Triphenylene Benzo-Fused Thiophene Hosts for OLED Energy Quenching

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Solution Overview

Problem

Current organic light emitting devices (OLEDs) face challenges in achieving high efficiency and stability, particularly in accommodating red, green, and blue phosphorescent dopants without energy quenching, and in balancing charge transport for improved device performance.

Innovation Solution

The development of triphenylene-containing benzo-fused thiophene and furan compounds, which serve as hosts or enhancement layers in OLEDs, offering high triplet energy and improved charge balance, thereby enhancing device efficiency and stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of energy

If conventional host materials are used in OLEDs, then device fabrication is simpler, but energy quenching occurs between host and phosphorescent dopants, reducing device efficiency

Engineering Contradiction:
Improveenergy quenchingVSAvoidhost material structure
Core Design Contradiction:
Loss of energyVSDevice complexity

Solution Approach 1:

The patent changes the energy parameter of the host material by incorporating triphenylene groups with high triplet energy levels (2.9-3.2 eV), which exceeds the energy of common phosphorescent dopants. This parameter change prevents energy quenching while maintaining compatibility with standard OLED fabrication processes

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite host materials by combining triphenylene core structures with various substituents (carbazole, dibenzothiophene, dibenzofuran groups) to achieve both high triplet energy and good charge transport properties, resolving the contradiction between energy matching and device performance

Inventive Principle:
Principle #40Composite materials

2Reliability

If standard organic materials are used in OLEDs, then cost is lower, but charge transport balance is poor, reducing device performance

Engineering Contradiction:
Improvecharge transport balanceVSAvoidmolecular structure
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies local quality by introducing specific functional groups (carbazole for hole transport, dibenzothiophene/dibenzofuran for electron transport) at strategic positions on the triphenylene core, creating molecules with balanced charge transport properties while maintaining overall structural simplicity

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The triphenylene-based host molecules serve multiple functions simultaneously: providing high triplet energy for phosphorescence, enabling balanced charge transport through integrated functional groups, and ensuring good film-forming properties, thereby improving reliability without proportionally increasing complexity

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

3Duration of action of moving object

If OLEDs use phosphorescent dopants with standard hosts, then device structure is simpler, but device lifetime is short due to energy quenching

Engineering Contradiction:
Improvedevice lifetimeVSAvoidhost compound structure
Core Design Contradiction:
Duration of action of moving objectVSDevice complexity

Solution Approach 1:

The patent changes the triplet energy parameter of the host material to 2.9-3.2 eV through triphenylene incorporation, which is higher than typical phosphorescent dopants (2.1-2.6 eV), preventing energy back-transfer and quenching, thereby extending device lifetime while maintaining manageable structural complexity

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

These compounds provide high efficiency and stability in OLEDs by accommodating phosphorescent dopants without energy quenching and improving charge balance, leading to extended device lifetime and performance.

Implementation Method 1

One application for phosphorescent emissive molecules is a full color display

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 2

accommodating red, green, and blue phosphorescent dopants without energy quenching

Methodology Applied
Scientific EffectEnergy transfer:

Data Source

PatentEP3159333B1Benzo-fused thiophene or furan compounds comprising a triphenylene group
Publication Date: 2020.04.22 UNIVERSAL DISPLAY CORP
  • EP3159333B1 patent drawingFigure 1
  • EP3159333B1 patent drawingFigure 2
  • EP3159333B1 patent drawingFigure 3

AI summary

A compound comprising a triphenylene containing benzo-fused thiophene or benzo-fused furan, wherein the compound is represented by the structure of Formula (IV) or Formula (V): wherein X is S or O; wherein R1, R2, and R3 are unfused substituents independently selected from the group consisting of CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH=CH-CnH2n+1, C≡C-CnH2n+1, Ar1, Ar1-Ar2, CnH2n-Ar1, or no substitution, and wherein each of R1, R2, and R3 may represent mono, di, tri, or tetra substitutions; wherein n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof; and wherein at least one of R1, R2, and R3 includes a triphenylene group.