Perylene-imide semiconductor polymers

• US 8,796,672 B2
• Filed: 02/05/2009
• Issued: 08/05/2014
• Est. Priority Date: 02/05/2008
• Status: Active Grant

• Current Assignee: Raynergy Tek, Inc.
• Original Assignee: BASF SE, Polyera Corporation
• Inventors: Facchetti, Antonio, Yan, He, Chen, Zhihua, Kastler, Marcel, Doetz, Florian
• Primary Examiner(s): Listvoyb, Gregory
• Application Number:
  US12/812,531
• Publication Number:
  US 20100283047A1
• Time in Patent Office: 2,007 Days
• Field of Search: 427/240, 427/358, 427/427.4, 427/430.1, 528/321, 528/322
• US Class Current: 257/40
• CPC Class Codes: C08G 61/10 only aromatic carbon atoms, e.g. polyphenylenes
• CPC Class Codes: C08G 61/12 Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
• CPC Class Codes: C09B 5/62 Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
• CPC Class Codes: C09B 69/102 containing a perylene dye
• CPC Class Codes: C09B 69/105 containing a methine or polymethine dye
• CPC Class Codes: C09B 69/106 containing an azo dye
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1458 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1483 containing nitrogen and sulfur as heteroatoms
• CPC Class Codes: H01B 1/127 comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 10/464 Lateral top-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 85/113 Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/151 Copolymers
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/621 Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
• CPC Class Codes: Y02E 10/549 Organic PV cells
• CPC Class Codes: Y02P 70/50 Manufacturing or production processes characterised by the final manufactured product

Abstract

Disclosed are new semiconductor materials prepared from perylene-imide copolymers. Such polymers can exhibit high n-type carrier mobility and/or good current modulation characteristics. In addition, the compounds of the present teachings can possess certain processing advantages such as solution-processability and/or good stability at ambient conditions.

Claims

1. A polymer selected from the formula:

2. The polymer of claim 1 selected from:

3. The polymer of claim 1, wherein R¹ and R² are independently selected from:

4. The polymer of claim 1, wherein R¹ and R² are independently a branched C_3-30 alkyl group or a branched C_3-30 alkenyl group.

5. The polymer of claim 1, wherein R¹ and R² are independently selected from an n-hexyl group, a 1-methylpropyl group, a 1-methylbutyl group, a 1-methylpentyl group, a 1-methylhexyl group, a 1-ethylpropyl group, a 1-ethylbutyl group, a 1-3,dimethylbutyl group, and a 2-octyldodecyl group.