is 3 or more and 12 or less.
- -
-
Page/Page column 43-45
(2011/01/12)
-
- Synthesis, characterization, and transistor response of semiconducting silole polymers with substantial hole mobility and air stability. Experiment and theory
-
Realizing p-channel semiconducting polymers with good hole mobility, solution processibility, and air stability is an important step forward in the chemical manipulation of charge transport in polymeric solids and in the development of low-cost printed electronics. We report here the synthesis and full characterization of the dithienosilole- and dibenzosilole-based homopolymers, poly(4,4-di-n-hexyldithienosilole) (TS6) and poly(9,9-di-n- octyldibenzosilole) (BS8), and their mono- and bithiophene copolymers, poly(4,4-di-n-hexyldithienosilole-alt-(bi)thiophene) (TS6T1, TS6T2) and poly(9,9-di-n-octyldibenzosilole-alt-(bi)thiophene) (BS8T1,BS8T2), and examine in detail the consequences of introducing dithienosilole and dibenzosilole cores into a thiophene polymer backbone. We demonstrate air-stable thin-film transistors (TFTs) fabricated under ambient conditions having hole mobilities as large as 0.08 cm2/V·s, low turn-on voltages, and current on/off ratios > 106. Additionally, unencapsulated TFTs fabricated under ambient conditions are air-stable, an important advance over regioregular poly(3-hexylthiophene) (P3HT)-based devices. Density functional theory calculations provide detailed insight into the polymer physicochemical and charge transport characteristics. A direct correlation between the hole injection barrier and both TFT turn-on voltage and TFT polymer hole mobility is identified and discussed, in combination with thin-film morphological characteristics, to explain the observed OTFT performance trends.
- Lu, Gang,Usta, Hakan,Risko, Chad,Wang, Lian,Facchetti, Antonio,Ratner, Mark A.,Marks, Tobin J.
-
p. 7670 - 7685
(2008/12/22)
-
- Dithienosilole- and dibenzosilole-thiophene copolymers as semiconductors for organic thin-film transistors
-
The synthesis and physicochemical properties of a new class of thiophene/arenesilole-containing π-conjugated polymers are reported. Examples of this new polymer class include the following: poly(2,5-bis(3′,3′′-dihexylsilylene-2′,2′′-bithieno)thiophene) (TS6T1), poly(2,5′-bis(3′′,3′″-dihexylsilylene-2′′,2′″-bithieno)bithiophene) (TS6T2), poly(2,5′-bis(2′′,2′″-dioctylsilylene-1′′,1′″-biphenyl)thiophene) (BS8T1), and poly(2,5′-bis(2′′,2′″-dioctylsilylene-1′′,1′″-biphenyl)bithiophene) (BS8T2). Organic field-effect transistors (OFETs) with hole carrier mobilities as high as 0.02-0.06 cm2/V s in air, low turn-on voltages, and current on/off ratios >105-106 are fabricated using solution processing techniques with the above polymers as the active channel layer. OFETs based on this polymer class exhibit excellent ambient operational stability. Copyright
- Usta, Hakan,Lu, Gang,Facchetti, Antonio,Marks, Tobin J.
-
p. 9034 - 9035
(2007/10/03)
-
- Alternating copolymers of N-(2-ethylhexyl)-carbazole derivatives with aniline units: Synthesis and properties
-
Alternating copolymers such as P(3,6-EHCZ-alt-Al), P(Bis-EHCZ-alt-Al) and P(2,7-EHCZ-alt-Al), based on blue-emitting carbazole and hole-transporting triarylamine units in the polymer backbone, were successfully synthesized by using palladium-catalyzed polycondensation reaction. P(Bis-EHCZ-alt-Al) exhibited blue shift both in UV-Vis absorption and PL emission, while P(2,7-EHCZ-alt-Al) showed red shift in UV-Vis absorption and blue shift in PL emission, compared to P(3,6-EHCZ-alt-Al). It was observed from the optical and electrochemical characterization that band gap energy (2.91~3.07 eV) and HOMO (-5.25~5.11 eV) levels of the copolymers could be fine-tuned by the carbazole content in the repeating unit and different reaction linkage on the carbazole ring.
- Wang, Hui,Ryu, Jeong-Tak,Han, Yoon Soo,Kim, Dae-Hwan,Choi, Byeong Dae,Park, Lee Soon,Kwon, Younghwan
-
p. 85/[365]-94/[374]
(2007/10/03)
-
- Poly(2,7-dibenzosilole): A blue light emitting polymer
-
2,7-Disubstituted dibenzosilole monomers have been prepared by the selective trans-lithiation of 4,4′-dibromo-2,2′-diiodobiphenyl followed by silylation with dichlorodihexylsilane. Suzuki copolymerization of dibromo and bis(boronate) monomers afforded poly(9,9-dihexyl-2,7-dibenzosilole) which showed better efficiency than the corresponding polyfluorene in a single layer light emitting device. Preliminary studies demonstrated this to be a promising blue light emitting polymer. Copyright
- Chan, Khai Leok,McKiernan, Mary J.,Towns, Carl R.,Holmes, Andrew B.
-
p. 7662 - 7663
(2007/10/03)
-
- Materials for injecting or transporting holes and organic electroluminescence devices using the same
-
The present invention relates to a novel compound that can significantly improve the lifespan, efficiency and thermal stability of an organic light emitting device, and to an organic electroluminescence device or light emitting device comprising the compound in an organic compound layer is also disclosed.
- -
-
-
- Biphenyl- and fluorenyl-based potential molecular electronic devices
-
New potential molecular electronics devices have been synthesized based on our knowledge of systems that we previously studied. Research has shown that simple molecular systems demonstrate negative differential resistance (NDR) and memory characteristics. The new molecules rely primarily on the redox properties of the compounds to improve upon the solid-state characteristics already observed. Electrochemical tests have been performed in order to evaluate the redox properties with the hope that the electrochemical results can be used as a predictive tool to evaluate the usefulness of those compounds in device configurations.
- Price Jr., David W.,Tour, James M.
-
p. 3131 - 3156
(2007/10/03)
-
- Synthesis of indoles via palladium[0]-mediated ullmann cross-coupling of o-halonitroarenes with α-halo-enones or -enals
-
(Matrix presented) Palladium[0]-mediated Ullmann cross-coupling of o-halonitrobenzene (1) and various related nitroarenes with a range of α-halo-enones (e.g., 2) or -enals readily affords the expected α-arylenones, e.g., 3, or -enals, which are converted into the corresponding indoles, e.g., 4, on reaction with dihydrogen in the presence of Pd on C.
- Banwell, Martin G.,Kelly, Brian D.,Kokas, Okanya J.,Lupton, David W.
-
p. 2497 - 2500
(2007/10/03)
-
- Dicationic dibenzofuran and dibenzothiophene compounds and methods of use thereof
-
Methods of treating Pneumocystis carinii pneumonia comprise administering a therapeutically effective amount of a dicationic dibenzofuran compound described by Formula (I). Methods of treating Pneumocystis carinii pneumonia also comprise administering a therapeutically effective amount of a dicationic dibenzothiophene compound described by Formula (II). Novel compounds are also disclosed, and are represented by the Formulae (I) and (II).
- -
-
-
- Synthesis and preliminary testing of molecular wires and devices
-
Presented here are several convergent synthetic routes to conjugated oligo(phenylene ethynylene)s. Some of these oligomers are free of functional groups, while others possess donor groups, acceptor groups, porphyrin interiors, and other heterocyclic interiors for various potential transmission and digital device applications. The syntheses of oligo(phenylene ethynylene)s with a variety of end groups for attachment to numerous metal probes and surfaces are presented. Some of the functionalized molecular systems showed linear, wire-like, current versus voltage (I(V)) responses, while others exhibited nonlinear I(V) curves for negative differential resistance (NDR) and molecular random access memory effects. Finally, the syntheses of functionalized oligomers are described that can form self-assembled monolayers on metallic electrodes that reduce the Schottky barriers. Information from the Schottky barrier studies can provide useful insight into molecular alligator clip optimizations for molecuar electronics.
- Tour, James M.,Rawlett, Adam M.,Kozaki, Masatoshi,Yao, Yuxing,Jagessar, Raymond C.,Dirk, Shawn M.,Price, David W.,Reed, Mark A.,Zhou, Chong-Wu,Chen, Jia,Wang, Wenyong,Campbell, Ian
-
p. 5118 - 5134
(2007/10/03)
-
- Dicationic dibenzofuran derivatives as anti-Pneumocystis carinii pneumonia agents: Synthesis, DNA binding affinity, and anti-P. carinii activity in an immunosuppressed rat model
-
Previous work from our laboratory shows that compounds with two cations linked by a carbazole spacer were highly potent anti-P. carinii agents. A prodrug approach designed to increase oral activity of the dicationic carbazoles by converting amidine groups to amidoxime groups was unsuccessful. The ring nitrogen was implicated as playing a role in the lack of activity of carbazole amidoximes. The current study was designed to determine if replacement of the carbazole ring nitrogen by isosteric oxygen to form dibenzofurans would improve effectiveness of amidoxime prodrugs. Eight dibenzofuran dicationic derivatives were synthesized and evaluated for anti- P. carinii activity in an immunosuppressed rat model. Since DNA binding has been hypothesized to play a key role in antimicrobial activity of dicationic compounds, the compounds were examined for their binding affinity to calf thymus DNA and a poly-dA·poly-dT oligomer. While several of the compounds were more potent anti-P. carinii agents than pentamidine, the corresponding amidoximes were significantly less effective than the amidoxime of pentamidine. No direct quantitative correlation was determined between DNA binding affinity and anti-P. carinii activity, but all active compounds were strong DNA binding agents.
- Wang, Sihe,Hall, James Edwin,Tanious, Farial A.,Wilson, W. David,Patrick, Donald A.,McCurdy, Donald R.,Bender, Brenden C.,Tidwell, Richard R.
-
p. 215 - 224
(2007/10/03)
-