IP Library Granted Patent US 8,147,989
Granted Patent B2
US 8,147,989 · App. 12/394,935 · Granted Apr 3, 2012

OLED device with stabilized green light-emitting layer

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Quick Facts
Patent No.
US 8,147,989
App. No.
12/394,935
Granted
Apr 3, 2012
Kind
B2
Abstract

The invention provides an OLED device including an anode, a cathode and a green light-emitting layer located therebetween, said light-emitting layer including an anthracene host, a bis-diarylamine 9,10-substituted anthracene and a stabilizer compound which is selected from a quinacridone or a biphenylstyrylamine. Devices of the invention provide improvement in features such as stability and efficiency while maintaining excellent color.

Claims (50)

1. An OLED device comprising an anode, a cathode and a green light-emitting layer located therebetween, said light-emitting layer comprising:

a) an anthracene host;

b) a bis-diarylamine 9,10-substituted anthracene emitter according to Formula (1):

wherein:

X is an aryl group of 6 to 30 nucleus carbon atoms;

n is 0 or 1;

Ar 1 , Ar 2 , Ar 3 and Ar 4 each independently represent a substituted or unsubstituted aryl group of 6 to 30 nucleus carbon atoms where Ar 1 and Ar 2 or Ar 3 and Ar 4 can optionally be joined together;

W is an alkyl, aryl or heterocyclic group; and

q is an integer of 0 to 2; and

c) a stabilizer compound which is selected from a quinacridone or a biphenylstyrylamine.

2. The OLED device of claim 1 wherein n is 0 in the bis-diarylamine 9,10-substituted anthracene.

3. The OLED device of claim 2 wherein the bis-diarylamine 9,10-substituted anthracene is according to Formula (1b):

wherein:

Ar 1 , Ar 2 , Ar 3 and Ar 4 each independently represent a substituted or unsubstituted aryl group of 6 to 10 nucleus carbon atoms where Ar 1 and Ar 2 or Ar 3 and Ar 4 can optionally be joined together;

W is an alkyl or aryl group; and

q is an integer of 0 to 2.

4. The OLED device of claim 3 wherein q is 0 and Ar 1 , Ar 2 , Ar 3 and Ar 4 are all individually substituted or unsubstituted phenyl or naphthyl groups.

5. The OLED device of claim 2 wherein the light emitting layer emits light with a CIE x coordinate in the range of 0.360-0.390 and a CIE y coordinate in the range of 0.600-0.610.

6. The OLED device of claim 1 wherein n is 1in the bis-diarylamine 9,10-substituted anthracene.

7. The OLED device of claim 6 wherein the bis-diarylamine 9,10-substituted anthracene is according to Formula (1d):

wherein:

Ar 1 , Ar 2 , Ar 3 and Ar 4 each independently represent a substituted or unsubstituted aryl group of 6 to 10 nucleus carbon atoms where Ar 1 and Ar 2 or Ar 3 and Ar 4 can optionally be joined together;

W is an alkyl or aryl group; and

q is an integer of 0 to 2.

8. The OLED device of claim 7 wherein the bis-diarylamine 9,10-substituted anthracene is according to Formula (1e):

wherein:

Ar 5 , Ar 6 , Ar 7 , Ar 8 are all individually substituted or unsubstituted phenyl or naphthyl; and

Z is hydrogen, alkyl, aryl, naphthyl or heterocyclic.

9. The OLED device of claim 6 wherein the light emitting layer emits light with a CIE x coordinate in the range of 0.250-0.300 and a CIE y coordinate in the range of 0.600-0.610.

10. The OLED device of claim 1 wherein the anthracene host is according to Formula (4):

wherein:

R 1 and R 6 each independently represent an aryl group having 6-24 carbon atoms;

R 2 -R 5 and R 7 -R 10 are each independently chosen from hydrogen, alkyl groups from 1-24 carbon atoms or aromatic groups from 5-24 carbon atoms.

11. The OLED device of claim 10 wherein:

R 1 and R 6 each represent an independently selected phenyl group, biphenyl group, or naphthyl group;

R 3 represents hydrogen or an aromatic group from 6-24 carbon atom; and

R 2 , R 4 , R 5 , R 7 -R 10 represent hydrogen.

12. The OLED device of claim 1 wherein the stabilizer compound is a quinacridone according to Formula (2):

wherein:

R 1 and R 2 are each independently alkyl or aryl;

X 1 and X 2 are each independently halogen; and

n and p are each independently 0 to 4.

13. The OLED device of claim 12 wherein the quinacridone is chosen from:

14. The OLED device of claim 1 wherein the stabilizer compound is a biphenylstyrylamine according to Formula (3):

wherein:

Ar 1 -Ar 4 are each independently an aryl group of 6 to 24 carbon atoms where Ar 1 -Ar 2 and Ar 3 -Ar 4 can be optionally joined together to form a ring system.

15. The OLED device of claim 14 where Ar1-Ar4 are each individually phenyl or alkyl substituted phenyl groups.

16. The OLED device of claim 15 wherein the biphenylstyrylamine is chosen from:

17. The OLED device of claim 1 wherein the light-emitting layer includes the bis-diarylamine 9,10-substituted anthracene in the range of 0.5-25% by volume and the stabilizer in the range of 0.5%-6% by volume.

18. The OLED device of claim 17 wherein the light-emitting layer includes the bis-diarylamine 9,10-substituted anthracene in the range of 3-15% by volume and the stabilizer in the range of 0.5%-6% by volume.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 11, 2010
From: EASTMAN KODAK COMPANY
To: GLOBAL OLED TECHNOLOGY LLC
Reel/Frame 024068/0468 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2009
From: KONDAKOVA, MARINA E.; KLUBEK, KEVIN P.; HELBER, MARGARET J.; BESSEY, PETER G.; VARGAS, J. R.; RICKS, MICHELE L.
To: EASTMAN KODAK COMPANY
Reel/Frame 022465/0832 →