Polymer comprising an unsymmetric diarylaminofluorene unit

Patent metadata

Field	Value
Publication number	US-9859499-B2
Application number	US-201314372529-A
Country	US
Kind code	B2
Filing date	Jan 16, 2013
Priority date	Jan 16, 2012
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

A polymer comprising one or more optionally substituted repeat units of formula (I): (I) wherein each Ar 1 independently represents a substituted or unsubstituted aromatic or heteroaromatic group; each Ar 2 independently represents a substituted or unsubstituted aromatic or heteroaromatic group; n and m in each occurrence is at least 1; and R 1 and R 2 are substituents wherein R 1 and R 2 are different.

First claim

The invention claimed is:

1. A polymer comprising one or more unsubstituted or substituted repeat units of formula (I):

wherein each Ar 1 independently represents a substituted or unsubstituted aromatic or heteroaromatic group; each Ar 2 independently represents a substituted or unsubstituted aromatic or heteroaromatic group; n and m in each occurrence is at least 1; and R 1 and R 2 are substituents wherein R 1 and R 2 are different; wherein R 1 is bound to the flourene ring through a sp 2 -hybridised carbon atom and R 2 is bound to the flourene unit through a sp 3 -hybridized carbon atom.

2. A polymer according to claim 1 , wherein R 2 is a substituted or unsubstituted, branched, linear, or cyclic alkyl group wherein one or more non-adjacent C atoms may be replaced with O, S, NR 5 , C═O or —COO—, and one or more H atoms may be replaced with F or D, and R 5 is H or a substituent.

3. A polymer according to claim 1 , wherein R 1 is bound to the fluorene unit through a group —(Ar 3 ) y wherein Ar 3 in each occurrence is a substituted or unsubstituted aromatic or heteroaromatic group; y is at least 1; and —(Ar 3 ) y forms a linear or branched chain of Ar 3 groups when y is greater than 2.

4. A polymer according to claim 3 , wherein Ar 3 in each occurrence is a substituted or unsubstituted phenyl.

5. A polymer according to claim 3 wherein Ar 3 is substituted with one or more substituents, selected from F; CN; NO 2 ; NR 5 2 ; a crosslinkable group; and C 1-20 alkyl wherein one or more non-adjacent C atoms may be replaced with unsubstituted or substituted aryl or heteroaryl, O, S, NR 5 , C═O or —COO— and wherein one or more H atoms may be replaced with F or D, and R 5 is H or a substituent.

6. A polymer according to claim 1 wherein each n is independently 1-3, and wherein each m is independently 1-3.

7. A polymer according to claim 1 wherein each Ar 1 and Ar 2 is independently an unsubstituted or substituted phenyl.

8. A polymer according to claim 1 wherein at least one Ar 2 is substituted with one or more substituents selected from F; CN; NO 2 ; NR 5 2 ; a crosslinkable group; and C 1-20 alkyl groups wherein one or more non-adjacent C atoms may be replaced with unsubstituted or substituted aryl or heteroaryl, O, S, NR 5 , C═O or —COO— and wherein one or more H atoms may be replaced with F or D, and R 5 is H or a substituent.

9. A polymer according to claim 1 wherein at least one position of at least one (Ar 2 ) m that is ortho- to the Ar 2 —N bond is substituted.

10. A polymer according to claim 1 wherein the polymer comprises a co-repeat unit of formula (IV):

wherein R 5 in each occurrence is the same or different and is H or a substituent, and
wherein the two groups R 5 may be linked to form a ring.

11. A polymer according to claim 1 comprising a repeat unit of formula (Ib):

wherein each Ar 1 independently represents a substituted or unsubstituted aromatic or heteroaromatic group; each Ar 2 independently represents a substituted or unsubstituted aromatic or heteroaromatic group; n and m in each occurrence is at least 1; and R 1 and R 2 are substituents wherein R 1 and R 2 are different.

12. A polymer according to claim 1 wherein the repeat unit of formula (I) and/or one or more co-repeat units of the polymer are substituted with at least one crosslinkable group.

13. An organic electronic device comprising a semiconductor layer wherein the semiconductor layer comprises a polymer according to claim 1 .

14. An organic electronic device according to claim 13 wherein the device is an organic light-emitting device comprising the semiconductor layer between an anode and a cathode.

15. An organic electronic device according to claim 14 wherein the semiconducting layer is a hole-transporting layer between the anode and a light-emitting layer.

16. A method of forming a polymer according to claim 1 comprising the step of polymerising a monomer of formula (II):

wherein Ar 1 , Ar 2 , R 1 , R 2 , n and m are as defined in claim 1 , and each L represents a reactive leaving group selected from the group consisting of halogen; boronic acids and esters thereof; and sulfonic acid esters.

17. A method according to claim 16 wherein the polymerisation is carried out in the presence of a metal catalyst.

Assignees

• Sumitomo Chemical Co
• Cambridge Display Tech Ltd

Inventors

• Pegington Ruth
• Heidenhain Sophie Barbara
• Mckiernan Mary J

Classifications

• C08G2261/3162

  Arylamines · CPC title

• C08G61/12

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

• C08G2261/3245

  containing nitrogen and oxygen as heteroatoms · CPC title

• C08G73/026

  Wholly aromatic polyamines · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title