Heteroatom Cycloalkyl Organic Compound for OLED Efficiency

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Solution Overview

Problem

Current blue-light organic electroluminescent materials suffer from low efficiency and short lifetime due to concentration quenching effects and isotropic characteristics during film formation, limiting their application in OLEDs.

Innovation Solution

A heteroatom- and cycloalkyl-containing organic compound with a boron-nitrogen structure and a cycloalkyl-containing fluorenyl group is introduced, enhancing molecular orientation and spin coupling, and extending conjugation to improve energy transfer and reduce photochromic blue shift.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If larger-plane conjugated groups are used to improve internal quantum efficiency through triplet-triplet fusion or thermally activated delayed fluorescence, then efficiency is improved, but concentration quenching effect increases significantly

Engineering Contradiction:
Improveinternal quantum efficiencyVSAvoidconcentration quenching effect
Core Design Contradiction:
Use of energy by moving objectVSLoss of energy

Solution Approach 1:

The patent introduces heteroatom-containing groups (such as triazole, tetrazole, pyrazole rings) and cycloalkyl groups at specific positions of the conjugated backbone. This creates local structural variations that modify electronic distribution and reduce non-radiative energy transfer between adjacent molecules, thereby suppressing concentration quenching while maintaining high internal quantum efficiency through the preserved conjugated system.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs composite molecular structures combining conjugated backbones with heteroatom-containing functional groups and cycloalkyl substituents. This composite approach allows the molecule to simultaneously achieve high triplet exciton utilization (through the conjugated system enabling triplet-triplet fusion or TADF) and reduced concentration quenching (through the heteroatom and cycloalkyl groups that space out electron density and reduce intermolecular interactions).

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If organic photoelectric materials are used with isotropic characteristics during film formation, then ease of manufacture is improved, but light emission is lost inside the device due to isotropic orientation

Engineering Contradiction:
Improvefilm formation processVSAvoidlight emission loss
Core Design Contradiction:
Ease of manufactureVSLoss of energy

Solution Approach 1:

The patent introduces asymmetric heteroatom-containing groups (such as chiral centers in certain triazole or tetrazole configurations) and cyclic structures that create inherent molecular asymmetry. This asymmetry translates to anisotropic packing and orientation in the film state, enabling preferential light emission directions that reduce internal light trapping and extraction losses while maintaining compatibility with standard vacuum deposition or solution processing methods.

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 significantly improves external quantum efficiency and lifetime performance of organic electroluminescent devices by avoiding concentration quenching and enhancing energy transfer, making it suitable for high-efficiency blue-light emission.

Implementation Method 1

The heteroatom- and cycloalkyl-containing organic compound of the present invention has a boron-nitrogen structure with multiple resonance effect

Methodology Applied
Scientific EffectResonance: Resonance

Implementation Method 2

by means of the heavy atom effect, the conjugation of a luminous moiety is extended while the efficiency is further improved

Methodology Applied
Scientific EffectHeavy atom effect:

Implementation Method 3

When energized, electrons and holes are respectively injected into, transported to and recombined in a light-emitting region, thus generating excitons and emitting light

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS12145952B2Heteroatom- and cycloalkyl-containing organic compound and organic electroluminescent device containing compound
Publication Date: 2024.11.19 SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
  • US12145952B2 patent drawing
  • US12145952B2 patent drawing
  • US12145952B2 patent drawing

AI summary

The present invention discloses a heteroatom- and cycloalkyl-containing organic compound and an organic electroluminescent device containing the compound. The general structural formula of the organic compound is as represented by Formula I. The organic compound has a boron-nitrogen structure with multiple resonance effect, wherein a cycloalkyl-containing fluorenyl structure is introduced on the basis of the boron-nitrogen structure. The molecular size is greatly expanded by means of the cycloalkyl group, thereby effectively avoiding a concentration quenching effect, while the molecular orientation is enhanced due to the planarity of the fluorenyl group. In order to further improve the efficiency, a heteroatom is introduced to improve the spin coupling effect, and the oscillator strength is enhanced to improve the energy transfer between a host and a guest; furthermore, by means of the heavy atom effect, the conjugation of a luminous moiety is extended while the efficiency is further improved, avoiding excessive photochromic blue shift, so that the organic compound of the present invention has a good efficiency and lifetime performance. Therefore, an organic electroluminescent device manufactured by using the organic compound of the present invention has a good performance in terms of external quantum efficiency and lifetime.