Double-Bridged Aromatic Compounds for OLED Thermal Stability

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Solution Overview

Problem

Current organic electroluminescent devices face challenges such as the need for simplified production, improved lifespan, thermal stability, emission color reproducibility, and efficiency, particularly for blue-emitting compounds, due to the limitations of existing host and transport materials like AlQ3, which are thermally unstable and lead to inefficiencies and color shifts.

Innovation Solution

Development of double-bridged aromatic systems with specific bridging structures and functional groups that enhance thermal stability and efficiency, allowing for their use as host, transport, and emitting materials in organic electroluminescent devices, enabling longer service life and improved performance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If conventional host materials and electron transport compounds (e.g., AlQ3) are used in OLEDs, then device production is possible, but thermal stability is insufficient leading to decomposition during sublimation and deposition

Engineering Contradiction:
Improvethermal stabilityVSAvoidsublimation and deposition process
Core Design Contradiction:
Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The patent modifies the molecular structure of host materials and electron transport compounds by introducing specific aromatic systems (triphenylene, triptycene, hexahydropyridine) and functional groups, which fundamentally changes their thermal properties. These structural parameter changes enable the materials to withstand sublimation temperatures without decomposition, directly resolving the thermal stability issue while maintaining manufacturability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining multiple aromatic systems and functional groups within single molecules. For example, electron transport compounds integrate triphenylene cores with specific substituent patterns, creating composite structures that achieve both thermal stability and electrical functionality, thereby solving the contradiction between stability and ease of manufacture

Inventive Principle:
Principle #40Composite materials

2Loss of energy

If AlQ3 is used as electron transport compound, then electron transport function is provided, but strong hygroscopy and low electron mobility lead to higher voltages and lower power efficiency

Engineering Contradiction:
Improvepower efficiencyVSAvoidelectron transport performance
Core Design Contradiction:
Loss of energyVSReliability

Solution Approach 1:

The patent systematically varies molecular parameters of electron transport compounds, including core structure (triphenylene vs. triptycene), substituent types, and molecular geometry, to optimize electron mobility. These parameter changes achieve higher electron mobility while reducing hygroscopy, thereby improving power efficiency without sacrificing electron transport reliability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates multiple analogues of electron transport compounds with systematically modified structures. By copying the basic functional motif (electron-transporting aromatic core) and varying substituents, the patent identifies structures with superior electron mobility and reduced hygroscopy, resolving the contradiction between energy loss and reliability

Inventive Principle:
Principle #26Copying

3Illumination intensity

If AlQ3 is used in blue OLEDs, then electron transport is achieved, but inherent yellow color causes color shifts due to reabsorption and weak re-emission

Engineering Contradiction:
Improveemission color purityVSAvoidefficiency
Core Design Contradiction:
Illumination intensityVSLoss of energy

Solution Approach 1:

The patent modifies the optical parameters of electron transport compounds by changing their molecular structures to have blue-shifted absorption spectra. The new compounds (with triphenylene, triptycene cores) exhibit absorption edges in the blue region rather than yellow, eliminating reabsorption losses and improving both color purity and efficiency simultaneously

Inventive Principle:
Principle #35Parameter changes

4Illumination intensity

If arylvinylamines are used as blue-emitting compounds, then deep blue emission is achieved, but thermal instability prevents evaporation without decomposition

Engineering Contradiction:
Improveemission colorVSAvoidthermal stability
Core Design Contradiction:
Illumination intensityVSStability of the object's composition

Solution Approach 1:

The patent creates composite emitting molecules by combining stable aromatic frameworks (triphenylene, triptycene, hexahydropyridine) with light-emitting functional groups. This composite structure provides both the thermal stability needed for vacuum deposition and the deep blue emission properties, resolving the contradiction between color performance and thermal stability

Inventive Principle:
Principle #40Composite materials

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 double-bridged aromatic systems provide enhanced thermal stability, improved efficiency, and reproducible results, allowing for the production of high-quality organic electroluminescent devices with longer service life and deeper blue emission without decomposition during sublimation, addressing the limitations of previous materials.

Implementation Method 1

The functional materials known in the art carry flexible units, such as olefinic double bonds, which increase the number of rotational degrees of freedom and thus increase the Stokes shift. In addition, the rigid building blocks in the compounds according to the invention ensure high thermal stability and a high glass transition temperature and can therefore be sublimated without decomposition.

Methodology Applied
Scientific EffectSublimation: Sublimation

Data Source

PatentEP2340290B1Novel materials for organic electroluminescence devices
Publication Date: 2015.11.25 MERCK PATENT GMBH
  • EP2340290B1 patent drawing
  • EP2340290B1 patent drawing
  • EP2340290B1 patent drawing

AI summary

The present invention relates to condensed aromatic compounds having multiple ring bridging according to the general formulas (1), (2), (3), (4) and (5). The invention also relates to the use of the compounds according to the invention in an organic electronic device and to a method for producing the compounds according to the invention. The invention also relates to an electronic device comprising the compounds according to the invention.