Ortho-Aryl Pyrene Compounds for OLED Blue Emission

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Solution Overview

Problem

Current organic light-emitting diode (OLED) technologies face challenges in achieving high efficiency blue emissions due to π-stacking in pyrene molecules, which leads to reduced photoluminescence and electroluminescent efficiency, and increased evaporation temperatures, making them less suitable for use as fluorescent blue emitters.

Innovation Solution

The development of pyrene compounds with specific substitutions, including at least two substitutions with an amine group having a six-membered aryl ring in the ortho position and an organic linker between the pyrene and amino group, which induces steric bulkiness and twisting of aryl rings, reducing π-stacking and enhancing photoluminescence and electroluminescent efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If pyrene molecules are used as fluorescent blue emitters in OLEDs, then blue emission is achieved, but photoluminescence and electroluminescent efficiency are reduced due to π-stacking

Engineering Contradiction:
Improvephotoluminescence efficiencyVSAvoidelectroluminescent efficiency
Core Design Contradiction:
Ease of manufactureVSLoss of energy

Solution Approach 1:

The pyrene molecule is segmented by introducing substitution groups at specific positions (at least two substitutions including amine group with six-membered aryl ring in ortho position). This segmentation disrupts the π-stacking interaction between pyrene molecules while maintaining the core pyrene emission properties, thereby improving photoluminescence efficiency without sacrificing electroluminescent efficiency

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

An organic linker is introduced as an intermediary between the pyrene core and the amino group. This linker acts as a spacer that prevents direct π-stacking between pyrene molecules while maintaining the electronic coupling necessary for efficient energy transfer, thus resolving the efficiency loss caused by π-stacking

Inventive Principle:
Principle #24Intermediary (Mediator)

2Ease of manufacture

If pyrene molecules are used as fluorescent blue emitters in OLEDs, then blue emission is achieved, but evaporation temperatures are increased

Engineering Contradiction:
Improvedeposition processabilityVSAvoidevaporation temperature
Core Design Contradiction:
Ease of manufactureVSTemperature

Solution Approach 1:

The pyrene molecule is segmented by introducing substitution groups at specific positions (at least two substitutions including amine group with six-membered aryl ring in ortho position). This segmentation disrupts the π-stacking interaction between pyrene molecules while maintaining the core pyrene emission properties, thereby improving photoluminescence efficiency without sacrificing electroluminescent efficiency

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The molecular structure parameters are changed by introducing specific substitution groups (amine group with six-membered aryl ring in ortho position connected via organic linker). These parameter changes reduce the molecular planarity and intermolecular interactions, thereby lowering the evaporation temperature and improving deposition processability

Inventive Principle:
Principle #35Parameter changes

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

These pyrene compounds exhibit high efficiency blue emissions with increased photoluminescence quantum yield and reduced evaporation temperatures, making them particularly suitable for use in OLED devices as fluorescent emitters.

Implementation Method 1

These pyrene compounds exhibit high efficiency blue emissions with increased photoluminescence quantum yield

Methodology Applied
Scientific EffectPhotoluminescence: Photoluminescence

Implementation Method 2

OLEDs make use of thin organic films that emit light when voltage is applied across the device

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS9293712B2Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same
Publication Date: 2016.03.22 UNIVERSAL DISPLAY CORP
  • US9293712B2 patent drawing
  • US9293712B2 patent drawing
  • US9293712B2 patent drawing

AI summary

Compounds according to Formula 1, devices containing the same and formulations containing the same are described. Formula 1 has the following structure:where at least two of R1—R10 are not H,where at least one of R1—R10 has the formula T1where L is an organic linker,where Y1 to Y4 are CR or N,where adjacent R moieties can form fused rings,where Rs and Rt are independently aryl or heteroaryl, either of which may independently be further substituted, andwhere Rs and Rt do not form fused rings with any part of the molecule.