Heterocyclic Compound Synthesis via Segmented Boron Introduction

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Solution Overview

Problem

Existing methods for preparing heterocyclic compounds with boron, such as those used in light-emitting devices, face challenges with low yields due to steric hindrance issues and by-product formation, especially during large-scale synthesis.

Innovation Solution

A method involving the reaction of an intermediate compound with a boron halide, followed by introducing specific groups, which improves yield and reduces by-product formation, allowing for high-yield production even with reactants having large steric hindrance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If existing methods are used to prepare heterocyclic compounds with boron, then the synthesis process can be completed, but the yield is low due to steric hindrance issues and by-product formation

Engineering Contradiction:
ImproveyieldVSAvoidby-product formation
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The synthesis process is divided into two distinct stages: first forming the heterocyclic compound structure without boron, then introducing the boron halide in a separate step. This segmentation allows each reaction to proceed under optimized conditions, avoiding the steric hindrance problems that occur when attempting to form both structures simultaneously.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The heterocyclic compound is prepared in advance before introducing the boron halide. This preliminary action creates a ready-to-receive intermediate structure that can then undergo boron substitution without encountering the steric hindrance issues present in conventional one-step methods.

Inventive Principle:
Principle #10Preliminary action

2Ease of manufacture

If conventional synthesis methods are used, then the process is simpler, but purification efficiency is reduced due to by-product formation

Engineering Contradiction:
Improveprocess simplicityVSAvoidpurification efficiency
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

By separating the heterocyclic compound formation from the boron introduction step, the method reduces by-product formation that complicates purification. Each stage produces fewer unwanted by-products, making the overall purification process more efficient despite adding a reaction step.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The method converts the potential harm of multiple reaction steps into a benefit by using the intermediate heterocyclic compound as a stable platform that facilitates cleaner boron substitution, ultimately improving purification efficiency.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Adaptability or versatility

If reactants with large steric hindrance are used in existing methods, then the desired compound can be synthesized, but the yield decreases significantly

Engineering Contradiction:
Improveability to synthesize compounds with steric hindranceVSAvoidyield
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The heterocyclic compound structure is built first using reactants with large steric hindrance, allowing these reactants to be fully utilized in forming the core structure. The boron halide is then introduced in a subsequent step under conditions that are less sensitive to steric hindrance, thereby maintaining high yield.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The method changes the reaction parameters by separating the synthesis into two stages with different optimal conditions. The first stage optimizes for heterocyclic compound formation with sterically hindered reactants, while the second stage optimizes for boron substitution, allowing each reaction to proceed with parameters suited to its specific requirements.

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

This method enhances the yield and purification efficiency of heterocyclic compounds, enabling large-scale synthesis and improving economic efficiency for light-emitting devices.

Implementation Method 1

preparing an intermediate compound by mixing the first reactant and the second reactant with a copper catalyst, a base, and optionally, an auxiliary solvent, to allow the first reactant and the second reactant to react

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS20240270761A1Method of preparing heterocyclic compound, heterocyclic compound prepared according to the method, light-emitting device including the heterocyclic compound, and electronic apparatus and electronic equipment including the light-emitting device
Publication Date: 2024.08.15 SAMSUNG DISPLAY CO LTD
  • US20240270761A1 patent drawing
  • US20240270761A1 patent drawing
  • US20240270761A1 patent drawing

AI summary

A method of preparing a heterocyclic compound represented by Formula 1, the method includes preparing a first reactant, preparing a second reactant represented by Formula 2-2, and preparing an intermediate compound by mixing the first reactant and the second reactant with i) a copper catalyst, ii) a base, and optionally, iii) an auxiliary solvent, to allow the first reactant and the second reactant to react, wherein the first reactant is a compound represented by Formula 2-1a, and the intermediate compound is a compound represented by Formula 2-3a, or the first reactant is a compound represented by Formula 2-1b, and the intermediate compound is a compound represented by Formula 2-3b:wherein more details of Formulae 1, 2-1a, 2-1b, 2-2, 2-3a, and 2-3b are as described herein.