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US 2018/0006247 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsLichang ZENG, Mingjuan SU, Edward BARRON, Zhiqiang JI, Chuanjun XIA
Life of this patent
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Abstract
New metal complexes containing a substituted fused aromatic moiety is disclosed. The substituents on the fused aromatic moiety fine-tune molecular energy levels and solid-state self-assembly, conducive to improved material performance in devices useful for phosphorescent organic light emitting devices.
Claims25
A compound comprising a first ligand LA having a structure of Formula I:
- wherein ring A is a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein Z1 is a negatively-charged donor atom, and is selected from nitrogen or carbon;
- wherein L1 is a linker selected from a group consisting of direct bond, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, aryl, heteroaryl, aryloxy, heteroaryloxy, and combinations thereof,
- wherein G1 comprises a fused aromatic structure containing at least four carbon atoms and two aromatic rings;
- wherein G2 is connected to one sp2-hybridized carbon atom which is involved in the conjugation system in G1;
- wherein R1 and R3 represent none to maximal number of substitutions;
- wherein R2 represents mono, di or tri substitutions;
- wherein R1, R3 are each independently selected from a group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, aryl, heteroaryl, aryloxy, heteroaryloxy, and combinations thereof;
- wherein R2, G2 are each independently selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, aryl, heteroaryl, aryloxy, heteroaryloxy, and combinations thereof;
- wherein any substituents R1, R2, and R3 are optionally joined or fused into a ring;
- wherein any of the hydrogen atom in LA is optionally replaced by a deuterium atom;
- wherein the ligand LA is coordinated to a metal M;
- 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.
12 more elements
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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 the structure of Formula I:
- wherein ring A is a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein Z1 is a negatively-charged donor atom, and is selected from nitrogen or carbon;
- wherein L1 is a linker selected from a group consisting of direct bond, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, aryl, heteroaryl, aryloxy, heteroaryloxy, and combinations thereof,
- wherein G1 comprises a fused aromatic structure containing at least four carbon atoms and two aromatic rings;
- wherein G2 is connected to one sp2-hybridized carbon atom which is involved in the conjugation system in G1;
- wherein R1 and R3 represent none to maximal number of substitutions;
- wherein R2 represents mono, di or tri substitutions;
- wherein R1, R3 are each independently selected from a group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, aryl, heteroaryl, aryloxy, heteroaryloxy, and combinations thereof;
- wherein R2, G2 are each independently selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, aryl, heteroaryl, aryloxy, heteroaryloxy, and combinations thereof;
- wherein any substituents R1, R2, and R3 are optionally joined or fused into a ring;
- wherein any of the hydrogen atom in LA is optionally replaced by a deuterium atom;
- wherein the ligand LA is coordinated to a metal M;
- 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.
16 more elements
(canceled)
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A consumer product comprising an organic light-emitting device 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 a structure according to Formula I,
- wherein ring A is a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein Z1 is a negatively-charged donor atom, and is selected from nitrogen or carbon;
- wherein L1 is a linker selected from a group consisting of direct bond, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, aryl, heteroaryl, aryloxy, heteroaryloxy, and combinations thereof,
- wherein G1 comprises a fused aromatic structure containing at least four carbon atoms and two aromatic rings;
- wherein G2 is connected to one sp2-hybridized carbon atom which is involved in the conjugation system in G1;
- wherein R1 and R3 represent none to maximal number of substitutions;
- wherein R2 represents mono, di or tri substitutions;
- wherein R1, R3 are each independently selected from a group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, aryl, heteroaryl, aryloxy, heteroaryloxy, and combinations thereof;
- wherein R2, G2 are each independently selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, aryl, heteroaryl, aryloxy, heteroaryloxy, and combinations thereof;
- wherein any substituents R1, R2, and R3 are optionally joined or fused into a ring;
- wherein any of the hydrogen atom in LA is optionally replaced by a deuterium atom;
- wherein the ligand LA is coordinated to a metal M;
- 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.
16 more elements
(canceled)
Dependencies are inferred from the claim text.