Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9935276-B2
Application number	US-201313867750-A
Country	US
Kind code	B2
Filing date	Apr 22, 2013
Priority date	Feb 21, 2013
Publication date	Apr 3, 2018
Grant date	Apr 3, 2018

Abstract

Compounds including a ligand L according to Formula I devices containing the same and formulations including the same are described.

In Formula I, B is a 5 or 6-membered carbocyclic or heterocyclic ring; C is a condensed aromatic ring system having at least two carbocyclic or heterocyclic rings; A-B represents a bonded pair of carbocyclic or heterocyclic rings coordinated to a metal M via a nitrogen atom in ring A and an sp 2 hybridized atom X 6 in ring B; R A , R B and R C can represent no substitutions or the maximum substitutions available on the respective ring; X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are carbon or nd nitrogen, and X 7 is carbon; at least one of R A and R C substituents adjacent to the bond between A and C is not hydrogen; and the ligand is coordinated to a metal, having an atomic number greater than 40.

First claim

We claim:

1. A heteroleptic compound having a structure of Formula II:

wherein n is 1 or 2;
wherein B is a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein C is a condensed aromatic ring system having at least two carbocyclic or heterocyclic rings;
wherein A-B represents a bonded pair of carbocyclic or heterocyclic rings coordinated to Ir via a nitrogen atom in ring A and an sp 2 hybridized atom X 6 in ring B;
wherein A-C represents a bonded pair of carbocyclic or heterocyclic rings;
wherein R A may represent mono, di, or tri substitutions, or no substitution;
wherein R B may represent any number of substitution from mono to up to the maximum possible number of substitution on ring B, or no substitution;
wherein R C may represent any number of substitution from mono to up to the maximum possible number of substitution on ring C, or no substitution;
wherein each R A , R B , and R C is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein X 1 , X 2 , X 3 , and X 4 are selected from C—R A , C—X 7 , and N;
wherein X 6 is selected from carbon and nitrogen;
wherein X 5 and X 7 are carbon;
wherein at least one of R A and R C is at least a mono-substitution;
wherein at least one of R A and R C adjacent to the bond between A and C is not hydrogen;
wherein L′ is monoanionic bidentate ligand selected from the group consisting of:

and
wherein:
R′, R 2′ , R″, and R′″ are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, aryl, and heteroaryl,
X is selected from the group consisting of S, NZ, O, Se, BZ, CZZ′, and C═O,
Z and Z′ are independently selected from the group consisting of hydrogen, alkyl, and aryl, and
R′, R″, and R′″ can join to form one or more fused rings.

2. The compound of claim 1 , wherein A is pyridine.

3. The compound of claim 1 , wherein B is phenyl.

4. The compound of claim 1 , wherein only one of R A and R C adjacent to the bond between A and C is not hydrogen.

5. The compound of claim 1 , wherein the R A and R C adjacent to the bond between A and C are independently selected from the group consisting of hydrogen; deuterium; linear, branched and cyclic alkyl; and combinations thereof.

6. The compound of claim 1 , wherein the R A and R C adjacent to the bond between A and C are independently 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.

7. The compound of claim 4 , wherein the only one of R A and R C adjacent to the bond between A and C that is not hydrogen is selected from the group consisting of deuterium, methyl, ethyl, and combinations thereof.

8. The compound of claim 1 , wherein n=1.

9. The compound of claim 1 , wherein n=2.

10. The compound of claim 1 , where L′ is

11. The compound of claim 1 , wherein bond between A and C is formed between X 2 and X 7 .

12. The compound of claim 1 , wherein bond between A and C is formed between X 3 and X 7 .

13. The compound of claim 1 , wherein C is selected from the group consisting of:

wherein A 1 to A 8 , Q 1 to Q 6 , B 1 to B 8 , J 1 to J 12 , K 1 to K 10 are independently selected from the group consisting of C and N;
wherein X and Y are independently selected from the group consisting of O, S, NR 3′ , and CR 3″ R 3′″ ; and
wherein R 3′ , R 3″ and R 3′″ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfanyl, sulfonyl, phosphino, and combinations thereof.

14. The compound of claim 1 , wherein C is selected from the group consisting of:

15. A compound selected from the group consisting of:

16. A first device comprising a 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 compound having a structure of Formula II:

wherein n is 1 or 2;
wherein B is a 5 or 6-membered carbocycl

Assignees

• Universal Display Corp

Inventors

• Alleyne Bert
• Kwong Raymond

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/185

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

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H01L51/5024

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic