Spiro OLED Materials for Thermal Stability and Low-Voltage Operation

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Solution Overview

Problem

Existing organic electroluminescent devices (OLEDs) face challenges in efficiency, lifetime, and operating voltage, particularly in hole-transport materials and phosphorescent OLEDs, with a need for improved thermal stability, low crystallinity, and high glass transition temperature.

Innovation Solution

Development of compounds with a rigid planar Spiro unit and flexible structure elements, enhancing thermal stability and solubility, suitable for use as hole-transport materials or matrix materials in OLEDs, facilitating easier handling and sublimation without decomposition.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional hole-transport materials are used in OLEDs, then the device structure is simpler, but the efficiency, lifetime, and operating voltage performance deteriorate

Engineering Contradiction:
Improvedevice efficiencyVSAvoidmolecular structure complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent employs composite molecular structures combining spirobifluorene or benzospirobifluorene cores with triarylamino groups and carbazole groups. This composite approach integrates the rigid spiro unit for thermal stability with electron-rich amine groups for hole transport capability, achieving both high device efficiency and functional performance through material composition rather than simple molecular modifications

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention introduces specific functional groups at strategic positions on the spirobifluorene core. The triarylamino groups and carbazole groups are localized at positions that optimize both hole transport and thermal stability, allowing different regions of the molecule to perform specialized functions - the spiro core provides structural rigidity while the peripheral groups enable charge transport

Inventive Principle:
Principle #3Local quality

2Duration of action of stationary object

If compounds with high thermal stability are used, then OLED lifetime is improved, but processing difficulty increases due to high sublimation temperature requirements

Engineering Contradiction:
ImproveOLED lifetimeVSAvoidprocessing ease
Core Design Contradiction:
Duration of action of stationary objectVSEase of manufacture

Solution Approach 1:

The patent modifies molecular parameters by introducing flexible substituents and adjusting the spiro core structure to achieve optimal glass transition temperatures and thermal stability. These parameter changes enable the materials to maintain structural integrity at high temperatures while remaining processable through vacuum evaporation, balancing lifetime requirements with manufacturing feasibility

Inventive Principle:
Principle #35Parameter changes

3Stability of the object's composition

If rigid planar spiro units are used, then thermal stability is improved, but solubility deteriorates

Engineering Contradiction:
Improvethermal stabilityVSAvoidsolubility
Core Design Contradiction:
Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The patent introduces flexible substituents and electron-rich groups at specific positions on the rigid spirobifluorene core. This local modification strategy maintains the structural rigidity and thermal stability of the spiro unit while the peripheral flexible groups enhance solubility and processability, allowing the material to exhibit both high thermal stability and good solution properties

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The invention creates composite structures where the rigid spirobifluorene core is combined with flexible triarylamino and carbazole groups. This composite material approach allows the rigid core to provide thermal stability while the flexible peripheral groups contribute to solubility, achieving a balance between stability and processability through material composition

Inventive Principle:
Principle #40Composite materials

4Use of energy by moving object

If conventional materials are used, then operating voltage is higher, but energy efficiency deteriorates

Engineering Contradiction:
Improveenergy efficiencyVSAvoidoperating voltage
Core Design Contradiction:
Use of energy by moving objectVSPower

Solution Approach 1:

The patent modifies electronic parameters by introducing electron-rich triarylamino groups and carbazole groups on the spirobifluorene core. These modifications change the HOMO-LUMO energy levels and improve hole transport efficiency, resulting in reduced operating voltage and enhanced energy efficiency through optimized electronic structure rather than increased power input

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

The compounds improve the lifetime and efficiency of OLEDs, reducing operating voltage and enabling easier processing through vacuum evaporation.

Implementation Method 1

The compounds of the present invention generally have high thermal stability and can therefore be sublimed without decomposition and without a residue

Methodology Applied
Scientific EffectSublimation: Sublimation

Implementation Method 2

The emitting materials employed here are increasingly organometallic complexes which exhibit phosphorescence instead of fluorescence

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 3

The emitting materials employed here are increasingly organometallic complexes which exhibit phosphorescence instead of fluorescence

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Data Source

PatentUS12486230B2Materials for organic electroluminescent devices
Publication Date: 2025.12.02 MERCK PATENT GMBH
  • US12486230B2 patent drawing
  • US12486230B2 patent drawing
  • US12486230B2 patent drawing

AI summary

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