Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11201299-B2
Application number	US-201815952797-A
Country	US
Kind code	B2
Filing date	Apr 13, 2018
Priority date	May 4, 2017
Publication date	Dec 14, 2021
Grant date	Dec 14, 2021

Abstract

The present invention includes novel heterocyclic materials for use as blue phosphorescent materials in OLED devices. The novel materials include two fused 5-membered aromatic or pseudoaromatic rings, which are bonded with 6 membered aromatic rings to serve as chelation ligands for a transition metal. The novel materials were determined computationally to have appropriate triplet energies for use as blue emitters and to possess sufficient chemical stability for use in devices.

First claim

We claim:

1. A compound of Formula I

wherein A is a fused ring system comprising a six-membered ring, which is fused to a five-membered ring, wherein the five-membered ring is fused to a second five-membered ring and the second five-membered ring is not a pyrazole ring;
wherein B is a five-membered or six-membered carbocyclic or heterocyclic ring;
wherein A and B are connected by a single bond between a carbon atom of A and an atom of B;
wherein each R A and R B independently represents mono to the possible maximum number of substitution, or no substitution;
wherein each R A and R B is 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;
wherein M is a metal having an atomic weight greater than 40;
wherein A is coordinated to M by a non-carbene dative bond;
wherein B is coordinated to M by a polar covalent bond between a carbon atom and M;
wherein M is bonded to one of the five-membered rings of A;
wherein L is a substituted or unsubstituted cyclometalated ligand, and each L can be the same or different; and
wherein m is at least 1, and m+n is the maximum number of ligands that may be attached to M.

2. The compound of claim 1 , wherein each R A and R B is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof.

3. The compound of claim 1 , wherein B is a six-membered aromatic ring.

4. The compound of claim 1 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

5. The compound of claim 1 , wherein M is Ir or Pt.

6. The compound of claim 1 , wherein B is benzene.

7. The compound of claim 1 , wherein the M-A fused ring system is selected from the group consisting of:

wherein C is a six-membered aromatic ring;
wherein R 1 represent mono to the maximum possible number of substitution, or no substitution;
wherein each X is independently selected from the group consisting of O, S, Se, NR, CRR′, SiRR′, BR, and PR;
wherein R 1 , R, and R′ are each 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any adjacent substituents in R 1 , R, and R′ are optionally joined or fused to form a ring; and
wherein the dashed line represents the bond to ring B.

8. The compound of claim 7 , wherein each R 1 , R, and R′ is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof.

9. The compound of claim 7 , wherein ring C comprises at least five carbons.

10. The compound of claim 1 , wherein the compound comprises a structure selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Lu Tongxiang (Aaron)
• Fitzgerald George
• Lahti Paul M
• Macinnis Morgan C
• Silverstein Daniel W
• Wolohan Peter
• Drennan Diana

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/361

  Polynuclear complexes, i.e. complexes comprising two or more metal centers · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C07C15/30

  Phenanthrenes · CPC title