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Peripheral Engineering of Multiple-Resonance Framework Targeting Efficient Organic Lasers.

Tuul Tsagaantsooj¹, Xun Tang¹, Tao Zhang²

¹Center for Organic Photonics and Electronics Research (OPERA), Kyushu University, 744 Motooka, Nishi, Fukuoka, 819-0395, Japan.

Angewandte Chemie (International Ed. in English)

|March 31, 2025

Summary

Peripheral substituents on 9-(phenylcarbazol-3-yl)-9H-carbazole-3-carbonitrile (CzBN) emitters significantly impact organic laser performance. Tert-butyl (t-Bu) groups enhance lasing by reducing aggregation, unlike phenyl (Ph) groups.

Keywords:

Excited State Absorption Molecular Aggregation Multiple Resonance Organic Lasers Peripheral Substituents

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Area of Science:

Organic electronics
Materials science
Photophysics

Background:

Multiple-resonance thermally activated delayed fluorescent (MR-TADF) emitters offer high oscillator strength and triplet utilization for organic lasers.
The 9-(phenylcarbazol-3-yl)-9H-carbazole-3-carbonitrile (CzBN) framework is a key structure for MR-TADF emitters.

Purpose of the Study:

To investigate how tert-butyl (t-Bu) and phenyl (Ph) substituents affect the photophysical properties and lasing performance of CzBN-based MR-TADF emitters.
To understand the role of molecular aggregation and excited-state dynamics in influencing laser characteristics.

Main Methods:

Synthesis and characterization of CzBN derivatives with t-Bu and Ph substituents.
Photophysical measurements including absorption, emission, and excited-state absorption (ESA) spectroscopy.
Fabrication and testing of distributed feedback (DFB) organic lasers using the synthesized emitters at various doping concentrations.

Main Results:

Both t-Bu and Ph substituents maintained large oscillator strengths but altered excited-state dynamics and aggregation.
Phenyl (Ph) substituents extended π-conjugation, leading to detrimental aggregation and a broadened ESA band, thus impairing lasing.
Tert-butyl (t-Bu) substituents reduced aggregation and separated the ESA band from the stimulated emission, resulting in optimal lasing performance.
CzBN-tBu achieved the lowest lasing threshold of 3.4 µJ cm⁻².

Conclusions:

Peripheral substituent choice critically influences molecular aggregation and excited-state dynamics in MR-TADF emitters.
Rational peripheral engineering is essential for optimizing molecular interactions and designing efficient organic laser molecules.
Minimizing aggregation, even at low doping levels, is crucial for achieving high-performance organic lasers.