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US 11,999,886 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsWalter Yeager, Zhiqiang Ji, Pierre-Luc T. Boudreault
Life of this patent
Estimating the term…
Abstract
Provided are compounds including a ligand LA of that are useful as emitters in OLEDs, where at least one of RA and RB is
Claims20
A compound comprising a ligand LA of Formula I
- wherein:
- K1 is N and K2, K3, and K4 are each C;
- ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- RA and RB each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;
- and
- RA and RB is independently a hydrogen or a substituent selected from the group consisting of Formula II, Formula III, Formula IV, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one of RA and RB comprising Formula II, Formula III, or Formula IV, wherein
- wherein:
- ring C is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- X in Formula II is N;
- Y for each occurrence is independently O, S, Se, or NR;
- each of G1-G8 is independently C or N;
- RII, RIII and RIV each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
- each of R, RII, RIII, and RIV is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- two substituents can be joined or fused together to form a ring, wherein the ligand LA is coordinated to a metal M through the two indicated dashed lines;
- M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au;
- the ligand LA can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- wherein at least one of the following is true:
- i) at least one RII is a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- ii) at least one RIII is partially or fully halogenated and/or a sulfanyl;
- iii) two RB join together to form a fused ring;
- or
- iv) Formula II, Formula III, or Formula IV bond to ring B when ring B is a 5-membered or 6-membered carbocyclic ring.
21 more elements
A compound comprising a ligand LA of Formula I
- wherein:
- K1 is N and K2, K3, and K4 are each C;
- ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- ring B is a 6-membered carbocyclic ring;
- RA and RB each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;
- wherein the ligand LA has a structure of Formula IB
- wherein:
- RA and RB is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one RB comprising a structure of Formula IIA, Formula IIB, Formula IVA, Formula IVB, or Formula V listed below:
- wherein:
- K5-K8 are each independently C or N;
- X10-X13 are each independently C or N;
- if RB is Formula IVB, then G8 is C;
- X in Formula IIA is N;
- Y for each occurrence is independently O, S, Se, or NR;
- ring C and ring D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- each of RII, RIIa, RIV, and RV is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- two substituents can be joined or fused together to form a ring, wherein the ligand LA is coordinated to a metal M through the two indicated dashed lines;
- M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au;
- and
- the ligand LA can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand.
17 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand LA of Formula I
- wherein:
- K1 is N and K2, K3, and K4 are each C;
- ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- RA and RB each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;
- and
- RA and RB is independently a hydrogen or a substituent selected from the group consisting of Formula II, Formula III, Formula IV, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one of RA and RB comprising Formula II, Formula III, or Formula IV, wherein
- wherein:
- ring C is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- X in Formula II is N;
- Y for each occurrence is independently O, S, Se, or NR;
- each of G1-G8 is independently C or N;
- RII, RIII, and RIV each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
- each of R, RII, RIII, and RIV is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- two substituents can be joined or fused together to form a ring, wherein the ligand LA is coordinated to a metal M through the two indicated dashed lines;
- M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au;
- the ligand LA can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- wherein at least one of the following is true:
- i) at least one RII is a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- ii) at least one RII is partially or fully halogenated and/or a sulfanyl;
- iii) two RB join together to form a fused ring;
- or
- iv) Formula II, Formula III, or Formula IV bond to ring B when ring B is a 5-membered or 6-membered carbocyclic ring.
24 more elements
Dependencies are inferred from the claim text.