IP Library Granted Patent US 7,183,365
Granted Patent B2
US 7,183,365 · App. 10/816,153 · Granted Feb 27, 2007

Electroactive fluorene polymers having perfluoroalkyl groups, process for preparing such polymers and devices made with such polymers

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Quick Facts
Patent No.
US 7,183,365
App. No.
10/816,153
Granted
Feb 27, 2007
Kind
B2
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.

Claims (25)

1. A process for preparing fluorene polymers having perfluoroalkyl groups, the steps comprising:

(A) forming a polymer having at least one monomeric unit having a Formula I or a polymer having at least one monomeric unit having a Formula I and monomeric unit having a Formula I(a):

 where:

R is a substituent on a carbon atom in an aromatic dng, which can be the same or different at each occurrence and is selected from hydrogen, alkyl, aryl, heteroalkyl, heteroaryl, F, —CN, —OR 1 , —CO 2 R 1 , —CO 2 R 1 , —C ψ H θ F λ , —OC ψ H θ F λ , —SR 1 , —N(R 1 ) 2 , —P(R 1 ) 2 , —SOR 1 , —SO 2 R 1 , —NO 2 , and beta-dicarbonyls having Formula XII:

 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

R 1 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=2 ψ +1;  (Equation A1);

R 2 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 —C ψ H θ F λ ,

R 3 is hydrogen, alkyl, aryl, heteroalkyl and heteroaryl;

δ is 0 or an integer from 1 to 12; and

(B) treating the polymer with a perfluoroalkylating reagent selected from (i) a perfluoroalkyl iodide and (ii) a perfluoroalkylsulfonyl chlodde in the presence of a ruthenium(ll) catalyst;

with the proviso that, after treating the polymer with the perfluoroalkylating reagent, the polymer contains at least one R substituent with the formula —C ψ H θ F λ .

2. The process of claim 1 , wherein ψ is an integer from 1–12.

3. The process of claim 1 , wherein at least one R is H, C 6 –C 12 alkyl, C 6 –C 20 aryl or C 2 –C 20 heteroaryl.

4. The process of claim 1 , wherein at least one R is C 1 –C 30 alkyl.

5. The process of claim 1 , wherein at least one R is C 1 –C 30 heteroalkyl.

6. The process of claim 1 , wherein at least one R is C 6 –C 20 aryl.

7. The process of claim 1 , wherein at least one R 2 is C 1 –C 30 alkyl.

8. The process of claim 1 , wherein at least one R 2 is C 1 –C 30 heteroalkyl.

9. The process of claim 1 , wherein at least one R 3 is alkyl or aryl.

10. The process of claim 1 , wherein at least one δ is 0.

11. The process of claim 1 , wherein the ruthenium (II) catalyst is dichlorotris(triphenylphosphine)ruthenium(II).

12. The process of claim 1 , wherein a perfluoroalkylating reagent is a perfluoroalkyl iodide having 1 to 12 carbon atoms.

13. The process of claim 1 , wherein a perfluoroalkylating reagent is a perfluoroalkylsulfonyl chloride having 1 to 12 carbon atoms.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 050150/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2019
From: UCKERT, FRANK P.; FEIRING, ANDREW EDWARD
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 048436/0646 →