Heterocycle-substituted poly(p-phenylene vinylene) for light-emitting devices

Yin, Shougen; Peng, Junbiao; Li, Chenxi; Huang, Wengqiang; Liu, Xingyuan; Li, Wenlian; He, Binglin

doi:10.1016/s0379-6779(97)04111-8

Cited by 62 publications

(3 citation statements)

References 10 publications

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“…The synthesis is shown in Figure 10 The oxadiazole moiety can be introduced in a sequence of several steps in the backbone of poly(p-phenylene vinylene) (PPV). 17,18 The re- action scheme is shown in Figure 10.5. Oligomers are obtained, which are soluble in both chloroform and tetrahydrofuran.…”

Section: Polycondensationmentioning

confidence: 99%

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Poly(oxadiazole)s

Fink

2008

High Performance Polymers

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Section: Polycondensationmentioning

confidence: 99%

“…43 The oxadiazole group may be part of the polymeric backbone, together with carbazole moieties or phenylene vinylene moieties. 14,17 Crosslinkable oxadiazole monomers with pending acrylic units have been described. 7 The synthesis is shown in Figure 10.2.…”

Section: Light-emitting Devicesmentioning

confidence: 99%

Poly(oxadiazole)s

Fink

2008

High Performance Polymers

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“…34,35 M-3 was synthesized by the starting products p-toluic acid (Scheme 2), and 4-6 were obtained according to the literature. 36,37 Bisphosphonium salts of 6 in refluxing toluene failed due to the poor solubility of the two salts. It only afforded the monophosphonium salts in the form of a white precipitate in a quantitative yield.…”

Section: Syntheses Of the Monomersmentioning

confidence: 99%

Synthesis and Characterization of Polybinaphthyls Incorporating Chiral (R) or (S)-2,2′-Binaphthyl Entities by Heck Reaction

Cheng

Chen

Song

et al. 2005

Polym J

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ABSTRACT:Four chiral conjugated polymer-1 (P-1), polymer-2 (P-2), polymer-3 (P-3) and polymer-4 (P-4) were obtained by the polymerization of (S)-6,60 -dibromo-2,2 0 -bisbutoxy-1,1 0 -binaphthyl ((S)-M-1) and (R)-6,6 0 -dibromo-2,2 0 -bisbutoxy-1,1 0 -binaphthyl ((R)-M-1) with 1,4-divinyl-2,5-dibutoxybenzene (M-2) and 1,3,4-oxadiazole-2,5- 1-4 (R) or (S)-1,1 0 -binaphthol (BINOL) have often been used as the starting materials for obtaining chiral binaphthyl compounds. The 2,2 0 -hydroxyl groups of BINOL can be easily converted into other functional groups and the 3,3 0 -and 6,6 0 -positions of binaphthyl skeletal structure of BINOL can be selectively functionalized at the well-defined molecular level, leading to a variety of binaphthyl derivatives which can exhibit remarkably stable chiral configuration as well as high chiral induction in molecular recognition, 5-9 asymmetric processes.10-15 These rigid and sterically chiral polybinaphthyl polymers also represent a new generation of materials for applications in chiral sensors, polarized light emission and nonlinear optical materials. [16][17][18][19][20] Conjugated polymers with rigid -systems often possess poor solubility, which seriously inhibits full structural elucidations and property investigations. We choose M-2 and M-3 as the conjugated molecular bridge linkers. Oxadiazole derivatives have been widely used as electron transporting/hole blocking materials in LED devices and LED blends because oxadiazole unit has many excellent properties on the better chromophore, high thermal and oxidative stability, and the good charge injection and transporting building blocks. [21][22][23] In our paper, M-3, 1,3,4-oxadiazole-2,5-bis(4-vinylbenzene) is introduced into the chiral polymers main chain backbone to maintain conjugation between the oxadiazole and binaphthyl segments so that the electron transporting properties of the polymers may be improved. In addition, by introducing oxadiazole, an electron deficient moiety into the main chain, the electron density may shift away from the vinyl bond, which could increase the stability of the resulting chiral polymers. 24,25 To make soluble conjugated polymers, the alkyl groups substitutents on the phenyl and binaphthyl rings as side chain of the polymers can improve solubility in organic solvents and facile electro-optical sensors. Heck, Suzuki, Stille and Sonogashira reactions are the most important C-C coupling reactions in organic chemistry synthesis. Herein, we present preliminary results of synthesis and properties of four polymers based on the chiral unit 1,1 0 -binaphthyl structure. The four chiral polymers containing vinylene linkages between naphthyl and phenyl groups can reduce steric hindrance between backbone rings and groups, and also have a beneficial effect on delocalizable -electronic conjugation structure of polymers. These polymers are green-blue light emitting materials with very good fluorescence quantum efficiencies. EXPERIMENTAL General1 H, 13 C NMR spectra measurements (all in CDCl 3 ) were recorded...

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Synthesis, photo-, and electroluminescent properties of the soluble poly[(2,5-diphenylene-1,3,4-oxadiazole)- 4,4?-vinylene]

Yin

Wang

Yang

et al. 1999

J. Appl. Polym. Sci.

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A novel soluble conjugated polymer, poly[(2,5-diphenylene-1,3,4-oxadiazole)-4,4Ј-vinylene] (O-PPV), containing an electron-transporting group on the main chain of PPV, was synthesized according to HORNER mechanism. The oligo-polymer with M w ϭ 1000 and T d ϭ 270°C is soluble in chloroform and tetrahydrofuran. The photoluminescent (PL) properties were investigated using different concentrations of solid-state O-PPV/PEO blends absorption and selective excitation measurements. The results show that PL arises from interchain charge-transfer states in solid-state O-PPV. Compared with the analogous single-layer device constructed with PPV (ITO/ PPV/Al), which emits two peaks at ϭ 520 nm and 550 nm (shoulder), the electroluminescence (EL) spectrum of the device [ITO/O-PPV (80 nm)/Al] is a broad peak at max ϭ 509 nm. The quantum efficiency (0.13%) of the device ITO/O-PPV/Al is much higher than that of the device ITO/PPV/Al, due to the introduction of the electron-transporting group-oxadiazole units in the main chain of PPV.

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Heterocycle-substituted poly(p-phenylene vinylene) for light-emitting devices

Cited by 62 publications

References 10 publications

Poly(oxadiazole)s

Poly(oxadiazole)s

Synthesis and Characterization of Polybinaphthyls Incorporating Chiral (R) or (S)-2,2′-Binaphthyl Entities by Heck Reaction

Synthesis, photo-, and electroluminescent properties of the soluble poly[(2,5-diphenylene-1,3,4-oxadiazole)- 4,4?-vinylene]

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