Condensed Cyclic Compound for TADF OLED Efficiency

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Solution Overview

Problem

Current organic light-emitting devices face limitations in achieving high efficiency and long lifespan due to challenges in exciton formation and charge transport in the emission layer, particularly in separating and utilizing triplet excited states for light emission.

Innovation Solution

The use of a condensed cyclic compound represented by Formula 1-1, 1-2, or 1-3, which includes electron donor and acceptor moieties, facilitates charge transfer and reduces orbital overlap, enabling thermally activated delayed fluorescence (TADF) and improving luminescence efficiency by allowing reverse intersystem crossing at room temperature, thus enhancing exciton utilization in the emission layer.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional organic light-emitting devices are used, then device structure is simple, but luminescence efficiency is low and lifespan is limited due to poor exciton formation and charge transport

Engineering Contradiction:
Improveluminescence efficiencyVSAvoiddevice structure
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent introduces a condensed cyclic compound with specific molecular structure parameters (Formula 1-1, 1-2, or 1-3) that changes the electronic properties of the emission layer. The compound features a core condensed cyclic structure with electron donor and acceptor moieties, where substituents R1-R6 can be selected from various functional groups. This parameter change in molecular structure enables thermally activated delayed fluorescence (TADF) and improves luminescence efficiency by allowing reverse intersystem crossing at room temperature.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite material approach by designing a condensed cyclic compound that integrates multiple functional moieties within a single molecular framework. The compound combines electron donor groups (such as carbazole, triphenamine) with electron acceptor groups (such as fluorinated aromatic rings) to create a multifunctional emission material that simultaneously achieves charge transport, exciton formation, and light emission functions in the emission layer.

Inventive Principle:
Principle #40Composite materials

2Loss of energy

If triplet excited states are not effectively utilized, then device operation is simple, but energy loss is high and quantum efficiency is low

Engineering Contradiction:
Improveenergy lossVSAvoidexciton management mechanism
Core Design Contradiction:
Loss of energyVSDevice complexity

Solution Approach 1:

The patent converts the harmful non-emissive triplet excited states into beneficial light-emitting states through thermally activated delayed fluorescence (TADF). The condensed cyclic compound is designed with appropriate HOMO-LUMO energy level separation and small singlet-triplet energy gaps, enabling triplet excitons to undergo reverse intersystem crossing to the singlet state and subsequently emit photons. This transforms the previously wasted triplet energy into useful light output, achieving high quantum efficiency.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The patent modifies the energy level parameters of the emission layer by incorporating the condensed cyclic compound with specific electronic structure. The compound's HOMO and LUMO levels are tuned to create an appropriate energy offset with adjacent layers, and the small singlet-triplet energy gap (ΔEST) is engineered to facilitate efficient reverse intersystem crossing. These parameter changes enable effective triplet exciton utilization without complex device architecture.

Inventive Principle:
Principle #35Parameter changes

3Speed

If charge transport is insufficient in the emission layer, then device structure is simple, but driving voltage is high and response speed is slow

Engineering Contradiction:
Improveresponse speedVSAvoidcharge transport mechanism
Core Design Contradiction:
SpeedVSDevice complexity

Solution Approach 1:

The condensed cyclic compound serves multiple functions simultaneously in the emission layer: it acts as the light-emitting species, facilitates charge transport through its electron donor and acceptor moieties, and enables exciton formation via its appropriate energy levels. The molecule's dual electron-donating and electron-accepting capabilities allow it to transport both holes and electrons, improving charge balance and response speed without requiring separate transport layers or complex device structures.

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

This approach results in an organic light-emitting device with improved luminescence efficiency, low driving voltage, extended lifespan, and high maximum quantum efficiency by effectively using triplet excitons for light emission and enhancing charge transport capabilities.

Implementation Method 1

facilitates charge transfer and reduces orbital overlap, enabling thermally activated delayed fluorescence (TADF) and improving luminescence efficiency by allowing reverse intersystem crossing at room temperature

Methodology Applied
Scientific EffectThermally activated delayed fluorescence (TADF): Thermoluminescence

Implementation Method 2

improving luminescence efficiency by allowing reverse intersystem crossing at room temperature, thus enhancing exciton utilization in the emission layer

Methodology Applied
Scientific EffectReverse intersystem crossing: Fluorescence

Implementation Method 3

Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may then recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS11818951B2Condensed cyclic compound and organic light-emitting device including the same
Publication Date: 2023.11.14 SAMSUNG DISPLAY CO LTD
  • US11818951B2 patent drawing
  • US11818951B2 patent drawing
  • US11818951B2 patent drawing

AI summary

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode and comprising an emission layer; and at least one condensed cyclic compound represented by Formula 1-1, 1-2, or 1-3:where in Formulae 1-1 to 1-3, at least one of R1(s) is an electron withdrawing group, at least one selected from R2(s) and R3(s) is an electron withdrawing group, and at least one selected from R4(s), R5(s), and R6(s) is an electron withdrawing group, wherein a case where the number of cyano groups in the electron withdrawing group included in the condensed cyclic compound represented by Formula 1-1 is two or more is excluded.