217-19-6

Usage

Uses

Used in Semiconductor Industry:
Naphtho[1,2-b:5,6-b']dithiophene is used as a semiconducting material for the synthesis of copolymers. These copolymers exhibit the highest mobility (>0.5 cm2 /Vs) in an NDT-based OFET (Organic Field-Effect Transistor) device to date, which is crucial for enhancing the performance and efficiency of these devices.

Upstream product

• 1207732-05-5 1,5-dichloro-6-(trifluoromethanesulfonyloxy)naphthalen-2-yl trifluoromethanesulfonate 
• 132178-76-8 1,5-dichloro-2,6-dihydroxynaphthalene 
• 581-43-1 2.6-dihydroxynaphthalene 
• 1207732-06-6 1,5-dichloronaphthalene-2,6-diyl bis(ethyne-2,1-diyl)bis(trimethylsilane) 

Relevant academic research and scientific papers

A new 2D-naphtho[1,2-b:5,6-b']dithiophene based donor small molecules for bulk-heterojunction organic solar cells

We present design and synthesis of three new symmetrical and linear A-D-A type π-conjugated donor small molecules (2D-NDT(TPD)2, 2D-NDT(Ester)2 and 2D-NDT(Amide)2) containing two dimensional (2D) naphthodithiophene (NDT) unit as the central donor core, end-capped with electron deficient unit such as thieno[3,4c]pyrrole-4,6-dione (TPD), 2-ethylhexyl 2-cyanoacetate (Ester) and 2-cyano-N-(2-ethylhexyl)acetamide (Amide) group respectively. We characterized these small molecules and further investigated the optical, electrochemical, morphological and photovoltaic properties. When solution–processed bulk heterojunction organic solar cells are fabricated using these small molecules, the morphology of 2D-NDT(Ester)2 or 2D-NDT(Amide)2 and [6,6]-PhenylC71-butyric acid methyl ester (PC71BM) blend film was optimized using 1,8 Diiodooctane (DIO) additive. DIO additive promotes the formation of nanoscopically well-connected molecular domains in the active blend film. A device based on (1% DIO, 1:1) 2D-NDT(Ester)2:PC71BM exhibited highest the efficiency of 1.22% with a short-circuit density (Jsc) of 3.75 mA/cm2, an open circuit voltage (Voc) of 0.91 V and fill factor (FF) of 35.50. Similarly for (1% DIO, 1:3) 2D-NDT(Amide)2:PC71BM device efficiency of 0.55%, with Jsc of 2.36 mA/cm2, Voc of 0.64 V and FF of 36.95 was observed. Whereas for (1:2) 2D-NDT(TPD)2:PC71BM device, due to the improper blending and phase separation between donor and acceptor efficiency restricted to 0.33% with Jsc of 1.66 mA/cm2, Voc of 0.73 V and FF of 27.2.

ORGANIC COMPOUND FOR ORGANIC EL DEVICE AND USING THE SAME

wherein A is an electron acceptor moiety, B represents a fused ring hydrocarbon units with two or three rings; m, n, L, and X are the same definition as described in the present invention.

Development of novel naphtho[1,2-b:5,6-b′]dithiophene and thieno[3,4-c]pyrrole-4,6-dione based small molecules for bulk-heterojunction organic solar cells

Two new small molecules, composed of naphthodithiophene (NDT) donor core and thienopyrroledione (TPD) group acceptor group end-capped with and without an alkyl-bithiophene, defined as NDT(TPD)2 and NDT(TPDTT)2 were designed and synthesized by stille coupling reactions. The thermal and electrochemical analyses carried out for both the small molecules revealed good thermal stability along with high decomposition temperature (>350?°C). NDT(TPD)2 showed a deep HOMO level (?5.38?eV), compared to slightly upshifted HOMO (?5.26?eV) of NDT(TPDTT)2. While X-ray diffractometry suggests crystalline and amorphous nature of NDT(TPD)2 and NDT(TPDTT)2 respectively, the space charge limited current analysis revealed high hole mobility in the former and appreciable charge balance in the later. The conventional organic solar cell (OSC) devices fabricated using NDT(TPD)2 and NDT(TPDTT)2 as donor show power conversion efficiency (PCE) of 0.26% and 0.8% respectively. While NDT(TPDTT)2 device after blending with additive, owing to the improved D-A heterojunction yielded maximum PCE of 1.31% resulting from enhanced Jsc 3.32?mA/cm2, Voc 0.75?V and FF of 52.44.

Organic compound and Light emitting diode and Organic light emitting diode display device using the same

Provided in the present invention is an organic compound having excellent hole injecting properties and electric-charge producing properties, and having a structure in which an electron withdrawing group is substituted for a naphtho[1,2-b:5,6-bandprime;]d

Modulation of electronic properties of π-conjugated copolymers derived from naphtho[1,2-b:5,6-b′]dithiophene donor unit: A structure-property relationship study

A set of three donor-acceptor conjugated (D-A) copolymers were designed and synthesized via Stille cross-coupling reactions with the aim of modulating the optical and electronic properties of a newly emerged naphtho[1,2-b:5,6-b′] dithiophene donor unit for polymer solar cell (PSCs) applications. The PTNDTT-BT, PTNDTT-BTz, and PTNDTT-DPP polymers incorporated naphtho[1,2-b:5,6- b′]dithiophene (NDT) as the donor and 2,2′-bithiazole (BTz), benzo[1,2,5]thiadiazole (BT), and pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP), as the acceptor units. A number of experimental techniques such as differential scanning calorimetry, thermogravimetry, UV-vis absorption spectroscopy, cyclic voltammetry, X-ray diffraction, and atomic force microscopy were used to determine the thermal, optical, electrochemical, and morphological properties of the copolymers. By introducing acceptors of varying electron withdrawing strengths, the optical band gaps of these copolymers were effectively tuned between 1.58 and 1.9 eV and their HOMO and LUMO energy levels were varied between -5.14 to -5.26 eV and -3.13 to -3.5 eV, respectively. The spin-coated polymer thin film exhibited p-channel field-effect transistor properties with hole mobilities of 2.73 × 10-3 to 7.9 × 10-5 cm2 V-1 s-1. Initial bulk-heterojunction PSCs fabricated using the copolymers as electron donor materials and [6,6]-phenyl C71 butyric acid methyl ester (PC71BM) as the acceptor resulted in power conversion efficiencies in the range of 0.67-1.67%.

Development of naphtho[1,2-b:5,6-b′]dithiophene based novel small molecules for efficient bulk-heterojunction organic solar cells

Two new small molecules with a rigid planar naphtho[1,2-b:5,6-b′] dithiophene (NDT) unit were designed and synthesized. Solution processed bulk-hetereojunction organic solar cells based on blends of the small molecules and [6,6]-phenyl-C71-buty

A crystalline D-π-A organic small molecule with naphtho[1,2-b:5,6- b′]dithiophene-core for solution processed organic solar cells

In this work, we have designed and synthesized a new naphtho[1,2-b:5,6- b′]dithiophene-containing enlarged π-conjugated donor-acceptor (D-A) small molecule, NDT(TTz)2, for use in solution-processed organic photovoltaics. NDT(TTz)2, which contains a thiophene-bridged naphtho[1,2-b:5,6-b′]dithiophene as the central fused core and triphenylamine-flanked thiophene thiazolothiazole as a spacer, was synthesized via sequential Suzuki and Stille coupling reactions. The thermal, physiochemical, and electrochemical properties of NDT(TTz)2 have been evaluated by differential scanning calorimetry, thermogravimetry, UV-Vis spectroscopy, photoluminescence spectroscopy, X-ray diffraction, and cyclic voltammetry. As desired for photovoltaic applications, NDT(TTz)2 possesses good solubility, thermal stability, and a well-ordered, π-π stacked, crystallinity. The optical band gap and HOMO level of NDT(TTz) 2 were determined to be 2.0 eV and -5.23 eV, respectively. In addition to organic thin film transistor studies, application of NDT(TTz) 2 to preliminary photovoltaic devices has also been investigated by fabricating solution-processed bulk heterojunction solar cells together with PC71BM in a typical layered device structure, ITO/PEDOT:PSS/NDT(TTz) 2:PC71BM/LiF/Al. Without extensive optimization of the device, NDT(TTz)2 in these devices shows a maximum power conversion efficiency of 1.44% under AM 1.5 illumination at a 100 mW/cm2 intensity.

Novel Compound, Method of Producing the Compound, Organic Semiconductor Material and Organic Semiconductor Device

There are provided a novel compound having a good field mobility, a method of producing of the compound, an organic semiconductor material containing the novel compound, and an organic semiconductor device. The novel compound which is represented by the following general formula (1), (2), (3) or (4) (where Z represents a sulfur atom or a selenium atom, and R represents a hydrogen atom, an alkyl group or a phenyl group in general formulae) has a structure having two benzene rings of naphthalene bonded with a thiophene ring and a selenophene ring, respectively. These compounds have a conjugate system in molecules due to an interaction between it orbitals, and show a strong molecular interaction through a sulfur atom or a selenium atom contained in a thiophene ring or a selenophene ring in each molecule, thereby having a good field mobility.

Synthesis, properties, crystal structures, and semiconductor characteristics of naphtho[1,2-b:5,6-b′]dithiophene and -diselenophene derivatives

(Chemical Equation Presented) In this paper we present the synthesis, structures, characterization, and applications to field-effect transistors (FETs) of naphtho[1,2-b:5,6-b′]dithiophene (NDT) and -diselenophene (NDS) derivatives. Treatment of 1,5-dichloro-2,6-diethynylnaphthalenes, easily derived from commercially available 2,6-dihydroxynaphthalene, with sodium chalcogenide afforded a straightforward access toNDTsand NDSsincluding the parent and dioctyl and diphenyl derivatives. Physicochemical evaluations ofNDT and NDS derivatives showed that these heteroarenes have a similar electronic structure with isomeric [1]benzothieno[2,3-b][1]benzothiophene (BTBT) and [1] benzoselenopheneno[2,3-b][1]benzoselenophene (BSBS) derivatives, respectively. Although attempts to fabricate solution-processed field-effect transistors (FETs) with soluble dioctyl-NDT (C8-NDT) and -NDS (C8-NDS) failed, diphenyl derivatives (DPh-NDTand DPh-NDS) afforded vapor-processed FETs showing field-effect mobility as high as 0.7 cm2 V-1 s-1. These results indicated that NDT and NDS are new potential heteroarene core structures for organic semiconducting materials. 2010 American Chemical Society.