Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10522769-B2
Application number	US-201615202866-A
Country	US
Kind code	B2
Filing date	Jul 6, 2016
Priority date	Aug 18, 2015
Publication date	Dec 31, 2019
Grant date	Dec 31, 2019

Abstract

This invention discloses iridium complexes with benzothienoquinoline, benzofuroquinoline, benzoselenophenoquinoline, and benzosiloloquinoline ligands. These complexes can be used as phosphorescent emitters in OLEDs.

First claim

We claim:

1. A compound of formula M(L A ) x (L B ) y (L C ) z ,
wherein ligand L A is:

wherein ligand L B is:

wherein ligand L C is:

wherein M is a metal having an atomic number greater than 40;
wherein x is 1, 2, or 3;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein Y 1 to Y 6 are carbon or nitrogen;
wherein Y is selected from the group consisting of S and Se;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R A , R B , R C , and R D each independently represent mono to the maximum possible number of substitution, or no substitution;
wherein each of R A , R B , R C , R D , R X , R Y , and R Z 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; and
wherein any adjacent substituents are optionally joined or fused into a ring.

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

3. The compound of claim 1 , wherein the compound has the formula selected from the group consisting of M(L A ) 2 (L C ) and M(L A )(L B ) 2 .

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

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl; and
wherein at least one of R 1 , R 2 , R 3 , and R 4 has at least two carbon atoms.

5. The compound of claim 1 , wherein ring C is benzene, and ring D is pyridine of which Y 6 is N.

6. The compound of claim 1 , wherein ligand L A is selected from the group consisting of:

7. The compound of claim 1 , wherein ligand L B is selected from the group consisting of:

wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d 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 acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

8. The compound of claim 1 , wherein ligand L B is selected from the group consisting of:

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

10. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having formula M(L A ) x (L B ) y (L C ) z ,
wherein ligand L A is:

wherein ligand L B is:

wherein ligand L C is:

wherein M is a metal having an atomic number greater than 40;
wher

Assignees

• Universal Display Corp

Inventors

• Xia Chuanjun
• Boudreault Pierre-Luc T

Classifications

• C07F15/0093

  without a metal-carbon linkage · CPC title

• C07F9/5045 Primary

  Complexes or chelates of phosphines with metallic compounds or metals · CPC title

• C07F7/0814

  said ring is substituted at a C ring atom by Si · CPC title

• C07F5/069

  without C-aluminium linkages · CPC title

• C07F7/0812

  comprising a heterocyclic ring · CPC title