Stability OLED materials and devices
AssigneeUniversal Display Corporation
InventorsChun Lin, Peter B. Mackenzie, Robert W. Walters, Jui-Yi Tsai, Cory S. Brown, Jun Deng
Life of this patent
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Abstract
Organic light emitting materials and devices comprising phosphorescent metal complexes comprising ligands comprising aryl or heteroaryl groups substituted at both ortho positions are described. An organic light emitting device, comprising: an anode; a hole transport layer; an organic emissive layer comprising an emissive layer host and an emissive dopant; an electron impeding layer; an electron transport layer; and a cathode disposed, in that order, over a substrate.
Claims19
A phosphorescent compound, wherein the phosphorescent compound is a neutral metal complex of a monodentate, bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand;
- wherein the ligand comprises at least one first aryl or heteroaryl ring directly bonded to the metal;
- wherein the first ring is substituted by a second aryl or heteroaryl ring which is not directly bonded to the metal,
- wherein the first ring is a moiety selected from the group consisting of naphthalene, quinoline, isoquinoline, pyrimidine, pyrrole, pyrazole, triazole, pyridazine, oxazole, oxadiazole, thiadiazole, furan, and thiophene, and the second ring is substituted at both ortho positions by aryl or heteroaryl;
- wherein the metal complex is an organometallic complex;
- wherein the ligand comprises at least one carbon bonded to the metal;
- and
- wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Cu and Au.
A phosphorescent compound, wherein the phosphorescent compound is a neutral metal complex of a monodentate, bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand;
- wherein the ligand comprises at least one first aryl or heteroaryl ring directly bonded to the metal;
- wherein the first ring is substituted by a second ring which is not directly bonded to the metal,
- wherein the first ring is a moiety selected from the group consisting of naphthalene, quinoline, isoquinoline, pyrimidine, pyridazine, pyrrole, oxazole, oxadiazole, thiadiazole, furan, thiophene, pyrazole, and triazole;
- wherein the metal complex is an organometallic complex;
- wherein the ligand comprises at least one carbon bonded to the metal;
- wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Cu and Au;
- and
- wherein, when the first ring is pyrrole, pyrazole, oxazole, or triazole, the second ring is selected from group A, and
- wherein, when the first ring is naphthalene, quinoline, isoquinoline, pyrimidine, pyridazine, oxadiazole, thiadiazole, furan, and thiophene, the second ring is selected from group A or group B,
- wherein group B consists of 2,3,4,5,6-pentamethylphenyl, 2,6-dimethyl-4-phenylphenyl, 2,6-dimethyl-4-(3,5-dimethylphenyl)phenyl, 2,6-dimethyl-4-(2,6-dimethylphenyl)phenyl, 2,6-dimethyl-4-(4-pyridyl)phenyl, 2,6-dimethyl-4-(2,6-dimethyl-4-pyridyl)phenyl, 2,4-dimethyl-3-naphthyl, 2,6-dimethyl-4-cyanophenyl, 2,6-dimethyl-4-(9-carbazolyl)phenyl, 2,6-dimethyl-4-(9-phenyl-3-carbazolyl)phenyl, 2,6-dimethyl-4-(2,6-dimethyl-4-cyanophenyl)phenyl, 1,8-dimethyl-9-carbazolyl, 2,6-di-isopropylphenyl, 2,4,6-triisopropylphenyl, 2,6-di-isopropyl-4-phenylphenyl, 2,6-di-isopropyl-4-(3,5-dimethylphenyl)phenyl, 2,6-di-isopropyl-4-(2,6-dimethylphenyl)phenyl, 2,6-di-isopropyl-4-(4-pyridyl)phenyl, 2,6-di-isopropyl-4-(2,6-dimethyl-4-pyridyl)phenyl, 2,4-di-isopropyl-3-naphthyl, 2,6-di-isopropyl-4-cyanophenyl, 2,6-di-isopropyl-4-(9-carbazolyl)phenyl, 2,6-di-isopropyl-4-(9-phenyl-3-carbazolyl)phenyl, 2,6-di-isopropyl-4-(2,6-dimethyl-4-cyanophenyl)phenyl, 2,6-di-tertbutylphenyl, 2,6-di-tert-butyl-4-(3,5-dimethylphenyl)phenyl,
- and
- wherein group A consists of 2,6-di-phenylphenyl, 2,6-di(4-isopropylphenyl)-4-isopropylphenyl, 2,6-di(4-isopropylphenyl)-4-methylphenyl, 2,6-di(4-isopropylphenyl)-4-tert-butylphenyl, 2,4,6-triphenylphenyl, 2,6-di-(4-isopropylphenyl)phenyl, 2,6-di-(3,5-dimethylphenyl)phenyl, 2,4,6-tri(4-isopropylphenyl)phenyl, 2,6-di-(4-tertbutylphenyl)phenyl, 2,6-di-(4-fluorophenyl)phenyl, 2,6-di-(9-carbazolyl)-4-isopropylphenyl, 2,6-di-(9-phenyl-3-carbazolyl)-4-isopropylphenyl, 2,6-di-(4-methoxyphenyl)phenyl, 2,6-diphenyl-4-fluorophenyl, 2,6-di-(2-triphenylenyl)phenyl, 2,6-di-(2-triphenylenyl)-4-isopropylphenyl, 2,6-di-(2,6-dimethyl-4-pyridyl)phenyl, 2,6-di-(4-cyanophenyl)-4-isopropylphenyl, 2,6-di-2-naphthylphenyl, 2,6-di-(4-phenylphenyl)-4-isopropylphenyl, 2,6-di-(3-phenylphenyl)-4-isopropylphenyl, 2,6-di-(4-diphenylaminophenyl)phenyl, 2,6-di-(4-dimethylaminophenyl)phenyl, 2,6-di-(4-trimethylsilylphenyl)phenyl, 2,6-di-(4-triphenylsilylphenyl)phenyl, 2,6-di-(4-diphenylmethylsilylphenyl)phenyl,
- wherein:
- for group B, R1a,e are each independently selected from alkyl;
- for group A, R1a,e are each independently selected from the group consisting of aryl and heteroaryl;
- R1b,d are each independently selected from the group consisting of H, F, cyano, alkoxy, aryloxy, hydrocarbyl, heteroatom substituted hydrocarbyl, aryl, and heteroaryl;
- any two of R1b-d may be linked to form a ring;
- and
- Ar1, Ar2, and Ar3 are each independently aryl or heteroaryl.
Dependencies are inferred from the claim text.