High performance solution processable semiconductor based on dithieno [2,3-D:2′, 3′-D′]benzo[1,2-B:4,5-B′] dithiophene

US8367717B2 · kind B2 · utility

Assignees

• BASF SE
• Max-Planck-Gesellschaft zur Föderung der Wissenschaften e.V. · US

Inventors

• Marcel Kastler · Mannheim, DE
• Silke Annika Koehler · Basel, CH
• Klaus Muellen · Cologne, DE
• Peng Gao · Mainz, DE
• Dirk Beckmann · Harxheim, DE
• Xinliang Feng · Mainz, DE
• Hoi Nok Tsao · Mainz, DE

Key dates

• Filing date: Jun 25, 2009
• Grant date: Feb 5, 2013
• Expiry date: Oct 24, 2029

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02E10/549
• WIPO field: Electrical machinery, apparatus, energy
• WIPO sector: Electrical engineering

Abstract

Dithienobenzodithiophenes of general formula (I) in which R1 to R6 are each independently selected from a) H, b) halogen, c) —CN, d) —NO2, e) —OH, f) a C1-20 alkyl group, g) a C2-20 alkenyl group, h) a C2-20 alkynyl group, i) a C1-20 alkoxy group, j) a C1-20 alkylthio group, k) a C1-20 haloalkyl group, I) a —Y—C3-10 cycloalkyl group, m) a —Y—C6-14 aryl group, n) a —Y-3-12 membered cyclo-heteroalkyl group, or o) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C2-20 alkynyl group, the C3-10 cycloalkyl group, the C6-14 aryl group, the 3-12 membered cyc-loheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-4 R7 groups, wherein R1 and R3 and R2 and R4 may also together form an aliphatic cyclic moiety, Y is independently selected from divalent a C1-6 alkyl group, a divalent C1-6 haloalkyl group, or a covalent bond; and m is independently selected from 0, 1, or 2. The invention also relates to the use of the dithienobenzodithiophenes according to any of claims 1 to 4 as semiconductors or charge transport materials, as thin-film transistors (TFTs), or in semiconductor components for organic ligh…