Organic materials for organic light emitting devices

Patent metadata

Field	Value
Publication number	US-9548459-B2
Application number	US-201514705103-A
Country	US
Kind code	B2
Filing date	May 6, 2015
Priority date	Mar 15, 2012
Publication date	Jan 17, 2017
Grant date	Jan 17, 2017

Abstract

Novel diarylamino phenyl carbazole compounds are provided. By appropriately selecting the nature of the diarylamino substituent and the substitution on the carbazole nitrogen, compounds with appropriate HOMO and LUMO energies can be obtained for use as materials in a secondary hole transport layer.

First claim

What is claimed is:

1. A compound having the formula:

wherein Ar 1 and Ar 2 are independently selected from the group consisting of aryl and heteroaryl; and
wherein X is selected from the group consisting of O, S, and Se;
wherein R 1 and R 2 independently represent mono, di, tri, tetra substitution, or no substitution; and
wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

2. The compound of claim 1 , wherein R 3 and R 4 are independently selected from the group consisting of alkyl, heteroalkyl, arylalkyl, aryl, and heteroaryl.

3. The compound of claim 1 , wherein R 3 and R 4 are hydrogen or deuterium.

4. The compound of claim 1 , wherein the compound has the formula:

5. The compound of claim 1 , wherein X is O or S.

6. The compound of claim 1 , wherein Ar 1 and Ar 2 are aryl.

7. A first device comprising an organic light emitting device, further comprising:
an anode;
a cathode;
an emissive layer disposed between the anode and the cathode;
a hole injection layer disposed between the anode and the emissive layer;
a first hole transport layer disposed between the hole injection layer and the emissive layer; and
a second hole transport layer disposed between the first hole transport layer and the emissive layer; and
wherein the second hole transport layer comprises a compound of formula:

wherein Ar 1 , Ar 2 , and Ar 5 are independently selected from the group consisting of aryl and heteroaryl; and
wherein R 3 and R 4 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

8. The first device of claim 7 , wherein the compound has the formula:

wherein X is selected from the group consisting of O, S, and Se;
wherein R 1 and R 2 independently represent mono, di, tri, tetra substitution, or no substitution; and
wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

9. The first device of claim 7 , wherein the second hole transport layer is disposed adjacent to the first hole transport layer.

10. The first device of claim 7 , wherein the first hole transport layer is thicker than the second hole transport layer.

11. The first device of claim 7 , wherein the first hole transport layer comprises a compound with the formula:

wherein Ar a , Ar b , Ar c and Ar d are independently selected from the group consisting of aryl and heteroaryl.

12. The first device of claim 7 , wherein the triplet energy of the compound of Formula II is higher than the emission energy of the emissive layer.

13. The first device of claim 7 , further comprising a first dopant material that is an emissive dopant comprising a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

wherein R a , R b , R c , and R d may represent mono, di, tri, or tetra substitution, or no substitution;
wherein R a , R b , R c , and R d are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a fused ring or form a multidentate ligand.

14. The first device of claim 7 , wherein the first device is a consumer product.

15. The first device of claim 7 , wherein the first device is an organic light-emitting device.

16. The first device of claim 7 , wherein the first device comprises a lighting panel.

17. A first device comprising an organic light emitting device, further comprising:
an anode;
a cathode;
a first organic layer disposed between the anode and the cathode; and
wherein the first organic layer comprises a compound of formula:

wherein Ar 1 and Ar 2 are independently selected from the group consisting of aryl and heteroaryl; and
wherein X is selected from the group consisting of O, S, and Se;
wherein R 1 and R 2 independently represent mono, di, tri, tetra substitution, or no substitution; and
wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

18. The first device of claim 17 , wherein the first organic layer is an emissive layer.

19. The first device of claim 18 , wherein the emissive layer is a phosphorescent emissive layer.

Assignees

• Universal Display Corp

Inventors

• Kwong Raymond
• Lam Siu Tung
• Lee Chi Hang
• Lam Sze Kui

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D409/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title