Condensed cyclic compound and organic light-emitting device including the same
Inventors
KIM, Sangmo • Kim, HyunJung • JEON, Soonok • CHUNG, Yeonsook • CHAE, Miyoung • HUH, Dalho • Kwon, Eunsuk • Kim, Jongsoo • SIM, Myungsun
Assignees
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Publication Number
US-12225817-B2
Publication Date
2025-02-11
Expiration Date
Abstract
A condensed cyclic compound represented by Formula 1: Ar1-L1-L2-Ar2 Formula 1 wherein Ar1, Ar2, L1, and L2 are the same as described in the specification.
Core Innovation
The document describes an organic light-emitting device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and comprising an emission layer. The emission layer comprises a host and a dopant, and the host comprises one or more condensed cyclic compounds represented by Formula 1, with Ar1 represented by Formula 2, Ar2 represented by Formula 3, CY1 selected from a fluorene group, a carbazole group, or a dibenzofuran group, and CY2 and CY3 each a benzene group.
The condensed cyclic compound further defines L1 and L2 by Formula 4 and Formula 5 relationships, including alternatives in which L1 and L2 are each independently a group represented by Formula 4. The structure also includes CY4 and CY5 selected from C5-C30 carbocyclic groups, and R1 to R4, R10, R20, R30, R40, and R50 selected from hydrogen, deuterium, a cyano group, and substituted or unsubstituted alkyl, alkenyl, alkynyl, and alkoxy groups, together with monovalent non-aromatic condensed polycyclic and heteropolycyclic groups and the group forms −Si(Q1)(Q2)(Q3), −N(Q4)(Q5), and −B(Q6)(Q7).
The disclosure associates the claimed structure with improved charge transfer characteristics, improved triplet energy, and favorable HOMO/LUMO and T1 energy characteristics, and describes improved device performance linked to frontier-orbital separation into moieties rather than localized HOMO/LUMO on similar-structured moieties. It also places the condensed cyclic compound in OLED emission-layer contexts and references delayed fluorescence embodiments, phosphorescent dopants, and evaluation examples comparing Compound 86 with hosts used in Examples 1 to 9 and a comparative compound.
Claims Coverage
The claim set includes two independent claims. Across these claims, the core inventive features are an organic light-emitting device in which the emission layer host comprises a specifically defined condensed cyclic compound represented by Formula 1, and the condensed cyclic compound of Formula 1 itself, defined by detailed structural selection constraints.
Organic light-emitting device with condensed cyclic host scaffold
An organic light-emitting device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and comprising an emission layer; wherein the emission layer comprises a host and a dopant, and wherein the host comprises one or more condensed cyclic compounds represented by Formula 1 with Ar1 represented by Formula 2, Ar2 represented by Formula 3, CY1 selected from a fluorene group, a carbazole group, or a dibenzofuran group, CY2 and CY3 each a benzene group, and L1 and L2 defined by Formula 4 and Formula 5 relationships.
Condensed cyclic compound represented by Formula 1
A condensed cyclic compound represented by Formula 1, with Ar1 represented by Formula 2, Ar2 represented by Formula 3, CY1 selected from a fluorene group, a carbazole group, or a dibenzofuran group, CY2 and CY3 each a benzene group, L1 and L2 defined by Formula 4 and Formula 5 relationships, and the recited substituent options, binding-site definitions, CY4 and CY5 selections, and group forms −Si(Q1)(Q2)(Q3), −N(Q4)(Q5), and −B(Q6)(Q7).
Overall, the claims focus on using a specific Formula 1-defined condensed cyclic scaffold as a host component in an emission layer, and separately on the scaffold itself under the same Formula 1 structural constraints.
Stated Advantages
Improved device performance associated with improved frontier-orbital separation into moieties rather than poor charge transfer and low electroluminescent efficiency.
Improved triplet energy and charge-transfer characteristics.
Improved or comparable device performance metrics are reported for examples versus Comparative Example 1, including driving voltage, luminous efficiency, power efficiency, quantum luminance efficiency, and T95 lifespan.
Improved hole transport and thermal stability.
Lower driving voltage.
Higher power efficiency, luminous efficiency, and quantum efficiency.
Longer lifespan.
Documented Applications
Use of the condensed cyclic compound as a host or dopant in an emission layer of an organic light-emitting device.
Use of the condensed cyclic compound in a hole transport region and/or an electron blocking layer, including combinations with a hole injection layer, hole transport layer, hole blocking layer, electron transport layer, and electron injection layer.
Delayed fluorescence embodiments using the described host/dopant emission-layer architecture.
Organic light-emitting device fabrication using an emission layer with Compound 86 as host compared against hosts used in Examples 1 to 9 and a comparative compound.
Use of the Formula 1 condensed cyclic compound in OLED organic layers, including as an emission layer host or dopant.
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