Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11968883-B2
Application number	US-201816042014-A
Country	US
Kind code	B2
Filing date	Jul 23, 2018
Priority date	Jul 26, 2017
Publication date	Apr 23, 2024
Grant date	Apr 23, 2024

Abstract

The present invention includes novel polycyclic alkyl amino carbenes as ligands for metal complexes. These compounds may be useful as emitter materials for phosphorescent electroluminescent devices.

First claim

We claim:

1. A compound comprising a ligand L A of Formula III, wherein the ligand L A is coordinated to a metal M, and M is optionally coordinated to other ligands

wherein Z is C or N;
wherein ring A is a 5-membered aromatic ring, a 5-membered heteroaromatic ring, a 6-membered aromatic ring having two adjacent R A together joined to form a 5-membered ring which is optionally further substituted, or ring A is pyridine wherein Z is C;
L 1 to L 4 are independently selected from CR or CRR′; and the bond between L 1 and L 2 , L 2 and L 3 , and L 3 and L 4 may be a single bond or a double bond;
R A represents mono to the maximum allowable substitution, or no substitution;
each of R A , R, and R′ 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 or any two adjacent substitutions in R A , R, and R′ can join to form a ring;
R″ is selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, ester, and combinations thereof;
wherein any two of L 1 , L 2 , L 3 , and L 4 can join to form a ring, or any one of L 1 , L 2 , and L 3 with R″ can join to form a bicyclic ring;
wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand
provided that at least one of conditions (i) and (ii) are met:
(i) two adjacent groups of L 1 , L 2 , L 3 , and L 4 are joined to form an aryl, and
(ii) a group of L 1 , L 2 , L 3 , and L 4 binds with a non-adjacent group of L 1 , L 2 , L 3 , and L 4 or with R″ to form a bicyclic ring.

2. The compound of claim 1 , wherein each R A , R, and R′ is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein the bond between L 1 and L 2 , and L 3 and L 4 , are double bonds, and at least one of L 1 and L 2 , or L 3 and L 4 , are CR, and together with R form a fused aromatic ring.

4. The compound of claim 1 , wherein R A includes a coordinating group to the metal M to form a tridentate ligand.

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

6. The compound of claim 1 , wherein the ligand L A is of the formula represented below, and the compound has a formula of M(L A ) x (L B ) y (L C ) z wherein L A can be the same or different, L B and L C are each a bidentate ligand; and x is 1, 2, or 3; y is 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M;

7. The compound of claim 6 , wherein the compound has a formula of Pt(L A )(L B ), or Pt(L A ) 2 , wherein L B is a bidentate ligand.

8. The compound of claim 6 , wherein the ligands L B and L C are independently selected from the group consisting of:

wherein each Y 1 to Y 13 are independently selected from the group consisting of carbon and nitrogen;
wherein Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
wherein R e and R f are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may independently represent from mono substitution to the maximum possible number of substitution, or no substitution;
wherein each R a , R b , R c , R d , R e , and R f 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; or optionally any two adjacent substituents of R a , R b , R c , and R d can join to form a ring or form a multidentate ligand.

9. The compound of claim 6 , wherein L B and L C are each independently selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Su Mingjuan
• Macinnis Morgan C
• Silverstein Daniel W
• Lu Tongxiang (Aaron)
• Fitzgerald George

Classifications

• H10K85/342 Primary

  comprising iridium · CPC title

• C07F9/5045 Primary

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

• C07F15/002

  Osmium compounds · CPC title

• C07F15/0033

  Iridium compounds · CPC title

• C07F15/0086

  Platinum compounds · CPC title