Polymers, their preparation and uses

Patent metadata

Field	Value
Publication number	US-11183648-B2
Application number	US-201615208582-A
Country	US
Kind code	B2
Filing date	Jul 12, 2016
Priority date	Nov 10, 2003
Publication date	Nov 23, 2021
Grant date	Nov 23, 2021

Abstract

A polymer containing an optionally substituted repeat unit of formula (I) wherein each R is the same or different and represents H or an electron withdrawing group, and each R 1 is the same or different and represents a substituent.

First claim

The invention claimed is:

1. A monomer of formula (II):

wherein each R is H; each R1 is the same or different and represents a substituent that is not aryl or heteroaryl; and each X is the same or different and is selected from the group consisting of boronic acid groups, boronic ester groups, borane groups and halide functional groups.

2. A monomer according to claim 1 wherein at least one R1 is a solubilizing group.

3. A monomer according to claim 1 wherein each R1 is the same or different and is independently selected from the group consisting of optionally substituted C1-20 alkyl, and optionally substituted C1-20 alkoxy.

4. A method of forming a polymer comprising the step of polymerizing a monomer according to claim 1 .

5. A method according to claim 4 wherein the polymer is a copolymer formed by polymerizing the monomer with one or more co-monomers.

6. A method according to claim 5 wherein the monomer is polymerized with a co-monomer for forming an optionally substituted aryl or heteroaryl repeat unit.

7. A method according to claim 5 wherein the co-monomer is a co-monomer for forming an optionally substituted fluorene repeat unit.

8. A method according to claim 5 wherein the copolymer is an alternating copolymer.

9. A method according to claim 5 wherein the copolymer is a random copolymer.

10. A method according to claim 5 wherein the copolymer is a block copolymer.

11. A method according to claim 4 wherein each X is the same or different and is a halide functional group, and the polymerization is performed in the presence of a nickel complex catalyst.

12. A method according to claim 4 comprising the step of polymerizing :
(a) a monomer of formula (II) wherein each X is a boron the same or different and is a boron derivative functional group selected from a boronic acid, a boronic ester and a borane, and an aromatic monomer having at least two reactive halide functional groups; or
(b) a monomer of formula (II) wherein each X is the same or different and is a reactive halide functional group, and an aromatic monomer having at least two boron derivative functional group selected from a boronic acid, a boronic ester and a borane; or
(c) a monomer of formula (II) wherein one X is a reactive halide functional group and the other X is a boron derivative functional group selected from a boronic acid, a boronic ester and a borane,
wherein the reaction mixture comprises a catalytic amount of a palladium catalyst suitable for catalyzing the polymerization of the aromatic monomers, and a base in an amount sufficient to convert the boron derivative functional groups into boronate anionic groups.

13. A monomer of formula (II):

wherein each R is H; each R1 is the same or different and represents a substituent; and
each X is the same or different and is selected from the group consisting of boronic acid groups, boronic ester groups, borane groups and halide functional groups, wherein each R1 is the same or different and is independently selected from the group consisting of optionally substituted C1-20 alkyl, and optionally substituted C1-20 alkoxy.

14. A monomer according to claim 13 wherein at least one R1 is a solubilizing group.

15. A method of forming a polymer comprising the step of polymerizing a monomer according to claim 13 .

16. A method according to claim 15 wherein the polymer is a copolymer formed by polymerizing the monomer with one or more co-monomers.

17. A method according to claim 16 wherein the monomer is polymerized with a co-monomer for forming an optionally substituted aryl or heteroaryl repeat unit.

18. A method according to claim 16 wherein the co-monomer is a co-monomer for forming an optionally substituted fluorene repeat unit.

19. A method according to claim 16 wherein the copolymer is an alternating copolymer.

20. A method according to claim 16 wherein the copolymer is a random copolymer.

21. A method according to claim 16 wherein the copolymer is a block copolymer.

22. A method according to claim 15 wherein each X is the same or different and is a halide functional group, and the polymerization is performed in the presence of a nickel complex catalyst.

23. A method according to claim 15 comprising the step of polymerizing :
(a) a monomer of formula (II) wherein each X is a boron the same or different and is a boron derivative functional group selected from a boronic acid, a boronic ester and a borane, and an aromatic monomer having at least two reactive halide functional groups; or
(b) a monomer of formula (II) wherein each X is the same or different and is a reactive halide functional group, and an aromatic monomer having at least two boron derivative functional group selected from a boronic acid, a boronic ester and a borane; or
(c) a monomer of formula (II) wherein one Xis a reactive halide functional group and the other X is a boron derivative functional group selected from a boronic acid, a boronic ester and a borane,
wherein the reaction mixture comprises a catalytic amount of a palladium catalyst suitable for catalyzing the polymerization of the aromatic monomers, and a base in an amount sufficient to convert the boron derivative functional groups into boronate anionic groups.

Assignees

• Cambridge Display Tech Ltd
• Cambridge Entpr Ltd

Inventors

• Towns Carl R
• Mak Chris
• Chan Khai Leok
• Holmes Andrew Bruce

Classifications

• C09K2211/1441

  Heterocyclic · CPC title

• C08G61/12 Primary

  Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule · CPC title

• C08G2261/148

  Side-chains having aromatic units · CPC title

• C08G2261/228

  Polymers, i.e. more than 10 repeat units · CPC title

• C07F7/08

  Compounds having one or more C—Si linkages · CPC title