Synthesis and properties of the polymers containing 3,3′-dicarbazyl units in the main chain and their model compounds

Grigalevičius, Saulius; Lideikis, E; Gražulevičius, Juozas V.; Gaidelis, Valentas; Antulis, J.; Jankauskas, Vygintas; Van, François Tran; Chevrot, C.

doi:10.1016/s0032-3861(02)00466-4

Cited by 32 publications

(8 citation statements)

References 17 publications

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“…Three classes of carbazole oligomers are studied, including the 3(6),9′-linked oligomers with their 9-position end-capped with an alkyl group (BCz1, TCz1), the 3(6),9′-linked oligomers with their 9-position end-capped with a substituted phenyl group (BCz2, TCz2), and one 3,3′-linked carbazole dimer, BCz3, for comparison. These compounds were synthesized by a modified Ullmann coupling reaction (BCz1, BCz2, TCz1, and TCz2) or by chemical oxidation (BCz3) by using procedures similar to protocols previously reported [12][13][14] (see Supporting Information for more details of syntheses and characterization). The four 3(6),9′-linked oligocarbazoles investigated exhibit fairly high thermal stability.…”

mentioning

confidence: 99%

3‐(9‐Carbazolyl)carbazoles and 3,6‐Di(9‐carbazolyl)carbazoles as Effective Host Materials for Efficient Blue Organic Electrophosphorescence

et al. 2007

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Linking topology in oligocarbazoles (see figure) has a strong influence on their electronic properties. 3(6),9′‐linked oligocarbazoles exhibit unusual suppression of electronic coupling between units, leading to localized excited states and very small reduction of triplet energies (compared to the monomer). Coupled with their excellent morphological stability, this makes them suitable as host materials for blue electrophosphorescence devices.

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confidence: 99%

3‐(9‐Carbazolyl)carbazoles and 3,6‐Di(9‐carbazolyl)carbazoles as Effective Host Materials for Efficient Blue Organic Electrophosphorescence

et al. 2007

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“…Despite the fact that the effective conjugation length in 3,6‐linked oligo‐ and polycarbazoles is generally limited to dimeric units (dyads), well defined oligomers demonstrate very different hole transport properties, with hole drift mobilities from time‐of‐flight (TOF) measurements ranging from ca. 10 −5 cm 2 · V −1 · s −1 for dimers9 to about 10 −3 cm 2 · V −1 · s −1 for pentamers 10. Related to these results, main chain polymers containing “isolated” oligocarbazole blocks of different length connected via aliphatic spacers should also exhibit rather different charge injection and transport properties.…”

Section: Introductionmentioning

confidence: 71%

“…Despite the very similar effective conjugation lengths and HOMO values, 3,6‐carbazole‐based oligomers have demonstrated very different hole transport properties, with a hole drift mobility from TOF measurements ranging from approximately 10 −5 cm 2 · V −1 · s −1 for dimers9 to about 10 −3 cm 2 · V −1 · s −1 for pentamers 10. In relation to these results, the copolymers 6 – 8 with different lengths of the oligocarbazole segments are expected to give different charge transport properties.…”

Section: Resultsmentioning

confidence: 99%

New Carbazole‐Based Copolymers as Amorphous Hole‐Transporting Materials for Multilayer Light‐Emitting Diodes

Grigalevičius

Qian

et al. 2007

Macro Chemistry & Physics

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New carbazole‐based copolymers, which contain various concentrations of 9‐alkyl‐3,6‐carbazole fragments in the main chain connected via alkylene spacers, have been synthesized by Ni(0)‐catalyzed Yamamoto‐type aryl‐aryl coupling reactions. Full characterization of the copolymer structure by NMR spectroscopy and elemental analysis is presented. These compounds represent amorphous materials of high thermal stability with glass transition temperatures of 151–162 °C and thermal decomposition starting at temperatures >390 °C. UV‐Vis absorption and photoluminescence emission of the copolymers confirmed that the effectively conjugated segment in the 3,6‐linked carbazole‐type copolymers is limited to dyads (dimeric units). However, copolymers with varying concentrations of the oligocarbazole chromophores demonstrate different charge injection and transport properties in multilayer light‐emitting diodes with the copolymers as the hole transport and Alq3 as the electroluminescent/electron transport layer. The device based on a copolymer composed of oligocarbazole blocks with an average length of around four carbazoles exhibited the best overall performance with a turn‐on voltage of 3.5 V, a maximal photometric efficiency of 4.1 cd · A−1 and maximum brightness of about 4 200 cd · m−2.

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“…[1][2][3][4][5][6][7][8][9][10][11][12] There are several reports of polymers with rigid carbazole derivatives that show not only optical properties but also high thermal stabilities. 13 Polymerizations at the 3,6-positions and 2,7-positions of carbazole have often been used to synthesize main-chaintype polymers, [14][15][16][17][18][19][20] which have carbazole units tailored into the main chain of the polymer. These polymers with carbazole units in the main chain usually exhibit poor solubility in common organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of poly(arylene ether ketone)s with 3,6-diphenyl-9H-carbazole pendants using C–N coupling reaction

Liu¹,

Chen²,

Lin³

et al. 2016

High Performance Polymers

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3,6-Diphenyl-9 H-carbazole pendants are grafted herein to poly(arylene ether ketone)s (PAEKs) via the Ullmann C–N coupling reaction. To the best of our knowledge, this is the first time that PAEKs containing a carbazole pendant (Cz) have been synthesized through the Ullmann C–N coupling reaction. The high molecular weights of PAEK-Cz (PAEKs with 3,6-diphenyl-9 H-carbazole pendants) are inherited from their precursors, owing to the high reactivity of their monomers. The obtained PAEK-Cz- x polymers exhibit good solubility in most common organic solvents and excellent thermal stabilities, with the 5% weight loss temperatures for all products being above 598°C under a nitrogen atmosphere. The glass transition temperatures are all above 199°C and can be controlled by adjusting the feed ratio of monomers. The polymer membranes obtained by the casting method are tough and thus have strong potential for practical applications.

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Synthesis and properties of the polymers containing 3,3′-dicarbazyl units in the main chain and their model compounds

Cited by 32 publications

References 17 publications

3‐(9‐Carbazolyl)carbazoles and 3,6‐Di(9‐carbazolyl)carbazoles as Effective Host Materials for Efficient Blue Organic Electrophosphorescence

3‐(9‐Carbazolyl)carbazoles and 3,6‐Di(9‐carbazolyl)carbazoles as Effective Host Materials for Efficient Blue Organic Electrophosphorescence

New Carbazole‐Based Copolymers as Amorphous Hole‐Transporting Materials for Multilayer Light‐Emitting Diodes

Synthesis and characterization of poly(arylene ether ketone)s with 3,6-diphenyl-9H-carbazole pendants using C–N coupling reaction

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