Polymer and device

Patent metadata

Field	Value
Publication number	US-9966534-B2
Application number	US-201314655237-A
Country	US
Kind code	B2
Filing date	Dec 23, 2013
Priority date	Dec 24, 2012
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

A copolymer comprising a repeat unit of Formula (I) and at least one further repeat unit: Formula (I) wherein: wherein: Ar 1 and Ar 2 are each independently selected from aryl and heteroaryl, each of which is independently unsubstituted or substituted with one or more substituents; each R is independently a substituent; each n is independently 0, 1 or 2; each m is independently 0, 1, 2 or 3, and at least one of the repeat units of the polymer is a partially conjugating repeat unit.

First claim

The invention claimed is:

1. A copolymer comprising a repeat unit of Formula (I) and at least one further repeat unit:

wherein:
Ar 1 and Ar 2 are each independently aryl or heteroaryl, each of which is independently unsubstituted or substituted with one or more substituents;
each R is independently a substituent;
each n is independently 0, 1, or 2;
each m is independently 0, 1, 2, or 3, and at least one of the repeat units of the polymer is a partially conjugating repeat unit;
wherein at least one repeat unit of the polymer is substituted with a crosslinkable group.

2. The copolymer of claim 1 , wherein at least one of m and n is at least 1, and each R is independently selected from the group consisting of:
C 1-20 alkyl wherein one or more non-adjacent C atoms may be replaced with O, S, NR 11 , C═O or COO; wherein R 11 is a substituent
aryl or heteroaryl that may be unsubstituted or substituted with one or more substituents;
a branched or linear chain of aryl or heteroaryl groups wherein each aryl or heteroaryl is independently unsubstituted or substituted with one or more substituents; and
a crosslinkable-group.

3. The copolymer of claim 1 , wherein each R is independently a C 1-40 hydrocarbyl group.

4. The copolymer of claim 1 , wherein n=2.

5. The copolymer of claim 1 , wherein the repeat unit of formula (I) has Formula (II):

wherein R 1 in each occurrence is a substituent; each y is independently 0, 1, 2, 3 or 4; and
each z is independently 0, 1, 2, 3, 4 or 5.

6. The copolymer of claim 1 , wherein the repeat unit of formula (I) is a partially conjugating repeat unit.

7. The copolymer of claim 6 wherein the repeat unit of formula (I) has formula (XIV):

wherein R, Ar 2 , n and m are as defined in claim 1 ;
wherein R 1 in each occurrence is a substituent;
y1 and y2 are each independently 0 or 1 with the proviso that at least one of y1 and y2 is 1; and
each y3 is independently 0, 1 or 2.

8. The copolymer of claim 1 , wherein a further repeat unit is a partially conjugating repeat unit.

9. The copolymer of claim 8 , wherein the partially conjugating repeat unit is a repeat unit of formula (IIIa), (IIIb) or (IIIc):

wherein p is 1, 2 or 3; q in each occurrence is independently 1, 2, 3 or 4; w is 0, 1, 2, 3 or 4;
and R 3 independently in each occurrence is a substituent.

10. The copolymer of claim 8 wherein the partially conjugating further repeat unit is a repeat unit of formula (VIIb) or (VIIc):

wherein R 3 and R 8 independently in each occurrence is a substituent.

11. The copolymer of claim 6 wherein the repeat unit of formula (I) is not a partially-conjugating repeat unit.

12. A formulation comprising the copolymer of claim 1 , and at least one solvent.

13. An organic light-emitting device comprising an anode, a cathode, a light-emitting layer between the anode and the cathode, and a hole transporting layer between the light emitting layer and the anode, wherein the hole transporting layer comprises a copolymer according to claim 1 .

14. The organic light-emitting device of claim 13 wherein the light-emitting layer comprises a fluorescent light-emitting material.

15. The organic light-emitting device of claim 13 wherein the light-emitting layer comprises a phosphorescent light-emitting material.

16. A method of forming an organic light-emitting device according to claim 13 comprising the steps of: forming the hole-transporting layer over the anode; forming the light-emitting layer over the hole-transporting layer; and forming the cathode over the light-emitting layer.

17. The method according to claim 16 wherein the hole-transporting layer is formed by depositing a formulation comprising a copolymer comprising a repeat unit of Formula (I) and at least one further repeat unit, and at least one solvent over the anode; and evaporating the at least one solvent:

wherein:
Ar 1 and Ar 2 are each independently selected from aryl and heteroaryl, each of which is independently unsubstituted or substituted with one or more substituents;
each R is independently a substituent;
each n is independently 0, 1 or 2;
each m is independently 0, 1, 2 or 3; and
a further repeat unit is a partially conjugating repeat unit.

18. The method according to claim 17 wherein the hole-transporting layer is crosslinked prior to formation of the light-emitting layer.

19. A copolymer comprising a repeat unit of Formula (XIV) and at least one further repeat unit:

wherein:
each Ar 2 is independently aryl or heteroaryl, each of which is independently unsubstituted or substituted with one or more substituents;
each R is independently a substituent;
each n is independently 0, 1 or 2;
each m is independently 0, 1, 2 or 3;
R 1 in each occurrence is a substituent;
y1 and y2 are each independently 0 or 1 with the proviso that at least one of y1 and y2 is 1; and
each y3 is independently 0, 1 or 2;
wherein the repeat unit of formula (XIV) is a partially conjugating repeat unit.

20. A copolymer comprising a repeat unit of Formula (I) and at least one further repeat unit:

wherein:
Ar 1 and Ar 2 are each independently aryl or heteroaryl, each of which is independently unsubstituted or substituted with one or more substituents;
each R is independently a substituent;
each n is independently 0, 1 or 2;
each m is independently 0, 1, 2 or 3, and at least one of the repeat units of the polymer is a partially conjugating repeat unit;
wherein a further repeat unit is a partially conjugating repeat unit and is a repeat unit of formula (IIIa), (IIIb) or (IIIc):

wherein p is 1, 2 or 3; q in each occurrence is independently 1, 2, 3 or 4; w is 0, 1, 2, 3 or 4;
and R 3 independently in each occurrence is a substituent.

21. A method of forming an organic light-emitting device comprising an anode, a cathode, a light-emitting layer between the anode and the cathode, and a hole transporting layer between the light emitting layer and the anode, wherein the hole transporting layer comprises a copolymer comprising a repeat unit of Formula (I) and at least one further repeat unit:

wherein:
Ar 1 and Ar 2 are each independently aryl or heteroaryl, each of w

Assignees

• Cambridge Display Tech Ltd
• Sumitomo Chemical Co

Inventors

• Stackhouse Philip
• Heidenhain Sophie Barbara
• Pegington Ruth
• Pillow Jonathan
• Humphries Martin
• Yoshida Tomoyasu

Classifications

• C08G61/12 Primary

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

• H01L51/5016

  Electricity · mapped topic

• H01L51/0085

  Electricity · mapped topic

• H01L51/0043

  Electricity · mapped topic

• C08G2261/3142

  fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene · CPC title