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US 10,707,427 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsTongxiang Lu, George Fitzgerald, Paul Lahti, Morgan C. MacInnis
Life of this patent
Estimating the term…
Abstract
This invention relates to the development of heterocyclic materials for use in OLED devices. The materials are based on a pair of 5-membered aromatic or psuedoaromatic rings bonded to one another and complexed to a transition metal.
Claims19
A compound of Formula I, comprising a ligand LA coordinated to a metal M, wherein ligand LA comprises ring A and ring B:
- wherein Y is carbon or nitrogen;
- wherein ring A is selected from the group consisting of:
- wherein ring B is selected from the group consisting of:
- wherein R3 substituents cannot join or fuse to form a ring;
- wherein rings C and D are five-, or six-member aromatic carbocyclic or heterocyclic rings;
- wherein X is selected from the group consisting of O, S, Se, and NR;
- wherein each of R2 to R4 independently represents mono to the possible maximum number of substitution, or no substitution;
- wherein each of R, and R2 to R4 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents are optionally joined or fused into a ring;
- wherein the metal M can be coordinated to other ligands;
- and
- wherein the compound has a formula of M(LA)n(LB)m-n;
- wherein M is Ir or Pt;
- wherein LB is a bidentate ligand;
- wherein when M is Ir, m is 3, and n is 1, 2, or 3;
- and
- when M is Pt, m is 2, and n is 1, or 2.
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, comprising a compound of Formula I comprising a ligand LA coordinated to metal M, wherein ligand LA comprises ring A and ring B:
- wherein Y is carbon or nitrogen;
- wherein ring A is selected from the group consisting of:
- wherein ring B is selected from the group consisting of:
- wherein R3 substituents cannot join or fuse to form a ring;
- wherein rings C and D are five-, or six-member aromatic carbocyclic or heterocyclic rings;
- X is selected from the group consisting of O, S, Se, and NR;
- wherein each of R2 to R4 independently represents mono to the possible maximum number of substitution, or no substitution;
- wherein each of R, and R2 to R4 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents are optionally joined or fused into a ring;
- wherein the metal M can be coordinated to other ligands;
- and
- wherein the compound has a formula of M(LA)n(LB)m-n;
- wherein M is Ir or Pt;
- wherein LB is a bidentate ligand;
- wherein when M is Ir, m is 3, and n is 1, 2, or 3;
- and
- when M is Pt, m is 2, and n is 1, or 2.
18 more elements
A formulation comprising a compound of Formula I comprising a first ligand LA coordinated to metal M, wherein ligand LA comprises ring A and ring B:
- wherein Y is carbon or nitrogen;
- wherein ring A is selected from the group consisting of:
- wherein ring B is selected from the group consisting of:
- wherein R3 substituents cannot join or fuse to form a ring;
- wherein rings C and D are five-, or six-member aromatic carbocyclic or heterocyclic rings;
- X is selected from the group consisting of O, S, Se, and NR;
- wherein each of R2 to R4 independently represents mono to the possible maximum number of substitution, or no substitution;
- wherein each of R, and R2 to R4 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents are optionally joined or fused into a ring;
- wherein the metal M can be coordinated to other ligands;
- and
- wherein the compound has a formula of M(LA)n(LB)m-n;
- wherein M is Ir or Pt;
- wherein LB is a bidentate ligand;
- wherein when M is Ir, m is 3, and n is 1, 2, or 3;
- and
- when M is Pt, m is 2, and n is 1, or 2.
14 more elements
Dependencies are inferred from the claim text.