Amine-Functionalized Polyfluorenes for OLED Efficiency

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Solution Overview

Problem

Current organic light-emitting devices (OLEDs) face limitations in light emission efficiency and color control due to the rapid non-radiative relaxation of triplet excited states, which hinders their performance and lifetime.

Innovation Solution

The development of polyfluorenes through imine condensation reactions with iridium (III) compounds and triarylamines, followed by reduction, to create amine-functionalized polymers that enhance emissive and transport properties, allowing for improved light emission efficiency and color control.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If phosphorescent materials are used to improve light emission efficiency through electrophosphorescence, then quantum efficiency is substantially increased, but triplet excited states rapidly undergo non-radiative relaxation to the ground state, limiting device lifetime and stability

Engineering Contradiction:
Improvequantum efficiencyVSAvoiddevice lifetime
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The patent introduces an iridium complex as an intermediary substance that mediates the phosphorescence process. The iridium complex accepts energy from the polyfluorene polymer and converts it to phosphorescent emission, allowing the polymer to benefit from phosphorescence without directly relying on its own triplet states which are prone to non-radiative relaxation. This intermediary approach resolves the contradiction by using the iridium complex's stable phosphorescent properties while maintaining the polymer's structural advantages.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent creates a composite material system combining polyfluorene polymer with iridium complexes. This composite approach allows the integration of the polymer's favorable properties (processability, stability) with the iridium complex's efficient phosphorescence. The composite structure enables energy transfer from the polymer to the iridium complex, achieving both high quantum efficiency through phosphorescence and improved device lifetime by avoiding direct reliance on the polymer's unstable triplet states.

Inventive Principle:
Principle #40Composite materials

2Device complexity

If conventional electroluminescent materials are used, then device structure is simpler, but light emission efficiency is limited due to rapid non-radiative relaxation of triplet excited states

Engineering Contradiction:
Improvematerial structureVSAvoidlight emission efficiency
Core Design Contradiction:
Device complexityVSUse of energy by moving object

Solution Approach 1:

The iridium complex serves as an intermediary that enables efficient light emission while maintaining relatively simple device structure. By incorporating the iridium complex into the polyfluorene system, the patent achieves phosphorescent emission without requiring complex multi-layer structures. The intermediary iridium complex handles the phosphorescence function, allowing the overall device structure to remain relatively simple while dramatically improving light emission efficiency.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Loss of energy

If phosphorescent materials are incorporated to achieve higher efficiency, then energy loss to radiationless decay is reduced, but control of color and efficiency requires more sophisticated material design

Engineering Contradiction:
Improveenergy loss to radiationless decayVSAvoidmaterial design sophistication
Core Design Contradiction:
Loss of energyVSDevice complexity

Solution Approach 1:

The patent utilizes parameter changes in the polyfluorene polymer structure to control the properties of the composite material. By modifying the polymer's chemical structure, molecular weight, and composition, the patent can tune the energy transfer characteristics, emission color, and efficiency of the iridium complex-containing system. This approach allows control over color and efficiency through relatively simple polymer parameter adjustments rather than complex material design, reducing the sophistication required while maintaining energy efficiency.

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

This approach results in polyfluorenes with increased light emission efficiency and extended device lifetime by attenuating emissive and transport properties, potentially leading to more efficient OLEDs with better temperature control.

Implementation Method 1

The development of polyfluorenes through imine condensation reactions with iridium (III) compounds and triarylamines, followed by reduction

Methodology Applied
Scientific EffectImine condensation: Chemical Bonding

Implementation Method 2

imine condensation reactions with iridium (III) compounds and triarylamines, followed by reduction

Methodology Applied
Scientific EffectReduction: Reduction

Implementation Method 3

Organic light emitting devices (OLEDs), which make use of thin film organic materials that emit light when subjected to a voltage bias

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Implementation Method 4

OLEDs capable of producing light by an alternate mechanism, electrophosphorescence, i.e. light emission from a triplet excited state formed by applying a voltage bias across a ground state electrofluorescecent material

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Data Source

PatentEP2373759B1Functionalized polyfluorenes for use in optoelectronic devices
Publication Date: 2015.11.11 GENERAL ELECTRIC CO
  • EP2373759B1 patent drawingFigure 1
  • EP2373759B1 patent drawing
  • EP2373759B1 patent drawing

AI summary

The present invention relates to process comprising reacting a polyfluorenes comprising at least one structural group of formula I with an iridium (III) compound of formula II wherein, R1 and R2 are independently alkyl, substituted alkyl, aryl, substituted aryl or a combination thereof; R5 is H or CHO; R3 and R4 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl or a combination thereof; R11 and R12 taken together form a substituted or unsubstituted monocyclic or bicyclic heteroaromatic ring; R13 is independently at each occurrence halo, nitro, hydroxy, amino, alkyl, aryl, arylalkyl, alkoxy, substituted alkoxy, substituted alkyl, substituted aryl, or substituted arylalkyl; Ar is aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a combination thereof; X is selected from a direct bond, alky, substituted alkyl, and combinations thereof; Y is CHO or NH2; Z is CHO or NH2 where Z does not equal Y; and p is O, 1 or 2. The invention also relates to the polyfluorenes, which are products of the reaction, and the use of the polyfluorenes in optoelectronic devices.