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US 2025/0063940 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsFadi M. Jradi, Hsiao-Fan Chen, Rasha Hamze
Life of this patent
Estimating the term…
Abstract
Provided are organometallic compounds wherein a central metal atom is coordinated by a tetradentate ligand comprising at least four 5- or 6-membered carbocyclic or heterocyclic rings, wherein one of the at least four 5- or 6-membered carbocyclic or heterocyclic rings is fused to an imidazole ring. Also provided are formulations comprising these organometallic compounds. Further provided are organic light emitting devices (OLEDs) and related consumer products that utilize these organometallic compounds.
Claims20
A compound of Formula I:
- wherein moieties A, B, C, and D are each 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;
- wherein K1—K4 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);
- wherein at least two of K1—K4 are direct bonds;
- wherein Z1—Z3 are each independently C or N;
- wherein one of Z1 and Z2 is C and the other of Z1 and Z2 is N;
- wherein L1, L2, and L3 are each independently a direct bond or selected from the group consisting of O, S, Se, NR, BR, BRR′, PR, CR, C═O, C═NR, C═CRR′, C═S, CRR′, SO, SO2, P(O)R, SiRR′, and GeRR′;
- wherein each of X1—X3 is independently C or N;
- wherein m and n are each independently 0 or 1;
- when m or n is 0, the corresponding L2 or L3 is not present;
- wherein m+n=1 or 2;
- wherein RA, RB, RC, and RD are each independently represent mono to the maximum allowable substitution, or no substitution;
- wherein each R, R′, Rα, Rβ, R1, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, boryl, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- wherein LA is coordinated to a metal M;
- wherein M is selected from the group consisting of Pd, Pt, Cu, Ag, or Au;
- wherein any two substituents may be joined or fused to form a ring;
- wherein at least one of K3 and K4 is a carbene bond;
- and
- with the proviso that two RB substituents do not join to form an imidazole ring.
15 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 of Formula I:
- wherein moieties A, B, C, and D are each 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;
- wherein K1—K4 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);
- wherein at least two of K1—K4 are direct bonds;
- wherein Z1— Z3 are each independently C or N;
- wherein one of Z1 and Z2 is C and the other of Z1 and Z2 is N;
- wherein L1, L2, and L3 are each independently a direct bond or selected from the group consisting of O, S, Se, NR, BR, BRR′, PR, CR, C═O, C═NR, C═CRR′, C═S, CRR′, SO, SO2, P(O)R, SiRR′, and GeRR′;
- wherein each of X1—X3 is independently C or N;
- wherein m and n are each independently 0 or 1;
- when m or n is 0, the corresponding L2 or L3 is not present;
- wherein m+n=1 or 2;
- wherein RA, RB, RC, and RD are each independently represent mono to the maximum allowable substitution, or no substitution;
- wherein each R, R′, Rα, Rβ, R1, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, boryl, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- wherein LA is coordinated to a metal M;
- wherein M is selected from the group consisting of Pd, Pt, Cu, Ag, or Au;
- wherein any two substituents may be joined or fused to form a ring;
- wherein at least one of K3 and K4 is a carbene bond.
18 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 of Formula I:
- wherein moieties A, B, C, and D are each 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;
- wherein K1—K4 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);
- wherein at least two of K1—K4 are direct bonds;
- wherein Z1— Z3 are each independently C or N;
- wherein one of Z1 and Z2 is C and the other of Z1 and Z2 is N;
- wherein L1, L2, and L3 are each independently a direct bond or selected from the group consisting of O, S, Se, NR, BR, BRR′, PR, CR, C═O, C═NR, C═CRR′, C═S, CRR′, SO, SO2, P(O)R, SiRR′, and GeRR′;
- wherein each of X1—X3 is independently C or N;
- wherein m and n are each independently 0 or 1;
- when m or n is 0, the corresponding L2 or L3 is not present;
- wherein m+n=1 or 2;
- wherein RA, RB, RC, and RD are each independently represent mono to the maximum allowable substitution, or no substitution;
- wherein each R, R′, Rα, Rβ, R1, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, boryl, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- wherein LA is coordinated to a metal M;
- wherein M is selected from the group consisting of Pd, Pt, Cu, Ag, or Au;
- wherein any two substituents may be joined or fused to form a ring;
- wherein at least one of K3 and K4 is a carbene bond.
18 more elements
Dependencies are inferred from the claim text.