Heterocyclic Compound for Stable Light-Emitting Element

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Solution Overview

Problem

Current light-emitting elements using organic compounds face challenges in achieving stable and efficient light emission due to limitations in the molecular structure of the electroluminescent layer, which affects the reliability and performance of the devices.

Innovation Solution

A novel heterocyclic compound with a stable molecular structure, where a heterocyclic skeleton is bonded to a fluorene skeleton through an arylene group, is developed for use in the electroluminescent layer, enhancing the light-emitting element's reliability and performance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional organic compounds are used in the electroluminescent layer, then the device structure is simpler, but the molecular structure stability and light emission efficiency are insufficient

Engineering Contradiction:
Improvelight emission stabilityVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent employs composite molecular structures combining heterocyclic skeletons (pyrimidine, triazine, oxadiazole, thiadiazole, or tetrazole rings) with fluorene skeletons through arylene group linkers. This composite approach creates molecules that exhibit enhanced stability and efficient light emission by integrating the electronic properties of different heterocyclic systems with the structural stability of fluorene, resolving the contradiction between simple structure and high performance.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent systematically varies key molecular parameters including the type of heterocyclic ring (pyrimidine, triazine, oxadiazole, thiadiazole, tetrazole), the arylene group substitution patterns, and the fluorene skeleton configuration. These parameter changes enable optimization of HOMO-LUMO energy gaps, charge transport properties, and photoluminescence characteristics while maintaining molecular stability, thereby achieving improved light emission performance without excessive structural complexity.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If the heterocyclic compound structure is optimized for stability, then the light emission reliability improves, but the synthesis difficulty increases

Engineering Contradiction:
Improvemolecular structure stabilityVSAvoidsynthesis difficulty
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The synthesis strategy divides the complex heterocyclic compound into modular components: pre-synthesized heterocyclic ring units, arylene linker units, and fluorene skeleton units. These segments are independently prepared and then coupled through standardized reaction protocols (such as Pd-catalyzed cross-coupling reactions), reducing overall synthesis difficulty while maintaining the stability benefits of the complete molecular structure.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent employs preliminary synthesis of key building blocks (heterocyclic rings with appropriate functional groups, arylene linkers, and fluorene derivatives) that can be stored and later assembled. This preliminary action allows optimization of each component's stability characteristics independently and simplifies the final coupling steps, making the overall manufacturing process more manageable despite the complexity of the target molecular structure.

Inventive Principle:
Principle #10Preliminary action

3Reliability

If conventional organic compounds are used, then the material solubility is adequate, but the purity and emission characteristics are insufficient

Engineering Contradiction:
Improveemission efficiencyVSAvoidmaterial purity
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent introduces specific functional groups and substituent patterns at localized positions within the molecular structure (such as electron-donating or electron-withdrawing groups on the arylene linkers or fluorene units) that simultaneously enhance purity through better crystallization behavior and improve emission characteristics through localized electronic effects, without requiring complete structural redesign.

Inventive Principle:
Principle #3Local quality

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 novel heterocyclic compound improves the solubility and purity of the light-emitting material, leading to a highly reliable and efficient light-emitting element with extended lifetime and improved emission characteristics.

Implementation Method 1

A light-emitting element using an organic compound as a luminous body... when a voltage is applied between a pair of electrodes with an electroluminescent layer (an EL layer) including a luminous body provided therebetween, electrons injected from the cathode and holes injected from the anode recombine in the light emission center of the EL layer to form molecular excitons, and energy is released and light is emitted when the molecular excitons return to the ground state

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS20210013421A1Heterocyclic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device
Publication Date: 2021.01.14 SEMICON ENERGY LAB CO LTD
  • US20210013421A1 patent drawing
  • US20210013421A1 patent drawing
  • US20210013421A1 patent drawing

AI summary

Provided is a novel heterocyclic compound, a novel heterocyclic compound that can be used in a light-emitting element, or a highly reliable light-emitting device, electronic device, and lighting device in each of which the light-emitting element using the novel heterocyclic compound is used. One embodiment of the present invention is a heterocyclic compound represented by General Formula (G1).In General Formula (G1), each of A1 and A2 independently represents nitrogen or carbon bonded to hydrogen, and at least one of A1 and A2 represents nitrogen; Ar represents a substituted or unsubstituted arylene group having 6 to 18 carbon atoms; B represents a substituted or unsubstituted fluorenyl group; and R1 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.