IP Library Patent Application 15795615
Patent Application
App. No. 15/795,615

EMITTERS BASED ON OCTAHEDRAL METAL COMPLEXES

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Patent No.
US None
App. No.
15/795,615
Abstract

Iridium, rhodium, and platinum complexes suitable for use as phosphorescent emitters or as delayed fluorescent and phosphorescent emitters having the following structures:

Claims (38)

1 . A compound of Formula I, Formula II, Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX or Formula X:

wherein:

M is Ir(III), Rh(III) or Pt(IV),

each of L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 , if present, is independently substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, carbene, or N-heterocyclic carbene, dione, cyanogen, or phosphine,

each of V 1 , V 2 , V 3 , V 4 , V 5 , and V 6 , if present, is coordinated with M and is independently N, C, P, B, or Si,

each of X, Y, and Z, if present, is independently CH 2 , CR 1 R 2 , C═O, CH 2 , SiR 1 R 2 , GeH 2 , GeR 1 R 2 , NH, NR 3 , PH, PR 3 , R 3 P═O, AsR 3 , R 3 As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR 3 , R 3 Bi═O, BiH, or BiR 3 ,

each of F 1 , F 2 , F 3 , F 4 , F 5 , and F 6 is independently present or absent, wherein at least one of F 1 , F 2 , F 3 , F 4 , F 5 , and F 6 is present, and each F 1 , F 2 , F 3 , F 4 , F 5 , and F 6 present is a fluorescent luminophore,

each of R a , R b , R c , R d , R e , and R f is independently present or absent, and if present each R a , R b , R c , R d , R e and R f independently represents mono-, di-, or tri-substitutions, and wherein each R a , R b , R c , R d , R e and R f present 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 , if present, 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 compound of claim 1 , wherein the compound has a neutral charge.

3 . The compound of claim 1 , wherein each of

if present, is independently one of the following structures:

4 . The compound of claim 1 , wherein each of

if present, is independently one of the following structures:

wherein R is 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.

5 . The compound of claim 1 , wherein each of F 1 , F 2 , F 3 , F 4 , F 5 , and F 6 , if present, is independently one of the following structures:

1. Aromatic Hydrocarbons and their Derivatives

2. Arylethylene, Arylacetylene and their Derivatives

3. Heterocyclic Compounds and their Derivatives

4. Other Fluorescent Luminophors

wherein:

each of R 11 , R 21 , R 31 , R 41 , R 51 , R 61 , R 71 , and R 81 , if present, is a mono-, di-, tri-, or tetra-substitution, valency permitting, and each R 11 , R 21 , R 31 , R 41 , R 51 , R 61 , R 71 , and R 81 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,

each of Y a , Y b , Y c , Y d , Y e , Y f , Y g , Y h , Y i , Y j , Y k , Y l , Y m , Y n , Y o , and Y p , if present, is independently C, N or B,

each of U a , U b , and U c , if present, is independently CH 2 , CR 1 R 2 , C═O, CH 2 , SiR 1 R 2 , GeH 2 , GeR 1 R 2 , NH, NR 3 , PH, PR 3 , R 3 P═O, AsR 3 , R 3 As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR 3 , R 3 Bi═O, BiH, or BiR 3 , and

each of W a , W b and W c , if present, is independently CH, CR 1 , SiR 1 , GeH, GeR 1 , N, P, B, Bi, or Bi═O.

6 . The compound of claim 1 , wherein each of X, Y, and Z, if present, is independently one of the following structures:

wherein:

x is an integer from 1 to 10, and

each of R sl , R tl , R ul , and R vl , if present, 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.

7 . The compound of claim 1 , wherein the compound is selected from any of Structures Ir-1 to Ir-25, Rh-1 to Rh-25, and Pt-1 to Pt-13.

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

9 . An emitter comprising the compound of claim 1 , wherein the emitter is a phosphorescent emitter.

10 . An emitter comprising the compound of claim 1 , wherein the emitter is a delayed fluorescent emitter.

11 . A device comprising a compound of claim 1 .

12 . The device of claim 11 , wherein the compound is selected to have 100% internal quantum efficiency in the device settings.

13 . The device of claim 11 , wherein the device is an organic light emitting diode.

14 . The compound of claim 1 , wherein polymeric comprises polyalkylene, polyester, or polyether.

15 . The compound of claim 14 , 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(COOCH 2 CH 3 )] n —CH 3 , or —[CH 2 CH(COO t Bu)] n —CH 3 , where n is an integer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 22, 2018
From: LI, JIAN; LI, GUIJIE
To: ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY
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