Method of forming polymers

Patent metadata

Field	Value
Publication number	US-10323123-B2
Application number	US-201715427155-A
Country	US
Kind code	B2
Filing date	Feb 8, 2017
Priority date	Nov 30, 2012
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

Methods of metal-catalysed polymerisation are described using a metal catalyst of formula (III):

wherein R 3 in each occurrence is independently selected from C 1-10 alkyl and aryl that may be unsubstituted or substituted with one or more substituents; y is 0 or 2; and Z − is an anion. Methods described include Buchwald-type and Suzuki-type polymerisation.

First claim

The invention claimed is:

1. A method of forming a polymer by polymerising a composition comprising at least one monomer of formula (IV) and at least one monomer of formula (V) at a temperature of less than 80° C.:
LG 1 -R 13 -LG 1   (IV)

LG 2 -R14-LG 2   (V)

wherein:
R 13 comprises an aromatic group that may be unsubstituted or substituted with one or more substituents;
R 14 comprises an aromatic group that may be unsubstituted or substituted with one or more substituents;
each LG 1 is a leaving group selected from bromine, chlorine, iodine and sulfonic acid esters, and each LG 1 is bound to an aromatic carbon atom of R 13 ;
each LG 2 is a leaving group selected from boronic acids and boronic acid ester and each LG 2 is bound to an aromatic carbon atom of R 14 ;
the monomers are polymerised in the presence of a palladium catalyst of formula (III):

wherein R 3 in each occurrence is independently selected from C 1-10 alkyl and aryl that may be unsubstituted or substituted with one or more substituents, with the proviso that at least one R 3 of at least one group PR 3 3 is C 1-10 alkyl;
y is 0 or 2; and
Z − is an anion.

2. A method according to claim 1 , wherein at least one of R 13 and R 14 is substituted with a crosslinkable group.

3. A method according to claim 2 , wherein the crosslinkable groups are selected from formulae:

wherein Sp is a spacer group; t is 0 or 1; R 10 in each occurrence is H, C 1-10 alkyl or C 1-10 alkoxy; R 11 in each occurrence is H or C 1-10 alkyl; and * represents a point of attachment of the crosslinkable substituent to R 13 or R 14 .

4. A method according to claim 3 , wherein t is 1 and Sp is selected from C 1-20 alkyl, phenyl and phenyl-C 1-20 alkyl wherein one or more C atoms of the C 1-20 alkyl groups may be replaced with O or S.

5. A method according to claim 1 , wherein at least one of groups R 13 and R 14 has formula —(Ar 6 ) v — wherein Ar 6 in each occurrence is independently an aryl or heteroaryl group that may be unsubstituted or substituted with one or more substituents and v is a positive integer.

6. A method according to claim 5 , wherein Ar 6 is selected from the group consisting of:

wherein q in each occurrence is 0, 1, 2, 3 or 4; d in each occurrence is 0, 1, 2 or 3; R 6 independently in each occurrence is a substituent and two groups R 6 may be linked to form a substituted or unsubstituted ring; and R 8 independently in each occurrence is a substituent.

7. A method according to claim 1 , wherein each R 3 is independently selected from C 1-10 alkyl; phenyl; and phenyl substituted with one or more C 1-5 alkyl groups.

8. A method according to claim 1 , wherein at least one R 3 of at least one group PR 3 3 is C 1-10 alkyl and at least one R 3 of the at least one group PR 3 3 is substituted or unsubstituted phenyl.

9. A method according to claim 1 , wherein y is 2.

10. A method according to claim 9 , wherein Z − is selected from C 1-10 alkoxy and halide.

11. A method according to claim 1 , wherein at least one of groups R 13 and R 14 has formula (VII):

wherein Ar 8 and Ar 9 in each occurrence are independently substituted or unsubstituted aryl or heteroaryl, g is greater than or equal to 1, R 15 is H or a substituent; c and d are each independently 1, 2 or 3; and any two of Ar 8 , Ar 9 and R 15 directly linked to a common N atom may be linked by a direct bond or a divalent linking group.

12. A method according to claim 8 , wherein Ar 8 and Ar 9 are each substituted or unsubstituted phenyl and R 15 is C 1-20 alkyl, Ar 10 , a branched or linear chain of Ar 10 groups, or a crosslinkable unit that is bound directly to the N atom of formula (VII) or spaced apart therefrom by a spacer group, wherein Ar 10 in each occurrence is independently optionally substituted aryl or heteroaryl.

13. A method according to claim 9 , wherein Ar 10 in each occurrence is independently an unsubstituted or substituted phenyl.

Assignees

• Cambridge Display Tech Ltd
• Sumitomo Chemical Co

Inventors

• Bourcet Florence
• Kamtekar Kiran
• Pegington Ruth
• Morey James

Classifications

• H01L51/0043

  Electricity · mapped topic

• H01L51/50

  Electricity · mapped topic

• C08G73/026 Primary

  Wholly aromatic polyamines · CPC title

• C08G2261/411

  Suzuki reactions · CPC title

• H01L51/5012

  Electricity · mapped topic