# US 12,010,908 B2 · Metal-assisted delayed fluorescent emitters employing benzo-imidazo-phenanthridine and analogues

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- Number: US 12,010,908 B2
- Document ID: US12010908B2
- Status: Granted
- Kind: B2
- Application number: 17/332,100
- Filed: 2021-05-27
- Published: 2022-11-24
- Granted: 2024-06-11
- Earliest claimed: 2017-05-19
- Assignees: Arizona Board of Regents on behalf of Arizona State University
- Applicants: Arizona Board of Regents on behalf of Arizona State University
- Inventors: Jian Li; Yunlong Ji
- Web page: https://patentgrep.com/patent/US12010908B2

## CPC

- C07F 15/006: {Palladium compounds}
- C07F 15/0033: {Iridium compounds}
- C07F 15/0086: {Platinum compounds}
- C09K 11/06: containing organic luminescent materials
- H10K 85/341: {Transition metal complexes, e.g. Ru(II)polypyridine complexes (H10K85/331 takes precedence)}
- H10K 85/342: {comprising iridium}
- H10K 85/346: {comprising platinum}
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1074: containing more than three nitrogen atoms as heteroatoms
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Metal-assisted delayed fluorescent emitters employing benzo-imidazo-phenanthridine and analogues for full color displays and lighting applications.

## Claims

### Claim 1

A complex represented by General Formula VIII or General Formula XII:
wherein:
M is Pt (II) or Pd (II),
N is nitrogen,
each of V1a-V1e, V2a-V2c, V3a, V4a-V4c, and V5a-V5d, if present, is independently N or C,
X1 is absent,
X represents CR7R8, SiR7R8, NR7, O, or S,
each of L1 and L2 is independently present or absent, and each L1 and L2 present independently represents a substituted or unsubstituted aryl or heteroaryl,
each of R1, R2, R3, R4, R5, R7, and R8 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each R1, R2, R3, R4, R5, R7, and R8 present independently represents deuterium, halogen, hydroxyl, thiol, nitro, cyanide, isocyanide, 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.

### Claim 2 (depends on 1)

A light emitting diode comprising the complex of claim 1.

### Claim 3 (depends on 2)

A light emitting device comprising the light emitting diode of claim 2.

### Claim 4 (depends on 1)

The complex of claim 1 represented by General Formula VIII-(i) or General Formula VIII-(ii):
wherein:
M is Pt (II) or Pd (II),
N is nitrogen,
each of V1b and V3a, if present, is independently N or C,
X is O, CR7R8, or SiR7R8, wherein, optionally, R7 and R8 may link together to form a fluorene ring,
X1 is absent,
each of L1 and L2 is independently present or absent, and each L1 and L2 present independently represents a substituted or unsubstituted aryl, heteroaryl, or N-heterocyclic carbene,
each R1, R2, R3, R4, R5, R6, R7 and R8 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each R1, R2, R3, R4, R5, R6, R7 and R8 present independently represents deuterium, halogen, hydroxyl, thiol, nitro, cyanide, isocyanide, 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.

### Claim 5 (depends on 4)

A light emitting diode comprising the complex of claim 4.

### Claim 6 (depends on 5)

A light emitting device comprising the light emitting diode of claim 5.

### Claim 7 (depends on 1)

The complex of claim 1 represented by General Formula XII-(i) or General Formula XII-(ii):
wherein:
M is Pt (II) or Pd (II),
N is nitrogen,
X is O, CR7R8, or SiR7R8, wherein, optionally, R7 and R8 may link together to form a fluorene ring,
L1 is present or absent, and each L1 present represents a substituted or unsubstituted aryl or heteroaryl,
each of R1, R2, R3, R4, R5, R7 and R8 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each R1, R2, R3, R4, R5, R7 and R8 present independently represents deuterium, halogen, hydroxyl, thiol, nitro, cyanide, isocyanide, 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.

### Claim 8 (depends on 7)

A light emitting diode comprising the complex of claim 7.

### Claim 9 (depends on 8)

A light emitting device comprising the light emitting diode of claim 8.