Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11424420-B2
Application number	US-201816116439-A
Country	US
Kind code	B2
Filing date	Aug 29, 2018
Priority date	Sep 7, 2017
Publication date	Aug 23, 2022
Grant date	Aug 23, 2022

Abstract

A metal-containing compound including a first ligand L A that is selected from one of the following structures:

is disclosed.

First claim

We claim:

1. A metal-containing compound comprising a first ligand L A

selected from the group consisting of:

and
wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein ring B is a 6-membered aromatic ring that is optionally present;
wherein Z 1 to Z 6 are each independently selected from the group consisting of carbon and nitrogen;
wherein R A , R B , R C , and R D each independently represent none to a maximum possible number of substituents;
wherein R 1 , R A , R B , R C , and R D are each independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any adjacent substitutions in R A , R B , and R C are optionally joined or fused into a ring;
wherein the ligand L A is coordinated to a metal M;
wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
wherein, when B is present and B and C are both benzene, (i) ring A is a 5-membered carbocyclic or heterocyclic ring, (ii) at least one pair of adjacent R B or R C are joined or fused together to form a ring, or (iii) both; and

wherein M is optionally coordinated to other ligands.

2. The compound of claim 1 , wherein R 1 , R A , R B , R C , and R D are each independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein the compound is selected from the group consisting of:

wherein A, B, C, D, and F are each independently a 5-membered or 6-membered aromatic ring;
wherein ring B may or may not be present;
wherein A is not 2-pyridyl;
wherein R A , R B , R C , R D , R E and R F are each independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , and Z 7 are each independently selected from the group consisting of C and N;
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 can be 0 or 1;
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; and
wherein L 1 , L 2 , and L 3 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.

4. The compound of claim 3 , wherein M is Pt.

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

6. The compound of claim 3 , wherein one of Z 6 and Z 7 is a neutral carbene carbon, and the other one of Z 6 and Z 7 is anionic carbon.

7. The compound of claim 3 , wherein at least one of L 1 , L 2 , and L 3 is not a direct bond.

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

9. The compound of claim 3 , wherein ring A is selected from the group consisting of phenyl, pyrimidine, triazine, pyrazole, triazole, imidazole, and imidazole derived carbene.

10. The compound of claim 3 , wherein rings B, C, D, and E are each independently selected from the group consisting of phenyl, pyridine, pyrimidine, triazine, pyrazole, triazole, imidazole, and imidazole derived carbene.

11. The compound of claim 3 , wherein L 3 and Z 4 are fused to form a 5-membered or 6-membered carbocyclic or heterocyclic ring.

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

wherein Z 1 Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 and Z 15 are each independently selected from the group consisting of C and N.

13. The compound of claim 3 , wherein the compound is the compound x having the formula (L Xi )Pt(L Yj ,)(L Zk );
wherein L Xi is a bidentate ligand;
wherein L Yj is a monodentate ligand;
wherein L Zk is a monodentate ligand;
wherein L Xi is linked to L Zk by a linking group L 3 ;
wherein L Zk is linked to L Yj by a direct bond;
wherein, when k is an integer from 1 to 40, x=30(i−1)+j+1830(k−1), i is an integer from 1 to 61, and j is an integer from 1 to 30;
wherein, when k=41 or 43, x=25(i−1)+j+1525(k−41)+73200, i is an integer from 1 to 61, and j is an integer from 15 to 25;
wherein L Xi is selected from the group consisting of:

wherein L Yj is selected from the group consisting of:

wherein L Zk is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Chen Hsiao-Fan
• Silverstein Daniel W
• Wolohan Peter

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• C09K2211/185

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

• H01L51/0087 Primary

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic