TADF Compounds with Aromatic Spacer Rings for OLEDs

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Solution Overview

Problem

Current OLED technologies face limitations due to the rarity, high cost, and toxicity of heavy metals used in second-generation phosphorescent emitters, and there is a need for improved compounds that can efficiently harness both singlet and triplet excitons for enhanced performance in display and lighting applications.

Innovation Solution

Development of Thermally Activated Delayed Fluorescence (TADF) compounds with specific aromatic spacer rings and heterocyclic moieties that segregate HOMO and LUMO, allowing efficient reverse intersystem crossing and radiative fluorescence, thereby overcoming the limitations of previous OLED generations.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If phosphorescent emitters with heavy metals are used, then both singlet and triplet excitons are harvested for emission, but the rarity, high cost and toxicity of these metals are important detracting features

Engineering Contradiction:
Improveexciton harvesting efficiencyVSAvoidrarity, cost and toxicity of heavy metals
Core Design Contradiction:
Use of energy by moving objectVSObject-affected harmful factors

Solution Approach 1:

The patent removes heavy metal elements from the emitter structure entirely, extracting the harmful component while preserving the desired functionality. The TADF mechanism achieves triplet exciton harvesting without requiring phosphorescent heavy metals, thus eliminating their rarity, cost and toxicity issues.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention replaces expensive, rare heavy metals with organic compounds based on common elements. The TADF emitters use readily available organic materials that are cheaper and less toxic, sacrificing the long-lived phosphorescent emission for shorter-lived but equally efficient TADF emission.

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

2Device complexity

If fluorescent emitters are used, then the device structure is simpler, but the efficiency is intrinsically capped at 25% due to only being able to recruit singlet excitons

Engineering Contradiction:
Improveemitter structure complexityVSAvoidexciton utilization efficiency
Core Design Contradiction:
Device complexityVSUse of energy by moving object

Solution Approach 1:

The patent changes the emission mechanism parameter from simple fluorescence to thermally activated delayed fluorescence. By introducing thermal energy activation and delayed emission components, the system can access both singlet and triplet excitons while maintaining organic material simplicity, achieving over 25% efficiency without complex phosphorescent structures.

Inventive Principle:
Principle #35Parameter changes

3Use of energy by moving object

If donor and acceptor moieties are placed nearly orthogonal to each other in TICT design, then a small energy gap between singlet and triplet excited states is achieved, but the emission wavelength may be limited

Engineering Contradiction:
Improveenergy gap between singlet and triplet statesVSAvoidemission wavelength range
Core Design Contradiction:
Use of energy by moving objectVSIllumination intensity

Solution Approach 1:

The patent applies local quality by positioning donor and acceptor moieties at specific orientations (including orthogonal arrangements) to create localized electronic structures with desired properties. This spatial arrangement enables small singlet-triplet energy gaps for efficient TADF while the specific molecular design allows tuning of emission wavelengths across different regions of the spectrum.

Inventive Principle:
Principle #3Local quality

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 TADF compounds exhibit improved efficiency, blue-shifted emission, and shorter emission lifetimes, leading to more robust and efficient light-emitting devices with reduced metal usage, addressing the drawbacks of previous OLED technologies while maintaining high performance.

Implementation Method 1

the electrons in the triplet state can return to the singlet state by reverse intersystem crossing (RISC) using thermal energy, followed by radiative fluorescence

Methodology Applied
Scientific EffectReverse intersystem crossing (RISC):

Implementation Method 2

small organic molecules, emitting via a thermally activated delayed fluorescence (TADF) mechanism

Methodology Applied
Scientific EffectThermally activated delayed fluorescence (TADF):

Implementation Method 3

The small ΔE ST is realized by spatial separation between HOMO and LUMO to minimize the electronic repulsion between these orbitals

Methodology Applied
Scientific EffectElectronic repulsion:

Implementation Method 4

harvest both singlet and triplet excitons for emission due to the enhanced intersystem crossing (ISC) mediated by the large spin-orbit coupling of heavy metals

Methodology Applied
Scientific EffectIntersystem crossing (ISC):

Implementation Method 5

enhanced intersystem crossing (ISC) mediated by the large spin-orbit coupling of heavy metals such as iridium(III) and platinum(II)

Methodology Applied
Scientific EffectSpin-orbit coupling:

Data Source

PatentEP3288956B1Light emitting devices and compounds
Publication Date: 2020.12.23 UNIV COURT OF THE UNIV OF ST ANDREWS
  • EP3288956B1 patent drawingFigure 1
  • EP3288956B1 patent drawingFigure 2
  • EP3288956B1 patent drawing

AI summary

Thermally Activated Delayed Fluorescence (TADF) compounds wherein two aromatic heterocyclic moieties are provided as acceptor groups, spaced apart from two donor moieties by an aromatic spacer ring, are described. Charged organic TADF species having a similar structure are also described. The TADF compounds and charged organic TADF species may be employed as emitter material in light emitting devices such as OLEDs and LEECs. Also described TADF compounds wherein at least one donor moiety is substituted by at least one substituent that is a phosphine oxide or a phosphine sulphide.