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

[31] Synthesis of Poly(4,4-dialkyl-cyclopenta[2,1-b:3,4-b′]dithiophene-alt-2,1,3-benzothiadiazole) (PCPDTBT) in a Direct Arylation Scheme
Kowalski, Sebastian
Allard, Sybille
Scherf, Ullrich
[J]. ACS MACRO LETTERS, 2012, 1 (04): : 465 - 468
[32] Catalytic intermolecular direct arylation of perfluorobenzenes
Lafrance, Marc
Rowley, Christopher N.
Woo, Tom K.
Fagnou, Keith
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (27) : 8754 - 8756
[33] Overview of the Mechanistic Work on the Concerted Metallation-Deprotonation Pathway
Lapointe, David
Fagnou, Keith
[J]. CHEMISTRY LETTERS, 2010, 39 (11) : 1119 - 1126
[34] Blue-light-emitting fluorene-based polymers with tunable electronic properties
Liu, B
Yu, WL
Lai, YH
Huang, W
[J]. CHEMISTRY OF MATERIALS, 2001, 13 (06) : 1984 - 1991
[35] Polycondensation of Dibromofluorene Analogues with Tetrafluorobenzene via Direct Arylation
Lu, Wei
Kuwabara, Junpei
Kanbara, Takaki
[J]. MACROMOLECULES, 2011, 44 (06) : 1252 - 1255
[36] Controlled polymerizations for the synthesis of semiconducting conjugated polymers
Okamoto, Ken
Luscombe, Christine K.
[J]. POLYMER CHEMISTRY, 2011, 2 (11) : 2424 - 2434
[37] Fluorine Substituted Conjugated Polymer of Medium Band Gap Yields 7% Efficiency in Polymer-Fullerene Solar Cells
Price, Samuel C.
Stuart, Andrew C.
Yang, Liqiang
Zhou, Huaxing
You, Wei
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) : 4625 - 4631
[38] Molecular engineering of the band gap of π-conjugated systems:: Facing technological applications
Roncali, J.
[J]. MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (17) : 1761 - 1775
[39] Suzuki Polycondensation: Polyarylenes a la Carte
Sakamoto, Junji
Rehahn, Matthias
Wegner, Gerhard
Schlueter, A. Dieter
[J]. MACROMOLECULAR RAPID COMMUNICATIONS, 2009, 30 (9-10) : 653 - 687
[40] Direct Arylation as a Synthetic Tool for the Synthesis of Thiophene-Based Organic Electronic Materials
Schipper, Derek J.
Fagnou, Keith
[J]. CHEMISTRY OF MATERIALS, 2011, 23 (06) : 1594 - 1600

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