Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorZhiqiang JI
Life of this patent
Estimating the term…
Abstract
A compound having a first ligand LA comprising a structure of Formula I is provided. In the compound, two RA are joined to form a cyclic moiety A1, which may be substituted by RA1; each of moieties A1 and C is a monocyclic ring or a polycyclic fused ring system; each of X1 to X6 is C or N; K is a direct bond or a linking group; Y is a linking group; each substituent is hydrogen or a General Substituent; LA is coordinated to a metal M. Formulations, OLEDs, and consumer products containing the compound are also provided.
Claims20
A compound having a first ligand LA comprising a structure of Formula I:
- wherein:
- two RA substituents are joined to form a cyclic moiety A1, which may be substituted by one or more substituents, RA1;
- each of moiety A1 and moiety C is independently a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of X1 to X6 is independently C or N;
- K is selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- Y is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
- RA represents di to the maximum allowable substitutions;
- each of RA1, RB, and RC independently represents mono to the maximum allowable substitutions, or no substitutions;
- each R, R′, Rα, Rβ, RA, RA1, RB, and RC is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- LA is coordinated to a metal M through the two dashed lines, selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- metal M may be coordinated to other ligands;
- LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- any two substituents may be joined or fused to form a ring, with the proviso that if Y is NR, then R and the RA substituent at X4 do not join to form a ring, and R and the RB substituent at X5 do not join to form a ring.
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 having a first ligand LA comprising a structure of Formula I:
- wherein:
- two RA substituents are joined to form a cyclic moiety A1, which may be substituted by one or more substituents, RA1;
- each of moiety A1 and moiety C is independently a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of X1 to X6 is independently C or N;
- K is selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- Y is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
- RA represents di to the maximum allowable substitutions;
- each of RA1, RB, and RC independently represents mono to the maximum allowable substitutions, or no substitutions;
- each R, R′, Rα, Rβ, RA, RA1, RB, and RC is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- LA is coordinated to a metal M through the two dashed lines, selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- metal M may be coordinated to other ligands;
- LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- any two substituents may be joined or fused to form a ring, with the proviso that if Y is NR, then R and the RA substituent at X4 do not join to form a ring, and R and the RB substituent at X5 do not join to form a ring.
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, wherein the organic layer comprises a compound having a first ligand LA comprising a structure of Formula I:
- wherein:
- two RA substituents are joined to form a cyclic moiety A1, which may be substituted by one or more substituents, RA1;
- each of moiety A1 and moiety C is independently a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of X1 to X6 is independently C or N;
- K is selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- Y is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
- RA represents di to the maximum allowable substitutions;
- each of RA1, RB, and RC independently represents mono to the maximum allowable substitutions, or no substitutions;
- each R, R′, Rα, Rβ, RA, RA1, RB, and RC is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- LA is coordinated to a metal M through the two dashed lines, selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- metal M may be coordinated to other ligands;
- LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- any two substituents may be joined or fused to form a ring, with the proviso that if Y is NR, then R and the RA substituent at X4 do not join to form a ring, and R and the RB substituent at X5 do not join to form a ring.
Dependencies are inferred from the claim text.