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US 2026/0107676 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsMatthew T. Tudge, Tyler Fleetham
Life of this patent
Estimating the term…
Abstract
Provided are organometallic compounds comprising a central metal atom which is coordinated by an at least two-dentate ligand comprising at least two rings A and B which are connected by a direct bond as well as a further linking group so that a 7-10 membered ring to which rings A and B are fused is formed. Also provided are formulations comprising these organometallic compounds. Further provided are organic light emitting devices (OLEDs) as well as related consumer products that utilize these organometallic compounds.
Claims20
A compound having a ligand LA comprising a structure of Formula I:
- wherein:
- ring A and ring B each can independently be a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- ring Z is a 7-, 8-, 9-, or 10-membered ring;
- X1, X2, X3, X4, X5, and X6 are each independently C or N, with the proviso that at least one of X2 and X5 is C;
- K1 and K2 are each independently selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- RA, RB, and RZ each independently represent zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
- each of Rα, Rβ, RA, RB, and RZ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- any two adjacent RA, RB, or RZ can be joined or fused to form a ring,
- wherein the ligand LA is coordinated to a metal M through the two indicated dashed lines;
- wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au, and can be coordinated to other ligands;
- wherein the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- wherein at least one of the following five conditions is true:
- (1) K1 is a direct bond, X1 forms a coordinate bond to M, and two RA substituents are joined to form a polycyclic fused ring system comprised of at least two carbocyclic or heterocyclic rings that is fused to ring A;
- (2) two RZ substituents are joined to form a polycyclic fused ring system comprised of at least two carbocyclic or heterocyclic rings that is fused to ring Z;
- (3) K2 is a direct bond, X4 forms an anionic bond to M, and two RB substituents are joined to form a monocyclic or polycyclic fused ring system comprising 5-membered to 10-membered carbocyclic or heterocyclic rings that is fused to ring B;
- (4) an RZ substituent is joined with an RA substituent or an RB substituent to form a 5-membered to 10-membered carbocyclic or heterocyclic ring D, which is further fused with two or more additional carbocyclic or heterocyclic rings;
- (5) at least one of K1 and K2 is not a direct bond.
16 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 having a ligand LA comprising a structure of Formula 1:
- wherein:
- ring A and ring B each can independently be a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- ring Z is a 7-, 8-, 9-, or 10-membered ring;
- X1, X2, X3, X4, X5, and X6 are each independently C or N, with the proviso that at least one of X2 and X5 is C;
- K1 and K2 are each independently selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- RA, RB, and RZ each independently represent zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
- each of Rα, Rβ, RA, RB, and RZ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- any two adjacent RA, RB, or RZ can be joined or fused to form a ring, wherein the ligand LA is coordinated to a metal M through the two indicated dashed lines;
- wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au, and can be coordinated to other ligands;
- wherein the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- wherein at least one of the following five conditions is true:
- (1) K1 is a direct bond, X1 forms a coordinate bond to M, and two RA substituents are joined to form a polycyclic fused ring system comprised of at least two carbocyclic or heterocyclic rings that is fused to ring A;
- (2) two RZ substituents are joined to form a polycyclic fused ring system comprised of at least two carbocyclic or heterocyclic rings that is fused to ring Z;
- (3) K2 is a direct bond, X4 forms an anionic bond to M, and two RB substituents are joined to form a monocyclic or polycyclic fused ring system comprising 5-membered to 10-membered carbocyclic or heterocyclic rings that is fused to ring B;
- (4) an RZ substituent is joined with an RA substituent or an RB substituent to form a 5-membered to 10-membered carbocyclic or heterocyclic ring D, which is further fused with two or more additional carbocyclic or heterocyclic rings;
- (5) at least one of K1 and K2 is not a direct bond.
20 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,
- wherein the organic layer comprises a compound having a ligand LA comprising a structure of Formula 1:
- wherein:
- ring A and ring B each can independently be a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- ring Z is a 7-, 8-, 9-, or 10-membered ring;
- X1, X2, X3, X4, X5, and X6 are each independently C or N, with the proviso that at least one of X2 and X5 is C;
- K1 and K2 are each independently selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- RA, RB, and RZ each independently represent zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
- each of Rα, Rβ, RA, RB, and RZ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- any two adjacent RA, RB, or RZ can be joined or fused to form a ring, wherein the ligand LA is coordinated to a metal M through the two indicated dashed lines;
- wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au, and can be coordinated to other ligands;
- wherein the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- wherein at least one of the following five conditions is true:
- (1) K1 is a direct bond, X1 forms a coordinate bond to M, and two RA substituents are joined to form a polycyclic fused ring system comprised of at least two carbocyclic or heterocyclic rings that is fused to ring A;
- (2) two RZ substituents are joined to form a polycyclic fused ring system comprised of at least two carbocyclic or heterocyclic rings that is fused to ring Z;
- (3) K2 is a direct bond, X4 forms an anionic bond to M, and two RB substituents are joined to form a monocyclic or polycyclic fused ring system comprising 5-membered to 10-membered carbocyclic or heterocyclic rings that is fused to ring B;
- (4) an RZ substituent is joined with an RA substituent or an RB substituent to form a 5-membered to 10-membered carbocyclic or heterocyclic ring D, which is further fused with two or more additional carbocyclic or heterocyclic rings;
- (5) at least one of K1 and K2 is not a direct bond.
20 more elements
Dependencies are inferred from the claim text.