Polycyclic Aromatic Hydrocarbon Derivatives with Cycloalkane Moieties
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Solution Overview
Problem
Current organic light emitting devices face challenges in achieving high efficiency, stability, and low voltage operation due to intermolecular interactions in their multilayer structures, particularly with polycyclic aromatic hydrocarbon derivatives like anthracene, naphthalene, pyrene, and rubrene.
Innovation Solution
A new organic compound is developed where at least one cycloalkane or polycycloalkane is directly linked to a polycyclic aromatic hydrocarbon as a core or substituent, reducing intermolecular interactions through steric protection and enhancing hyperconjugative effects, thereby improving light-emitting efficiency, color purity, and thermal stability.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If polycyclic aromatic hydrocarbon derivatives are used in organic light emitting devices, then light emission function is achieved, but intermolecular interactions cause reduced efficiency and stability
Solution Approach 1:
The patent introduces bulky cycloalkane or polycycloalkane groups at specific positions (9,10-positions) of the anthracene core to create localized steric protection. This local structural modification prevents intermolecular interactions at critical sites while preserving the overall light-emitting functionality of the polycyclic aromatic hydrocarbon derivative.
Solution Approach 2:
The patent creates composite molecular structures by combining polycyclic aromatic hydrocarbon cores (anthracene, naphthalene, pyrene, rubrene) with cycloalkane or polycycloalkane groups. This composite approach integrates the desirable light-emitting properties of PAHs with the steric protection and thermal stability of cycloalkane moieties, resolving the contradiction between efficiency and stability.
2Productivity
If conventional organic layer materials are used, then device structure is simple, but efficiency and stability are insufficient
Solution Approach 1:
The patent modifies molecular parameters by changing the core structure from conventional materials to polycyclic aromatic hydrocarbon derivatives with cycloalkane/polycycloalkane groups. This parameter change enhances efficiency and stability while maintaining reasonable structural complexity through systematic molecular design.
3Duration of action of stationary object
If standard operating voltage is applied, then device operates normally, but energy consumption is high and lifespan is limited
Solution Approach 1:
The bulky cycloalkane or polycycloalkane groups create localized steric protection that stabilizes cation radicals at critical positions, preventing degradation pathways. This local stabilization reduces energy loss through degradation reactions and extends device lifespan while enabling lower operating voltages.
Solution Approach 2:
The patent converts the potential harm of intermolecular interactions into benefit by using the bulky groups to direct interactions toward desirable pathways while blocking harmful ones. The steric protection transforms what would be degradation-prone regions into stabilized zones, reducing energy consumption and extending lifespan.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The compound effectively reduces intermolecular interactions, leading to enhanced light-emitting efficiency, high color purity, extended device lifespan, and the ability to operate at low voltage, while also stabilizing cation radicals and preventing crystallization-induced breakdown.
Implementation Method 1
can maximally decrease interaction between compounds by bulky cycloalkane or polycycloalkane moieties (steric protection)
Implementation Method 2
can further exhibit induction effect and hyperconjugative effect
Implementation Method 3
can further exhibit induction effect andhyperconjugative effect
Implementation Method 4
Since Pope, Kallman and Magnate have found electro-luminescence in anthracene single crystal in 1963
Implementation Method 5
holes and electrons injected are combined together to form excitons. Further, when the excitons drop to a ground state, lights are emitted
Data Source
AI summary
The present invention provides an organic light emitting device comprising a first electrode, at least one organic layer and a second electrode, laminated successively, in which at least one layer of the organic layer has a polycyclic aromatic hydrocarbon as a core and comprises at least one of a derivative in which a substituted or unsubstituted C2-30 cycloalkane, or a substituted or unsubstituted C5-50 polycycloalkane is directly fused to the core or fused to a substituent of the core; and a new organic compound usable in the organic light emitting device. Furthermore, the present invention provides a charge carrier extracting, injecting or transporting material which has a polycyclic aromatic hydrocarbon as a core and comprises a derivative in which a substituted or unsubstituted C2-30 cycloalkane, or a substituted or unsubstituted C5-50 polycycloalkane is directly fused to the core or fused to a substituent of the core.