Amino fluorene monomers, polymers, and organic electronic devices

Patent metadata

Field	Value
Publication number	US-10396287-B2
Application number	US-201314372534-A
Country	US
Kind code	B2
Filing date	Jan 16, 2013
Priority date	Jan 16, 2012
Publication date	Aug 27, 2019
Grant date	Aug 27, 2019

Abstract

An organic electronic device comprising an anode, a cathode, a semiconducting layer between the anode and the cathode and a hole transporting layer between the anode and the semiconducting layer, the hole-transporting layer comprising a co-polymer comprising repeat units of formula (I) and one or more co-repeat units: (I) wherein: Ar 1 independently in each occurrence represents a fused aryl or fused heteroaryl group that may be unsubstituted or substituted with one or more substituents; Ar 2 represents an aryl or heteroaryl group that may be unsubstituted or substituted with one or more substituents; R independently in each occurrence represents a substituent; and m is 1 or 2, preferably 1; and each Ar 1 is directly bound to an aromatic or heteroaromatic group of a co-repeat unit.

First claim

The invention claimed is:

1. An organic electronic device comprising an anode, a cathode, a semiconducting layer between the anode and the cathode, and a hole transporting layer between the anode and the semiconducting layer, the hole-transporting layer comprising a co-polymer comprising repeat units of formula (I) and at least two different co-repeat units:

wherein:
Ar 2 represents an aryl or heteroaryl group that may be unsubstituted or substituted with one or more substituents; R independently in each occurrence represents a substituent; and m is 1or 2;
each Ar 1 is directly bound to an aromatic or heteroaromatic group of a co-repeat unit; and
Ar 1 is of formula (II):

wherein R 6 in each occurrence is independently H or a substituent; R 7 in each occurrence is independently a substituent; and x in each occurrence is independently 0, 1, 2or 3.

2. An organic electronic device according to claim 1 wherein R is an aryl or heteroaryl group that may be unsubstituted or substituted with one or more substituents.

3. An organic electronic device according to claim 1 wherein Ar 2 is a fused aryl.

4. An organic electronic device according to claim 1 wherein at least one co-repeat unit is an aromatic group that may be unsubstituted or substituted with one or more substituents.

5. An organic electronic device according to claim 4 wherein at least one of the co-repeat units is a repeat unit of formula (III):

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

6. An organic electronic device according to claim 4 wherein at least one of the co-repeat units is a repeat unit of formula (IV):

wherein R 3 in each occurrence is the same or different and is H or a substituent, and wherein the two groups R 3 may be linked to form a ring; R 8 is a substituent; and d is 0, 1, 2 or 3.

7. An organic electronic device according to claim 1 wherein the co-polymer is crosslinked.

8. An organic electronic device according to claim 1 wherein the device is an organic light-emitting device, and the semiconducting layer is an organic light-emitting layer.

9. An organic electronic device comprising an anode, a cathode, a semiconducting layer between the anode and the cathode, and a hole transporting layer between the anode and the semiconducting layer, the hole-transporting layer comprising a co-polymer comprising repeat units of formula (I) and one or more co-repeat units:

wherein:
Ar 2 represents an aryl or heteroaryl group that may be unsubstituted or substituted with one or more substituents; R independently in each occurrence represents a substituent; and m is 1or 2;
each Ar 1 is directly bound to an aromatic or heteroaromatic group of a co-repeat unit; and
Ar 1 is of formula (II):

wherein R 6 in each occurrence is independently H or a substituent; R 7 in each occurrence is independently a substituent; x in each occurrence is independently 0, 1, 2 or 3;
wherein at least one co-repeat unit is an aromatic group that may be unsubstituted or substituted with one or more substituents; and
wherein at least one of the co-repeat units is a repeat unit of formula (IV):

wherein R 3 in each occurrence is the same or different and is H or a substituent, and wherein the two groups R 3 may be linked to form a ring; R 8 is a substituent; and d is 0, 1, 2 or 3.

10. An organic electronic device comprising an anode, a cathode, a semiconducting layer between the anode and the cathode, and a hole transporting layer between the anode and the semiconducting layer, the hole-transporting layer comprising a co-polymer comprising repeat units of formula (I) and one or more co-repeat units:

wherein:
Ar 2 represents an aryl or heteroaryl group that may be unsubstituted or substituted with one or more substituents; R independently in each occurrence represents a substituent; and m is 1or 2;
each Ar 1 is directly bound to an aromatic or heteroaromatic group of a co-repeat unit; and
Ar 1 is of formula (II):

wherein R 6 in each occurrence is independently H or a substituent; R 7 in each occurrence is independently a substituent; x in each occurrence is independently 0, 1, 2 or 3; and
wherein the co-polymer is crosslinked.

11. A method of forming an organic electronic device according to claim 1 , the method comprising the steps of: forming the hole-transporting layer over the anode; forming the semiconducting layer over the hole-transporting layer; and forming the cathode over the semiconducting layer.

12. A method according to claim 11 wherein the hole transporting layer is formed by depositing a formulation comprising the polymer comprising repeat units of formula (I) and one or more solvents and evaporating the one or more solvents.

13. A method according to claim 11 wherein the hole-transporting layer is crosslinked prior to formation of the semiconducting layer.

Assignees

• Sumitomo Chemical Co
• Cambridge Display Tech Ltd

Inventors

• Pillow Jonathan
• Wilson Richard J
• Heidenhain Sophie Barbara
• Pegington Ruth
• Doust Alexander
• Owoare Richard

Classifications

• C09K2211/185

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

• C08G73/026

  Wholly aromatic polyamines · CPC title

• C08G2261/3162

  Arylamines · CPC title

• C08G2261/76

  crosslinking · CPC title

• C07C211/61 Primary

  with at least one of the condensed ring systems formed by three or more rings · CPC title