Dibenzofuran and dibenzothiophene derivatives and organic light-emitting devices containing them

Patent metadata

Field	Value
Publication number	US-11136303-B2
Application number	US-201716083470-A
Country	US
Kind code	B2
Filing date	Mar 7, 2017
Priority date	Mar 8, 2016
Publication date	Oct 5, 2021
Grant date	Oct 5, 2021

Abstract

A compound of formula (I) wherein Z is a group of formula (II) and Core is selected from groups of formula (IIIa) or (IIIb) wherein X is S or O; R1 is a substituent; n is 0 or a positive integer; Ar1 independently in each occurrence is an arylene group; R2 is a substituent; R3 is a substituent; R4 is an arylene or heteroarylene group; Y is C or Si; a is 1, 2 or 3; b is 0 or a positive integer; and c is 0 or a positive integer. The compound of formula (I) may be used as a host for a light-emitting dopant in an organic light-emitting device.

First claim

The invention claimed is:

1. A compound of formula (I):
Z-Core-Z  (I)

wherein:
Z in each occurrence is independently a group of formula (II):

X is S or O;
R 1 independently in each occurrence is a substituent;
n is 0 or a positive integer;
-* is a direct bond to Core; and
Core is of formula (IIIb):

wherein
R 3 is a substituent;
R 4 is an arylene or heteroarylene group that may independently in each occurrence be unsubstituted or substituted with one or more substituents;
Y is C;
and
c is 1.

2. A compound according to claim 1 wherein each R 4 is a phenylene group that may be unsubstituted or substituted with one or more substituents.

3. A compound according to claim 1 wherein each R 3 is an aryl or heteroaryl group which may be unsubstituted or substituted with one or more substituents.

4. A compound according to claim 1 having a HOMO level of at least 5.8 eV from vacuum level as measured by square wave voltammetry.

5. A composition comprising a compound according to claim 1 and at least one light-emitting dopant.

6. A composition according to claim 5 wherein the light-emitting dopant is a phosphorescent dopant.

7. A composition according to claim 5 wherein the light-emitting dopant is a blue light-emitting material.

8. A composition according to claim 5 wherein the light-emitting dopant is a metal complex comprising at least one unsubstituted or substituted phenylimidazole or phenyltriazole ligand.

9. A formulation comprising a compound according to claim 1 and one or more solvents.

10. An organic light-emitting device comprising an anode, a cathode and a light-emitting layer between the anode and the cathode wherein the light-emitting layer comprises a compound according to claim 1 .

11. An organic light-emitting device comprising an anode, a cathode and a light-emitting layer between the anode and the cathode wherein the organic light-emitting layer comprises a composition according to claim 5 .

12. An organic light-emitting device according to claim 10 wherein the device comprises at least one further light-emitting layer.

13. An organic light-emitting device according to claim 10 wherein the device emits white light.

14. A method of forming an organic light-emitting device according to claim 10 comprising the step of forming the light-emitting layer over one of the anode and the cathode and forming the other of the anode and the cathode over the light-emitting layer.

15. A method according to claim 14 wherein the light-emitting layer is formed by depositing a formulation comprising the compound of formula (I) and one or more solvents and evaporating the one or more solvents.

16. A compound of formula (I):
Z-Core-Z  (I)

wherein:
Z in each occurrence is independently a group of formula (II):

X is S or O;
R 1 independently in each occurrence is a substituent;
n is 0 or a positive integer;
-* is a direct bond to Core; and
Core is of formula (IIIb):

wherein each R 3 is an aryl or heteroaryl group which may be unsubstituted or substituted with one or more substituents;
R 4 is an arylene or heteroarylene group that may independently in each occurrence be unsubstituted or substituted with one or more substituents;
Y is C; and
c independently in each occurrence is 0 or a positive integer.

17. A composition comprising a compound according to claim 16 and at least one light-emitting dopant.

18. A formulation comprising a compound according to claim 16 and one or more solvents.

19. An organic light-emitting device comprising an anode, a cathode, and a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a compound according to claim 16 .

20. A method of forming an organic light-emitting device according to claim 19 comprising the step of forming the light-emitting layer over one of the anode and the cathode and forming the other of the anode and the cathode over the light-emitting layer.

Assignees

• Cambridge Display Tech Ltd
• Sumitomo Chemical Co

Inventors

• Humphries Martin
• Tarran William
• Kamtekar Kiran
• Stackhouse Philip
• Lee James

Classifications

• C07F7/0814

  said ring is substituted at a C ring atom by Si · CPC title

• C07D307/91 Primary

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• C07D333/76

  Dibenzothiophenes · CPC title

• C07D407/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D407/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title