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US 11,903,305 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsPierre-Luc T. Boudreault, Bin Ma, Zhiqiang Ji, Alan Deangelis
Life of this patent
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Abstract
A compound having a structure of formula Ir(LA)m(LB)n, where ligand LA has Formula I and ligand LB has Formula II that is useful as an emitter in OLEDs is disclosed.
Claims18
A compound of formula Ir(LA)m(LB)n;
- wherein LA has
- and LB has
- wherein,
- m and n are each 1 or 2;
- m+n=3;
- X1 to X10 are each independently C or N;
- the maximum number of N atoms that can connect to each other in each ring is two;
- R1 and R2 represent mono to the maximum allowable number of substituents, or no substituent;
- each of R1 , R2, and R3 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- at least one of R1 and R2 is a substituent selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, R4 and R5 are each selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, cycloheteroalkyl, and combinations thereof;
- at least one of R4 and R5 comprises five or more carbon atoms;
- and
- at least one of X1 to X10 is N.
10 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and an organic layer, disposed between the anode and the cathode, comprising a compound of formula Ir(LA)m(LB)n;
- wherein LA has
- and LB has
- wherein,
- m and n are each 1 or 2;
- m+n=3;
- X1-X10 are each independently C or N;
- the maximum number of N atoms that can connect to each other in each ring is two;
- R1 and R2 represent mono to the maximum allowable number of substituents, or no substituent;
- each of R1, R2, and R3 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- at least one of R1 and R2 is a substituent selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- R4 and R5 are each selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, cycloheteroalkyl, and combinations thereof;
- at least one of R4 and R5 is comprises five or more carbon atoms;
- and
- at least one of X1 to X10 is N.
14 more elements
A consumer product comprising an organic light-emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound of formula Ir(LA)m(LB)n;
- wherein LA has
- and LB has
- wherein,
- m and n are each 1 or 2;
- m+n=3;
- X1-X10 are each independently C or N;
- the maximum number of N atoms that can connect to each other in each ring is two;
- R1 and R2 represent mono to the maximum allowable number of substituents, or no substituent;
- each of R1, R2, and R3 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- at least one of R1 and R2 is a substituent selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- R4 and R5 are each selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, cycloheteroalkyl, and combinations thereof;
- at least one of R4 and R5 is comprises five or more carbon atoms;
- and
- at least one of X1 to X10 is N.
15 more elements
Dependencies are inferred from the claim text.