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US 12,742,114 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsAlexey Borisovich Dyatkin, Jui-Yi Tsai, Zhiqiang Ji, Suman Layek, Pierre-Luc T. Boudreault
Life of this patent
Estimating the term…
Abstract
Provided are organometallic compounds. Also provided are formulations comprising these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.
Claims18
A compound comprising a ligand LA of Formula I:
- wherein:
- moiety A is a monocyclic or multicyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;
- A1 and A2 are both independently a one-atom, two-atom, or three-atom linking group, with one of A1 or A2 being O, S, or CRR′ and the other of A1 or A2 being a two-atom or three-atom linking group consisting of carbon atoms, wherein at least two atoms of the linking group are connected to each other by a double bond;
- each of RA and RB independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;
- each X is independently C, CR, or N, wherein the X connecting to Z2 is C, and the X connecting to K2 is C or N;
- X1, X2, and X3 are each independently C or N;
- Z1 and Z2 are each independently C or N;
- K1, and K2 are each independently a direct bond, O, or S;
- each of R, R′, 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, 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 substituents can be joined or fused together to form a ring;
- wherein the ligand LA is coordinated to a metal M through the indicated two dash lines;
- wherein M is selected from the group consisting of Ru, Os, Ir, Pd, Pt, Cu, Ag, and Au;
- wherein the ligand LA can be joined with other ligands to form a tetradentate, pentadentate, or hexadentate ligand;
- and
- if one of A1 or A2 has the structure
- in which each RW can be the same or different and is independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof, and the two RW join to form a ring, then said ring is a heteroaromatic ring or a saturated ring.
14 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:
- moiety A is a monocyclic or multicyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;
- A1 and A2 are both independently a one-atom, two-atom, or three-atom linking group, with one of A1 or A2 being O, S, or CRR′ and the other of A1 or A2 being a two-atom or three-atom linking group consisting of carbon atoms, wherein at least two atoms of the linking group are connected to each other by a double bond;
- each of RA and RB independently represents zero, mono, or up to maximum allowed substitutions to its associated ring;
- each X is independently C, CR, or N, wherein the X connecting to Z2 is C, and the X connecting to K2 is C or N;
- X1, X2, and X3 are each independently C or N;
- Z1 and Z2 are each independently C or N;
- K1, and K2 are each independently a direct bond, O, or S;
- each of R, R′, 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, 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 substituents can be joined or fused together to form a ring;
- wherein the ligand LA is coordinated to a metal M through the indicated two dash lines;
- wherein M is selected from the group consisting of Ru, Os, Ir, Pd, Pt, Cu, Ag, and Au;
- wherein the ligand LA can be joined with other ligands to form a tetradentate, pentadentate, or hexadentate ligand;
- and
- if one of A1 or A2 has the structure
- in which each RW can be the same or different and is independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof, and the two RW join to form a ring, then said ring is a heteroaromatic ring or a saturated ring.
19 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:
- moiety A is a monocyclic or multicyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;
- A1 and A2 are both independently a one-atom, two-atom, or three-atom linking group, with one of A1 or A2 being O, S, or CRR′ and the other of A1 or A2 being a two-atom or three-atom linking group consisting of carbon atoms, wherein at least two atoms of the linking group are connected to each other by a double bond;
- each of RA and RB independently represents zero, mono, or up to maximum allowed substitutions to its associated ring;
- each X is independently C, CR, or N, wherein the X connecting to Z2 is C, and the X connecting to K2 is C or N;
- X1, X2, and X3 are each independently C or N;
- Z1 and Z2 are each independently C or N;
- K1, and K2 are each independently a direct bond, O, or S;
- each of R, R′, 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, 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 substituents can be joined or fused together to form a ring;
- wherein the ligand LA is coordinated to a metal M through the indicated two dash lines;
- wherein M is selected from the group consisting of Ru, Os, Ir, Pd, Pt, Cu, Ag, and Au;
- wherein the ligand LA can be joined with other ligands to form a tetradentate, pentadentate, or hexadentate ligand;
- and
- if one of A1 or A2 has the structure
- in which each RW can be the same or different and is independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof, and the two RW join to form a ring, then said ring is a heteroaromatic ring or a saturated ring.
19 more elements
Dependencies are inferred from the claim text.