Spiroacridine OLED Emitters Narrow Blue Spectrum

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Solution Overview

Problem

Current electroluminescent compounds, such as iridium complexes and fluorescent molecules, are expensive and inefficient, with broad emission spectra and low photoluminescence quantum yield, making them unsuitable for cost-effective and efficient light emission in organic light-emitting diodes (OLEDs) with desired peak wavelengths between 400 nm and 500 nm.

Innovation Solution

A composition comprising a compound with a specific structure, where A1 to A8 are independently CR12 or N, J1 is C or Si, and J2 is C(R13)n, O, (C(R13)n)2, S, NR13, or Se, is used to create a layer in OLEDs, allowing for efficient light conversion and narrow emission spectra, achieved through a method involving a mixture of the compound, a base with a pKa of 8 or higher, and a reactant like methanesulfonyl or trifluoromethanesulfonyl derivatives.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If iridium complexes are used as emissive materials, then photoluminescence quantum yield is improved, but cost increases

Engineering Contradiction:
Improvephotoluminescence quantum yieldVSAvoidcost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent replaces expensive iridium complexes with organic fluorescent molecules that are cheaper to manufacture. The invention uses small molecular weight organic compounds with specific structural features (spirobifluorene core with electron-donating groups) to achieve cost-effective emissive materials that maintain acceptable performance for OLED applications.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent modifies molecular parameters by changing the chemical structure from traditional fluorescent molecules to spirobifluorene-based compounds with specific substituents. This structural parameter change enables narrow emission spectra while maintaining high photoluminescence quantum yield, resolving the contradiction between performance and cost.

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If traditional fluorescent molecules are used, then cost is reduced, but conversion efficiency of current into emitted light deteriorates

Engineering Contradiction:
ImprovecostVSAvoidconversion efficiency
Core Design Contradiction:
Ease of manufactureVSUse of energy by moving object

Solution Approach 1:

The patent changes key molecular parameters by introducing spirobifluorene core structures with specific electron-donating groups (such as carbazole, triphen胺, or their derivatives). These parameter changes in molecular structure lead to improved charge injection and transport properties, thereby enhancing conversion efficiency while maintaining cost-effectiveness compared to iridium complexes.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures combining spirobifluorene cores with electron-donating aromatic groups. This composite approach allows the molecule to exhibit both good fluorescent properties (maintaining low cost) and improved charge transport characteristics (enhancing conversion efficiency), thus resolving the contradiction between cost and efficiency.

Inventive Principle:
Principle #40Composite materials

3Ease of manufacture

If traditional fluorescent molecules are used, then cost is reduced, but emission spectrum width deteriorates

Engineering Contradiction:
ImprovecostVSAvoidemission spectrum width
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent achieves narrow emission spectra by carefully controlling molecular parameters - specifically using spirobifluorene cores with rigid aromatic substituents and limited rotational freedom. This parameter control in molecular design narrows the emission spectrum to full width at half maximum (FWHM) of 50-80 nm, providing precise color control while maintaining the cost advantages of organic fluorescent materials.

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 solution provides a cost-effective and efficient conversion of current into emitted light with a narrow emission spectrum and high photoluminescence quantum yield, approaching 100%, suitable for blue-color emission in OLEDs, combining the advantages of fluorescent and phosphorescent emitters.

Implementation Method 1

efficient conversion of current into emitted light

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Implementation Method 2

high photoluminescence quantum yield, approaching 100%

Methodology Applied
Scientific EffectPhotoluminescence: Photoluminescence

Data Source

PatentUS11114617B2Spiroacridine derivatives
Publication Date: 2021.09.07 DDP SPECIALTY ELECTRONICS MATERIALS US LLC
  • US11114617B2 patent drawing
  • US11114617B2 patent drawing
  • US11114617B2 patent drawing

AI summary

Provided is a composition comprising a compound having structure (I) wherein each of A1, A2, A3, A4, A5, A6, A7, and A8 is independently CR12 or N; wherein one to four of A1, A2, A3, A4, A5, A6, A7, and A8 are N; wherein J1 is C or Si; wherein J2 is C(R13)n, O, (C(R13)n)2, S, NR13, or Se; wherein n is 1 or 2; wherein each of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, and R13 is independently H, deuterium, or an organic group. Also provided is a method of making the composition, a method of making an organic light-emitting diode using the composition, and an organic light-emitting diode made by that method.