Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9540329-B2
Application number	US-201213553495-A
Country	US
Kind code	B2
Filing date	Jul 19, 2012
Priority date	Jul 19, 2012
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

Heteroleptic complexes having at least one diarylamino or carbazole group, as shown in Formula (I), are provided:

wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each represent mono, di, tri, tetra, or penta substitutions or no substitution; wherein Z is a single bond connecting the two phenyl rings, or is absent, wherein when Z is absent, the positions on the phenyl rings may be substituted by R 5 or R 6 ; wherein any two adjacent substituents are optionally joined together to form a ring, which may be further substituted; wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently selected from various substituents; and wherein m is 1 or 2. Devices, such as organic light emitting devices (OLEDs) that comprise phosphorescent light emitting materials are also provided.

First claim

The invention claimed is:

1. A first device comprising a first organic light emitting device, the first organic light emitting device further comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a heteroleptic metal complex of Formula (V):

wherein R 1 , R 2 , R 3 , and R 4 each represent mono, di, tri, tetra, or penta substitutions or no substitution;
wherein R 5 and R 6 represent no substitutions;
wherein any two adjacent substituents are optionally joined together to form a ring, which may be further substituted;
wherein each of R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof; and
wherein m is 1 or 2.

2. The first device of claim 1 , wherein the heteroleptic metal complex is a compound of Formula (VI):

3. The first device of claim 1 , wherein m is 1.

4. The first device of claim 1 , wherein m is 2.

5. The first device of claim 1 , wherein the heteroleptic metal complex is selected from the group consisting of:

6. The first device of claim 1 , wherein the heteroleptic metal complex is selected from the group consisting of:

7. The first device of claim 1 , wherein each of R 1 , R 2 , R 3 , and R 4 is selected from the group consisting of: hydrogen, deuterium, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, and partially or fully deuterated variations thereof.

8. The first device of claim 1 , wherein each of R 1 , R 2 , R 3 , and R 4 is selected from the group consisting of: hydrogen, deuterium, alkyl, and combinations thereof.

9. The first device of claim 1 , wherein each of R 1 , R 2 , R 3 , and R 4 is selected from the group consisting of: hydrogen, deuterium, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, and combinations thereof.

10. The first device of claim 1 , wherein the first device is a consumer product.

11. The first device of claim 1 , wherein the first device is an organic light-emitting device.

12. The first device of claim 1 , wherein the first device comprises a lighting panel.

13. The first device of claim 1 , wherein the organic layer is an emissive layer and the complex is an emissive dopant.

14. The first device of claim 1 , wherein the organic layer is an emissive layer and the complex is a non-emissive dopant.

15. The first device of claim 1 , wherein the organic layer further comprises a host.

16. The first device of claim 15 , wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;
wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C≡CC n H 2n+1 , Ar 1 , Ar 1 -Ar 2 , and C n H 2n —Ar 1 ;
wherein n is from 1 to 10; and
wherein Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

17. The first device of claim 15 , wherein the host is selected from the group consisting of:

and combinations thereof.

18. The first device of claim 15 , wherein the host comprises a metal complex.

Assignees

• Beers Scott
• Xia Chuanjun
• Layek Suman
• Wendt Harvey
• Universal Display Corp

Inventors

• Beers Scott
• Xia Chuanjun
• Layek Suman
• Wendt Harvey

Classifications

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C07D213/74 Primary

  Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals · CPC title

• C09K2211/185

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

• C09K2211/1011

  Condensed systems · CPC title

• H05B33/10

  Apparatus or processes specially adapted to the manufacture of electroluminescent light sources · CPC title