IP Library › Granted Patent US 10,519,178
Granted Patent B2
US 10,519,178 · App. 15/314,256 · Granted Dec 31, 2019

Bi-nuclear main group metal phosphorescent emitter

Inventors: Ana-Maria Krestel (Erlangen, DE); Anna Maltenberger (Leutenbach, DE); Marina A Petrukhina (Schenectady, NY); Guenter Schmid (Hemhofen, DE)
Assignee: SIEMENS AKTIENGESELLSCHAFT
C07F9/94C07F15/0033C09K11/06H01L51/009C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/188H01L51/5016Y02E10/52Y02E10/549
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Quick Facts
Patent No.
US 10,519,178
App. No.
15/314,256
Granted
Dec 31, 2019
Kind
B2
Abstract

A bi-nuclear phosphorescent emitter according to the following formula is disclosed. The emitter may include metal atoms M 1 and M 2 , fluorescent emitter ligands L F , L F ′, terminal ligands L T , L T ′, and bridging ligands L V , L V ′, wherein M 1 and M 2 are In, Tl, Sn, Pb, Sb, and Bi; L F and L F ′ are comprise substituted or non-substituted C6-C70 aromatics or heteroaromatics; L V and L V ′ are fluorinated or non-fluorinated, bi-dentate C2-C30 heteroalkyl or heteroaromatics; L T and L T ′ are fluorinated or non-fluorinated, mono-, bi-, or tri-dentate C2-C30 O—, S—, N, heteroalkyl or heteroaromatics; and n and m are 1 or 2 independently of one another.

Claims (23)

1. A bi-nuclear phosphorescent emitter according to the following formula

wherein the emitter comprises metal atoms M 1 and M 2 , fluorescent emitter ligands L F , L F ′, terminal ligands L T , L T ′, and bridging ligands L V , L V ′,

wherein each of M 1 and M 2 is an element selected from the group consisting of In, Tl, Sn, Pb, Sb, and Bi;

wherein each of L F , L F ′ is selected from the group consisting of 4,7-di(9H-carbazol-9-yl)-1,10-phenanthroline, 2,6-bis(3-(9H-carbazol-9-yl)phenyl)pyridine, and 3,5-bis(3-(9H-carbazol-9-yl)phenyl)pyridine;

wherein each of L V and L V ′ is a compound selected from the group consisting of fluorinated and non-fluorinated, bi-dentate C2-C30 heteroalkyl and heteroaromatics;

wherein each of L T and L T ′ is a compound selected from the group consisting of fluorinated and non-fluorinated, mono-, bi-, or tri-dentate C2-C30 O—, S—, N—, heteroalkyl or heteroaromatics; and

wherein n is 1 or 2, and m is 1 or 2.

2. The emitter of claim 1 , wherein:

M 1 and M 2 are selected independently of one another from the group consisting of Sb, As, and Bi; and

n, m=2.

3. The emitter of claim 1 , wherein:

M 1 and M 2 are selected independently of one another from the group consisting of Pb and Sn.

4. The emitter of claim 1 , wherein the emitter is a homonuclear emitter with M 1 =M 2 =Bi.

5. The emitter of claim 1 , wherein distances between at least one metal atom and the ligands L V , L V ′, L T , L T ′ coordinated thereon are greater than or equal to 2.2 Å and less than or equal to 3.0 Å.

6. The emitter of claim 1 , wherein at least one of L V , L V ′ is selected from the group consisting of fluorinated and non-fluorinated C2-C30 O—, S—, N—, heteroalkyl, heterocycloalkyl, and heteroaromatics.

7. The emitter of claim 1 , wherein the emitter corresponds to the following formula:

wherein R 1 , R 2 are selected independently of one another from the group consisting of fluorinated and non-fluorinated C1-C30 alkyl, cycloalkyl, aryl, heteroalkyl, heterocycloalkyl, and heteroaryl; and

wherein E 1 , E 2 , E 3 , E 4 are selected independently of one another from the group consisting of O, S, and NR, wherein R═H, D.

8. The emitter of claim 1 , wherein at least one of the ligands L V , L V ′ is selected from the group consisting of fluorinated and non-fluorinated aliphatic and aromatic C2-C30 carboxylates.

9. The emitter of claim 1 , wherein at least one of the ligands L V , L V ′ is selected from the group consisting of acetate, fluoroacetate, fluorobenzoate, fluoromethylbenzoate, fluoromethylfluorobenzoate, di-fluoromethyl-benzoate, and di-fluoromethyl-fluorobenzoate.

10. The emitter of claim 1 , wherein at least one of the ligands L T , L T ′ is selected from the group consisting of fluorinated or non-fluorinated aliphatic and aromatic C2-C30 alcoholates, carboxylates, benzoates, v acetylacetonates.

11. The emitter of claim 1 , wherein at least one of the ligands L T , L T ′ is selected from the group consisting of acetate, fluoroacetate, fluorobenzoate, fluoromethylbenzoate, fluoromethylfluorobenzoate, di-fluoromethyl-benzoate, and di-fluoromethyl-fluorobenzoate.

12. The emitter of claim 1 , wherein each of the ligands L V , L V ′, L T , L T ′ is selected from the group comprising acetate, fluoroacetate, fluorobenzoate, fluoromethylbenzoate, fluoromethylfluorobenzoate, di-fluoromethyl-benzoate, and di-fluoromethyl-fluorobenzoate.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 28, 2016
From: KRESTEL, ANA-MARIA; MALTENBERGER, ANNA; SCHMID, GUENTER
To: SIEMENS AKTIENGESELLSCHAFT
Reel/Frame 040432/0250 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 28, 2016
From: PETRUKHINA, MARINA A.
To: THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK
Reel/Frame 040432/0333 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 28, 2016
From: THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK
To: SIEMENS AKTIENGESELLSCHAFT
Reel/Frame 040432/0482 →
Continuity (2)
Provisional Application 62004486 · May 29, 2014
Related Publication 20180240975A1 · Aug 23, 2018