Universal Display Corporation

Mingjuan Su

Chuanjun Xia

Bin Ma

Walter H Yeager

Lichang Zeng

Jui-Yi Tsai

Zhiqiang Ji

Edward Barron

Alexey Borisovich Dyatkin

Alan Deangelis

Chun Lin

Eric A Margulies

Pierre-Luc T Boudreault

Scott Joseph

Michael Stewart Weaver

Julia J Brown

Harvey Wendt

Alan DeAngelis

Hsiao-Fan Chen

Tongxiang (Aaron) Lu

Vadim Adamovich

Bert Alleyne

Jerald Feldman

George Fitzgerald

Ting-Chih Wang

Daniel W Silverstein

Morgan C MacInnis

Lech Michalski

Jason Brooks

Michael Stuart Weaver

Paul M Lahti

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.

Organic electroluminescent materials and devices

Metal complexes with cyclic ligands having Formula (I), are disclosed. Ligands with cyclic structure are believed to be beneficial to the rigidity and stability of the metal complexes, which is desirable for improving OLED device performance.

A compound having a Pt tetradentate structure of Formula 1, is provided. In the structure of Formula 1, rings C and D each independently represent 5- or 6-membered carbocyclic or heterocyclic ring; L, L, and Lare each independently a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO, SiRR', GeRR′, alkyl, cycloalkyl, or a combination thereof; the sum of n1 and n2 is 1 or 2; X is selected from NR, O, S, and Se; Xand Xeach independently carbon or nitrogen; and one of Q, Q, and Qis oxygen, and the remaining two of Q, Q, and Qeach represents a direct bond. Formulations and devices, such as an OLEDs, that include the compound of Formula 1 are also described.

A compound is disclosed that has a metal coordination complex structure having at least two ligands coordinated to the metal; wherein the compound has a first substituent Rat one of the ligands' periphery; wherein a first distance is defined as the distance between the metal and one of the atoms in Rwhere that atom is the farthest away from the metal among the atoms in R; wherein the first distance is also longer than any other atom-to-metal distance between the metal and any other atoms in the compound; and wherein when a sphere having a radius r is defined whose center is at the metal and the radius r is the smallest radius that will allow the sphere to enclose all atoms in the compound that are not part of R, the first distance is longer than the radius r by at least 2.9 Å.

A compound having a metal coordination complex structure, where the compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature is disclosed. The compound has a first ligand coordinated to a metal. The free-state of the first ligand has a first triplet energy T1 of Eat 77K, while the compound has a first triplet energy T1 of E at 77K, and the difference in energy (ΔE) between E and Eis ≤250 meV. The compound has a triplet emission spectrum with a FWHM value of no more than 45 nm. Organic light emitting devices, consumer products, and formulations containing the compounds are also disclosed.

A compound comprising a ligand L, having a structure of Formula I, is provided. In Formula I, Ato Aare each independently CR or N; at least two adjacent ones of Ato Aare CR and the Rs are joined together to form a six-membered ring fused to ring A or ring C; X is O, S, or Se; each R and Ris independently hydrogen or a substituent; any adjacent substituents are optionally joined or fused into a ring; the ligand Lis coordinated to a metal M; the metal M is bonded to ring A through a M-C bond; the metal M can be coordinated to other ligands; and the ligand Lis optionally linked with other ligands. Formulations, OLEDs, and consumer products containing such compounds are also disclosed.

A compound is disclosed that has a metal coordination complex structure having at least two ligands coordinated to the metal; wherein the compound has a first substituent Rat one of the ligands' periphery; wherein a first distance is defined as the distance between the metal and one of the atoms in Rwhere that atom is the farthest away from the metal among the atoms in R; wherein the first distance is also longer than any other atom-to-metal distance between the metal and any other atoms in the compound; and wherein when a sphere having a radius r is defined whose center is at the metal and the radius r is the smallest radius that will allow the sphere to enclose all atoms in the compound that are not part of R, the first distance is longer than the radius r by at least 2.9 &#x212b;.

A compound having a Pt tetradentate structure of Formula 1, is provided. In the structure of Formula 1, rings C and D each independently represent 5- or 6-membered carbocyclic or heterocyclic ring; L, L, and Lare each independently a direct bond, BR, NR, PR, O, S, Se, C&#x2550;O, S&#x2550;O, SO, SiRR', GeRR&#x2032;, alkyl, cycloalkyl, or a combination thereof; the sum of n1 and n2 is 1 or 2; X is selected from NR, O, S, and Se; Xand Xeach independently carbon or nitrogen; and one of Q, Q, and Qis oxygen, and the remaining two of Q, Q, and Qeach represents a direct bond. Formulations and devices, such as an OLEDs, that include the compound of Formula 1 are also described.

Novel metal compounds having a first ligand Lthat has the following formula: Formula I useful as emitters in OLED application are disclosed.

A compound having a metal coordination complex structure, where the compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature is disclosed. The compound has a first ligand coordinated to a metal. The free-state of the first ligand has a first triplet energy T1 of Eat 77K, while the compound has a first triplet energy T1 of E at 77K, and the difference in energy (&#x394;E) between E and Eis &#x2264;250 meV. The compound has a triplet emission spectrum with a FWHM value of no more than 45 nm. Organic light emitting devices, consumer products, and formulations containing the compounds are also disclosed.

A compound having a formula (L)Ir(L)having a structure selected from is disclosed. In the structures of formula (L)Ir(L), m is 1 or 2, R, R, R, R, and Rare each independently selected from hydrogen, deuterium, C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, and, Ris selected from C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof.

A composition including a first compound capable of functioning as a phosphorescent emitter in an OLED is provided. The first compound has at least one aromatic ring and at least one substituent R directly bonded to one of the at least one aromatic rings. Each substituent R has the formula of where (a) Gis selected from NR, SiRR, GeRR, alkyl, cycloalkyl, and combinations thereof; and Gis a non-aromatic polycyclic group; (b) Gis a direct bond; and Gis a non-aromatic spiro polycyclic group; or (c) Gis selected from direct bond, NR, SiRR, GeRR, alkyl, cycloalkyl, and combinations thereof; Gis a non-aromatic polycyclic group; and R is directly bonded to a phenyl, pyridine, or triazine. R, R, and Rare a variety of substituents. Formulations and devices, such as an OLEDs, that include the first compound are also described.

A compound having a formula: Formula I useful as emitters in OLEDs is disclosed.

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Ewing, NJ, United States of America

Mingjuan Su