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US 2011/0086994 A1Published application
Methods for preparing benzodithiophenes
AssigneeXerox Corporation
InventorsAnthony James Wigglesworth, Yiliang Wu, Ping Liu, Nan-Xing Hu
Life of this patent
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Abstract
Methods of adding substituents to a benzodithiophene are disclosed. A benzodithiophene is reacted with a reagent to directly add the substituent to the benzene core of the benzodithiophene. This method eliminates steps from prior process and eliminates the need for hydrogenation, allowing for a safer and more scaleable process. The resulting benzodithiophenes are suitable for use in semiconductor polymers and have no loss of performance.
Claims20
A method of producing a 4,8-disubstituted benzodithiophene of Formula (I):
- wherein R1 is independently selected from linear alkyl, branched alkyl, and aryl;
- the method comprising:
- reacting a benzoquinone-dithiophene with a reagent having a pKa of at least 35 and having the formula M-R1, wherein M is MgX or Li, X is a halogen, and R1 is alkyl, aryl, or heteroaryl;
- and
- reducing the resulting intermediate to form the 4,8-disubstituted benzodithiophene of Formula (I).
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A method of producing a semiconductor polymer of Formula (II):
- wherein R1 and R2 are independently selected from alkyl, aryl, and heteroaryl;
- and n is from 2 to about 5,000;
- the method comprising:
- reacting a benzoquinone-dithiophene with a reagent of the formula M-R1, wherein M is MgX or Li, X is a halogen, and R1 is alkyl, aryl, or heteroaryl;
- reducing the resulting intermediate to form the 4,8-disubstituted benzodithiophene of Formula (I):
- coupling a 3-R2-thiophene to the 2 and 6 positions of the benzodithiophene, wherein R2 is alkyl, aryl, or heteroaryl, to obtain a repeating unit;
- and
- polymerizing the repeating unit to obtain the polymer of Formula (II).
5 more elements
Dependencies are inferred from the claim text.