Synthesis of π-Conjugated Polymers Containing Fluorinated Arylene Units via Direct Arylation: Efficient Synthetic Method of Materials for OLEDs

被引：137

作者：

Lu, Wei ^{[1
]}

Kuwabara, Junpei ^{[1
]}

Iijima, Takayuki ^{[2
]}

Higashimura, Hideyuki ^{[2
]}

Hayashi, Hideki ^{[3
]}

Kanbara, Takaki ^{[1
]}

机构：

[1] Univ Tsukuba, Tsukuba Res Ctr Interdisciplinary Mat Sci TIMS, Grad Sch Pure & Appl Sci, Tsukuba, Ibaraki 3058573, Japan

[2] Sumitomo Chem Co Ltd, Adv Mat Res Lab, Tsukuba, Ibaraki 3003294, Japan

[3] Nagoya Municipal Ind Res Inst, Atsuta Ku, Nagoya, Aichi 4560058, Japan

来源：

MACROMOLECULES | 2012年 / 45卷 / 10期

关键词：

LIGHT-EMITTING POLYMERS; CATALYZED DIRECT ARYLATION; POLYCONDENSATION; COPOLYMERS; MECHANISM; THIOPHENE; HOLE;

D O I：

10.1021/ma3004899

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Polycondensation via direct arylation of tetrafluorobenzene or octafluorobiphenyl was investigated for the synthesis of pi-conjugated polymers consisting of fluorinated arylene units. The optimization of reaction conditions revealed that a combination of Pd(OAc)(2) and (PBu2Me)-Bu-t-HBF4 is the most efficient catalytic system for the polycondensation reactions. The polycondensation reactions produced four types of pi-conjugated polymers having low highest occupied molecular orbital (HOMO) levels due to the strong electron-withdrawing nature of the fluorine substituents. Owing to the low HOMO levels, the synthesized polymers served as an efficient hole-blocking layer (HBL) in OLEDs.

引用

页码：4128 / 4133

页数：6

共 49 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
Ackermann, Lutz
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
[2] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
Ackermann, Lutz
Vicente, Ruben
Kapdi, Anant R.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
[3] Ahn T, 2001, MACROMOL CHEM PHYSIC, V202, P3180, DOI 10.1002/1521-3935(20011101)202:16<3180::AID-MACP3180>3.3.CO
[4] 2-M
[5] Novel fluorine containing polyfluorenes with efficient blue electroluminescence
Assaka, AM
Rodrigues, PC
de Oliveira, ARM
Ding, LM
Bin, H
Karasz, FE
Akcelrud, L
[J]. POLYMER, 2004, 45 (21) : 7071 - 7081
[6] Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates
Bellina, Fabio
Rossi, Renzo
[J]. TETRAHEDRON, 2009, 65 (50) : 10269 - 10310
[7] Bernius MT, 2000, ADV MATER, V12, P1737, DOI 10.1002/1521-4095(200012)12:23<1737::AID-ADMA1737>3.0.CO
[8] 2-N
[9] Synthesis of 5-Alkyl[3,4-c]thienopyrrole-4,6-dione-Based Polymers by Direct Heteroarylation
Berrouard, Philippe
Najari, Ahmed
Pron, Agnieszka
Gendron, David
Morin, Pierre-Olivier
Pouliot, Jean-Remi
Veilleux, Justine
Leclerc, Mario
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) : 2068 - 2071
[10] Processable Low-Bandgap Polymers for Photovoltaic Applications
Boudreault, Pierre-Luc T.
Najari, Ahmed
Leclerc, Mario
[J]. CHEMISTRY OF MATERIALS, 2011, 23 (03) : 456 - 469

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