Spiro TADF Compounds for Durable, Efficient OLED Emission

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Solution Overview

Problem

Existing organic light-emitting devices using compounds A-1 and A-2 suffer from inefficiencies in luminous efficiency and driving durability.

Innovation Solution

An organic compound represented by formula [1] or [2] with a spiro structure, containing an electron-withdrawing carbonyl group and an electron-donating acridine ring, is used in the light-emitting layer, which has a small S-T gap, wide band gap, and is less likely to undergo molecular association, enhancing exciton utilization and durability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If compounds A-1 or A-2 are used in the light-emitting layer, then the device can operate with various emission wavelengths, but the luminous efficiency is insufficient

Engineering Contradiction:
Improveemission wavelength varietyVSAvoidluminous efficiency
Core Design Contradiction:
Adaptability or versatilityVSLoss of energy

Solution Approach 1:

The patent modifies the molecular structure parameters of the light-emitting compound by introducing a spiro structure with specific substituents (X1-X18, X21-X38) and functional groups (Y, Z). This structural parameter change optimizes the HOMO-LUMO energy levels and S1-T1 gap, enabling both high luminous efficiency and tunable emission wavelengths across different device embodiments

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite material strategies by combining the spiro structure compound with different host materials (EM1-EM14) and assist materials (GD1-GD9) in the light-emitting layer. This composite approach allows optimization of energy transfer pathways and exciton management, achieving high luminous efficiency while maintaining emission wavelength versatility

Inventive Principle:
Principle #40Composite materials

2Device complexity

If conventional organic compounds are used in the light-emitting layer, then the device structure can be simplified, but the driving durability is reduced

Engineering Contradiction:
Improvedevice structure simplicityVSAvoiddriving durability
Core Design Contradiction:
Device complexityVSReliability

Solution Approach 1:

The patent applies local quality enhancement by introducing the spiro structure at the molecular level, which creates steric hindrance and prevents molecular association locally. This local structural modification prevents aggregation-induced degradation and improves driving durability without requiring complex device architecture changes

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

Instead of trying to improve durability through complex device structures or additional protective layers, the patent inverts the approach by embedding durability-enhancing features directly into the molecular structure of the light-emitting compound itself. The spiro structure's inherent properties (steric hindrance, amorphous film formation) provide durability without increasing device complexity

Inventive Principle:
Principle #13The other way round (Inversion)

3Ease of manufacture

If molecules are allowed to associate in the light-emitting layer, then material deposition is simplified, but exciton utilization efficiency decreases

Engineering Contradiction:
Improvematerial deposition simplicityVSAvoidexciton utilization efficiency
Core Design Contradiction:
Ease of manufactureVSLoss of energy

Solution Approach 1:

The patent employs asymmetry through the spiro structure, which creates an asymmetric three-dimensional geometry that prevents planar stacking and molecular association. This asymmetric structure maintains molecular dispersion in the light-emitting layer, ensuring high exciton utilization efficiency while remaining compatible with standard vacuum deposition processes

Inventive Principle:
Principle #4Asymmetry

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 compound achieves high luminous efficiency and driving durability by facilitating delayed fluorescence and preventing molecular association, leading to stable amorphous films and reduced impurity-related degradation.

Implementation Method 1

the compound has a small difference between the excited singlet state (S1) and the excited triplet state (T1), and thus can be used for light emission of delayed fluorescence

Methodology Applied
Scientific EffectDelayed fluorescence: Fluorescence

Implementation Method 2

The injection of electrons and holes from these pairs of electrodes generates excitons in the light-emitting organic compound in the organic compound layer, and when the excitons return to the ground state, the organic light-emitting device emits light

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS12384799B2Organic compound and organic light-emitting device
Publication Date: 2025.08.12 CANON KK
  • US12384799B2 patent drawing
  • US12384799B2 patent drawing
  • US12384799B2 patent drawing

AI summary

An organic compound, represented by formula [1] or [2], suitably used for a thermally activated delayed fluorescent device:where X1 to X18 and X21 to X38 are each independently selected from the group consisting of a hydrogen atom, and substituents, Y is oxygen, sulfur, selenium, tellurium, a CR1R2 group, or a carbonyl group, where R1 and R2 are each independently selected from the group consisting of a hydrogen atom, and substituents, and Z is an alkyl group, an aryl group, or a heterocyclic group.