Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues

Patent metadata

Field	Value
Publication number	US-2016359125-A1
Application number	US-201615168942-A
Country	US
Kind code	A1
Filing date	May 31, 2016
Priority date	Jun 3, 2015
Publication date	Dec 8, 2016
Grant date	—

Abstract

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

First claim

What is claimed is:

1 . A complex of Formula AI, Formula AII, Formula AIII or Formula AIV:

wherein:
M is Pt or Pd,
each of V 1 , V 2 , V 3 , and V 4 is coordinated with M and is independently N, C, P, B, or Si,
each of L 1 , L 2 , L 3 , and L 4 is independently substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, carbene, or N-heterocyclic carbene,
each of A 1 , A 2 , A 3 , A 4 and A 5 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 and X 2 is independently CR 1 , SiR 1 , GeR 1 , N, P, P═O, As, As═O, B, R 3 Bi═O or Bi,
each of R a , R b , R c , and R d is independently present or absent, and if present each of R a , R b , R c , and R d is independently a mono-, di-, or tri-substitution as valency permits, and each of R a , R b , R c , and R d 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, and
each of R x and R y 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 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 has the structure of Formula AV, Formula AVI, Formula AVII, Formula AVIII, Formula AIX, Formula AX, Formula AXI or Formula AXII:

wherein:
M is Pt or Pd,
each of V 1 , V 2 , V 3 , and V 4 is coordinated with M and is independently N, C, P, B, or Si,
each of L 1 , L 2 , L 3 , and L 4 is independently substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, carbene, or N-heterocyclic carbene,
each of A 1 , A 2 , A 3 , A 4 and A 5 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,
each of R a , R b , R c , and R d is independently present or absent, and if present each of R a , R b , R c , and R d is independently a mono-, di-, or tri-substitution as valency permits, and each of R a , R b , R c , and R d 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
wherein each of R x , R y and R z 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 and
wherein 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.

3 . The complex of claim 1 , wherein the complex has a neutral charge.

4 . A complex represented by one of the chemical structures in Structure 1-Structure 47.

5 . The complex of claim 1 , wherein each of

is independently one of the following structures:

Assignees

• Univ Arizona State

Inventors

• Li Jian
• Li Guijie

Classifications

• H01L51/5012

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/0084

  Electricity · mapped topic

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title