Cyano-Substituted Benzene Compounds for Delayed Fluorescence
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Solution Overview
Problem
Existing compounds with substituted amino groups and cyano groups, such as those described in PTL 1, are not verified for their usefulness as light-emitting materials beyond host material applications, and there is a need for compounds with excellent light emission characteristics for organic light-emitting devices.
Innovation Solution
Development of specific compounds with particular structures, represented by general formulas (1) and (1'), incorporating cyano groups and various substituents, which are used as light-emitting materials or delayed fluorescence emitters in organic light-emitting devices, enhancing light emission efficiency.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If compounds with substituted amino groups and cyano groups are used as host materials, then device structure and material properties are established, but their usefulness as light-emitting materials is not verified and light emission efficiency is insufficient
Solution Approach 1:
The patent modifies the molecular structure parameters of compounds by introducing specific substituents (carbazolyl groups, diphenylamino groups, cyano groups) at defined positions on the benzene ring. This structural parameter change transforms the compound's properties from suitable only as host materials to capable of functioning as light-emitting materials with high efficiency, thereby resolving the contradiction between reliability in light emission and adaptability of application
Solution Approach 2:
The patent develops compounds that can serve multiple functions: they can act as both host materials and light-emitting materials within the same organic light-emitting device. This multi-functionality increases the adaptability of the compounds while maintaining high light emission efficiency, as the same compound class can be applied in different functional roles
2Productivity
If conventional light-emitting materials are used, then device operation is achieved, but light emission efficiency and cost-effectiveness are insufficient
Solution Approach 1:
The patent employs compounds with relatively simple molecular structures that can be synthesized using conventional organic synthesis methods. These compounds achieve high light emission efficiency without requiring complex or expensive rare materials, making them cost-effective for manufacturing while maintaining high productivity in terms of light output
Solution Approach 2:
The patent creates composite functional compounds by combining electron-rich groups (carbazolyl, diphenylamino) with electron-deficient cyano groups on a benzene core. This composite structure enables the material to exhibit both good charge transport properties and high light emission efficiency, achieving high productivity while remaining cost-effective through conventional synthesis routes
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 identified compounds achieve high light emission efficiency and can be used inexpensively in organic light-emitting devices, emitting delayed fluorescent light, thereby improving the performance of these devices.
Implementation Method 1
U. Hoyer et al., Highly efficient organic light-emitting diodes from delayed fluorescence, Nature, Vol. 492, 13 December 2012, pages 234 to 238 report a novel pathway to attain the greatest possible electroluminescence efficiency from simple aromatic compounds that exhibit efficient thermally activated delayed fluorescence with high photoluminescence efficiency.
Data Source
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AI summary
A compound represented by the general formula (1) is useful as a light-emitting material. R1, R3, and R5 each represent a cyano group, or R1, R2, R4, and R5 each represent a cyano group; and the others of R1 to R6 each represent a group represented by any one of the following general formula (4), etc.