Novel Fluorene Compound for Solution-Processed OLEDs

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Solution Overview

Problem

Existing methods for manufacturing organic light emitting devices using a deposition process face challenges such as significant material loss and difficulty in producing large area devices, prompting the need for alternative materials suitable for solution processes.

Innovation Solution

A novel compound represented by Chemical Formula 1 is introduced, which includes a fluorene group, a curable group, and a halogen group, providing excellent solubility in organic solvents and forming a deep HOMO energy level to enhance hole mobility. This compound is used in a coating composition for forming organic material layers in organic light emitting devices.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If a deposition process is used to manufacture organic light emitting devices, then manufacturing precision and device performance are improved, but material loss increases and large area device production becomes difficult

Engineering Contradiction:
Improvedevice performanceVSAvoidmaterial loss
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The patent replaces the deposition process (mechanical/physical vapor deposition) with a solution process involving coating compositions. The compound of Formula 1 is dissolved in solvents to form coating compositions that can be applied via solution-based methods, eliminating the material loss inherent in deposition processes while enabling large area fabrication.

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

Solution Approach 2:

The invention changes the physical and chemical parameters of the organic compound by introducing specific functional groups (curable groups Xz1 and Xz2, fluorene groups, and halogen groups) that enable the compound to be processed in solution form. This parameter change allows transition from deposition-based manufacturing to solution-based coating, resolving the contradiction between precision and material efficiency.

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If a deposition process is used to manufacture organic light emitting devices, then device performance is improved, but the ability to manufacture large area devices deteriorates

Engineering Contradiction:
Improvedevice performanceVSAvoiddevice area
Core Design Contradiction:
Manufacturing precisionVSArea of stationary object

Solution Approach 1:

The patent substitutes deposition processes with solution-based coating processes using the coating composition. Solution processes inherently enable large area fabrication through techniques like spin coating, dip coating, or inkjet printing, while the specific molecular structure of Compound 1 maintains the performance characteristics needed for functional devices.

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

Solution Approach 2:

The compound of Formula 1 is designed with multiple functional groups that provide both the electroluminescent functionality needed for device performance and the solubility characteristics needed for solution processing. This multi-functionality allows the same material to achieve both high performance and large area manufacturability.

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

3Area of stationary object

If conventional compounds are used in solution processes, then large area device production is enabled, but driving voltage and light emission efficiency deteriorate

Engineering Contradiction:
Improvedevice areaVSAvoiddriving voltage
Core Design Contradiction:
Area of stationary objectVSUse of energy by moving object

Solution Approach 1:

The patent optimizes the molecular parameters of the organic compound by incorporating fluorene groups (which provide deep HOMO energy levels for low driving voltage) and curable groups (which enable crosslinking for stable coating formation). These parameter changes allow solution processing for large area devices while maintaining low driving voltage and high efficiency.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The compound combines multiple functional moieties (fluorene groups, curable groups, halogen groups, and aromatic hydrocarbon groups) into a single molecular structure. This composite molecular design integrates the benefits of low driving voltage, solution processability, and crosslinking capability, achieving all requirements simultaneously.

Inventive Principle:
Principle #40Composite materials

4Area of stationary object

If conventional compounds are used in solution processes, then large area device production is enabled, but light emission efficiency and device lifetime deteriorate

Engineering Contradiction:
Improvedevice areaVSAvoiddevice lifetime
Core Design Contradiction:
Area of stationary objectVSReliability

Solution Approach 1:

The patent modifies the chemical structure parameters by introducing curable groups that enable crosslinking reactions. This crosslinking creates a stable, insoluble network that prevents material degradation and maintains device performance over time, thereby extending device lifetime while preserving solution processability for large area fabrication.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The curable groups enable a crosslinking reaction that creates a continuous, stable network structure within the organic material layer. This continuous crosslinked structure provides long-term stability and reliability, preventing material degradation during device operation while allowing initial solution-based processing.

Inventive Principle:
Principle #20Continuity of useful action

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 use of the novel compound in organic light emitting devices achieves low driving voltage, high light emission efficiency, and extended device lifetime, while enabling the manufacture of large area devices using a solution process.

Implementation Method 1

forming a deep HOMO energy level to enhance hole mobility

Methodology Applied
Scientific EffectCharge transport: Conduction (electrical)

Implementation Method 2

Xz1 and Xz2 are the same as or different from each other, and each independently a curable group

Methodology Applied
Scientific EffectCrosslinking: Chemical Bonding

Implementation Method 3

When an organic material layer is placed between an anode and a cathode and a current is applied between the two electrodes, electrons and holes are injected to the organic material layer from the cathode and the anode, respectively. The holes and the electrons injected to the organic material layer recombine to form excitons, and light emits when these excitons fall back to the ground state.

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentEP4186892B1Novel compound, coating composition comprising same, organic light-emitting device using same, and manufacturing method therefor
Publication Date: 2025.03.05 LG CHEM LTD
  • EP4186892B1 patent drawingFigure 1
  • EP4186892B1 patent drawing
  • EP4186892B1 patent drawing

AI summary

The present disclosure relates to a compound represented by Chemical Formula 1, a coating composition including the compound represented by Chemical Formula 1, an organic light emitting device using the same, and a method for manufacturing the same.