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US 12,751,198 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsNeil Palmer, Wei-Chun Shih, George Fitzgerald, Joseph A. Macor, Rasha Hamze, Pierre-Luc T. Boudreault, Geza Szigethy
Life of this patent
Estimating the term…
Abstract
Provided are compounds comprising ligands LA that are ligands of Pt and Ir complexes for OLED applications. Also provided are formulations comprising these compounds comprising ligands LA that are ligands of Pt and Ir complexes for OLED applications. Further provided are OLEDs and related consumer products that utilize these compounds comprising ligands LA that are ligands of Pt and Ir complexes for OLED applications.
Claims20
A compound comprising a ligand LA of Formula I:
- wherein
- ring A and ring B each independently represents a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
- Z1, Z2, Z3 and Z4 are each independently C or N;
- L is a direct bond or selected from the group consisting of O, S, NR″, CR′R″, SiR′R″, BR′, P(O)R, and BR′R″;
- K1 and K2 are each independently selected from the group consisting of direct bond, O, and S;
- RA represents mono to the maximum allowable substitution;
- at least one of RA or RB comprises a structure of Formula II or Formula III:
- the dashed lines of Formula II and Formula III indicate direct bond to ring A or ring B;
- X is selected from the group consisting of BR′, C═O, C═S, C═NR′, CR′R″ and SiR′R″;
- Y1 and Y2 are each independently selected from the group consisting of O, S, NR′, and BR′;
- ring C is a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
- RB and RC each independently represent mono to the maximum allowable substitution, or no substitution;
- each R, R′, R″, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, 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 dashed lines of Formula I, forming a 5-membered or 6-membered chelate ring;
- M is optionally coordinated to other ligands;
- LA is optionally joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- any two of adjacent R, R′, R″, RA, RB, and RC can be joined or fused together to form a ring;
- when Y1 and Y2 of Formula II are independently selected from the group consisting of O and NR′, X is not CR′R″;
- and
- when one of ring A or ring B is a 5-membered ring and one of RA or RB comprises a structure of Formula II, then X is not CR′R″.
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
- ring A and ring B each independently represents a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
- Z1, Z2, Z3 and Z4 are each independently C or N;
- L is a direct bond or selected from the group consisting of O, S, NR″, CR′R″, SiR′R″, BR′, P(O)R, and BR′R″;
- K1 and K2 are each independently selected from the group consisting of direct bond, O, and S;
- RA represents mono to the maximum allowable substitution;
- at least one of RA or RB comprises a structure of Formula II or Formula III:
- the dashed lines of Formula II and Formula III indicate direct bond to ring A or ring B;
- X is selected from the group consisting of BR′, C═O, C═S, C═NR′, CR′R″ and SiR′R″;
- Y1 and Y2 are each independently selected from the group consisting of O, S, NR′, and BR′;
- ring C is a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
- RB and RC each independently represent mono to the maximum allowable substitution, or no substitution;
- each R, R′, R″, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, 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 dashed lines of Formula I, forming a 5-membered or 6-membered chelate ring;
- M is optionally coordinated to other ligands;
- LA is optionally joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- any two of adjacent R, R′, R″, RA, RB, and RC can be joined or fused together to form a ring;
- when Y1 and Y2 of Formula II are independently selected from the group consisting of O and NR′, X is not CR′R″;
- and
- when one of ring A or ring B is a 5-membered ring and one of RA or RB comprises a structure of Formula II, then X is not CR′R″.
22 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 comprising a ligand LA of Formula I:
- wherein
- ring A and ring B each independently represents a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
- Z1, Z2, Z3 and Z4 are each independently C or N;
- L is a direct bond or selected from the group consisting of O, S, NR″, CR′R″, SiR′R″, BR′, P(O)R, and BR′R″;
- K1 and K2 are each independently selected from the group consisting of direct bond, O, and S;
- RA represents mono to the maximum allowable substitution;
- at least one of RA or RB comprises a structure of Formula II or Formula III:
- the dashed lines of Formula II and Formula III indicate direct bond to ring A or ring B;
- X is selected from the group consisting of BR′, C═O, C═S, C═NR′, CR′R″ and SiR′R″;
- Y1 and Y2 are each independently selected from the group consisting of O, S, NR′, and BR′;
- ring C is a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
- RB and RC each independently represent mono to the maximum allowable substitution, or no substitution;
- each R, R′, R″, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, 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 dashed lines of Formula I, forming a 5-membered or 6-membered chelate ring;
- M is optionally coordinated to other ligands;
- LA is optionally joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- any two of adjacent R, R′, R″, RA, RB, and RC can be joined or fused together to form a ring;
- when Y1 and Y2 of Formula II are independently selected from the group consisting of O and NR′, X is not CR′R″;
- and
- when one of ring A or ring B is a 5-membered ring and one of RA or RB comprises a structure of Formula II, then X is not CR′R″.
21 more elements
Dependencies are inferred from the claim text.