IP Library Granted Patent US 9,722,183
Granted Patent B2
US 9,722,183 · App. 14/361,662 · Granted Aug 1, 2017

Display

Inventors: Omrane Fadhel (Dresden, DE); Ramona Pretsch (Dresden, DE); Carsten Rothe (Dresden, DE); Rudolf Lessmann (Duesseldorf, DE); Francois Cardinali (Dresden, DE)
Assignee: Novaled GmbH
H01L51/0054C07D221/18C07F9/64C09B15/00H01L27/3206H01L27/3244H01L51/0067H01L51/0071H01L51/0072H01L51/5076
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Quick Facts
Patent No.
US 9,722,183
App. No.
14/361,662
Granted
Aug 1, 2017
Kind
B2
Abstract

Display comprising at least one organic light emitting diode, wherein the at least one organic light emitting diode comprises an anode, a cathode, a light emitting layer between the anode and the cathode, and at least one layer comprising a compound according to formula (I) between the cathode and the light emitting layer: wherein A 1 and A 2 are independently selected from halogen, CN, substituted or unsubstituted C 1 -C 20 -alkyl or heteroalkyl, C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, C 1 -C 20 -alkoxy or C 6 -C 20 -aryloxy, A 3 is selected from substituted or unsubstituted C 6 -C 40 -aryl or C 5 -C 40 -heteroaryl, m=0, 1 or 2, n=0, 1 or 2.

Claims (44)

1. A display comprising at least one organic light emitting diode, wherein the at least one organic light emitting diode comprises an anode, a cathode, a light emitting layer arranged between the anode and the cathode, and at least one layer arranged between the cathode and the light emitting layer, the at least one layer comprising a compound according to formula (I):

wherein A 1 and A 2 are independently selected from halogen, CN, substituted or unsubstituted C 1 -C 20 -alkyl or heteroalkyl, substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, or substituted or unsubstituted C 1 -C 20 -alkoxy or C 6 -C 20 -aryloxy,

A 3 is selected from substituted or unsubstituted C 6 -C 40 -aryl or C 5 -C 40 -heteroaryl,

m is 0, 1 or 2, and

n is 0, 1 or 2.

2. The display according to claim 1 , wherein the compound of formula (I) has a structure according to generic formula (II):

wherein each R 1 -R 4 is independently selected from H, halogen, CN, substituted or unsubstituted C 1 -C 20 -alkyl or heteroalkyl, substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, or substituted or unsubstituted C 1 -C 20 -alkoxy or C 6 -C 20 -aryloxy,

Ar is a substituted or unsubstituted C 6 -C 24 arene or substituted or unsubstituted C 5 -C 24 -heteroarene,

j is 1 or 2, and

each R 5 is independently selected from substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, H, F, or

wherein each R 1′ -R 4′ is independently selected from H, halogen, CN, substituted or unsubstituted C 1 -C 20 -alkyl or heteroalkyl, substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, or substituted or unsubstituted C 1 -C 20 -alkoxy or C 5 -C 20 -aryloxy.

3. The display according to claim 2 , wherein each of R 1 -R 4 is independently selected from H, substituted or unsubstituted C 6 -C 20 aryl, or substituted or unsubstituted C 5 -C 20 -heteroaryl.

4. The display according to claim 1 , wherein A 3 comprises at least one group selected from the group consisting of phosphine oxide and phosphine sulfide.

5. The display according to claim 1 , wherein A 3 is

wherein R 6 is selected from H, F, CN, or substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl,

each of R 7 and R 8 is independently selected from C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl which is unsubstituted or substituted,

R 9 is O or S,

r is 0, 1, 2, 3 or 4,

k is 0 or 1, and

q is 1, 2 or 3.

6. The display according to claim 1 , wherein the layer comprising the compound according to formula (I) comprises an additional material selected from a redox n-dopant, an alkaline metal complex, or alkaline earth metal complex.

7. The display according to claim 1 , wherein the layer comprising the compound according to formula (I) is an exciton blocking layer.

8. The display according to claim 1 , wherein the at least one organic light emitting diode emits white light.

9. The display according to claim 1 , wherein the device comprises a first and a second organic light emitting diode, wherein the first organic light emitting diode emits light in a first color, and the second organic light emitting diode emits light in a second color other than the first color.

10. The display according to claim 9 , wherein the compound according to formula (I) of the first organic light emitting diode and the compound according to formula (I) of the second organic light emitting diode are the same compounds.

11. A compound according to formula (I):

wherein A 1 and A 2 are independently selected from halogen, CN, substituted or unsubstituted C 1 -C 20 -alkyl or heteroalkyl, substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, or substituted or unsubstituted C 1 -C 20 -alkoxy or C 6 -C 20 -aryloxy,

m and n are independently selected from 0, 1 or 2,

A 3 is

wherein R 6 is selected from H, halogen, CN, substituted or unsubstituted C 1 -C 20 -alkyl or C 1 -C 20 -heteroalkyl, substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, or substituted or unsubstituted C 1 -C 20 -alkoxy or C 6 -C 20 -aryloxy;

each of R 7 and R 8 is independently selected from substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl;

q is selected from 1, 2, or 3;

k is 0 or 1,

r is selected from 0, 1, 2, 3 or 4,

R 9 is O or S;

wherein the following compounds are excluded:

12. The compound according to claim 11 having the formula (IV)

wherein each of R 18 -R 22 is independently selected from H, halogen, CN, substituted or unsubstituted C 1 -C 20 -alkyl or C 1 -C 20 -heteroalkyl, substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, or substituted or unsubstituted C 1 -C 20 -alkoxy or C 6 -C 20 -aryloxy;

each of R 23 and R 24 is independently selected from substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, and

R 25 is O or S.

13. The compound according to claim 12 , wherein each of R 18 -R 21 in formula (IV) is independently selected from H, substituted or unsubstituted C 1 -C 20 -alkyl, substituted or unsubstituted C 1 -C 20 -heteroalkyl, substituted or unsubstituted C 1 -C 20 -alkoxy, or substituted or unsubstituted C 6 -C 20 -aryloxy;

R 22 is selected from H, substituted or unsubstituted C 6 -C 20 -aryl, or substituted or unsubstituted C 5 -C 20 -heteroaryl; each of R 23 and R 24 is independently selected from substituted or unsubstituted C 6 -C 20 -aryl or substituted or unsubstituted C 5 -C 20 -heteroaryl, and R 25 is O.

14. The compound according to claim 11 having a structure according to one of the following formulas:

15. The display according to claim 5 , wherein R 6 is selected from:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2014
From: FADHEL, OMRANE; PRETSCH, RAMONA; ROTHE, CARSTEN; LESSMANN, RUDOLF; CARDINALI, FRANCOIS
To: NOVALED GMBH
Reel/Frame 034152/0769 →
Priority Claims (2)
EP 11191345 · Nov 30, 2011 · regional
EP 11193070 · Dec 12, 2011 · regional
Continuity (1)
Related Publication 20140332790A1 · Nov 13, 2014