Polymers, monomers and methods of forming polymers

Patent metadata

Field	Value
Publication number	US-9562136-B2
Application number	US-201214130920-A
Country	US
Kind code	B2
Filing date	Jul 3, 2012
Priority date	Jul 4, 2011
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

A method of forming a crosslinked polymer comprising the step of reacting a crosslinkable group in the presence of a polymer, wherein: the crosslinkable group comprises a core unit substituted with at least one crosslinkable unit of formula (I): the crosslinkable group is bound to the polymer or is a crosslinkable compound mixed with the polymer; Ar is aryl or heteroaryl which may be unsubstituted or substituted with one or more substituents independently selected from monovalent substituents and a divalent linking group linking the unit of formula (I) to the core unit; and R is independently in each occurrence H, a monovalent substituent or a divalent linking group linking the unit of formula (I) to the core unit, with the proviso that at least one R is not H.

First claim

The invention claimed is:

1. A method of forming a crosslinked polymer having a conjugated polymer backbone, the method comprising the step of reacting a crosslinkable group in the presence of a polymer, wherein:
the crosslinkable group comprises a core unit substituted with at least one crosslinkable unit of formula (I):

the crosslinkable group is a repeat unit of the polymer of formula (IIIa) or (IIIb):

wherein:
RU represents a conjugated core repeat unit comprised in a backbone of the polymer, wherein RU is at least partially conjugated to one or both adjacent repeat units in the polymer backbone;
Sp 2 represents a spacer group;
m is 0 or 1;
p is at least 1;
Ar is aryl or heteroaryl which is unsubstituted or is substituted with one or more substituents independently selected from monovalent substituents and a divalent linking group linking the unit of formula (I) to the core unit; and
R is independently in each occurrence H, a monovalent substituent, or a divalent linking group linking the unit of formula (I) to the core unit, with the proviso that at least one R is a linear or branched C 3-20 alkyl,
and wherein the polymer backbone is substituted with a crosslinkable double bond unit.

2. A method according to claim 1 wherein Ar is phenyl.

3. A method according to claim 2 wherein the at least one unit of formula (I) has formula (Ia):

4. A method according to claim 1 wherein only one R is not H.

5. A method according to claim 1 wherein the crosslinkable group comprises at least two units of formula (I).

6. A method according to claim 1 wherein the crosslinkable group is a crosslinkable compound mixed with the polymer.

7. A method according to claim 1 wherein RU has formula (XVI):

wherein Ar 6 represents a substituted or unsubstituted aryl or heteroaryl group and * represents a bond to Sp 2 , Ar or R.

8. A method according to claim 7 wherein Ar 6 is selected from the group consisting of phenyl, fluorene and indenofluorene, each of which is substituted or unsubstituted.

9. A method according to claim 1 wherein the repeat unit of formula (IIIa) or (IIIb) has formula (IIIc):

wherein R 1 and R 2 are independently in each occurrence H or a substituent with the proviso that at least one of R 1 and R 2 has formula -(Sp 2 ) m -XL; XL is a crosslinkable unit of formula (I); and a is at least 1.

10. A method according to claim 1 wherein Sp 2 is selected from the group consisting of a C 1-20 n-alkyl chain and an optionally substituted aryl or heteroaryl, and wherein one or more non-adjacent C atoms of the n-alkyl chain are optionally replaced with optionally substituted aryl or heteroaryl, O, S, substituted N, substituted Si, —C═O, or —COO—, and one or more H atoms of the n-alkyl chain are optionally replaced with C 1-5 alkyl, F, or an aryl or heteroaryl group.

11. A method according to claim 1 wherein the reaction is performed by heating the reactants or exposing the reactants to UV light.

12. A method according to claim 11 wherein the reaction is performed at a temperature of less than 180° C.

13. A method according to claim 1 wherein the repeat units of formula (IIIa) or (IIIb) form up to 25 mol % of the repeat units of the polymer.

14. A method according to claim 1 wherein the crosslinkable double bond unit is a group of formula (V):
*—CR 7 ═CHR 7    (V),

wherein R 7 independently in each occurrence is H or a substituent and * is a point of attachment of the crosslinkable double bond unit to the polymer backbone, and wherein the group of formula (V) is bound directly to the polymer backbone or is spaced apart therefrom by a spacer group.

15. A method of forming a crosslinked polymer comprising the step of reacting a crosslinkable group in the presence of a polymer, wherein:
the crosslinkable group comprises a core unit substituted with at least one crosslinkable unit of formula (I):

the crosslinkable group is a repeat unit of the polymer of formula (IIIa) or (IIIb):

wherein:
RU represents a conjugated core repeat unit comprised in a backbone of the polymer, wherein RU is at least partially conjugated to one or both adjacent repeat units in the polymer backbone;
Sp 2 represents a spacer group;
m is 0 or 1;
p is at least 1;
Ar is aryl or heteroaryl which is unsubstituted or is substituted with one or more substituents independently selected from monovalent substituents and a divalent linking group linking the unit of formula (I) to the core unit; and
R is independently in each occurrence H, a monovalent substituent, or a divalent linking group linking the unit of formula (I) to the core unit, with the proviso that at least one R is a branched C 3-20 alkyl.

Assignees

• Humphries Martin
• Bourcet Florence
• Zuberi Sheena
• Cambridge Display Tech Ltd
• Sumitomo Chemical Co

Inventors

• Humphries Martin
• Bourcet Florence
• Zuberi Sheena

Classifications

• H10K85/151

  Copolymers · CPC title

• C08G61/12 Primary

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

• C08G2261/12

  Copolymers · CPC title

• H01L51/5044

  Electricity · mapped topic

• C08G73/026 Primary

  Wholly aromatic polyamines · CPC title