Pyrimidinyl Derivatives for OLED Efficiency and Stability

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Solution Overview

Problem

Existing optoelectronic devices, such as OLEDs, face challenges in achieving high efficiency and stability due to the limitations of metal complexes used in organic electroluminescent materials, particularly in emitting light in the blue, sky-blue, or green spectral range with sufficient photoluminescence quantum yields and thermally activated delayed fluorescence.

Innovation Solution

Development of purely organic molecules with specific chemical structures, comprising a first and second chemical moiety linked via a single bond, exhibiting emission maxima between 420 nm and 520 nm, and possessing thermally activated delayed fluorescence (TADF) properties, which are used in optoelectronic devices to enhance efficiency and stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If metal complexes are used as emitter materials in OLEDs, then device efficiency can be improved, but device stability deteriorates

Engineering Contradiction:
Improvedevice efficiencyVSAvoiddevice stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent replaces stable but inefficient metal complexes with purely organic molecules that have shorter lifetimes but higher efficiency. The organic emitters achieve better device efficiency while maintaining acceptable stability through molecular design optimization, effectively trading material longevity for performance improvement.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent systematically modifies molecular parameters including substituent groups (electron-donating and electron-withdrawing groups), molecular weight, and structural configuration to optimize the balance between efficiency and stability. By adjusting these parameters, the organic emitters achieve high photoluminescence quantum yields while maintaining sufficient device operational stability.

Inventive Principle:
Principle #35Parameter changes

2Illumination intensity

If organic molecules are designed for blue-green emission, then emission wavelength is improved, but photoluminescence quantum yield deteriorates

Engineering Contradiction:
Improveemission wavelengthVSAvoidphotoluminescence quantum yield
Core Design Contradiction:
Illumination intensityVSLoss of energy

Solution Approach 1:

The patent introduces different substituent groups at specific positions on the pyrimidine core structure. Electron-donating groups (such as dialkylamino groups) are placed at positions that enhance electron injection and energy transfer, while electron-withdrawing groups (such as cyano and trifluoromethyl groups) are positioned to optimize energy level alignment. This localized functional differentiation enables blue-green emission with improved quantum yields.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent creates composite molecular structures by combining the pyrimidine core with various aromatic hydrocarbon groups and heterocyclic substituents. These composite structures leverage the complementary properties of different molecular fragments to achieve both the desired emission wavelength and improved photoluminescence quantum yield through synergistic effects.

Inventive Principle:
Principle #40Composite materials

3Illumination intensity

If molecular structure complexity is increased to improve emission properties, then emission characteristics are improved, but manufacturing complexity deteriorates

Engineering Contradiction:
Improveemission characteristicsVSAvoidmanufacturing complexity
Core Design Contradiction:
Illumination intensityVSEase of manufacture

Solution Approach 1:

The patent divides the emitter molecule into modular components: a pyrimidine core structure and separate substituent groups. This segmentation allows independent optimization of each component's properties and simplifies the synthesis process, as the core structure can be prepared once and then functionalized with different substituents to achieve various emission characteristics without redesigning the entire molecule.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent develops a universal pyrimidine core structure that can serve as a platform for multiple emitter variants. By maintaining the same core and only modifying the substituent groups, the patent achieves multi-functionality where a single core structure can produce emitters with different emission wavelengths, quantum yields, and other properties, thereby reducing overall manufacturing complexity.

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 organic molecules achieve higher efficiency and stability in OLEDs with improved photoluminescence quantum yields and emission characteristics, maintaining comparable color performance to traditional emitter materials.

Implementation Method 1

The organic molecules exhibit in particular thermally activated delayed fluorescence (TADF). The photoluminescence quantum yields of the organic molecules according to the invention are, in particular, 35 % or more.

Methodology Applied
Scientific EffectThermally activated delayed fluorescence (TADF): Photoluminescence

Data Source

PatentEP3398945B1Pyrimidinyl derivatives and their use in optoelectronic devices
Publication Date: 2022.11.02 SAMSUNG DISPLAY CO LTD
  • EP3398945B1 patent drawingFigure 1~2
  • EP3398945B1 patent drawingFigure 3~4
  • EP3398945B1 patent drawingFigure 5~6

AI summary

Summary The invention relates to an organic molecule, in particular for the application in organic optoelectronic devices. According to the invention, the organic molecule consists of - a first chemical moiety consisting of a structure of Formula I, and - one second chemical moiety consisting of a structure of Formula II, wherein the first chemical moiety is linked to the second chemical moiety via a single bond; wherein T and W are independently from another the binding site of a single bond linking the first chemical moiety to the second chemical moiety or is selected from the group consisting of R2, CN and CF3; X, Y are independently from another selected from the group consisting of R2, CN and CF3; V is hydrogen or the binding site of a single bond linking the first chemical moiety to the second chemical moiety; wherein one substituent selected from the group consisting of T, W, X, and Y is CN or CF3, and one substituent selected from the group consisting of T, V and W represents the binding site of a single bond linking the first chemical moiety and the second chemical moiety.