Terpene-Substituted Small Molecules for OLED Solution Processing

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Solution Overview

Problem

Current methods for producing organic light-emitting diodes (OLEDs) are complex and costly, especially for high-molecular-weight compounds, and there is a need for compounds that can be processed from solution with improved solubility and efficiency.

Innovation Solution

Development of small molecules with terpene groups that enhance solubility and orientation, allowing for efficient solution processing and improved performance in OLEDs as fluorescent or phosphorescent emitting compounds, hosts, or host materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If vacuum deposition methods are used to produce OLEDs, then good device performance is achieved, but the process becomes complex and costly

Engineering Contradiction:
Improvedevice performanceVSAvoidprocess complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent changes the processing method from vacuum deposition to solution processing, fundamentally altering the manufacturing parameters. This allows small molecules with terpene groups to be processed from solution, simplifying the manufacturing process while maintaining device performance

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces the mechanical vacuum deposition system with a chemical solution processing approach. Instead of using vacuum chambers and deposition equipment, the invention uses solution-based methods to deposit organic compounds, thereby reducing equipment complexity and cost

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

2Device complexity

If small molecules are processed from solution, then manufacturing complexity is reduced, but solubility properties must be sufficient

Engineering Contradiction:
Improveprocessing complexityVSAvoidsolubility properties
Core Design Contradiction:
Device complexityVSReliability

Solution Approach 1:

The patent introduces terpene groups at specific positions on the small molecule structure. These local structural modifications (adding terpene substituents) provide the necessary solubility enhancement without compromising the overall molecular function and device performance

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent creates composite molecular structures by combining small molecule cores with terpene groups. This composite approach integrates the functional properties of small molecules with the solubility benefits of terpene structures, achieving both processability and performance

Inventive Principle:
Principle #40Composite materials

3Ease of manufacture

If terpene groups are added to small molecules, then solubility and orientation are improved, but molecular structure becomes more complex

Engineering Contradiction:
ImprovesolubilityVSAvoidmolecular structure
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent segments the molecular structure into distinct functional components: a small molecule core providing electronic function and terpene groups providing solubility and orientation. This segmentation allows each component to be optimized independently for its specific function

Inventive Principle:
Principle #1Segmentation

4Productivity

If conventional small molecules are used, then processing is simpler, but OLED efficiency is lower

Engineering Contradiction:
ImproveOLED efficiencyVSAvoidprocessing ease
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent incorporates terpene groups into the small molecule structure during synthesis, preliminarily establishing the solubility and orientation properties needed for efficient solution processing. This preliminary structural design enables subsequent easy processing while achieving high device efficiency

Inventive Principle:
Principle #10Preliminary action

Data Source

PatentUS11737352B2Materials for organic electroluminescent devices
Publication Date: 2023.08.22 MERCK PATENT GMBH
  • US11737352B2 patent drawing
  • US11737352B2 patent drawing
  • US11737352B2 patent drawing

AI summary

The present invention relates to compounds of the formulae (1) to (4), which are suitable for use in electronic devices, in particular organic electroluminescent devices, to intermediate compounds for the compounds or formulae (1) to (4) and to electronic devices, which comprise the compounds of formulae (1) to (4).