Organic EL Compound for Coating via Segmented Molecular Design

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Solution Overview

Problem

Current organic electroluminescence (EL) devices lack materials suitable for coating methods, particularly for large-sized displays and lighting panels, as existing compounds with fused nitrogen-containing rings and biscarbazole or tricarbazole groups are not adequately addressed in previous patents, and materials for coating methods do not meet the diverse performance requirements.

Innovation Solution

A compound represented by formula (1) with various substituents is developed, allowing for layer formation via coating methods and meeting the necessary properties for EL devices, produced through specific coupling reactions involving amine compounds and basic catalysts, enabling efficient and easy synthesis.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of energy

If a compound with fused nitrogen-containing ring and biscarbazole or tricarbazole groups is used, then the light emission efficiency is improved, but the solubility and heat resistance required for coating methods are not satisfied

Engineering Contradiction:
Improvelight emission efficiencyVSAvoidsolubility and heat resistance for coating
Core Design Contradiction:
Loss of energyVSEase of manufacture

Solution Approach 1:

The compound is divided into distinct functional modules: a fused nitrogen-containing ring core (providing high light emission efficiency) and separately attached carbazole groups (providing solubility and processability). This segmentation allows each part to fulfill its specific function without compromising the other.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent creates a composite molecular structure combining the fused nitrogen-containing ring (such as triazine, pyrimidine, or pyridine rings) with multiple carbazole groups. This composite structure integrates the high efficiency characteristics of the fused ring with the favorable processing characteristics of carbazole groups, achieving both high light emission efficiency and good solubility/heat resistance for coating methods.

Inventive Principle:
Principle #40Composite materials

2Reliability

If a material is designed for vapor deposition method, then the device performance is improved, but the material cannot be used for coating method which is required for large-sized display production

Engineering Contradiction:
Improvedevice performanceVSAvoidapplicability to coating method
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The compound is designed to be universally applicable to multiple manufacturing methods. By incorporating carbazole groups with appropriate substituents, the material achieves both the high device performance required for vapor deposition and the solubility/heat resistance properties needed for coating methods, making it versatile for different production scales and techniques.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent modifies molecular parameters (such as adding alkyl groups, aryl groups, or other substituents to the carbazole moieties) to adjust the physical properties of the compound. These parameter changes enhance solubility and thermal stability without significantly compromising the light emission efficiency, enabling the material to meet the requirements of coating methods while maintaining high device performance.

Inventive Principle:
Principle #35Parameter changes

3Quantity of substance

If existing compounds are used, then the synthesis process is complex, but the production efficiency and ease of manufacture are reduced

Engineering Contradiction:
Improveproduction efficiencyVSAvoidsynthesis process complexity
Core Design Contradiction:
Quantity of substanceVSDevice complexity

Solution Approach 1:

The patent employs preliminary action by using pre-synthesized carbazole-containing building blocks with predetermined structures. These building blocks are then coupled with the fused nitrogen-containing ring through standardized reactions, avoiding the need to synthesize complex structures from scratch and significantly simplifying the overall synthesis process while maintaining production efficiency.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent simplifies synthesis by changing the approach from multi-step complex reactions to more straightforward coupling reactions. By using readily available carbazole derivatives and standard coupling reagents, the synthesis process becomes less complex and more scalable, improving production efficiency without sacrificing molecular complexity or device performance.

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 compound can be efficiently produced and forms layers suitable for organic EL devices by coating methods, meeting the required properties and diverse performance needs, enhancing the capabilities of organic EL devices.

Implementation Method 1

produced through specific coupling reactions involving amine compounds and basic catalysts

Methodology Applied
Scientific EffectCoupling reaction: Chemical Bonding

Implementation Method 2

holes and electrons injected into the light emitting layer are recombined to form excitons, and the exciton energy is released as light

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS10032991B2Compound, organic electroluminescence element material, ink composition, organic electroluminescence element, electronic device, and method for producing compound
Publication Date: 2018.07.24 IDEMITSU KOSAN CO LTD
  • US10032991B2 patent drawing
  • US10032991B2 patent drawing
  • US10032991B2 patent drawing

AI summary

A compound represented by formula (1):wherein *a, *b, R1, X1, L1, L2, n, A1, and A2 are as defined in the description, and a production method of the compound represented by formula (1) are provide. In the production method, A1 is introduced under a reaction condition in which the reactivity of Hal2 in a compound represented by formula (I):wherein *c, *d, R1, X1, L1, L2, n, A1, A2, Hal1, and Hal2 are as defined in the description,is extremely low as compared with that of Hal1 and then A2 which is different from A1 is introduced under a reaction condition in which the reactivity of Hal2 is high. The compound represented by formula (1) is formed into a layer by a coating method and meets various performance requirements of an organic EL device.