Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12428438-B2
Application number	US-202217965283-A
Country	US
Kind code	B2
Filing date	Oct 13, 2022
Priority date	Dec 1, 2016
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

Metal complexes with cyclic ligands having Formula (I),

are disclosed. Ligands with cyclic structure are believed to be beneficial to the rigidity and stability of the metal complexes, which is desirable for improving OLED device performance.

First claim

The invention claimed is:

1. A compound comprising a bidentate ligand L A of Formula I:

wherein G 1 has at least one 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein G 2 has at least two 5-membered or 6-membered carbocyclic or heterocyclic ring fused together;
wherein G 1 and G 2 are linked by a chemical group L having at least three backbone atoms;
wherein L is not fused with G 1 or G 2 ;
wherein L A is coordinated to a metal M;
wherein G 2 comprises a first ring directly bonded to metal M and a second ring that is directly bonded to L, but not directly bonded to metal M;
wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
wherein M is optionally coordinated to other ligands; and
wherein at least one of the following is true:
(1) G 1 is a 5-membered ring coordinated to metal M by N or carbene C and G 2 either includes at least one 5-membered ring or includes a total of at least three rings;
(2) G 1 is a 6-membered ring and at least one of the following conditions is true: (i) L comprises a moiety selected from the group consisting of cycloalkyl, aryl, heteroaryl, and silyl, (ii) G 2 includes at least one 5-membered ring, or (iii) G 2 comprises at least three 5-membered or 6-membered carbocyclic or heterocyclic rings;
(3) ligand L A has a structure selected from the group consisting of

 wherein, in the first structure, two R 2 are not joined or fused to form a ring; or
(4) ligand L A has a structure of

 where two R 1 or two R 2 are joined or fused to form a ring;
wherein R 1 , R 2 , and R 3 each independently represents none to a maximum allowable number of substituents;
wherein X is selected from a group consisting of O, S, Se, and NR 4 ;
wherein each of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , and Z 12 is independently selected from a group consisting of carbon and nitrogen;
wherein R 1 , R 2 , R 3 , and R 4 each is independently selected from the group consisting of hydrogen, deuterium, halogen, nitrile, carbonyl, silyl, alkyl, cycloalkyl, alkyloxyl, cycloalkyloxyl, aryl, heteroaryl, and combinations thereof; and
wherein any two R 1 , R 2 , R 3 and R 4 are optionally joined to form 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 the ligand L A is selected from the group consisting of

and

5. The compound of claim 1 , wherein L comprises a moiety selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and silyl.

6. The compound of claim 1 , wherein G 1 is a 6-membered ring, L is bonded to ring G 2′ , and G 2 includes at least one 5-membered ring.

7. The compound of claim 1 , wherein G 1 is a 5-membered ring coordinated to metal M by N or carbene C, L is bonded to ring G 2′ , and G 2 either includes at least one 5-membered ring or includes a total of at least three rings.

8. The compound of claim 1 , wherein G 1 is a 6-membered ring, L is bonded to ring G 2′ , and G 2 is comprises at least three 5-membered or 6-membered carbocyclic or heterocyclic rings.

9. The compound of claim 1 , wherein the ligand L A is

and
wherein two R 1 or two R 2 are joined to form a ring.

10. The compound of claim 1 , wherein the compound has formula (L A ) m Pt(L C ) 2-m ; wherein L C is a bidentate ligand; and m is 1, or 2.

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

L A4 to L A6 represented by

wherein in L A4 , X = O;

wherein in L A5 , X = S; and

wherein in L A6 , X = Se;

L A7 to L A9 represented by

wherein in L A7 , X = O;

wherein in L A8 , X = S; and

wherein in L A9 , X = Se;

LA 10 to LA 12 represented by

wherein in LA 10 , X = O;

wherein in LA 11 , X = S; and

wherein in LA 12 , X = Se;

L A13 to L A15 represented by

wherein in L A13 , X = O;

wherein in L A14 , X = S; and

wherein in L A15 , X = Se;

L A16 to L A18 represented by

wherein in L A16 , X = O;

wherein in L A17 , X = S; and

wherein in L A18 , X = Se;

L A19 to L A21 represented by

Assignees

• Universal Display Corp

Inventors

• Zeng Lichang
• Ji Zhiqiang
• Su Mingjuan T
• Barron Edward
• Lin Chun

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K85/346

  comprising platinum · CPC title

• H10K85/342

  comprising iridium · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title