Aromatic Amine Hole-Transport Material for Low-Index OLED Layers

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Solution Overview

Problem

Existing organic light-emitting devices face challenges with low outcoupling efficiency due to refractive index differences between layers, which affect carrier-transport properties and reliability, making it difficult to form low refractive index layers without compromising device performance.

Innovation Solution

Development of novel aromatic amine compounds for hole-transport and hole-injection layers with specific refractive indices and carrier-transport properties, including monoamine compounds with aromatic groups bonded to a nitrogen atom, sp3 hybrid orbital configurations, and fluorene skeletons, to enhance emission efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of energy

If a low refractive index layer is formed in the EL layer, then outcoupling efficiency is improved, but carrier-transport property deteriorates

Engineering Contradiction:
Improveoutcoupling efficiencyVSAvoidcarrier-transport property
Core Design Contradiction:
Loss of energyVSReliability

Solution Approach 1:

The patent changes the chemical structure parameters of the organic compound by introducing specific saturated hydrocarbon groups (sp3 hybridized carbon atoms) into the molecular structure. This structural modification reduces the refractive index while maintaining carrier-transport capability through the aromatic amine core structure, thus resolving the trade-off between outcoupling efficiency and carrier-transport property

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining aromatic amine groups (for carrier transport) with saturated hydrocarbon groups (for low refractive index). This molecular-level composite allows simultaneous achievement of high outcoupling efficiency and good carrier-transport property by integrating the beneficial properties of different structural motifs

Inventive Principle:
Principle #40Composite materials

2Loss of energy

If a low refractive index layer is formed in the EL layer, then external quantum efficiency is improved, but device reliability deteriorates

Engineering Contradiction:
Improveexternal quantum efficiencyVSAvoiddevice reliability
Core Design Contradiction:
Loss of energyVSReliability

Solution Approach 1:

The patent modifies molecular parameters by controlling the proportion of sp3 hybridized carbon atoms (saturated hydrocarbon content) to achieve optimal refractive index reduction while maintaining device reliability through the stable aromatic amine framework, thus improving external quantum efficiency without sacrificing reliability

Inventive Principle:
Principle #35Parameter changes

3Reliability

If organic compounds with many unsaturated bonds are used, then carrier-transport property is improved, but refractive index increases

Engineering Contradiction:
Improvecarrier-transport propertyVSAvoidrefractive index
Core Design Contradiction:
ReliabilityVSIllumination intensity

Solution Approach 1:

The patent changes the hybridization state parameter of carbon atoms in the molecular structure, specifically incorporating sp3 hybridized (saturated) hydrocarbon groups instead of purely sp2 unsaturated structures. This parameter change reduces the refractive index while the aromatic amine core maintains adequate carrier-transport property through its electronic structure

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS12435266B2Material for hole-transport layer, material for hole-injection layer, organic compound, light-emitting device, light-emitting apparatus, electronic device, and lighting device
Publication Date: 2025.10.07 SEMICON ENERGY LAB CO LTD
  • US12435266B2 patent drawing
  • US12435266B2 patent drawing
  • US12435266B2 patent drawing

AI summary

A material for a hole-transport layer includes a monoamine compound. The first aromatic group, the second aromatic group, and the third aromatic group are bonded to the nitrogen atom of the monoamine compound. The first and second aromatic groups each independently include 1 to 3 benzene rings. One or both of the first and second aromatic groups have one or more hydrocarbon groups each having 1 to 12 carbon atoms each forming a bond only by the sp3 hybrid orbitals. The total number of the carbon atoms in the hydrocarbon group in the first or second aromatic group is 6 or more. The total number of the carbon atoms in all of the hydrocarbon groups in the first and second aromatic groups is 8 or more. The third aromatic group is a substituted or unsubstituted monocyclic condensed ring or a substituted or unsubstituted bicyclic or tricyclic condensed ring.