Fluorene Spirobifluorene Matrix for OLED Lifetime and Voltage

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current organic electroluminescent devices face limitations in lifetime, efficiency, and operating voltage, particularly with matrix materials for phosphorescent emitters, which also require high thermal stability and compatibility with ketoketonate ligands.

Innovation Solution

The use of fluorene and spirobifluorene derivatives substituted with triazine or other electron-deficient nitrogen heterocycles as matrix materials in organic electroluminescent devices, which enhance efficiency, lifetime, and reduce operating voltage, even when used with phosphorescent emitters containing ketoketonate ligands.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of stationary object

If conventional matrix materials like carbazole derivatives are used, then the device structure is simple and ease of manufacture is good, but the lifetime and glass-transition temperature are insufficient

Engineering Contradiction:
ImprovelifetimeVSAvoidmaterial structure complexity
Core Design Contradiction:
Duration of action of stationary objectVSDevice complexity

Solution Approach 1:

The patent employs composite matrix materials combining carbazole derivatives with fluorene and spirobifluorene derivatives. This composite approach leverages the beneficial properties of both material types: carbazole provides good hole transport and structural simplicity, while fluorene/spirobifluorene components enhance thermal stability and glass-transition temperature, thereby extending device lifetime without excessive complexity increase

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent modifies molecular parameters of matrix materials by introducing specific substituents and core structures (fluorene, spirobifluorene) to carbazole derivatives. These parameter changes in molecular weight, rigidity, and thermal stability directly improve the glass-transition temperature and lifetime while maintaining compatibility with existing device fabrication processes

Inventive Principle:
Principle #35Parameter changes

2Productivity

If ketones are used as matrix materials, then low operating voltage and long lifetime are achieved, but efficiency and compatibility with ketoketonate ligands are insufficient

Engineering Contradiction:
ImproveefficiencyVSAvoidcompatibility with ketoketonate ligands
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent introduces fluorene and spirobifluorene derivatives as intermediary matrix materials that mediate between the electrical excitation and the phosphorescent emitters containing ketoketonate ligands. These intermediaries provide optimal energy transfer pathways while maintaining chemical compatibility with the sensitive ketoketonate ligands, thereby simultaneously improving efficiency and reliability

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent applies local quality optimization by designing matrix materials with specific functional regions: the fluorene/spirobifluorene core provides rigid structural support and appropriate HOMO-LUMO levels for efficient energy transfer, while peripheral substituents ensure chemical compatibility with ketoketonate ligands. This localized functional differentiation achieves both high efficiency and reliable compatibility

Inventive Principle:
Principle #3Local quality

3Stability of the object's composition

If metal complexes like BAlq are used as matrix materials, then chemical stability is improved, but operating voltage increases and handling difficulty increases due to hydrolysis sensitivity

Engineering Contradiction:
Improvechemical stabilityVSAvoidhandling ease
Core Design Contradiction:
Stability of the object's compositionVSEase of operation

Solution Approach 1:

The patent replaces sensitive metal complex matrix materials with purely organic fluorene and spirobifluorene derivatives that, while having different stability characteristics, eliminate the handling difficulties associated with hydrolysis-sensitive metal complexes. The organic nature of these materials makes them inherently more stable toward moisture and easier to handle, even if their absolute chemical stability differs from metal complexes

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

Solution Approach 2:

The patent substitutes metal-based matrix materials with purely organic alternatives, replacing the metal-ligand coordination system with organic π-conjugated systems. This substitution eliminates the hydrolysis sensitivity inherent in metal complexes while maintaining the necessary electronic and optical properties for phosphorescent emitter support, thereby improving ease of operation

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

4Use of energy by stationary object

If phosphine oxides and sulfones are used as matrix materials, then operating voltage is reduced, but efficiency and compatibility with ketoketonate ligands are insufficient

Engineering Contradiction:
Improveoperating voltageVSAvoidefficiency
Core Design Contradiction:
Use of energy by stationary objectVSProductivity

Solution Approach 1:

The patent designs fluorene and spirobifluorene derivative matrix materials with multi-functional capabilities: they provide appropriate energy levels for low operating voltage operation, maintain chemical compatibility with ketoketonate ligands, and enable efficient energy transfer to phosphorescent emitters. This universal functionality across multiple performance dimensions achieves low operating voltage without sacrificing efficiency

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

These materials result in organic electroluminescent devices with high efficiency, long lifetimes, and low operating voltages, overcoming previous limitations and improving performance across various parameters.

Implementation Method 1

phosphorescent organic electroluminescent devices which comprise fluorene and spirobifluorene derivatives as matrix materials

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 2

simultaneously have high efficiencies, long lifetimes and low operating voltages, including with phosphorescent emitters which contain ketoketonate ligands

Methodology Applied
Scientific EffectEnergy transfer:

Implementation Method 3

organic electroluminescent device comprising, in at least one emitting layer, (A) at least one phosphorescent compound and (B) at least one compound of the formula (1) or formula (2)

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS8951647B2Organic electroluminescence device
Publication Date: 2015.02.10 MERCK PATENT GMBH
  • US8951647B2 patent drawing
  • US8951647B2 patent drawing
  • US8951647B2 patent drawing

AI summary

The present invention relates to organic electroluminescent devices which comprise fluorene derivatives and spirobifluorene derivatives as matrix material for phosphorescent emitters.