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US 2002/0177679 A1Published application
Electroactive fluorene polymers having perfluoroalkyl groups, process for preparing such polymers and devices made with such polymers
AssigneeE. I. Du Pont De Memours and Company
InventorsFrank P. Uckert, Andrew Edward Feiring
Life of this patent
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Abstract
The present invention is generally directed to perfluoroalkylated fluorene polymers. It further relates to a process for preparing the polymers and devices that are made with the polymers.
Claims20
A polymer comprising one or more first monomeric unit having a Formula I shown in FIG. 1, where:
- R is a substituent on a carbon atom in an aromatic ring, which can be the same or different at each occurrence and is selected from hydrogen, alkyl, aryl, heteroalkyl, heteroaryl, F, —CN, —OR1, —CO2R1, —CψHθFλ, —OCψHθFλ, —SR1, —N(R1)2, —P(R1)2, —SOR1, —SO2R1, —NO2, and beta-dicarbonyls having Formula XII shown in FIG. 12;
- or
- adjacent R groups together can form a ring selected from 5-membered cycloalkyl, 6-membered cycloalkyl, 5-membered aryl, 6-membered aryl. 5-membered heteroaryl and 6-membered heteroaryl,
- such that:
- R1 is a substituent on a heteroatom which can be the same or different at each occurrence and is selected from alkyl, aryl, heteroalkyl and heteroaryl;
- and
- ψ is an integer between 1 and 20, and θ and λ are integers satisfying Equation A1 below:
- θ+λ=2ψ+1;
- (Equation A1)
- R2 is a substituent on a carbon atom not in an aromatic ring, which can be the same or different at each occurrence and is selected from hydrogen, alkyl, aryl, heteroalkyl, heteroaryl and —CψHθFλ,
- with the proviso that the polymer contains at least one R substituent with the formula —CψF2ψ+1.
8 more elements
16 The device of claim 13, wherein the device comprises an electron injection/transport layer comprising the polymer of claim 1.
A process for preparing fluorene polymers having perfluoroalkyl groups, the steps comprising:
- forming a polymer having at least one first monomeric unit having a Formula I shown in FIG. 1 where:
- R is a substituent on a carbon atom in an aromatic ring, which can be the same or different at each occurrence and is selected from hydrogen, alkyl, aryl, heteroalkyl, heteroaryl, F, —CN, —OR1, —CO2R1, —CψHθFλ,
- —OCψHθFλ, —SR1, —N(R1)2, —P(R1)2, —SOR1, —SO2R1, —NO2, and beta-dicarbonyls having Formula XII shown in FIG. 12;
- or
- adjacent R groups together can form a ring selected from 5-membered cycloalkyl, 6-membered cycloalkyl, 5-membered aryl, 6-membered aryl. 5-membered heteroaryl and 6-membered heteroaryl,
- such that:
- R1 is a substituent on a heteroatom which can be the same or different at each occurrence and is selected from alkyl, aryl, heteroalkyl and heteroaryl;
- and
- ψ is an integer between 1 and 20, and θ and λ are integers satisfying Equation A1 below:
- θ+λ=2ψ+1;
- (Equation A1);
- R2 is a substituent on a carbon atom not in an aromatic ring, which can be the same or different at each occurrence and is selected from hydrogen, alkyl, aryl, heteroalkyl, heteroaryl and —C104 HθFλ,
- with the proviso that the polymer contains at least one R substituent with the formula —CψF2ψ+1;
- treating the polymer with a perfluoroalkylating reagent selected from (i) a perfluoroalkyl iodide and (ii) a perfluoroalkylsulfonyl chloride in the presence of a ruthenium(II) catalyst.
11 more elements
Dependencies are inferred from the claim text.