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US 2021/0265576 A1Published application
Organic Electroluminescent Materials and Devices
AssigneeUniversal Display Corporation
InventorsJui-Yi Tsai, Gregg Kottas
Life of this patent
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Abstract
This invention discloses metal complexes containing carborane moiety. The metal complexes showed desired properties in term of EQE, LT, and CIE.
Claims22
A compound comprising a first ligand LA having Formula I:
- wherein ring A is a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RA represents mono to the possible maximum number of substitution, or no substitution;
- wherein Z1 and Z2 are each independently selected from the group consisting of carbon or nitrogen;
- wherein Z1 is neutral donor atom;
- wherein G1 is a carborane group having formula of C2BnHn, which can be further substituted;
- wherein n is an integer of 3 to 10;
- wherein each RA 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 acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents are optionally joined or fused into a ring;
- wherein the ligand LA is coordinated to a metal M, wherein M is selected from the group consisting of Ir and Os;
- wherein the metal M can be coordinated to other ligands;
- and
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand,
- with the proviso that when LA is
- wherein n=10, at least one of the following is true:
- (a) the compound is homoleptic;
- (b) RA represents mono to the possible maximum number of substitution and each RA is independently selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- or
- (c) the compound further comprises a second ligand LB wherein LB is selected from the group consisting of:
- wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
- wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
- wherein R′ and R″ are optionally fused or joined to form a ring;
- wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- wherein R′, R″, Ra, Rb, Rc, and Rd are each 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 acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.
22 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 comprising a first ligand LA having Formula I:
- wherein ring A is a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RA represents mono to the possible maximum number of substitution, or no substitution;
- wherein Z1 and Z2 are each independently selected from the group consisting of carbon or nitrogen;
- wherein Z1 is neutral donor atom;
- wherein G1 is a carborane group having formula of C2BnHn;
- which can be further substituted;
- wherein n is an integer of 3 to 10;
- wherein each RA 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 acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents are optionally joined or fused into a ring;
- wherein the ligand LA is coordinated to a metal M, wherein M is selected from the group consisting of Ir and Os;
- wherein the metal M can be coordinated to other ligands;
- and
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand,
- with the proviso that when LA is
- wherein n=10, at least one of the following is true:
- (a) the compound is homoleptic;
- (b) RA represents mono to the possible maximum number of substitution and each RA is independently selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- or
- (c) the compound further comprises a second ligand LB wherein LB is selected from the group consisting of:
- wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
- wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
- wherein R′ and R″ are optionally fused or joined to form a ring;
- wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- wherein R′, R″, Ra, Rb, Rc, and Rd are each 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 acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.
27 more elements
(canceled)
(canceled)
A formulation comprising a compound comprising a first ligand LA having Formula I:
- wherein ring A is a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RA represents mono to the possible maximum number of substitution, or no substitution;
- wherein Z1 and Z2 are each independently selected from the group consisting of carbon or nitrogen;
- wherein Z1 is neutral donor atom;
- wherein G1 is a carborane group having formula of C2BnHn;
- which can be further substituted;
- wherein n is an integer of 3 to 10;
- wherein each RA 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 acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents are optionally joined or fused into a ring;
- wherein the ligand LA is coordinated to a metal M, wherein M is selected from the group consisting of Ir and Os;
- wherein the metal M can be coordinated to other ligands;
- and
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand,
- with the proviso that when LA is
- wherein n=10, at least one of the following is true:
- (d) the compound is homoleptic;
- (e) RA represents mono to the possible maximum number of substitution and each RA is independently selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- or
- (f) the compound further comprises a second ligand LB wherein LB is selected from the group consisting of:
- wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
- wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
- wherein R′ and R″ are optionally fused or joined to form a ring;
- wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- wherein R′, R″, Ra, Rb, Rc, and Rd are each 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 acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.
23 more elements
Dependencies are inferred from the claim text.