US 2026/0314251 A1Published application

Organic electroluminescent materials and devices

AssigneeUniversal Display Corporation

InventorsJui-Yi TSAI, Alexey Borisovich DYATKIN, Zhiqiang JI, Wei-Chun SHIH, Wystan Neil PALMER, Tyler FLEETHAM, Robert DYER

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Abstract

A compound of formula Ir(LA)x(LB)y(LC)z is provided where x is 1, 2, or 3; each of y and z is 0, 1, or 2; and x+y+z=3. In the compound, the first ligand LA includes a structure of Formula I, where each of moiety A and, when present, moiety C is a monocyclic ring or a polycyclic fused ring system; each of Z1, Z2, and X1 to X6 is C or N; each of Y1 and Y2 is a linker; K is a direct bond or a linker; each R, R′, Rα, Rβ, RA, RB, and, when present, RC is hydrogen or a General Substituents defined herein. Compositions, OLEDs, and consumer products containing the compound are also provided.

Claims20

Dependent claims

A compound comprising a formula of Ir(LA)x(LB)y(LC)z, wherein:

x is 1, 2, or 3;
each of y and z is independently 0, 1, or 2;
and x+y+z=3;
first ligand LA comprises a structure of Formula I,
each of moiety A and, when present, 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 Z1, Z2, and X1 to X6 is independently C or N;
each of Y1 and Y2 is independently selected from O, S, Se, NR, BR, BRR′, PR, PRR′, CR, C═O, C═NR′, C═CRR′, C═S, C═Se, CRR′, S═O, SO2, P(O)R, SiRR′, and GeRR′;
K is selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), β(Rα), C(Rα)(Rβ), or Si(Rα)(Rβ);
each of RA, RB, and, when present, RC independently represents mono to the maximum allowable substitutions, or no substitutions;
each R, R′, Rα, Rβ, RA, RB, and, when present, 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;
any two substituents may be joined or fused to form a ring;
LA is bonded to the Ir atom through the indicated dashed lines;
LA may join with LB, LC, or both to form a tetradentate or hexadentate ligand;
and
at least one of the following is true:
(1) at least one RB or RC substituent comprises a moiety selected from the group consisting of silyl, germyl, and electron-withdrawing groups;
(2) moiety C comprises at least three 6-membered rings;
(3) moiety C comprises two fused 6-membered rings, and at least one of Y1 or Y2 is CRR′ or SiRR′;
(4) moiety C comprises a saturated ring;
(5) moiety A is not unfused pyridine, and Z2 is bonded to X2, X3, or X4;
(6) moiety C comprises a 5-membered ring;
(7) moiety A is a polycyclic fused ring system comprising at least three rings;
(8) moiety C is a benzene ring and moiety A is not unfused pyridine;
(9) one of Y1 or Y2 is CRR′ or Se, and moiety A is an imidazole or its derivatives;
or
(10) one of Y1 or Y2 is Se.

23 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 formula of Ir(LA)x(LB)y(LC)z, wherein:
x is 1, 2, or 3;
each of y and z is independently 0, 1, or 2;
and x+y+z=3;
first ligand LA comprises a structure of Formula I,
each of moiety A and, when present, 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 Z1, Z2, and X1 to X6 is independently C or N;
each of Y1 and Y2 is independently selected from O, S, Se, NR, BR, BRR′, PR, PRR′, CR, C═O, C═NR′, C═CRR′, C═S, C═Se, CRR′, S═O, SO2, P(O)R, SiRR′, and GeRR′;
K is selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), or Si(Rα)(Rβ);
each of RA, RB, and, when present, RC independently represents mono to the maximum allowable substitutions, or no substitutions;
each R, R′, Rα, Rβ, RA, RB, and, when present, 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;
any two substituents may be joined or fused to form a ring;
LA is bonded to the Ir atom through the indicated dashed lines;
LA may join with LB, LC, or both to form a tetradentate or hexadentate ligand;
and
at least one of the following is true:
(1) at least one RB or RC substituent comprises a moiety selected from the group consisting of silyl, germyl, and electron-withdrawing groups;
(2) moiety C comprises at least three 6-membered rings;
(3) moiety C comprises two fused 6-membered rings, and at least one of Y1 or Y2 is CRR′ or SiRR′;
(4) moiety C comprises a saturated ring;
(5) moiety A is not unfused pyridine, and Z2 is bonded to X2, X3, or X4;
(6) moiety C comprises a 5-membered ring;
(7) moiety A is a polycyclic fused ring system comprising at least three rings;
(8) moiety C is a benzene ring and moiety A is not unfused pyridine;
(9) one of Y1 or Y2 is CRR′ or Se, and moiety A is an imidazole or its derivatives;
or
(10) one of Y1 or Y2 is Se.

27 more elements

A compound, or a neutral molecular form thereof, or a monovalent or polyvalent form thereof, or a monomeric or polymeric form thereof, or a macromolecular or supramolecular form thereof;

wherein the compound comprises a formula of Ir(LA)x(LB)y(LC)z, wherein:
x is 1, 2, or 3;
each of y and z is independently 0, 1, or 2;
and x+y+z=3;
first ligand LA comprises a structure of Formula I,
each of moiety A and, when present, 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 Z1, Z2, and X1 to X6 is independently C or N;
each of Y1 and Y2 is independently selected from O, S, Se, NR, BR, BRR′, PR, PRR′, CR, C═O, C═NR′, C═CRR′, C═S, C═Se, CRR′, S═O, SO2, P(O)R, SiRR′, and GeRR′;
K is selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), or Si(Rα)(Rβ);
each of RA, RB, and, when present, RC independently represents mono to the maximum allowable substitutions, or no substitutions;
each R, R′, Rα, Rβ, RA, RB, and, when present, 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;
any two substituents may be joined or fused to form a ring;
LA is bonded to the Ir atom through the indicated dashed lines;
LA may join with LB, LC, or both to form a tetradentate or hexadentate ligand;
and
at least one of the following is true:
(1) at least one RB or RC substituent comprises a moiety selected from the group consisting of silyl, germyl, and electron-withdrawing groups;
(2) moiety C comprises at least three 6-membered rings;
(3) moiety C comprises two fused 6-membered rings, and at least one of Y1 or Y2 is CRR′ or SiRR′;
(4) moiety C comprises a saturated ring;
(5) moiety A is not unfused pyridine, and Z2 is bonded to X2, X3, or X4;
(6) moiety C comprises a 5-membered ring;
(7) moiety A is a polycyclic fused ring system comprising at least three rings;
(8) moiety C is a benzene ring and moiety A is not unfused pyridine;
(9) one of Y1 or Y2 is CRR′ or Se, and moiety A is an imidazole or its derivatives;
or
(10) one of Y1 or Y2 is Se.

24 more elements

Dependencies are inferred from the claim text.

Facts

Application: 19/562,872Filed 11 Mar 2026
Priority: 19 Mar 2025
Published: 8 Oct 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification18 codes

H10K 85/342
Transition metal complexes, e.g. Rupolypyridine complexes: comprising iridium
C07B 59/004
Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se: acyclic, carbocyclic or heterocyclic compounds…
C07F 15/0033
Compounds of the platinum group: iridium compounds
C09K 11/06
Luminescent materials, e.g. electroluminescent or chemiluminescent: containing organic luminescent materials