Metallopolymers and use thereof

Patent metadata

Field	Value
Publication number	US-9790325-B2
Application number	US-201414766605-A
Country	US
Kind code	B2
Filing date	Feb 7, 2014
Priority date	Feb 7, 2013
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

Metallopolymers of formula (I) where R 1 and R 1 ′; and R 2 and R 2 ′ are independently of each other, a C 2 -C 10 alkyl group; X is CR3R3′ or NR4; R 3 and R 3 ′ are, independently of each other, as is R 4 , a C 2 -C 10 alkyl group; L is a C 4 -C 10 alkylene group; Ln 1 and Ln 2 are, independently of each other, chosen from the lanthanide cations; L 1 and L 2 are, independently of each other, chosen from the α-diketonate ligands; T is a neutral bidentate Lewis base including two coordinating nitrogen atoms; → represents a coordination of group T via the two nitrogen atoms of T to Ln 1 and Ln 2 respectively; Ln 1 and Ln 2 are, independently of each other, chosen from the lanthanide cations; L 1 and L 2 are, independently of each other, chosen from the β-diketonate, picolinate or dipicolinate monoanionic ligands; 0.01<x<0.50; 0<y<0.49, with x+y=0.50.

First claim

The invention claimed is:

1. A metallopolymer consisting_of repeat units of Formula I

in which
R 1 and R 1′ are, independently of one another, a C 2 -C 10 alkyl group;
R 2 and R 2′ are, independently of one another, a C 2 -C 10 alkyl group;
X is CR 3 R 3′ or NR 4 ;
R 3 and R 3′ are, independently of one another, a C 2 -C 10 alkyl group;
R 4 is a C 2 -C 10 alkyl group;
L is a C 4 -C 10 alkylene group;
T is a neutral bidentate Lewis base that comprises two coordinating nitrogen atoms;
→ shows a coordination of the group T via the two nitrogen atoms from T to Ln 1 and Ln 2 respectively;
Ln 1 and Ln 2 are, independently of one another, selected from among the lanthanide cations;
L 1 and L 2 are, independently of one another, selected from among the β-diketonate, picolinate or dipicolinate monoanionic ligands;
x is from 0.01 to 0.50;
y is from 0 to 0.49, with the sum of x +y being equal to 0.50.

2. The metallopolymer according to claim 1 , consisting of repeat units of Formula IA

in which R 1 , R 1′ , R 2 , R 2′ , R 3 , R 3′ , L, T, Ln 1 , Ln 2 , L 1 , L 2 , x and y are as previously defined.

3. The metallopolymer according to claim 1 , consisting of repeat units of Formula IB

in which R 1 , R 1′ , R 2 , R 2′ , R 4 , L, T, Ln 1 , Ln 2 , L 1 , L 2 , x, y, and n are as previously defined.

4. The metallopolymer according to claim 1 , consisting of repeat units of Formula I′

in which R 1 , R 1′ , R 2 , R 2′ , X, L, Ln 1 , Ln 2 , L 1 , L 2 , x and y are as previously defined.

5. The metallopolymer according to claim 1 , in which R 1 and R 1′ are n-octyl.

6. The metallopolymer according to claim 1 , in which R 2 and R 2′ are n-octyl.

7. The metallopolymer according to claim 1 , in which L is n-butylene.

8. The metallopolymer according to claim 1 , in which Ln 1 and Ln 2 are both Eu 3+ , and L 1 and L 2 are both thenoyltrifluoroacetonate.

9. The metallopolymer according to claim 1 , in which Ln 1 is Eu 3+ and Ln 2 is Tb 3+ , and L 1 and L 2 are both thenoyltrifluoroacetonate.

10. A conjugated polymer consisting of repeat units of Formula II

in which
R 1 and R 1′ are, independently of one another, a C 2 -C 10 alkyl group;
R 2 and R 2′ are, independently of one another, a C 2 -C 10 alkyl group;
X is CR 3 R 3′ or NR 4 ;
R 3 and R 3′ are, independently of one another, a C 2 -C 10 alkyl group;
R 4 is a C 4 -C 10 alkyl group;
x is from 0.01 to 0.50;
y is from 0 to 0.49, with the sum of x +y being equal to 0.50;
L is a C 4 -C 10 alkylene group;
T is a neutral bidentate Lewis base that comprises two coordinating nitrogen atoms.

11. A method of manufacturing a polymer light-emitting diode which comprises placing a metallopolymer according to claim 1 between an anode and a cathode.

12. A light-emitting_diode comprising a layer of a metallopolymer according to claim 1 .

13. The metallopolymer_according to claim 2 , in which R 1 and R 1′ are n-octyl.

14. The metallopolymer_according to claim 2 , in which R 2 and R 2′ are n-octyl.

15. The metallopolymer according to claim 2 , in which L is n-butylene.

16. The metallopolymer_according to claim 2 , in which Ln 1 and Ln 2 are both Eu 3+ , and L 1 and L 2 are both thenoyltrifluoroacetonate.

17. The metallopolymer -— according to claim 2 , in which Ln 1 is Eu 3+ and Ln 2 is Tb 3+ , and L 1 and L 2 are both thenoyltrifluoroacetonate.

Assignees

• Commissariat Energie Atomique
• Centre Nat De La Rech Scientifique—Cnrs
• Ecole Polytech

Inventors

• Sergent Alessandra
• Zucchi Gael
• Tondelier Denis
• Geffroy Bernard

Classifications

• C08G2261/3241

  containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C08G61/124 Primary

  with a five-membered ring containing one nitrogen atom in the ring · CPC title

• C09K2211/1466

  containing nitrogen as the only heteroatom · CPC title

• C08G2261/5242

  electrophosphorescent · CPC title