Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2017229663-A1
Application number	US-201715407337-A
Country	US
Kind code	A1
Filing date	Jan 17, 2017
Priority date	Feb 9, 2016
Publication date	Aug 10, 2017
Grant date	—

Abstract

Novel Iridium complexes having three different bidentate ligands useful for phosphorescent emitters in OLEDs are disclosed. At least one of the three different bidentate ligands is a carbene ligand.

First claim

1 . A compound having a formula M(L A ) x (L B ) y (L C ) z :
wherein the ligand L A is

the ligand L B is

and the ligand L C is

wherein M is a metal having an atomic number greater than 40;
wherein x is 0, 1, or 2;
wherein y is 1, 2, or 3;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein L A is different from L B , and when x, y, or z is larger than 1, each plurality of L A , L B , or L C are also different;
wherein rings A, B, 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 substitution up to the maximum possible number of substitutions, or no substitution;
wherein Z 1 and Z 2 are each independently selected from the group consisting of carbon or nitrogen;
wherein C 1 is an anionic donor carbon atom, C 2 is a neutral carbene carbon atom;
wherein each of R A , R B , R C , R D , R X , R Y , and R Z 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 any adjacent substitutents 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 M is Ir or Pt.

4 . The compound of claim 1 , wherein Z 1 is a neutral donor nitrogen atom, Z 2 is an anionic donor carbon atom.

5 . The compound of claim 1 , wherein rings A, B, and C are 6-membered aromatic rings, and ring D is a 5-member aromatic rings.

6 . The compound of claim 1 , wherein Rings B and C are benzene.

7 . The compound of claim 1 , wherein the compound is selected from the group consisting of: Ir(L A )(L B )(L C ), Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ),Pt(L A )(L B ), and Pt(L B ) 2 .

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

wherein each X 1 to X 17 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 up to the maximum possible number of substitutions, 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.

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

wherein each X 1 to X 8 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 up to the maximum possible number of substitutions, 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.

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

wherein R X1 , R X2 , R Z1 , and R Z2 are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;
wherein at least one of R X1 , R X2 , R Z1 , and R Z2 has at least two carbon atoms.

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

wherein each R a , R b , R c , and R d may represent from mono substitution up to the maximum possible number of substitutions, or no substitution;
wherein 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.

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

Assignees

• Universal Display Corp

Inventors

• Tsai Jui-Yi
• Xia Chuanjun
• Lin Chun
• Palacios Adrian U
• Oñate Enrique
• Esteruelas Miguel A
• Boudreault Pierre-Luc T

Classifications

• H10K50/12

  comprising dopants · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H01L51/5016

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/0085 Primary

  Electricity · mapped topic