Boron Hydroxyl Organic Compounds for OLED Stability

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Solution Overview

Problem

Current organic thermally activated delayed fluorescence materials lack improved luminescence properties and diverse electron acceptor units, particularly boron hydroxyl-containing light-emitting materials have not been developed, limiting the selection and performance of pure organic luminescent materials.

Innovation Solution

A series of boron hydroxyl-containing organic compounds are synthesized using xanthene or thioxanthene as electron acceptor units and triarylamine or carbazole derivatives as electron donor units, with a method involving reactions such as Suzuki coupling and Buchwald-Hartwig coupling to create compounds with enhanced stability and luminous efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If conventional electron acceptor units are used in thermally activated delayed fluorescence materials, then the materials can achieve acceptable luminous efficiency, but the luminescence properties and material diversity are limited

Engineering Contradiction:
Improvematerial diversityVSAvoidluminescence properties
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent changes the chemical structure parameters of electron acceptor units by introducing boron hydroxyl-containing xanthene and thioxanthene units with novel molecular configurations. This structural parameter change enables diverse material design while maintaining excellent luminescence properties through the unique electron-accepting characteristics of the boron hydroxyl group

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures by combining boron hydroxyl-containing electron acceptor units with various electron donor units (aromatic amines, carbazoles, triarylamines). This composite approach generates a series of new TADF materials with diversified properties while ensuring reliable luminescence performance through the synergistic interaction between donor and acceptor units

Inventive Principle:
Principle #40Composite materials

2Reliability

If pure organic thermally activated delayed fluorescence materials are used, then the internal quantum efficiency can reach approximately 100%, but the stability and luminous efficiency need further improvement

Engineering Contradiction:
ImprovestabilityVSAvoidluminous efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent introduces rigid boron hydroxyl-containing xanthene and thioxanthene units at specific positions in the molecular structure to enhance stability. The local rigid structure restricts molecular vibration and rotation, reducing non-radiative decay pathways, while the overall molecular design maintains efficient charge recombination for high luminous efficiency

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent designs molecules with continuous π-conjugated systems connecting electron donor and acceptor units, enabling efficient electron-hole recombination and continuous radiative decay pathways. This continuous action ensures high luminous efficiency while the rigid boron hydroxyl unit provides ongoing structural stability

Inventive Principle:
Principle #20Continuity of useful action

3Reliability

If the energy gap between singlet energy level (S1) and triplet energy level (T1) is reduced, then triplet excitons can acquire thermal energy and achieve thermally activated delayed fluorescence, but the luminescence properties need further improvement

Engineering Contradiction:
Improveluminescence propertiesVSAvoidenergy gap
Core Design Contradiction:
ReliabilityVSUse of energy by moving object

Solution Approach 1:

The patent precisely adjusts the energy gap parameter between S1 and T1 levels by modifying the boron hydroxyl-containing electron acceptor unit structure. The energy gap is optimized to be small enough to allow thermal activation of triplet excitons but large enough to maintain high photoluminescence quantum yield and prevent energy loss

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 boron hydroxyl-containing organic compounds improve the stability and luminous efficiency of organic electronic devices, such as OLEDs, by optimizing the structure and concentration, resulting in high-efficiency, high-brightness, and stable performance for full-color displays and lighting.

Implementation Method 1

triplet excitons (T1) can acquire thermal energy from the environment and thus the radioluminescence, also known as thermally activated delayed fluorescence, of singlet excitons (S1) is realized through a reverse intersystem crossing process

Methodology Applied
Scientific EffectThermally activated delayed fluorescence: Luminescence

Implementation Method 2

the dotted line represents a hydrogen bond formed between X (oxygen or sulfur atom) and the hydrogen atom in the hydroxyl (OH)

Methodology Applied
Scientific EffectHydrogen bond:

Data Source

PatentUS12134627B2Boron hydroxyl-containing organic compound, method for preparing same and use thereof
Publication Date: 2024.11.05 JIANGSU UNIV OF SCI & TECH
  • US12134627B2 patent drawing
  • US12134627B2 patent drawing
  • US12134627B2 patent drawing

AI summary

The present invention relates to a boron hydroxyl-containing organic compound having a structural formula shown in formula I. The present invention also relates to a method for preparing the boron hydroxyl-containing organic compound and use thereof in an organic electronic device, particularly an organic light-emitting diode. The present invention further relates to an organic electronic device, particularly an organic light-emitting diode, including the boron hydroxyl-containing organic compound according to the present invention and use thereof in display and lighting technology. By optimizing the structure of the device and altering the concentration of the boron hydroxyl-containing organic compound in the substrate, the optimal device performance can be achieved so as to produce an OLED device with high efficiency, high brightness and high stability, which provides a better material option for use in full-color display and lighting.