Polymer and organic electronic device

Patent metadata

Field	Value
Publication number	US-10290810-B2
Application number	US-201414909045-A
Country	US
Kind code	B2
Filing date	Jul 29, 2014
Priority date	Jul 31, 2013
Publication date	May 14, 2019
Grant date	May 14, 2019

Abstract

A polymer comprising a repeat unit of formula (I): wherein R 1 in each occurrence is independently H or a substituent, and the two groups R 1 may be linked to form a ring; R 2 in each occurrence is independently a substituent; Ar 1 in each occurrence is independently an aryl or heteroaryl group that may be unsubstituted or substituted with one or more substituents; R 3 in each occurrence is independently a substituent; each n independently is 0, 1, 2 or 3 with the proviso that at least one n=1; and each m is independently 0 or 1. The polymer may be a light-emitting 103 of an organic light-emitting device.

First claim

The invention claimed is:

1. A conjugated polymer comprising a repeat unit of formula (III):

wherein:
R 1 in each occurrence is independently H or a substituent, and the two groups R 4 are optionally linked to form a ring;
R 2 in each occurrence is independently a substituent selected from a C 1-20 alkyl group, wherein one or more non-adjacent C atoms are optionally replaced with O, S, NR 4 , C═O, or —COO—, R 4 is a substituent, and wherein one or more H atoms of the C 1-20 alkyl group are optionally replaced with F; and an aryl or heteroaryl group that is substituted or unsubstituted with one or more substituents;
Ar 1 in each occurrence is independently an aryl or heteroaryl group that is unsubstituted or substituted with one or more substituents;
R 3 in each occurrence is independently a substituent;
n is 0, 1, 2 or 3; and
each m is independently 0 or 1.

2. The polymer according to claim 1 , wherein the repeat unit of formula (III) has formula:

3. The polymer according to claim 1 , wherein each R 1 is independently selected from the group consisting of a C 1-30 alkyl group, wherein one or more non-adjacent C atoms are optionally replaced with O, S, NR 4 , C═O, or —COO—, wherein R 4 is a substituent, and wherein one or more H atoms of the C 1-30 alkyl group are optionally replaced with F; and an aryl or heteroaryl group that is substituted or unsubstituted with one or more substituents.

4. The polymer according to claim 1 , wherein each R 2 is independently a C 1-10 alkyl group.

5. The polymer according to claim 1 , wherein n is 0.

6. The polymer according to claim 1 , wherein each m is 0.

7. The polymer according to claim 1 , wherein at least one m is 1.

8. The polymer according to claim 7 , wherein Ar 1 in each occurrence is independently a phenyl group that is unsubstituted or substituted with one or more substituents.

9. The polymer according to claim 7 , wherein R 3 in each occurrence is independently a C 1-40 hydrocarbyl group.

10. The polymer according to claim 1 , wherein the polymer comprises 1-50 mol % of the repeat unit of formula (I).

11. A monomer of formula (IIIm):

wherein:
R 1 in each occurrence is independently H or a substituent;
R 2 in each occurrence is independently a substituent selected from a C 1-20 alkyl group, wherein one or more non-adjacent C atoms are optionally replaced with O, S, NR 4 , C═O, or —COO—, R 4 is a substituent, and wherein one or more H atoms of the C 1-20 alkyl group are optionally replaced with F; and an aryl or heteroaryl group that is substituted or unsubstituted with one or more substituents;
Ar 1 in each occurrence is independently an aryl or heteroaryl group that is unsubstituted or substituted with one or more substituents;
R 3 in each occurrence is independently a substituent;
n is 0, 1, 2 or 3;
each m is independently 0 or 1; and
LG is a leaving group.

12. The monomer according to claim 11 , wherein each LG is independently selected from boronic acid, boronic acid ester, halogen, and sulfonic acid ester.

13. A method of forming a polymer comprising the step of polymerizing a monomer according to claim 11 .

14. The method according to claim 13 , wherein the polymerizing step is performed in the presence of a metal catalyst.

15. A formulation comprising a polymer according to claim 1 and one or more solvents.

16. An organic electronic device comprising a first layer comprising a polymer according to claim 1 .

17. The organic electronic device according to claim 16 , wherein the device is an organic light-emitting device comprising an anode, a cathode, and at least one organic semiconducting layer including an organic light-emitting layer between the anode and the cathode, wherein the at least one organic semiconducting layer comprises the first layer.

18. A method of forming an organic light-emitting device comprising an anode, a cathode, and an organic semiconducting layer, the method comprising the steps of:
depositing the formulation according to claim 15 over one of the anode and cathode;
evaporating the one or more solvents to form the organic semiconducting layer comprising the polymer; and

forming the other of the anode and cathode over the organic semiconducting layer.

19. The method according to claim 18 , wherein the formulation is deposited by inkjet printing.

20. The polymer according to claim 6 , wherein the repeat unit of formula (III) is bound directly to aromatic carbon atoms of adjacent repeat units.

Assignees

• Cambridge Display Tech Ltd
• Sumitomo Chemical Co

Inventors

• Heidenhain Sophie Barbara
• Owoare Richard
• Watts Gary
• Pillow Jonathan

Classifications

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• H01L51/0039 Primary

  Electricity · mapped topic

• C09K2211/1433

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• H01L51/0043

  Electricity · mapped topic

• C08G2261/3245

  containing nitrogen and oxygen as heteroatoms · CPC title