Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10975113-B2
Application number	US-201815948059-A
Country	US
Kind code	B2
Filing date	Apr 9, 2018
Priority date	Apr 21, 2017
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

An organometallic complex including a ligand L A having a structure represented by one of the following formulas

Formula III useful as emitters in OLEDs is provided.

First claim

We claim:

1. A compound comprising a first ligand L A selected from the group consisting of:

or the compound has one of the following formulas:

wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein Z 1 to Z 5 are each independently carbon, nitrogen, oxygen, or phosphorus;
wherein X 1 to X 8 , Z 7 and Z 8 are each independently carbon or nitrogen;
wherein Z 6 is selected from the group consisting of carbon, nitrogen, oxygen, sulfur, phosphorus, and boron;
wherein R 1′ , R 2′ , R 1 , R 2 , R B , R C , and R A each independently represents none to a maximum possible number of substitutions;
wherein each R 1′ , R 2′ , R 1 , R 2 , and R A 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 any two substitutions in R 1′ , R 2′ , R 1 , R 2 , and R A are optionally joined or fused into a ring;
wherein the ligand L A is coordinated to a metal M;
wherein if L A has a formula according to Formula II or Formula III, it is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
wherein for Formula II and Formula III, M is optionally coordinated to other ligands;
wherein m1, m2 and m3 are each independently an integer of 0 or 1;
when m2 is 0, each m1 and m3 is 1; when m2 is 1, each m1 and m3 are each independently 0 or 1;
wherein at least one of m1 and m3 is not 0;
wherein when m1 is 0, L 1 is not present;
when m2 is 0, L 2 is not present;
when m3 is 0, L 3 is not present;
wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
wherein R B , R C , R, and R′ are each 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;
wherein any two substitutions are optionally joined or fused into a ring;
wherein Q 1 and Q 2 are each independently a direct bond or oxygen;
wherein when any of Z 7 and Z 8 is nitrogen, the Q 1 and Q 2 attached thereto is a direct bond; and
wherein M is Pt or Pd.

2. The compound of claim 1 , wherein each R 1 , R 2 , and R A is independently selected from 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 the compound has one of the following formulas:

4. The compound of claim 3 , wherein each Q 1 and Q 2 is a direct bond.

5. The compound of claim 3 , wherein one of Q 1 and Q 2 is oxygen, and the other one of Q 1 and Q 2 is direct bond.

6. The compound of claim 3 , wherein one of Z 7 and Z 8 is carbon, and the other one of Z 7 and Z 8 is nitrogen.

7. A compound comprising a first ligand L A selected from the group consisting of:

or the compound has one of the following formulas:

wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein Z 1 to Z 5 are each independently carbon, nitrogen, oxygen, or phosphorus;
wherein X 1 to X 8 , Z 7 and Z 8 are each independently carbon or nitrogen;
wherein Z 6 is selected from the group consisting of carbon, nitrogen, oxygen, sulfur, phosphorus, and boron;
wherein R 1′ , R 2′ , R 1 , R 2 , R B , R C , and R A each independently represents none to a maximum possible number of substitutions;
wherein each R 1′ , R 2′ , R 1 , R 2 , and R A 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 any two substitutions in R 1′ , R 2′ , R 1 , R 2 , and R A are optionally joined or fused into a ring;
wherein the ligand L A is coordinated to a metal M;
wherein if L A has a formula according to Formula II or Formula III, it is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
wherein for Formula II and Formula III, M is optionally coordinated to other ligands;
wherein m1, m2 and m3 are each independently an integer of 0 or 1;
when m2 is 0, each m1 and m3 is 1; when m2 is 1, each m1 and m3 are each independently 0 or 1;
wherein at least one of m1 and m3 is not 0;
wherein when m1 is 0, L 1 is not present;
when m2 is 0, L 2 is not present;
when m3 is 0, L 3 is not present;
wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
wherein R B , R C , R, and R′ are each 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;
wherein any two substitutions are optionally joined or fused into a ring;
wherein Q 1 and Q 2 are each independently a direct bond or oxygen;
wherein when any of Z 7 and Z 8 is nitrogen, the Q 1 and Q 2 attached thereto is a direct bond;
wherein M is Pt or Pd; and
wherein one of the following conditions is true:
one of Z 7 and Z 8 is a neutral carbene carbon, the other one of Z 7 and Z 8 is anionic carbon; or
each L 1 , L 2 , and L 3 is not a direct bond when they are present.

8. The compound of claim 3 , wherein L 2 is a direct bond.

9. The compound of claim 3 , wherein the rings of A, B, and C are each independently selected from the group consisting of phenyl, pyridine, imidazole, and imidazole derived carbene.

10. The compound of claim 3 , wherein the compound has at least one Pt-carbene bond.

11. The compound of claim 3 , wherein the compound is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Chen Hsiao-Fan
• Lin Chun
• Feldman Jerald
• Ji Zhiqiang
• Silverstein Daniel W

Classifications

• C09K2211/185

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

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• H10K85/346

  comprising platinum · CPC title