IP Library Granted Patent US 9,617,291
Granted Patent B2
US 9,617,291 · App. 15/354,280 · Granted Apr 11, 2017

Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues

Inventors: Jian Li (Tempe, AZ); Guijie Li (Hangzhou Zhejiang, CN)
Assignee: Arizona Board of Regents on behalf of Arizona State University
C07F15/0033C09K11/06H01L51/0085C09K2211/185H01L51/5016H01L2251/5376
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Quick Facts
Patent No.
US 9,617,291
App. No.
15/354,280
Granted
Apr 11, 2017
Kind
B2
Abstract

Tetradentate and octahedral metal complexes suitable for use as phosphorescent or delayed fluorescent and phosphorescent emitters in display and lighting applications.

Claims (19)

1. A complex of Formula BI, Formula BII, Formula BIII, or Formula BIV:

wherein:

Ar is substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, carbene, or N-heterocyclic carbene,

each of A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 is independently a single bond, CR 1 R 2 , C═O, SiR 1 R 2 , GeR 1 R 2 , NR 3 , PR 3 , R 3 P═O, AsR 3 , R 3 As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BR 3 , R 3 Bi═O, or BiR 3 ,

each of X 1 , X 2 , and X 3 is independently CR 1 , SiR 1 , GeR 1 , N, P, P═O, As, As═O, B, R 3 Bi═O or Bi,

m=1, n=2 or m=2, n=1,

each of R a , R b , R c , R d , R e , R f , R g , R h , and R i is independently present or absent, and if present each of R a , R b , R c , R d , R e , R f , R g , R h , and R i is independently a mono-, di-, or tri-substitution as valency permits, and each of R a , R b , R c , R d , R e , R f , R g , R h , and R i is independently deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof, and

each of R 1 , R 2 and R 3 is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof.

2. The complex of claim 1 , wherein the complex is one of the following structures:

3. An emitter comprising the complex of claim 1 , wherein the emitter is a phosphorescent emitter.

4. An emitter comprising the complex of claim 1 , wherein the emitter is a delayed fluorescent emitter.

5. An emitter comprising the complex of claim 1 , wherein the emitter is a delayed fluorescent and phosphorescent emitter.

6. The complex of claim 1 , wherein polymeric comprises polyalkylene, polyester, or polyether.

7. The complex of claim 6 , wherein polymeric comprises —(CH 2 O) n —CH 3 , —(CH 2 CH 2 O) n —CH 3 , —[CH 2 CH(CH 3 )] n —CH 3 , —[CH 2 CH(COOCH 3 )] n —CH 3 , —[CH 2 CH(COO CH 2 CH 3 )] n —CH 3 , or —[CH 2 CH(COO t Bu)] n —CH 3 , where n is an integer.

8. A device comprising a complex of claim 1 .

9. The complex of claim 1 , wherein the complex is a complex of Formula BI:

10. The complex of claim 1 , wherein the complex is a complex of Formula BII:

11. The complex of claim 1 , wherein the complex is a complex of Formula BIII:

12. The complex of claim 1 , wherein the complex is a complex of Formula BIV:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 7, 2016
From: LI, JIAN; LI, GUIJIE
To: ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY
Reel/Frame 040588/0253 →
Continuity (4)
Division 15168942 · May 31, 2016
Provisional Application 62170283 · Jun 3, 2015
Provisional Application 62254011 · Nov 11, 2015
Related Publication 20170066792A1 · Mar 9, 2017