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US 12,514,108 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsMingjuan Su, Morgan C. MacInnis, Daniel W. Silverstein, Tongxiang (Aaron) Lu, George Fitzgerald
Life of this patent
Estimating the term…
Abstract
The present invention includes novel polycyclic alkyl amino carbenes as ligands for metal complexes. These compounds may be useful as emitter materials for phosphorescent electroluminescent devices.
Claims19
A compound comprising a ligand LA selected from Formula I or Formula II,
- or the ligand LA is selected from the group consisting of:
- wherein the ligand LA is coordinated to a metal M, and M is optionally coordinated to other ligands;
- wherein ring A is a 5-membered aromatic ring or a 6-membered aromatic ring;
- Z is C or N;
- X1 to X5 are independently selected from CRR′ or NRN, wherein optionally, X1 and X2 of Formula I join to form an additional ring;
- wherein E is selected from the group consisting of BRN, NRN, PRN, O, S, Se, C═O, S═O, SO2, SiRR′ and GeRR′;
- Y1, Y2 and Y3 are independently selected from CR or N, wherein one of Y1, Y2, and Y3 is N;
- RA represents mono to the maximum allowable substitution, or no substitution;
- each of RA, RB, R, and R′ are 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;
- or any two adjacent substitutions in RA, RB, R, and R′ can join to form a ring;
- each RN is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, ester, and combinations thereof;
- or
- wherein n is 1 or 2;
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- wherein when the compound is represented by Formula I, then at least one of conditions (i) to (iii) is satisfied:
- (i) at least one of X1, X2, and X3 represents NRN;
- (ii) Z is N;
- and
- (iii) Y1 and Y3 are N.
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, the organic layer comprising a compound that includes a Ligand LA selected from Formula I or Formula II,
- or the ligand LA is selected from the group consisting of:
- wherein the ligand LA is coordinated to a metal M, and M is optionally coordinated to other ligands;
- wherein ring A is a 5-membered aromatic ring or a 6-membered aromatic ring;
- Z is C or N;
- X1 to X5 are independently selected from CRR′ or NRN, wherein optionally, X1 and X2 of Formula I join to form an additional ring;
- wherein E is selected from the group consisting of BRN, NRN, PRN, O, S, Se, C═O, S═O, SO2, SiRR′ and GeRR′;
- Y1, Y2 and Y3 are independently selected from CR or N, wherein one of Y1, Y2, and Y3 is N;
- RA represents mono to the maximum allowable substitution, or no substitution;
- each of RA, RB, R, and R′ are 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;
- or any two adjacent substitutions in RA, RB, R, and R′ can join to form a ring;
- each RN is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, ester, and combinations thereof;
- or
- wherein n is 1 or 2;
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- wherein when the compound is represented by Formula I, then at least one of conditions (i) to (iii) is satisfied:
- (i) at least one of X1, X2, and X3 represents NRN;
- (ii) Z is N;
- and
- (iii) Y1 and Y3 are N.
20 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, the organic layer comprising a compound that includes a Ligand LA selected from Formula I or Formula II,
- or the ligand LA is selected from the group consisting of:
- wherein the ligand LA is coordinated to a metal M, and M is optionally coordinated to other ligands;
- wherein ring A is a 5-membered aromatic ring or a 6-membered aromatic ring;
- Z is C or N;
- X1 to X5 are independently selected from CRR′ or NRN, wherein optionally, X1 and X2 of Formula I join to form an additional ring;
- wherein E is selected from the group consisting of BRN, NRN, PRN, O, S, Se, C═O, S═O, SO2, SiRR′ and GeRR′;
- Y1, Y2 and Y3 are independently selected from CR or N, wherein one of Y1, Y2, and Y3 is N;
- RA represents mono to the maximum allowable substitution, or no substitution;
- each of RA, RB, R, and R′ are 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;
- or any two adjacent substitutions in RA, RB, R, and R′ can join to form a ring;
- each RN is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, ester, and combinations thereof;
- or
- wherein n is 1 or 2;
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- wherein when the compound is represented by Formula I, then at least one of conditions (i) to (iii) is satisfied:
- (i) at least one of X1, X2, and X3 represents NRN;
- (ii) Z is N;
- and
- (iii) Y1 and Y3 are N.
20 more elements
Dependencies are inferred from the claim text.