Electron-Accepting Conjugated Materials Based on 2-Vinyl-4,5-dicyanoimidazoles for Application in Organic Electronics

被引:78
作者
Shin, Richard Y. C. [1 ]
Sonar, Prashant [1 ]
Siew, Pei Sann [1 ]
Chen, Zhi-Kuan [1 ]
Sellinger, Alan [1 ]
机构
[1] ASTAR, IMRE, Singapore 117602, Singapore
关键词
FIELD-EFFECT TRANSISTORS; HETEROJUNCTION SOLAR-CELLS; LIGHT-EMITTING-DIODES; LOW BANDGAP POLYMERS; FILM MICROSTRUCTURE; THIOPHENE OLIGOMERS; PHOTOVOLTAIC CELLS; CRYSTAL-STRUCTURE; PERYLENE DIIMIDE; BUILDING-BLOCKS;
D O I
10.1021/jo802720m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the Heck coupling of 2-vinyl-4,5-dicyanoimidazole (vinazene) with selected di- and trihalo aromatics in an effort to prepare linear and branched electron-accepting conjugated materials for application in organic electronics. By selecting the suitable halo-aromatic moiety, it is possible to tune the HOMO-LUMO energy levels, absorption, and emission properties for a specific application. In this regard, materials with strong photoluminescence from blue -> green -> red are reported that may have potential application in organic light-emitting diodes (OLEDs). Furthermore, derivatives with strong absorption in the-visible spectrum, coupled with favorable HOMO-LUMO levels, have been used to prepare promising organic photovoltaic devices (OPVs) when combined with commercially available semiconducting donor polymers.
引用
收藏
页码:3293 / 3298
页数:6
相关论文
共 63 条
[1]   n-Type organic field-effect transistors with very high electron mobility based on thiazole oligomers with trifluoromethylphenyl groups [J].
Ando, S ;
Murakami, R ;
Nishida, J ;
Tada, H ;
Inoue, Y ;
Tokito, S ;
Yamashita, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) :14996-14997
[2]   New air-stable n-channel organic thin film transistors [J].
Bao, ZA ;
Lovinger, AJ ;
Brown, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (01) :207-208
[3]   Highly ordered vacuum-deposited thin films of metallophthalocyanines and their applications in field-effect transistors [J].
Bao, ZN ;
Lovinger, AJ ;
Dodabalapur, A .
ADVANCED MATERIALS, 1997, 9 (01) :42-&
[4]   VISIBLE-LIGHT EMISSION FROM SEMICONDUCTING POLYMER DIODES [J].
BRAUN, D ;
HEEGER, AJ .
APPLIED PHYSICS LETTERS, 1991, 58 (18) :1982-1984
[5]   Polymer-perylene diimide heterojunction solar cells [J].
Breeze, AJ ;
Salomon, A ;
Ginley, DS ;
Gregg, BA ;
Tillmann, H ;
Hörhold, HH .
APPLIED PHYSICS LETTERS, 2002, 81 (16) :3085-3087
[6]   The development of light-emitting dendrimers for displays [J].
Burn, Paul L. ;
Lo, Shih-Chun ;
Samuel, Ifor D. W. .
ADVANCED MATERIALS, 2007, 19 (13) :1675-1688
[7]   LIGHT-EMITTING-DIODES BASED ON CONJUGATED POLYMERS [J].
BURROUGHES, JH ;
BRADLEY, DDC ;
BROWN, AR ;
MARKS, RN ;
MACKAY, K ;
FRIEND, RH ;
BURN, PL ;
HOLMES, AB .
NATURE, 1990, 347 (6293) :539-541
[8]   Connecting electrical and molecular properties of semiconducting polymers for thin-film transistors [J].
Chabinyc, Michael L. ;
Jimison, Leslie H. ;
Rivnay, Jonathan ;
Salleo, Alberto .
MRS BULLETIN, 2008, 33 (07) :683-689
[9]   Relationship between the ionization and oxidation potentials of molecular organic semiconductors [J].
D'Andrade, BW ;
Datta, S ;
Forrest, SR ;
Djurovich, P ;
Polikarpov, E ;
Thompson, ME .
ORGANIC ELECTRONICS, 2005, 6 (01) :11-20
[10]   Flexible, conjugated polymer-fullerene-based bulk-heterojunction solar cells: Basics, encapsulation, and integration [J].
Dennler, G ;
Lungenschmied, C ;
Neugebauer, H ;
Sariciftci, NS ;
Labouret, A .
JOURNAL OF MATERIALS RESEARCH, 2005, 20 (12) :3224-3233